US 20140200140A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0200140 A1 KEDA (43) Pub. Date: Jul. 17, 2014

(54) METHOD OF CONTROLLING PESTS (57) ABSTRACT (71) Applicant: SUMITOMO CHEMICAL COMPANY., LIMITED, Tokyo (JP) The present invention relates to a method of controlling 9 s weeds in a crop field, the method including treating the crop (72) Inventor: Hajime IKEDA, Kasai-shi (JP) field with crystal of flumioxazin described in the specifica tion, before sowinggorp or planting, 9. at the same time of sowing9. or (73) Assignee: SUMITOMO CHEMICAL planting, or after Sowing or planting crop seeds or vegetative COMPANY., LIMITED, Tokyo (JP) organs such as tubers, bulbs, or stem fragments which are treated with one or more compounds selected from the fol (21) Appl. No.: 14/144,083 lowing group B; 1-1. Group B: neonicotinoid type compounds, diamide type com (22) Filed: Dec. 30, 2013 pounds, carbamate type compounds, organic phosphorous Publication Classification type compounds, biological nematicidal compounds, other insecticidal compounds and nematicidal compounds, azole (51) Int. Cl. type compounds, strobilurin type compounds, metalaxyl AOIN 43/84 (2006.01) type compounds, SDHI compounds, and other fungicidal (52) U.S. Cl compounds and plant growth regulators. CPC ...... A0IN 43/84 (2013.01) According to the method of controlling pests of the present USPC ...... 504/128:504/225; 504/130 invention, weeds in clop fields can be efficiently controlled. US 2014/0200140 A1 Jul. 17, 2014

METHOD OF CONTROLLING PESTS TABLE 1-continued BACKGROUND OF THE INVENTION 20 value () 0001 1. Field of the Invention 3 crystal 7.7 + 0.1, 10.9 + 0.1, 13.5 + 0.1, 14.6+ 0.1, 15.0 + 0.1 0002 The present invention relates to a pest control 4 crystal 7.7 + 0.1, 10.7 + 0.1, 13.4 + 0.1, method, that is, a method of controlling pests such as harmful 14.3 + 0.1, 14.8 + 0.1 arthropod pests, nematodes, plant pathogens, and/or weeds. 5' crystal 5.5 + 0.1, 10.3 + 0.1, 10.9 + 0.1, 0003 2. Description of the Related Art 13.20.1 6 crystal 7.7 + 0.1, 8.6 + 0.1, 11.0 + 0.1, 0004 Various compounds are known as effective compo 13.2 + 0.1, 14.7 + 0.1, 15.1 + 0.1, nents for insecticides, nematicides, or fungicides. Also, flu 7" crystal 14.5 + 0.1, 18.7 + 0.1 mioxazin is known as an effective component for herbicides. PRIOR ART LITERATURE 0014) 2A method of controlling pests in a crop field, the Patent Literature method including the steps of 0005 Patent Literature 1: U.S. Pat. No. 3,799,758. Non 0015 treating crop seeds or vegetative organs such as Patent Literatures tubers, bulbs, or stem fragments with one or more compounds 0006 Non-Patent Literature 1: Crop Protection Hand selected from the group B: neonicotinoid type compounds, book, vol. 98 (2012) Meister Publishing Company, ISBN: diamide type compounds, carbamate type compounds, 1-892829-25-8) organic phosphorous type compounds, biological nemati 0007. Non-Patent Literature 2: Compendium of Pesticide cidal compounds, other insecticidal compounds and nemati Common Names (http//www.alanwood.net/pesticides/) cidal compounds, azcle type compounds, strobilurin type compounds, metalaxyl type compounds, SDHI compounds, SUMMARY OF THE INVENTION and other fungicidal compounds and plant growth regulators; and 0008. It is an object of the present invention to provide a method for producing an excellent effect on pest control in 0016 treating the crop field with crystal of fluraicxazin, crop fields. before sowing or planting, at the same time of sowing or 0009. The present invention relates to a method of control planting, or after sowing or planting the crop seeds or Veg ling pests grown in a crop field by treating the crop field with etative organs such as tubers, bulbs, or stem fragments which flumioxazin constituted of a specific crystal structure before are treated with the compounds of the group B, Sowing or planting, at the same time of sowing or planting, or 0017 wherein the crystal of flumioxazin is one or more after Sowing or planting crop seeds or vegetative organs Such selected from the group consisting of 1 crystal. 2" crystal, as tubers, bulbs, or stem fragments which are treated with one 3" crystal, 4" crystal, 5" crystal, 6" crystal and 7" crystal, or more specific insecticidal compounds, nematicidal com pounds, or fungicidal compounds. 0018 each of the crystals showing a powder X-Ray dif 0010. The present invention is as follows. fraction pattern which has diffraction peaks with 20 values () 0011 1A method of controlling weeds in a crop field, the shown in the corresponding right column of Table 1, method including treating the crop field with crystal of flu mioxazin, before sowing or planting, at the same time of TABLE 1 Sowing or planting, or after sowing or planting crop seeds or 20 value () Vegetative organs such as tubers, bulbs, or stem fragments 1 crystal 7.5 + 0.1, 11.9 + 0.1, 15.3 + 0.1 which are treated with one or more compounds selected from 2” crystal 8.7 + 0.1, 9.4 + 0.1, 14.7 + 0.1, the following group B; 18.8 0.1 Group B: neonicotinoid type compounds, diamide type com 3 crystal 7.7 + 0.1, 10.9 + 0.1, 13.5 + 0.1, pounds, carbamate type compounds, organic phosphorous 14.6+ 0.1, 15.0 + 0.1 4" crystal 7.7 + 0.1, 10.7 + 0.1, 13.4 + 0.1, type compounds, biological nematicidal compounds, other 14.3 + 0.1, 14.8 + 0.1 insecticidal compounds and nematicidal compounds, azole 5th crystal 5.5 + 10.1, 10.3 + 0.1, 10.9 + 0.1, type compounds, strobilurin type compounds, metalaxyl type 13.20.1 compounds, SDHI compounds, and other fungicidal com 6" 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, pounds and plant growth regulators, 7th crystal 14.5 + 0.1, 18.7 + 0.1 0012 wherein the crystal of flumioxazin is one or more selected from the group consisting of 1 crystal. 2" crystal, 3' crystal, 4' crystal, 5' crystal, 6' crystal and 7' crystal, 0019. 3. The control method according to 1 or 2. 0013 each of the crystals showing a powder X-Ray dif wherein the group B is the following compounds: fraction pattern which has diffraction peaks with 20 values () shown in the corresponding right column of Table 1, group B: TABLE 1. 0020 B-1. neonicotinoid type compounds: clothianidin, thiamethoxam, imidacloprid, dinotefuran, nitenpyram, 20 value () acetamiprid, and thiacloprid; 1 crystal 7.5 + 0.1, 11.9 + 0.1, 15.3 + 0.1 2” crystal 8.7 + 0.1,9.4 + 0.1, 14.7 + 0.1, 0021 diamide type compounds: flubendiamide, chlorant 18.8 0.1 raniliprole, cyantraniliprole, and compounds represented by the formula (I): US 2014/0200140 A1 Jul. 17, 2014

fludioxonil, ethaboxam, 3-chloro-5-phenyl-6-methyl-4-(2,6- (I) difluorophenyl)pyridazine, 3-cyano-5-phenyl-6-methyl-4- Br (2,6-difluorophenyl)pyridazine, and N-(1,1,3-trimethylin dan-4-yl)-1-methyl-3-difluoromethylpyrazole-4-carboxylic acid amide (racemic or enantiomer, containing a mixture of O W \ R-enantiomer and S-enantiomer (optional ratio)); and Br N1 Cl; 0031 B-11. plant growth inhibitors: ethephon, chlo NH rmeduat-chloride, mepiduat-chloride, and 4-oxo-4-(2-phe nylethyl)aminobutyric acid. 0032. 4 The control method according to any one of 1 C to 3, wherein the crop is soybean, peanut, common bean, C. O / \ pea, corn, cotton, wheat, rice, Sunflower, potato, Sugar cane, HN or vegetables. CH3 0033 5. The control method according to any one of 2 to 4, wherein the pests are weeds and/or arthropods and/or plant pathogens. - 0034 (6) The control method according to any one of 2 to 4, wherein the pests are weeds. 0022 B-2. carbamate type compounds: aldicarb, oxamyl, 0035 Pests in crop fields can be controlled by the method thiodicarb, carbofuran, carbosulfan, and dimethoate; of controlling pests according to the present invention. 0023 B-3. organic phosphorous type compounds: fenami phos, imicyafos, fensulfothion, terbufos, fosthiazate, phos DETAILED DESCRIPTION OF THE PREFERRED phocarb, dichlofenthion, isamidofos, isaZophos, ethopro EMBODIMENTS phos, cadusafos, chlorpyrifos, heterofos, mecarphon, phorate, thionazin, triaZophos, diamidafos, fosthietan, and 0036. A method of controlling pests according to the phosphamidon; present invention (hereinafter referred to as a method of the 0024 B-4. biological nematicidal compounds: Harpin present invention) includes the steps of: Protein, Pasteuria nishizawae, Pasteuria penetrans, Myroth 0037 (1) treating crop seeds or vegetative organs such as ecium verrucaria, Burholderia cepacia, Bacillus chitono tubers, bulbs, or stem fragments with one or more compounds sporus, Paecilomyces lilacinus, Bacillus amyloliquefaciens, selected from the group B consisting of specific insecticidal Bacillus firmus, Bacillus subtilis, Bacillus pumulis, Tricho compounds, nematicidal compounds, and fungicidal com derma harzianum, Hirsutella rhossiliensis, Hirsutella minine pounds; and Sotensis, Verticillium chlamydosporum, and Arthrobotry's 0038 (2) treating a crop field with crystal of flumioxazin, dactyloides, before sowing or planting, at the same time of sowing or 0025 B-5. other insecticidal compounds and nematicidal planting, or after sowing or planting the crop seeds or Veg compounds: fipronil, ethiprole, Sulfoxaflor, flupyradifurone, etative organs such as tubers, bulbs, or stem fragments which beta-cyfluthrin, tefluthrin, chlorpyrifos, abamectin, spirotet are treated with the compounds of the group B, wherein the ramat, and fluenSulfone; crystal of flumioxazin is one or more selected from the group 0026 B-6. azole type compounds: azaconazole, biter consisting of 1 crystal, 2" crystal, 3" crystal, 4" crystal, 5" tanol, bromuconazole, cyproconazole, diphenoconazole, crystal, 6" crystal and 7" crystal, diniconazole, epoxyconazole, fenbuconazole, fluquincona 0039 each of the crystals showing a powder X-Ray dif Zole, flusilaZole, flutriafol, hexaconazole, imibenconazole, fraction pattern which has diffraction peaks with 28 values () ipconazole, metconazole, mycrobutanil, penconazole, propi shown in the corresponding right column of Table 1, conazole, prothioconazole, Simeconazole, tebuconazole, tet raconazole, triadimenol, triticonazole, fenarimol, nuarimol, TABLE 1 pyrifenox, imazalil, Oxpoconazole-fumarate, pefurazoate, prochloraz, and triflumizol; 20 value () 0027 B-7. Strobilurin type compounds: kresoxim-methyl, 1 crystal 7.5 + 0.1, 11.9 + 0.1, 15.3 + 0.1 2” crystal 8.7 + 0.1, 9.4 + 0.1, 14.7 + 0.1, azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, 18.8 0.1 pyraclostrobin, dimoxystrobin, pyribencarb, metominos 3 crystal 7.7 + 0.1, 10.9 + 0.1, 13.5 + 0.1, trobin, orysastrobin, and N-methyl-2-[2-(2,5-dimethylphe 14.6+ 0.1, 15.0 + 0.1 noxy)methylphenyl-2-methoxy-acetamide (racemic or 4" crystal 7.7 + 0.1, 10.7 + 0.1, 13.4 + 0.1, 14.3 + 0.1, 14.8 + 0.1 enantiomer, containing a mixture of R-enantiomer and 5th crystal 5.5 + 10.1, 10.3 + 0.1, 10.9 + 0.1, S-enantiomer (optional ratio)); 13.20.1 0028 B-8. metalaxyl type compounds: metalaxyl and 6" crystal 7.7 + 0.1, 8.6 + 0.1, 11.0 + 0.1, metalaxyl-M; 13.2 + 0.1, 14.7 + 0.1, 15.1 + 0.1, 0029 B-9. SDHI compounds: sedaxane, penflufen, car 7th crystal 14.5 + 0.1, 18.7 + 0.1 boxin, boScalid, furametpyr, flutolanil, fluxapyroxad, isopy razam, fluopyram, and thifluZamide; 0040. Hereinafter, the crystal of flumioxazin is referred to 0030 B-10. other fungicidal compounds: tolclophos-me as “1” crystal of flumioxazin, 2" crystal of flumioxazin, 3" thyl, thiram, Captan, carbendazim, thiophanate-methyl, man crystal of flumioxazin, 4" crystal of flumioxazin, 5" crystal cozeb, thiabendazole, isotianil, triazoxide, (RS)-2-methoxy of flumioxazin, 6" crystal of flumioxazin and 7" crystal of N-methyl-2-C.-(2,5-xylyloxy)-o-tolyl)acetamide, flumioxazin, respectively'. US 2014/0200140 A1 Jul. 17, 2014

0041. Examples of the crops to which the method of the Soybeans and cotton resistant to glyphosate, and they have present invention is applied include food crops such as Soy already been commercially available under the trade names of bean, corn, cotton, wheat, barley, rye, triticale, rice, peanut, RoundupReady (registered trade mark), Agrisure (registered common bean, lima bean, azuki bean, cowpeas, mung bean, trademark) GT, Gly-Tol (registered trademark) and the like. blacklentil, Scarlet runner bean, Vigna umbellate, moth bean, Similarly, there are corn, soybeans and cotton resistant to tepary bean, broad bean, pea, garbanzo bean, lentil, lupine, glufosinate by genetic modification technologies, and they pigeon pea, and potato; forage crops such as Sorghum, oat, have already been commercially available under the trade and alfalfa, industrial crops such as Sugar beet, Sunflower, names of LibertyLink (registered trademark) and the like. rapeseed, and Sugar cane; and garden crops such as Solan There are varieties of corn and soybeans under the trade aceae vegetables (for example, eggplant, tomato, green pep names of Optimum (registered trademark) GAT (registered per, bell pepper, and hot pepper), Cucurbitaceae vegetables trademark), which are resistant to both of glyphosate and (for example, cucumber, pumpkin, Zucchini, watermelon, acetolactic acid synthase inhibitor. Similarly, there are Soy and melon), Cruciferous vegetables (for example, Japanese beans resistant to imidazolinone type acetolactic acid syn radish, turnip, horseradish, kohlrabi, Chinese cabbage, cab thase inhibitors by genetic modification technologies, and bage, brown mustard, broccoli, and cauliflower), Compositae they have been developed under the name of Cultivance. Vegetables (for example, burdock, garland chrysanthemum, Similarly, there is cotton resistant to bromoxynil by genetic artichoke, and lettuce), Liliaceae vegetables (for example, modification technologies, and this has already been com Welsh onion, onion, garlic, asparagus), Umbelliferae Veg mercially available under the trade name of BXN (registered etables (carrot, parsley, celery, and parsnip), Chenopodiaceae trademark). Similarly, there is a variety of soybean sold under Vegetables (for example, spinach and Swiss chard), Labiatae the trade name of RoundupReady (registered trademark) 2 Vegetables (for example, Japanese mint, mint, basil, and lav Xtend as a Soybean resistant to both of glyphosate and ender), Strawberry, Sweet potato, yam, and aroid. dicamba by genetic modification technologies. Similarly, 0042. The method of the present invention is applied par there has been developed cotton resistant to both of glypho ticularly to soybean, peanut, common bean, pea, corn, cotton, sate and dicamba by genetic modification technologies. wheat, rice, Sunflower, potato, Sugar cane, or vegetables. 0047 A gene encoding aryloxyalkanoate dioxygenase 0043. When the method of the present invention is applied may be introduced to produce a crop which becomes resistant to Sugarcane, stem fragments cut so as to have one stalk may to phenoxy acid type herbicides such as 2,4-D, MCPA, be used as the stem fragment of Sugarcane, or stem fragments dichlorpropand mecoprop, and aryloxyphenoxypropionic having a size of 2 cm to 15 cm may be used in the cultivation acid type herbicides Such as quizalofop, haloxyfop, fluazifop, of Sugar cane. Sugar cane cultivation methods using Such diclofop, fenoxaprop, metamifop, cyhalofop and clodinafop stem fragments are publicly known (WO 09/000,0398, WO (Wright et al. 2010: Proceedings of National Academy of 09/000,399, WO 09/000,400, WO 09/000,401, and WO Science. 107 (47): 20240-20245). Cultivars of soybean and 09/000,402) and performed under the brand name of Plene cotton, which show the resistance to 2,4-D, have been devel (trademark). oped under the brand of Enlist. 0044) The above crops include plants to which resistance 0048. A gene encoding a 4-hydroxyphenyl pyruvic acid to Protoporphyrinogen IX oxidase inhibitors such as flumi dioxygenase (hereinafter referred to as HPPD) inhibitor, the oxazin: 4-hydroxyphenylpyrubic acid dioxygenase inhibitors gene having resistance to HPPD, may be introduced to create Such as isoxaflutole; acetolactic acid synthase inhibitors such a plant resistant to a HPPD inhibitor (US2004/0058427). A as imazethapyr and thifensulfuron-methyl; 5-enolpyru gene capable of synthesizing homogentisic acid which is a Vylshikimate-3-phosphoric acid synthase inhibitors such as product of HPPD in a separate metabolic pathway even if glyphosate; glutamine synthetase inhibitors such as glufosi HPPD is inhibited by a HPPD inhibitoris introduced, with the nate; auxin type herbicides such as 2,4-D and dicamba; and result that a plant having resistance to the HPPD inhibitor can herbicides such as bromoxinyl are imparted by classical be created (WO02/036787). A gene expressing excess HPPD breeding methods or genetic modification technologies. may be introduced to produce HPPD in such an amount as not 0045. As examples of crops to which resistance has been to adversely affect the growth of plants even in the presence of imparted by classical breeding methods, corn resistant to a HPPD inhibitor, with the result that a planthaving resistance imidazolinone type acetolactic acid synthase inhibitory her to the HPPD inhibitor can be created (WO96/38567). Besides bicides such as imazethapyr is given and has already been introduction of the gene expressing excess HPPD, a gene commercially available under the trade name of Clearfield encoding prephenate dehydrogenase is introduced in order to (trademark). Examples of such crops include STS soybeans increase the yield of p-hydroxyphenyl pyruvic acid which is resistant to Sulfonylureatype acetolactic acid synthase inhibi a substrate of HPPD to create a plant having resistance to the tory herbicides such as thifensulfuron-methyl. Similarly, HPFD inhibitor (Rippert Pet. al., 2004 Engineering plant examples of a plant to which resistance to an acetyl CoA shikimate pathway for production of tocotrienol and improv carboxylase inhibitor Such as triune oxime-based or arylox ing herbicide resistance. Plant Physiol. 134: 92-100). yphenoxypropionic acid-based herbicide has been imparted 0049. Examples of a method of producing crops resistant by classical breeding methods include SR corn. to herbicides include, other than the above, the gene introduc 0046 Examples of a plant to which resistance has been ing methods described in WO98/20144, WO2002/46387, and imparted by genetic modification technologies include corn, 1382005/O2468OO. US 2014/0200140 A1 Jul. 17, 2014

0050. The above crops include, for example, crops which BollGard (registered trademark) II (cotton variety expressing can synthesize selective toxins and the like known as the Cry1Ac and Cry2Ab toxins), BollGard (registered trade genus Bacillus by using genetic modification technologies. mark) III (cotton variety expressing Cry1Ac, Cry2Ab and 0051 Examples of the toxins developed in such geneti VIP3R toxins), VipCot (registered trademark) (cotton variety cally modified plants include insecticidal proteins derived expressing VIP3A and Cry1Ab toxins), WideStrike (regis from Bacillus cereus and Bacillus popilliae: Ö-endotoxins tered trademark) (cotton variety expressing Cry1Ac and such as Cry1Ab, Cry1Ac, Cry 1F, Cry1 Fa2, Cry2Ab, Cry3A, Cry 1F toxins) and the like. Cry3Bb1, Cry9C, Cry34, and Cry35ab derived from Bacillus 0055 Examples of the plant used in the present invention thuringiensis, insecticidal proteins such as VIP1, VIP2, also include plants such as Soybeans into which a Ragl (Re VIP3, and VIP3A; insecticidal proteins derived from nema sistance Aphid Gene 1) gene is introduced to impart resis todes; toxins produced by animals such as Scorpion toxins, tance to an aphid. spider toxins, bee toxins, and neurotoxins specific to insects; filamentous fungus toxins; plant lectins; agglutinin; trypsin 0056. The plants to be used in the present invention inhibitors, serine protease inhibitors, and protease inhibitors include those provided with resistance to nematodes by using Such as patatin, cystatin, and papain inhibitors; ribosome a classical breeding method or genetic modification technolo inactivating proteins (RIP) such as lysine, corn-RIP, abrin, gies. Examples of the genetic modification technologies used lufin, Saporin, and bryodin; steroid metabolic enzymes Such to provide the resistance to nematodes include RNAi. as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyl 0057 The above crops include those to which the ability to transferase, and cholesterol oxidase; ecdysone inhibitors; produce antipathogenic Substances having a selective effect is HMG-CoA reductase; ion channel inhibitors such as sodium imparted using genetic modification technologies. For channel and calcium channel inhibitors; juvenile hormone example, PR proteins are known as an example of the esterase: diuretic hormone receptors; stilbene synthase; antipathogenic substance (PRPs, EP-A-0392225). Such bibenzyl synthase; chitinase; and glucanase. antipathogenic Substances and genetically modified plants 0052. The toxins expressed in these transgenic plants producing these antipathogenic Substances are described in, include hybrid toxins, partially deficient toxins and modified for example, EP-A-0392225, WO 95/33818, and EP-A- toxins, which derive from Ö-endotoxin proteins such as 0353191. Examples of the antipathogenic substances devel Cry1Ab, Cry1Ac, Cry 1F, Cry1 Fa2, Cry2Ab, Cry3A, oped in Such genetically modified plants include ion channel Cry3Bb1, Cry9C, Cry34Ab and Cry35Ab, and insecticidal inhibitors such as a sodium channel inhibitor and calcium proteins such as VIP1, VIP2, VIP3 and VIP3A. The hybrid channel inhibitor (KP1, KP4, and KP6 toxins produced by toxins are created by new combinations of domains having virus are known); stilbene synthase; bibenzyl synthase; chiti different proteins by using genetic modification technologies. nase; glucanase; PR protein; antipathogenic Substances pro As the partially defective toxins, Cry1Ab in which part of the duced by microorganisms such as peptide antibiotics, antibi amino acid sequences is missing is known. In the modified otics having a heteroring, and a protein factor (referred to as toxin, one or more of amino acids of a natural type toxin is replaced. Examples of these toxins and genetically modified a plant disease resistant gene and described in WO plants capable of synthesizing these toxins are described in, 03/000906) relating to plant disease resistance. for example, EP-A-0374753, WO 93/07278, WO95/34656, 0058. The above crops include plants to which useful traits EP-A-0427529, EP-A-451878, and WO 03/052073. Resis Such as an oil component reformation and amino acid-content tance to noxious insects belonging to order Coleoptera, order reinforcing trait are given by genetic modification technolo Diptera, and order Lepidoptera is imparted to plants by toxins gies. Examples of these plants include VISTIVE (trademark) contained in these genetically modified plants. (low linolenic Soybean having a reduced linolenic content), 0053 Also, genetically modified plants which contain one high-lysine (high oil) corn (corn having an increased lysine or or more insecticidal genes resistant to harmful insects and oil content) and the like. develop one or more toxins have been already known and 0059 Moreover, the above crops include stuck varieties Some of these plants have been put on the market. Examples obtained by combining two or more useful traits such as the of these genetically modified plants include YieldGard (reg above classical herbicide trait or herbicide resistant gene, istered trademark) (corn variety expressing Cry1Ab toxin), gene resistant to insecticidal noxious insects, antipathogenic YieldGard Rootworm (registered trademark) (corn variety Substance-producing gene, oil component reformation, expressing Cry3Bb1 toxin). YieldGard Plus (registered trade amino acid-content reinforcing trait, and allergen reduction mark) (corn variety expressing Cry1Aband Cry3Bb1 toxins), trait. Herculex I (registered trademark) (corn variety expressing 0060. In the method of the present invention, examples of phosphinothricin N-acetyltransferase (PAT) for imparting the compounds of the group B including specific insecticidal resistance to a Cry1 Fa2 toxin and glufosinate), NatureGard compounds, nematicidal compounds, fungicidal compounds, (registered trademark), AGRISURE (registered trademark) or plant growth regulators used to treat crop seeds or vegeta CB Advantage (Bt11 corn borer (CB) trait), Protecta (regis tive organs such as tubers, bulbs, or stem fragments include tered trademark); and the like. neonicotinoid type compounds, diamide type compounds, 0054 Also, genetically modified cotton which contains carbamate type compounds, organic phosphorous type com one or more insecticidal genes resistant to harmful insects and pounds, biological nematicidal compounds, other insecti develops one or more toxins has been already known and cidal compounds and nematicidal compounds, azole type Some of cotton have been put on the market. Examples of compounds, strobilurin type compounds, metalaxyl type these genetically modified cotton include BollGard (regis compounds, SDHI compounds, and other fungicidal com tered trademark) (cotton variety expressing Cry1Ac toxin), pounds and plant growth regulators. US 2014/0200140 A1 Jul. 17, 2014

0061 Examples of the neonicotinoid type compounds in 0075 Examples of the strobilurin type compounds in the the present invention include the followings: present invention include the followings: 0062 clothianidin, imidacloprid, nitenpyram, acetami 0076 kresoxim-methyl, azoxystrobin, trifloxystrobin, prid, thiamethoxam, thiacloprid, and dinotefuran. fluoxastrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, 0063 Examples of the diamide type compounds in the pyribencarb, metominostrobin, orysastrobin, and N-methyl present invention include the followings: 2-2-(2,5-dimethylphenoxy)methylphenyl-2-methoxyac 0064 flubendiamide, chlorantraniliprole, cyantranilip etamide (racemic or enantiomer, containing a mixture of role, and compounds represented by the formula (I): R-enantiomer and S-enantiomer (optional ratio), hereinafter referred to as a compound 1). 0077. Examples of the metalaxyl type compounds include (I) the followings: Br 0078 metalaxyl and metalaxyl-M and mefenoxam. 0079. Examples of the SDHI compounds in the present invention include the followings: N o 4 / 0080 sedaxane, penflufen, carboxin, boscalid, furamet B r N Cl. pyr, flutolanil, fluxapyroxad, isopyrazam, fluopyram, and thi NH fluzamide. N I0081 Examples of the other fungicidal compounds in the present invention include the followings: I0082 tolclophos-methyl, thiram, Captan, carbendazim, O thiophanate-methyl, mancoZeb, thiabendazole, isotianil, tria C.HN Zoxide, (RS)-2-methoxy-N-methyl-2-O-(2,5-xylyloxy)-o- tolyl)acetamide, fludioxonil, ethaboxam, 3-chloro-5-phenyl 6-methyl-4-(2,6-difluorophenyl)pyridazine (hereinafter referred to as a compound 2), 3-cyano-5-phenyl-6-methyl-4- " (2,6-difluorophenyl)pyridazine (hereinafter referred to as a compound 3), and N-(1,1,3-trimethylindan-4-yl)-1-methyl 3-difluoromethylpyrazole-4-carboxylic acid amide (racemic 0065. Examples of the carbamate type compounds in the or enantiomer, containing a mixture of R-enantiomer and present invention include the followings: S-enantiomer (optional ratio), hereinafter referred to as a 0066 aldicarb, oxamyl, thiodicarb, carbofuran, carbosul compound 4). fan, and dimethoate. I0083. Examples of the plant growth regulators in the 0067 Examples of the organic phosphorous type com present invention include the followings: pounds in the present invention include the followings: I0084 ethephon, chlormeduat-chloride, mepiduat-chlo 0068 fenamiphos, imicyafos, fensulfothion, terbufos, fos ride, and 4-oxo-4-(2-phenylethyl)aminobutyric acid (herein thiazate, phosphocarb, dichlofenthion, isamidofos, isaZo after referred to as a compound 5). phos, ethoprophos, cadusafos, chlorpyrifos, heterofos, I0085. In the present invention, the compounds of the group mecarphon, phorate, thionazin, triaZophos, diamidafos, fos Bused to treatcrop seeds, or vegetative organs such as tubers, thietan, and phosphamidon. bulbs, or stem fragments are publicly known compounds, and 0069. Examples of the biological nematicidal compounds may be synthesized based on well known patent documents. in the present invention include the followings: Also, commercially available preparations or standard prod 0070 Harpin Protein, Pasteuria nishizawae, Pasteuria ucts may be purchased and used as the compounds of the penetrans, Pasteuria usage, Myrothecium verrucaria, group B. Burholderia cepacia, Bacillus chitonosporus, Paecilomyces I0086. In the step of treating crop seeds or vegetative lilacinus, Bacillus amyloliquefaciens, Bacillus firmus, Bacil organs such as tubers, bulbs, or stem fragments with the lus subtilis, Bacillus pumulis, Trichoderma harzianum, Hir compounds of the group B in the present invention, the com Sutella rhossiliensis, Hirsutella minnesotensis, Verticillium pounds of the group B are usually mixed with a carrier Such as chlamydosporum, and Arthrobotry's dactyloides. a solid carrier or liquid carrier and further added with auxil 0071 Examples of the other insecticidal compounds and iaries for preparations such as Surfactants according to the nematicidal compounds in the present invention include the need to be formulated into preparations. The dosage is pref followings: erably an aqueous suspension preparation. 0072 fipronil, ethiprole, flupyradifurone, sulfoxaflor, I0087 As the compounds of the group B used to treat crop beta-cyfluthrin, tefluthrin, chlorpyrifos, abamectin, spirotet seeds or vegetative organs such as tubers, bulbs, or stem ramat, and fluenSulfone. fragments in the present invention, a preparation constituted 0073. Examples of the azole type compounds in the of a single component may be used, two or more preparations present invention include the followings: each constituted of a single component may be used in com 0074 azaconazole, bitertanol, bromuconazole, cypro bination, or a preparation constituted of two or more compo conazole, difenoconazole, diniconazole, epoxyconazole, fen nents may be used. buconazole, fluguinconazole, flusilaZole, flutriafol, hexa I0088. The compounds of the group B used for the above conazole, imibenconazole, ipconazole, metconazole, treatment are applied in an amount of usually 0.2 to 5000 g, myclobutanil, penconazole, propiconazole, prothioconazole, and preferably 0.5 to 1000 g based on 100 kg of the crop seeds simeconazole, tebuconazole, tetraconazole, triadimenol, or vegetative organs such as tubers, bulbs, or stem fragments. triticonazole, fenarimol, nuarimol, pyrifenox, imazalil, Oxpo Examples of a method for applying effective components to conazole fumarate, pefurazoate, prochloraZ, and triflumizol. the crop seeds or vegetative organs such as tubers, bulbs, or US 2014/0200140 A1 Jul. 17, 2014

stem fragments include a method in which the crop seeds or azin. It is also possible to use a solution or a Suspension of a Vegetative organs such as tubers, bulbs, or stem fragments are synthetic reaction crude product containing flumioxazin. powder-coated with a preparation containing effective com 0097. The organic solvent to be used for the crystallization ponents; a method in which the crop seeds or vegetative includes alcohols such as methanol, 2-methoxyethanol, organs such as tubers, bulbs, or stem fragments are dipped in 2-ethoxyethanol, ethers such as tetrahydrofuran, acetone, a preparation containing effective components; a method in 1,4-dioxane, halogenated hydrocarbons such as chloroform, which a preparation containing effective components is 1.2-dichloroethane orchlorobenzene, and aromatic hydrocar sprayed on the crop seeds or vegetative organs such as tubers, bons such as Xylene or toluene. bulbs, or stem fragments; and a method in which the crop 0098. It is also possible to use seed crystals in crystalliza seeds or vegetative organs such as tubers, bulbs, or stem tion for producing the crystal of the present invention. In that fragments are coated with a carrier containing effective com case, it is preferred to use crystals having a crystal form to be ponents. prepared. The amount of seed crystals to be added is prefer 0089. The present invention includes the step of treating a ably from 0.0005 parts by weight to 0.02 parts by weight, and crop field with one or more crystals selected from the group more preferably from 0.001 part by weight to 0.01 part by consisting of 1 crystal of flumioxazin to 7" crystal of flumi weight, based on 1 part by weight offlumioxazin. The crystals oxazin before sowing or planting, at the same time of sowing of the present invention may be a solvate or a non-Solvate. or planting, or after Sowing or planting the crop seeds or Vegetative organs such as tubers, bulbs, or stem fragments 0099. When a specific hydrophilic organic solvent is used which are treated with the compounds of the group B. as a crystallization solvent, the obtained crystals are some 0090. The 1 crystal of flumioxazin, 2" crystal of flumi times crystals of a solvate. The crystals of a non-Solvate can oxazin, 3" crystal of flumioxazin, 4" crystal of flumioxazin, be obtained by heating to dry the crystals of a solvate under 5' crystal of flumioxazin, 6' crystal of flumioxazin and 7" reduced pressure. crystal of flumioxazin (hereinafter, referred to as 1 crystal of 0100. The degree of drying of the crystals can be deter flumioxaxin to 7" crystal of flumioxaxin) used in the method mined by analytical means such as gas chromatography. of the present invention can be produced by the methods 0101. It is also possible to determine the purity of the disclosed in Example and modified methods thereof. crystal form of the crystal by subjecting the crystal to the 0091. The 1 crystal of flumioxaxin to 7' crystal of flu powder X-ray diffraction measurement Such as CuKO. rays mioxaxin in the present invention can be obtained, for diffraction analysis, followed by analyzing the obtained dif example, by conducting the following steps. fraction pattern about the presence or absence of diffraction 0092 First, a starting material is dissolved in an organic peaks peculiar to crystal of a Solvate, and the height of the Solvent to obtain a solution which contains flumioxazin at the peaks. concentration generally in the range of 2 mg to 200 mg. 0102 The crystal of the present invention can be produced preferably in the range of 5 mg to 120 mg, per ml of the with high purity, can remain unchanged in crystal form even Solvent, and setting the temperature of the obtained solution after a heat treating step for formulation, can also exhibit generally within the range of 40° C. to 80° C., preferably physical and chemical properties which are more advanta within the range of 50° C. to 75° C. geous for the production of a formulation, and can maintain 0093. Then, the heated solution may be heated to rapidly Such properties even after being stored for a long period. Volatilizing its solvent, for example by dropping the Solution 0103) In the step of treating a field with the one or more onto the heated glass plate or the like to form and isolate crystals selected from the group consisting of 1 crystal of crystals. flumioxazin to 7" crystal of flumioxazin, the one or more 0094. The heated solvent is preferably cooled to its tem crystals selected from the group consisting of 1 crystal of perature generally from about 0° C. to less than 25° C. flumioxazin to 7" crystal of flumioxazin is usually mixed preferably from about 10° C. to 25° C. to form a crystal. with a carrier Such as a Solid carrier or liquid carrier and Preferably the step of cooling the heated solution is gradually further added with auxiliaries for preparations such as Surfac conducted, specifically by lowering the solution preferably at tants according to the need to be formulated into preparations. 5° C. to 15° C. per hour, more preferably at around 10° C. per 0104 Examples of a method for applying the one or more hour. Water or other solvent at the same temperature as that of crystals selected from the group consisting of 1 crystal of the heated solution can be added to the solution before cool flumioxazin to 7" crystal of flumioxazinto a field include a ing for easily forming crystals. After cooling the solution, the method in which the one or more crystals selected from the cooled Solution is maintained at the lowered temperature to group consisting of 1 crystal of flumioxazinto 7" crystal of form a crystal. The time of maintenance for the solution flumioxazin is sprayed on field soil and a method in which the depends on the scale, temperature or other conditions of the one or more crystals selected from the group consisting of 1 solution, which can be arbitrarily determined. crystal of flumioxazinto 7" crystal of flumioxazin is sprayed 0095. The crystals of the present invention can be col on weeds after the weeds are grown. lected in a known manner, for example, by filtration, by 0105. The amount of the one or more crystals selected concentration, by centrifugation or by decantation. The crys from the group consisting of 1 crystal of flumioxazin to 7" tal may be washed with an appropriate solvent, if necessary. crystal of flumioxazin used in the step of applying the one or The crystal may be subjected to the method comprising the more crystals selected from the group consisting of 1 crystal above-mentioned steps or slurry filtration for improving its offlumioxazinto 7" crystal of flumioxazinto a field is usually purity or quality. 5 to 5000 g, preferably 10 to 1000 g, and more preferably 20 0096. It is possible to use, as the starting material for to 500g per 10000 m. In this case, adjuvants may be added producing the crystal of the present invention, a solution or a to the one or more crystals selected from the group consisting Suspension of flumioxazin, or a mixture containing flumioX of 1 crystal of flumioxazin to 7" crystal of flumioxazin to US 2014/0200140 A1 Jul. 17, 2014 apply the one or more crystals selected from the group con Cydia pamonella, Gracillarlidae such as Caloptilia theivora sisting of 1 crystal of flumioxazin to 7" crystal of flumiox and Phyllonorycter ringoneella, Carposimidae such as Car azin to the field. posina niponensis, hyonetiidae Such as Lyonetia spp., 0106. In the present invention, the crop seeds or vegetative Lymantriidae such as Lymantriidae spp. and Euproctis spp., organs such as tubers, bulbs, or stem fragments treated with Yponameutidae such as Plutella xylostella, Gelechiidae such the compounds of the group B are Sowed or planted in a field as Pectinophora gossypiella and Phthorimaea operculella, by a usual method. In the method of controlling pests accord Arctiidae such as Hyphantria cunea, and Tineidae such as ing to the present invention, a crop field may be treated with Tinea translucens and Tineola bisselliella, the one or more crystals selected from the group consisting of 0113 noxious insects belonging to order Thripidae: Thys 1 crystal of flumioxazin to 7" crystal of flumioxazin before anoptera Such as Frankliniella Occidentalis, Thrips parmi, Sowing or planting, at the same time of sowing or planting, or Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, after sowing or planting the crop seeds or vegetative organs and Frankliniella fisca, Such as tubers, bulbs, or stem fragments. 0114 noxious insects belonging to order Diptera: 0107. When a crop field is treated with the one or more Agromyzidae such as Musca domestics, Culex popiens pal crystals selected from the group consisting of 1 crystal of lens, Tabanus trigonus, Hyleraya antique, Hyllemya platura, flumioxazin to 7" crystal of flumioxazin before sowing or Anopheles sinensis, Agromyza Oryzae, Hydrellia griseola, planting the crop seeds or vegetative organs such as tubers, Chlorops Oryzae, and Liriomyza trifolii, Dacus cucurbitae, bulbs, or stem fragments, the one or more crystals selected and Ceratitis capitata, from the group consisting of 1 crystal of flumioxazin to 7" 0115 Noxious insects belonging to order Coleoptera: crystal of flumioxazin is applied before 50 days to immedi Epillachna vigintioctopunctata, Aulacophora femoralis, ately before sowing or planting, preferably before 30 days to Phyllotreta Striolata, Culema Oryzae, Echinocnemus squa immediately before Sowing or planting, more preferably meus, Lissorhoptrus Oryzophilus, Anthonomus grandis, Cal before 20 days to immediately before Sowing or planting, and losobruchus chinensis, Sphenophorus venatus, Popillia even more preferably before 10 days to immediately before japonica, Anomala cuprea, Diabrotica spp., Leptinotarsa Sowing or planting. deceniineata, Agriotes spp., Lasioderma serricorne, Anthre 0108. When a crop field is treated with the one or more nus verbasci, Tribolium castaneum, Lyctus brunneus, Ano crystals selected from the group consisting of 1 crystal of plophora malasiaca, and Tomicus piniperda, flumioxazin to 7" crystal of flumioxazin after sowing or 0116 noxious insects belonging to order Orthoptera: planting the crop seeds or vegetative organs such as tubers, Locusts migratoria, Gryllotalpa africana, Oxya yezoensis, bulbs, or stem fragments, the one or more crystals selected from the group consisting of 1 crystal of flumioxazin to 7" and Oxya japonica, crystal of flumioxazin is applied immediately after to 50 days 0117 noxious insects belonging to order Hymenoptera: after sowing or planting. Athalia rosae, Acromyrmex spp., and Solenopsis spp.; 0109 The method of controlling pests according to the 0118 noxious insects belonging to order Blattodea: Blat present invention ensures that harmful arthropods, noxious tella germanica, Periplaneta fuliginosa, Periplaneta ameri nematodes and/or plant pathogens, and pests such as weeds in cana, Periplaneta brunnea, and Blatta Orientalis; and crop fields can be controlled. 0119 noxious insects belonging to order Acarina: Tet 0110. As harmful arthropods, the following examples are ranychidae such as Tetranychus urticae, Panonychus citri, given. and Oligonychus spp., Eriophyidae such as Aculops pelle 0111 Noxious insects belonging to order Hemiptera: Del kassi, Tarsonemidae Such as Polyphagotarisonemus latus, phacidae Such as Laodelphax striatellus, Nilaparvata lugens, Tenuipalpidae, Tuckerellidae, Acaridae such as Trophagus and Sogatella fircifera, Deltocephalidae Such as Nephotettix putrescentiae, Dermanyssidae Such as Dermatophagoides cincticeps and Nephotettix virescens, Aphididac Such as farina and Dermatophagoides ptrenyssinus, and Cheyletidae Aphis gossypii, Myzus persicae, Brevicoryne brassicae, Mac Such as Cheyletus eruditus, Cheyletus malaccensis, and rosiphum euphorbiae, Aulacorthum Solani, Rhopalosiphun Cheyletus moorei. padi, and Toxoptera citricidus, Pentatomidae Such as Nezara 0.120. As the plant pathogens, the following examples can antennata, Riptortus clavetus, Leptocorisa chinensis, Eysar be given. coris parvus, Haiyomorpha mista, and Lygus lineolaris, 0121 Cercospora gossypina, Cercospora kikuchii, Cer Aleyrodidae Such as Trialeurodes vaporariorum, Bemisia cospora zeae-maydis, Cercospora sojina, Phakopsora gos tabaci, and Bemisia argentifolii, Coccidae such as Aonidiella sypii, Rhizoctonia Solani, Colletotrichum gossypii, Perono aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplas spora gossypina, Aspergillus spp., Penicillium spp., tes rubens, and Icerya purchase, Tingidae, and Psyllidae; Fusarium spp., Tricoderma spp., Thielaviopsis spp., Rhizo 0112 noxious insects belonging to order Lepidoptera: pus spp., Mucor spp., Corticium spp., Phoma spp., Diplodia Pyralidae such as Chilo suppressalis, Tryporyza incertulas, spp., Verticillium spp., Puccinia spp., Mycosphaerella spp., Cnaphalocrocis medinalis, Notarcha derogate, Plodia inter Phytophthora spp. (for example, Phytophthora sojae, Phy punctella, Ostrinia furnacalis, Ostrinia nubilaris, Hellula tophthora nicotianae var. nicotianae, Phytophthora undalis, and Pediasia teterrellus, Noctuidae such as infestans, and Phytophthora erythroseptica), Pythium spp. Spodoptera litura, Spodoptera exigua, Pseudaletia separate, (for example, Pythium debaryanum, Pythium Sylvaticum, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Tri Pythium graminicola, Pythium irregular, and Pythium ulti choplusia spp., Heliothis spp., and Belicoverpa spp., Pieridae mum), Microsphaera diffusa, Diaporthe phaseolorum var. such as Pieris rapae, Tortricidae such as Adoxophyes app., sojae, Septoria glycines, Phakopsora pachyrhizi, Sclerotinia Grapholita molesta, Leguminivora glycinivorella, Matsumu sclerotiorum, Elsinoeglycines, Ustilago maydis, Cochliobo raeses azukivora, Adoxophyes Orana fasciata, Adoxophyes lus heterostrophus, Gloeocercospora Sorghi, and Alternaria sp., Homona magnanima, Archips fiascocupreanus, and spp. US 2014/0200140 A1 Jul. 17, 2014

0122. As the weeds, the following examples are given. 0144 weeds of the family Primulaceae: Anagallis arven 0123 Weeds of the family Urticaceae: Urtica urens, Sis, 0.124 weeds of the family Polygonaceae: Polygonum con 0145 weeds of the family Asclepiadaceae: Asclepias Syri volvulus, Polygonum lapathifolium, Polygonum pensylvani aca and Ampellamus albidus, cum, Polygonum persicaria, Polygonum longisetum, 0146 weeds of the family Rubiaceae: Galium aparine, Polygonum aviculare, Polygonum arenastrum, Polygonum Galium spuriura var. echinospermon, Spermacoce latifolia, cuspidatum, Rumex japonicas, Rumex Crispus, Rumex obtusi Richardia brasiliensis, and Borreria alata, folius, and Rumex acetosa, 0147 weeds of the family Convolvulaceae: Ipomoea nil, 0.125 weeds of the family Portulacaceae: Portulaca olera Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacea Ced. var. integriuscula, Ipomoea lacunose, Ipomoea triloba, Ipo 0126 weeds of the family Caryophyllaceae: Stellaria moea acuminate, Ipomoea hederifolia, Ipomoea coccinea, media, Cerastium holosteoides, Cerastium glomeratum, Ipomoea quamoclit, Ipomoea grandifolia, Ipomoea aristolo Spergula arvensis, and Silene gallica, chiafolia, Ipomoea cairica, Convolvulus arvensis, Calystegia 0127 weeds of the family Molluginaceae: Mollugo verti hederacea, Calystegia japonica, Merremia hedeacea, Mer cillata, remia aegyptia, Merremia cissoids, and Jacquemonitia tam 0128 weeds of the family Chenopodiaceae: Chenopo nifolia, dium album, Chenopodium ambrosioides, Kochia scoparia, 0148 weeds of the family Boraginaceae: Myosotis arven Salsola kali, and Atriplex spp.; Sis, 0129 weeds of the family Amaranthaceae: Amaranthus 0149 weeds of the family Lamiaceae: Lamium pur retroflexus, Amaranthus viridis, Amaranthus lividus, Ama pureum, Lamium amplexicaule, Leonotis nepetaefolia, Hyp ranthus spinosus, Amaranthus hybridus, Amaranthus palm tis suaveolens, Hyptis lophanta, Leonurus Sibiricus, and eri, Amaranthus rudis, Amaranthus patulus, Amaranthus Stachys arvensis, tuberculatos, Amaranthus blitoides, Amaranthus deflexus, 0150 weeds of the family Solanaceae: Datura stramo Amaranthus quitensis, Alternanthera philoxeroides, Alter nium, Solanum nigrum, Solanum americanum, Solariumpty nanthera sessilis, and Alternanthera tenella, canthum, Solanum Sarrachoides, Solanum rostratum, 0130 weeds of the family Papaveraceae: Papaverrhoeas Solanum aculeatissimuru, Solanum Sisymbriifolium, and Argemone mexicana, Solarium carolinense, Physalis angulata, Physalis subgla 0131 weeds of the family Brassicaceae: Raphanus brata, and Nicandra physaloides; raphanistrum, Raphanus sativus, Sinapis arvensis, Capsella 0151 weeds of the family Scrophulariaceae: Veronica bursa-pastoris, Brassica juncea, Brassica campestris, Des hederaefolia, Veronica persica, and Veronica arvensis, curainia pinnata, Rorippa islandica, Rorippa Sylvestris, 0152 weeds of the family Plantaginaceae: Plantago asi Thlaspi arvense, Myagrum rugosum, Lepidium virginicum, atica, and Coronopus didymus, 0153 weeds of the family Asteraceae: Xanthium pensyl 0132 weeds of the family Capparaceae: Cleome affinis, vanicum, Xanthium occidentale, Helianthus annuus, Matri 0.133 weeds of the family Fabaceae: Aeschynomene caria chamomilla, Matricaria perforate, Chrysanthemum indica, Aeschynomene rudis, Sesbania exaltata, Cassia segetum, Matricaria matricaricides, Artemisia princeps, obtusifolia, Cassia Occidentalis, Desmodium tortuosum, Artemisia vulgaris, Artemisia verlotorum, Solidago Desmodium adscendens, Trifolium repens, Pueraria lobata, altissima, Taraxacum officinale, Galinsoga ciliate, Galinsoga Viola angustifolia, Indigofera hirsute, Indigofera truxilensis, parviflora, Senecio vulgaris, Senecio brasiliensis, Senecio and Vigna sinensis, grisebachii, Conyza bonariensis, Conyza Canadensis, 0134 weeds of the family Oxalidaceae: Oxalis cornicu Ambrosia artemisiaefolia, Ambrosia trifida, Bidens pilosa, late, Oxalis strica, and Oxalis Oxyptera, Bidens frondosa, Bidens subalternans, Cirsium arvense, Cir 0135 weeds of the family Geraniaceae: Geranium caro sium vulgare, Silybum marianum, Carduus nutans, Lactuca linense and Erodiura cicutarium, serriola, Sonchus oleraceus, Sonchus asper; Wedelia glauca, 0.136 weeds of the family Euphorbiaceae: Euphorbia Melampodiumperfoliaturn, Emilia Sonchifolia, Tagetes helioscopia, Euphorbia maculate, Euphorbia humistrata, minuta, Blainvillea latifolia, Tridax procumbens, Porophyl Euphorbia esula, Euphorbia heterophylla, Euphorbia brasil lum ruderale, Acanthospermum australe, Acanthospermum iensis, Acalypha australis, Croton glandulosus, Croton loba hispidum, Cardiospermum halicacabum, Ageratum tus, Phyllanthus Corcovadensis, and Ricinus communis, convzoides, Eupatorium perfoliatum, Eclipta alba, Erechtites 0.137 weeds of the family Malvaceae: Abutilon theo hieracifolia, Gamochaeta spicata, Gnaphalium spicatum, phrasti, Sida rhonibiforia, Sida cordifolia, Sida spinosa, Sida Jaegeria hirta, Parthenium hysterophorus, Siegesbeckia ori glaziovii, Sida Santaremmensis, Hibiscus trionum, Anoda entalis, and Soliva sessilis, cristata, and Malvastrum Coromandelianum, 0154 weeds of the family Liliaceae: Allium canadense 0138 weeds of the family Sterculiaceae: Waltheria and Allium vineale, indica, 0155 weeds of the family Commelinaceae: Commelina 0139 weeds of the family Violaceae: Viola arvensis, and communis, Commelina bengharensis, and Commelina Viola tricolor, erecta, 0140 weeds of the family Cucurbitaceae: Sicyos angula 0156 weeds of the family Poaceae: Echinochloa crus tus, Echinocystis lobata, and Momordica charantia, galli, Setaria viridis, Setaria faberi, Setaria glauca, Setaria 0141 weeds of the family Lythraceae: Lythrum salicaria, geniculate, Digitaria ciliaris, Digitaria sanguinalis, Digi 0142 weeds of the family Apiaceae: Hydrocotyle Sibthor taria horizontalis, Digitaria insularis, Eleusine indica, pioides, Poaannua, Allospecurus aequalis, Alopecurus myosuroides, 0143 weeds of the family Sapindaceae: Cardiospermum Avena fatua, Sorghum halepense, Sorghum vulgare, Agropy halicacabum, ron repens, Lolium multiflorum, Lolium perenne, Lolium rigi US 2014/0200140 A1 Jul. 17, 2014

dum, Bromus secalinus, Bromus tectorum, Hordeum juba saflufenacil, cinidon, cinidon-ethyl, SulfentraZone, pyra tum, Aegilops cylindrica, Phalaris arundinacea, Phalaris clonil, pyraflufen, pyraflufen-ethyl, butafenacil, fluazolate, minor; Apera spica-venti, Panicum dichotomiflorum, Pani fluthiacet, fluthiacet-methyl, flufenpyr, flufenpyr-ethyl, flu cum texanum, Panicum maximum, Brachiaria platyphylla, miclorac, flumiclorac-pentyl, pentoxazone, oxyfluorfen, aci Brachiaria ruziziensis, Brachiaria plantaginea, Brachiaria fluorfen, aclonifen, chlomethoxynil, chloronitrofen, nitrofen, decumbens, Brachiaria brizantha, Brachiaria humidicola, bifenox, fluoroglycofene, fluoroglycofene-ethyl, fomesafen, Cenchrus echinatus, Cenchrus pauciflorus, Eriochloa vil fomesafen-Sodium salt, lactofen, benzobicyclon, bicyclopy losa, Pennisetum setosum, Chloris gayana, Eragrostis pilosa, rone, mesotrione, Sulcotrione, tefuryltrione, tembotrione, Rhynchelitrum repens, Dactyloctenium aegyptium, Ischae isoxachlortole, isoxaflutole, benzofenap, pyrasulfotole, pyra mum rugosum, Oryza sativa, Paspalum notatum, Paspalum Zolynate, pyrazoxyfen, toprameZone, diflufenican, picolin maritimum, Pennisetum clandestinum, Pennisetum setosum, and Rottboelia cochinchinensis, afen, beflubutamid, norflurazon, fluridone, fluorochloridone, 0157 weeds of the family Cyperaceae: Cyperus microiria, flurtamone, ioxynil, ioxynil octanoate, bentaZone, pyridate, Cyperus iria, Cyperus Odoratus, Cyperus rotundus, Cyperus bromoxynil, bromoxynil octanoate, chlorotoluron, dimefu esculentus, and Kyllinga gracillina; and ron, diuron, linuron, fluometuron, isoproturon, isouron, 0158 weeds of the family Equisetaceae: Equisetum tebuthiuron, benzthiaZuron, methabenzthiaZuron, propanil, metobromuron, metoxuron, monolinuron, Siduron, simazine, arvense and Equisetum palustre. atrazine, propazine, cyanazine, ametryn, simetryn, 0159. In the method of the present invention, one or more other agrochemicals may be used in combination with the dimethametryn, prometryn, terbumeton, terbuthylazine, ter compounds of the group B or the one or more crystals selected butryn, trietazine, hexaZinone, metamitron, metribuzin, ami from the group consisting of 1 crystal of flumioxazin to 7" carbazone, bromacil, lenacil, terbacil, chlcridazon, desme crystal of flumioxazin either simultaneously or separately. dipham, phenmedipham, propachior, metaZachlor, alachlor, Examples of the other agrochemicals include insecticides, acetochlor, metolachlor, S-metolachlor, butachler, preti acaricides, nematicides, fungicides, herbicides, plant growth lachlor, thenylchlor, indanofan, cafenstrole, fentraZamide, regulators, and safeners. dimethenamid, dimethenamid-P, mefenacet, pyroxasulfone, 0160. As the above herbicides, plant growth regulators, fenoxasulfone, naproanilide, anilofos, flufenacet, trifluralin, and safeners, the following examples are given. pendimethalin, ethafluralin, benfluralin, prodiamine, indazi 0161 Herbicides: pyrithiobac, pyrithiobac-sodium salt, flam, triaziflam, butamifos, dithiopyr, thiazopyr, dicamba and pyriminobac, pyriminobac-methyl, bispyribac, bispyribac a salt thereof (diglycolamine salt, dimethylammonium salt, Sodium salt, pyribenzoxim, pyrimisulfan, pyriftalid, triafa isopropylammonium salt, potassium salt, Sodium salt, and mone, amidosulfuron, azimsulfuron, benSulfuron, benSulfu choline salt), 2,4-D and a salt or ester thereof (butotyl ester, ron-methyl, chlorimuron, chlorimuron-ethyl, dimethylammonium salt, diolamine salt, ethylhexyl ester, cyclosulfamuron, ethoxysulfuron, flaZaSulfuron, flucetosul isooctyl ester, isopropylammoniumsalt, sodium salt, and tri furon, flupyrsulfuron, flupyrsulfuron-methyl-Sodium, foram isopropanolamine salt), 2,4-DB and a salt or ester thereof Sulfuron, halosulfuron, halosulfuron-methyl, imaZoSulfuron, (dimethylammonium salt, isooctyl ester, and choline salt), mesosulfuron, mesosulfuron-methyl, metazosulfuron, nico MCPA and a salt or ester thereof (dimethylammonium salt, Sulfuron, orthosulfamuron, oxasulfuron, primisulfuron, pri 2-ethylhexylester, isooctyl ester, sodium salt, and choline misulfuron-methyl, propyrisulfuron, pyrazosulfuron, pyra salt), MCPB, mecopropand a salt or ester thereof (dimethy ZoSulfuron-ethyl, rimsulfuron, Sulfometuron, Sulfometuron lammonium salt, diolamine salt, ethadyl ester, 2-ethylhexyl methyl, sulfosulfuron, trifloxysulfuron-sodium salt, ester, isooctyl ester, methyl ester, potassium salt, Sodium salt, trifloxysulfuron, chlorsulfuron, cinosulfuron, ethametsulfu tololamine salt, and choline salt), mecoprop-P and a salt or ron, ethametSulfuron-methyl, iodosulfuron, iodosulfuron ester thereof (dimethylammonium salt, 2-ethylhexyl ester, methyl-Sodium, iofensulfuron, iofensulfuron-sodium, met isobutyl salt, potassium salt, and choline salt), dichlorprop Sulfuron, metSulfuron-methyl, prosulfuron, thifensulfuron, and a salt or ester thereof (butotyl ester, dimethylammonium thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron salt, 2-ethylhexyl ester, isooctyl ester, methyl ester, potas methyl, triflusulfuron, triflusulfuron-methyl, tritosulfuron, sium salt, sodium salt, and choline salt), dichlorprop-P, bencarbazone, flucarbazone, flucarbazone-sodium salt, dichlorprop-P dimethylammonium salt, triclopyrand a salt or ipfencarbazone, propoxycarbazone, propoxycarbazone-so ester thereof (butotyl ester and triethylammonium salt), flu dium salt, thiencarbazone, thiencarbazone-methyl, cloransu oroxypyr, fluoroxypyr-meptyl, picloram and a salt thereof lam, cloranSulam-methyl, dicloSulam, florasulam, flumetsu (potassium salt, triisopanolammonium salt, and choline salt), lam, metoSulam, penoXSulam, pyroxSulam, imazamethabenz, quinclorac, quinmerac, aminopyralid and a salt thereof (po imazamethabenZ-methyl, imaZamox, imaZamox-ammonium tassium salt, triisopanolammonium salt, and choline salt), salt, imazapic, imazapic-ammonium salt, imazapyr, imaza clopyralid and a salt thereof (olamine salt, potassium salt, pyr-isopropyl-ammonium salt, imazaquin, imazaquin-am triethylammonium salt, and choline salt), clomeprop, glufo monium salt, imazethapyr, imazethapyr-ammonium salt, clo sinate, glufosinate-ammonium salt, glufosinate-P. glufosi dinafop, clodinafop-propargyl, cyhalofop, cyhalofop-butyl, nate-P-Sodium salt, bialaphos, isoxaben, dichlobenil, methio diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, Zolin, diallate, butylate, triallate, chlorpropham, asulam, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-bu phenisopham, benthiocarb, molinate, esprocarb, pyributi tyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-me carb, prosulfocarb, orbencarb, EPTC, dimepiperate, swep, thyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pro aminocyclopyrachlor, aminocyclopyrachlor-methyl, ami paquizafop, quizalofop, quizalofop-ethyl, quizalofop-P, nocyclopyrachlor-potassium, difenoXuron, methyl dymron, quizalofop-P-ethyl, alloxydim, clethodim, Sethoxydim, bromobutide, dymron, cumyluron, diflufenZopyr, etobenza tepraloxydim, tralkoxydim, pinoxaden, azafenidin, oxadia nide, tridiphane, amitrole, fenchlorazole, clomaZone, maleic Zon, oxadiargyl, carfentraZone, carfentraZone-ethyl, acid hydrazide, oxaziclomefone, cinmethylin, benfuresate, US 2014/0200140 A1 Jul. 17, 2014

ACN, dalapon, chlorthiamid, flupoxam, bensulide, paraquat, 0176 a combination of one or more crystals selected from paraquat-dichloride, diguat, and diquat-dibromide. the group consisting of 1' crystal of flumioxazinto 7" crystal 0162 Plant growth regulators: hymexazol, paclobutrazol, of flumioxazin and 2,4-D-dimethylammonium salt; uniconazole, uniconazole-P, inabenfide, prohexadione-cal 0177 a combination of one or more crystals selected from cium, 1-methylcyclopropene, and trinexapac. the group consisting of 1 crystal of flumioxazinto 7" crystal 0163 Safeners: benoxacor, cloquintocet, cloquintocet of flumioxazin and 2,4-D-diolamine salt; mexyl, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, 0.178 a combination of one or more crystals selected from dietholate, fenchlorazole, fenchlorazole-ethyl, fenclorim, the group consisting of 1 crystal of flumioxazinto 7" crystal flurazole, fluxofenim, furilazole, isoxadifen, isoxadifen of flumioxazin and 2,4-D-ethylhexyl ester; ethyl, mefenpyr, mefenpyr-diethyl, mephenate, naphthalic 0179 a combination of one or more crystals selected from anhydride, and oxabetrinil. the group consisting of 1' crystal of flumioxazinto 7" crystal 0164. In the method of the present invention, a glufosi of flumioxazin and 2,4-D-isooctyl ester; nate-ammonium salt, chlorimuron-ethyl, cloranSulam-me 0180 a combination of one or more crystals selected from thyl, pyroxasulfone, imazethapyr-ammonium salt, the group consisting of 1 crystal of flumioxazinto 7" crystal metribuzin, 2,4-D, 2,4-D-butotyl ester, 2,4-D-dimethylam of flumioxazin and 2,4-D-isopropylammonium salt; monium salt, 2,4-D-diolamine salt, 2,4-D-ethylhexyl ester, 0181 a combination of one or more crystals selected from 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt, 2,4-D- the group consisting of 1 crystal of flumioxazinto 7" crystal Sodium salt, 2,4-D-triisopropanolamine salt, dicamba, of flumioxazin and 2,4-D-Sodium salt; dicamba-diglycolamine salt, dicamba-dimethylammonium 0182 a combination of one or more crystals selected from salt, dicamba-isopropylammonium salt, dicamba-potassium the group consisting of 1 crystal of flumioxazinto 7" crystal salt, dicamba-Sodium salt, dicamba-choline salt, mesotrione, of flumioxazin and 2,4-D-triisopropanolamine salt; tembotrione, isoxaflutole, and ametryn are particularly pref 0183 a combination of one or more crystals selected from erable as the herbicides which may be simultaneously used in the group consisting of 1' crystal of flumioxazinto 7" crystal combination with the one or more crystals selected from the of flumioxazin and dicamba; group consisting of 1 crystal of flumioxazinto 7" crystal of 0.184 a combination of one or more crystals selected from flumioxazin. the group consisting of 1 crystal of flumioxazinto 7" crystal 0.165. In the present invention, cyprosulfamide, mefenpyr of flumioxazin and dicamba-diglycolamine salt; diethyl, and isoxadifen-ethyl are particularly preferable as the 0185 a combination of one or more crystals selected from safener which may be simultaneously used in combination the group consisting of 1 crystal of flumioxazinto 7" crystal with the one or more crystals selected from the group con of flumioxazin and dicamba-dimethylammonium salt; sisting of 1 crystal of flumioxazin to 7" crystal of flumiox 0186 a combination of one or more crystals selected from aZ1. the group consisting of 1 crystal of flumioxazinto 7" crystal 0166 The followings are more preferable as the combina of flumioxazin and dicamba-isopropylammonium salt; tions of the herbicide and/or safener which may be used in 0187 a combination of one or more crystals selected from combination with the one or more crystals selected from the the group consisting of 1' crystal of flumioxazinto 7" crystal group consisting of 1 crystal of flumioxazinto 7" crystal of of flumioxazin and dicamba-potassium salt; flumioxazin: 0188 a combination of one or more crystals selected from 0167 a combination of one or more crystals selected from the group consisting of 1' crystal of flumioxazinto 7" crystal the group consisting of 1 crystal of flumioxazinto 7" crystal of flumioxazin and dicamba-sodium salt; of flumioxazin and glufosinate-ammonium salt; 0189 a combination of one or more crystals selected from 0168 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal the group consisting of 1 crystal of flumioxazinto 7" crystal of flumioxazin and dicamba-choline salt; of flumioxazin and chlorimuron-ethyl: 0.190 a combination of one or more crystals selected from 0169 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal the group consisting of 1' crystal of flumioxazinto 7" crystal of flumioxazin, dicamba, and isoxadifen-ethyl; of flumioxazin and cloranSulam-methyl; 0191 a combination of one or more crystals selected from 0170 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal the group consisting of 1' crystal of flumioxazinto 7" crystal of flumioxazin, dicamba-diglycolamine salt, and isoxadifen of flumioxazin, chlorimuron-ethyl, and pyroxasulfone; ethyl: 0171 a combination of one or more crystals selected from 0.192 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal the group consisting of 1 crystal of flumioxazinto 7" crystal of flumioxazin and pyroxasulfone; offlumioxazin, dicamba-dimethylammonium salt, and isoxa 0172 a combination of one or more crystals selected from dlfen-ethyl: the group consisting of 1 crystal of flumioxazinto 7" crystal 0193 a combination of one or more crystals selected from of flumioxazin and imazethapyr-ammonium salt, the group consisting of 1' crystal of flumioxazinto 7" crystal 0173 a combination of one or more crystals selected from of flumioxazin, dicamba-isopropylammonium salt, and the group consisting of 1 crystal of flumioxazinto 7" crystal isoxadifen-ethyl; of flumioxazin and metribuzin, 0194 a combination of one or more crystals selected from 0.174 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal the group consisting of 1' crystal of flumioxazinto 7" crystal of flumioxazin, dicamba-potassium salt, and isoxadifen of flumioxazin and 2,4-D; ethyl: 0175 a combination of one or more crystals selected from 0.195 a combination of one or more crystals selected from the group consisting of 1' crystal of flumioxazinto 7" crystal the group consisting of 1' crystal of flumioxazinto 7" crystal of flumioxazin and 2,4-D-butotyl ester; of flumioxazin, dicamba-sodium salt, and isoxadifen-ethyl; US 2014/0200140 A1 Jul. 17, 2014

0196) a combination of one or more crystals selected from The 1 crystals of flumioxazin were obtained by the same the group consisting of 1' crystal of flumioxazinto 7" crystal method as mentioned above except that methanol or of flumioxazin, dicamba-choline salt, and isoxadifen-ethyl; 2-ethoxyethanol was used instead of 2-methoxyethanol. 0.197 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal Production Example 2 of flumioxazin and mesotrione; 0198 a combination of one or more crystals selected from 0209 Flumioxazin (100 mg) was dissolved in tetrahydro the group consisting of 1 crystal of flumioxazinto 7" crystal furan THF at 60° C. so as to adjust its concentration to 51.0 of flumioxazin and tembotrione; mg/mL. The obtained mixture was gradually dropped onto a 0199 a combination of one or more crystals selected from glass plate heated at 100° C. to rapidly volatilize its solvent the group consisting of 1 crystal of flumioxazinto 7" crystal therefrom, to obtain crystals. of flumioxazin and isoxaflutole; 0210. The pattern of the obtained crystals had the peaks 0200 a combination of one or more crystals selected from with 20 values as shown in Table 3 to find them 2" crystals of the group consisting of 1' crystal of flumioxazinto 7" crystal flumioxazin of flumioxazin and ametryn; 0201 a combination of one or more crystals selected from TABLE 3 the group consisting of 1' crystal of flumioxazinto 7" crystal of flumioxazin, isoxaflutole, and cyprosulfamide; 20 value () d value (A) Relative intensity (%) 8.7 10.1555 20.4 0202 a combination of one or more crystals selected from 9.4 9.4007 43.5 the group consisting of 1' crystal of flumioxazinto 7" crystal 14.7 6.02.11 62.O of flumioxazin, tembotrione, and isoxadifen; and 18.8 4.7162 1OO.O 0203 a combination of one or more crystals selected from the group consisting of 1 crystal of flumioxazinto 7" crystal of flumioxazin and saflufenacil. The 2" crystals of flumioxazin were obtained by the same method as mentioned above except that acetone was used EXAMPLES instead of THF. The crystals were obtained by adding metha nol instead of THF to flumioxazin, gradually cooling to 20° 0204 Hereinbelow, the present invention will be C., followed by leaving it to stand. described in detail by way of examples, but the present inven tion is not limited to these examples. Production Example 3 Production Example 0211 Flumioxazin (100 mg) was dissolved in 1,2-dichlo roethane at 60° C. so as to adjust its concentration to 50.9 0205 Production Example of 1 crystal of flumioxazinto mg/mL. Then the obtained solution was gradually cooled to 7" crystal of flumioxazin used in the method of the present 20° C. at the rate of 10° C. per hour and then left to stand, invention will be shown below. followed by blow its solvent with nitrogen gas to obtain crystals. Production Example 1 0212. The pattern of the obtained crystals had the peaks 0206. The powder X-ray diffraction patterns of the with 20 values as shown in Table 4 to find them 3" crystals of obtained crystals were measured by X'Pert Pro MPD (manu flumioxazin. factured by PANalytical B.V., Netherlands) at a scanning range from 2.0° to 40.0° (20) using CuKO. rays (40 kV, 30 TABLE 4 mA). 20 value () d value (A) Relative intensity (%) Production Example 1 7.7 11472O 1OO.O 10.9 8.11 O2 21.5 0207. Flumioxazin (100 mg) was dissolved in 2-methoxy 13.5 6.5535 41.1 ethanol at 60° C. so as to adjust its concentration to 16.8 14.6 6.0621 9.5 mg/mL. Then 10 times volumes of water relative to the vol 1S.O S.9013 12.6 ume of 2-methoxyethanol were heated to 60° C. and gradu ally added to the obtained solution. The obtained mixture was gradually cooled to 20° C. at the rate of 10° C. per hour and The 3" crystals of flumioxazin were obtained by the same then left to stand, followed by filtrating it to collect crystals. method as mentioned above except that chlorobenzene was 0208. The pattern of the obtained crystals had the peaks used instead of 1,2-dichloroethane with 20 values as shown in Table 2 to find them 1 crystals of flumioxazin. Production Example 4 0213 Flumioxazin (100 mg) was dissolved in toluene at TABLE 2 60° C. so as to adjust its concentration to 13.3 mg/mL. Then 20 value () d value (A) Relative intensity (%) the obtained solution was gradually cooled to 20° C. at the rate of 10°C. per hour and then left to stand, followed by blow 7.5 11.7774 22.5 its solvent with nitrogen gas to obtain crystals. 11.9 7.4308 61.9 15.3 5.8241 11.0 0214. The pattern of the obtained crystals had the peaks with 20 values as shown in Table 5 to find them 4" crystals of flumioxazin. US 2014/0200140 A1 Jul. 17, 2014 12

TABLE 5 Production Example 7 20 value () d value (A) Relative intensity (%) 0221 Flumioxazin (100mg) was dissolved in 1,4-dioxane at 60° C. so as to adjust its concentration to 50.9 mg/mL. The 7.7 S.9013 1OO.O 10.7 8.2613 13.9 1,4-dioxane Solution was added gradually to 10 times Vol 13.4 6.6O22 25.5 umes of water relative to the volume of 1,4-dioxane at 60° C. 14.3 6.1886 4.6 The obtained mixture was gradually cooled to 20° C. at the 14.8 5.9806 6.8 rate of 10° C. per hour and then left to stand, followed by filtrating it to collect crystals. 0222. The pattern of the obtained crystals had the peaks with 20 values as shown in Table 8 to find them 7" crystals of Production Example 5 flumioxazin. 0215 Flumioxazin 100 mg) was dissolved in Xylene at 60° C. So as to adjust its concentration to 10.0 mg/mL. Then the TABLE 8 obtained solution was gradually cooled to 20° C. at the rate of 10° C. per hour and then left to stand, followed by blow its 20 value () d value (A) Relative intensity (%) Solvent with nitrogen gas at 20°C. to obtain crystals. 14.5 6.1037 15.6 0216. The pattern of the obtained crystals had the peaks 18.7 4.7412 36.4 with 20 values as shown in Table 6 to find them 5" crystals of flumioxazin. The 7" crystals of flumioxazin were obtained by the same method as mentioned above except that heptane was used TABLE 6 instead of water. 20 value () d value (A) Relative intensity (%) Test Examples 5.5 16.0548 23.1 0223 First, given are the standard of evaluation of a pest 10.3 8.5812 68.2 10.9 8.11 O2 29.7 control effect (harmful arthropod control effect, plant patho 13.2 6.7018 37.6 gen control effect, and herbicidal effect) and that of crop injuries, which will be shown in examples hereinafter. 0224 Harmful Arthropod Control Effect 0225. In the evaluation of the harmful arthropod control Production Example 6 effect, each insect at the time of investigation is examined by 0217 Flumioxazin (100 mg) was dissolved in chloroform discriminating whether the insect is alive or dead to calculate at 60° C. so as to adjust its concentration to 102.8 mg/mL. The a controlling value by the following equation. chloroform solution was added gradually to 10 times volumes Controlling value (%)=100x (1-T/C) of heptane relative to the volume of chloroform at 60°C. The 0226 wherein C represents the number of insects to be obtained mixture was gradually cooled to 20° C. at the rate of observed in an untreated area, and 10°C. per hour and then left to stand, followed by filtrating it 0227 Trepresents the number of insects to be observed in to collect crystals. a treated area 0218. The pattern of the obtained crystals had the peaks 0228 Plant Pathogen Control Effect with 20 values as shown in Table 7 to find them 6" crystals of 0229. In the evaluation of the plant pathogen control flumioxazin. effect, the symptom of each test plant in a treated area is compared with that in an untreated area and when there is no TABLE 7 or almost no difference in symptom between the treated area and the untreated area at the time of investigation, the case is 20 value () d value (A) Relative intensity (%) given “0”, and when no or almost no change in Symptom 7.7 11.472O 1OO.O caused by plant pathogens is observed at the time of investi 8.6 10.2733 5.8 gation, the case is given '100', thereby grading each sample 11.0 8.0367 14.4 13.2 6.7018 6.7 between 0 to 100. 14.7 6.02.11 7.4 0230 Herbicidal Effect and Crop Injuries 15.1 5.862S 9.2 0231. In the evaluation of the herbicidal effect, the germi nation or growth condition of each test weed in a treated area is compared with that in an untreated area and when there is The 6" crystals of flumioxazin were obtained by the same no or almost no difference in germination or growth condition method as mentioned above except that THF was used instead between the treated area and the untreated area at the time of of chloroform. investigation, the case is given “0”, and when the test plant 0219. The solution obtained by adding 2 times volumes of perfectly withers and dies, or the germination or growth of the THF relative to the volume of chloroform to flumioxazin plant is perfectly restricted at the time of investigation, the instead of chloroform, was added to 10 times Volumes of case is given “100, thereby grading each sample between 0 water relative to the volume of THF and gradually cooled to to 100. 20°C., followed by leaving it to stand. 0232. In the evaluation of crop injuries, the case where 0220. The crystals were obtained by adding THF, 1,4- almost no crop injury is observed is expressed as “harmless'. dioxane or pyridine instead of chloroform to flumioxazin and, the case where mild crop injuries are observed is expressed as gradually cooling to 20°C., followed by concentrating it. “small, the case where moderate crop injuries are observed US 2014/0200140 A1 Jul. 17, 2014

is expressed as “middle', and the case where severe crop Example 6 injuries are observed is expressed as “large'. 0238. One or more compounds selected from the group B are attached to corn seeds at a dose of 1, 10, or 100 g/100 kg Example 1 seeds. Next, a pot is filled with soil and the corn seeds and 0233. A potis filled with soil and weeds are sowed, and the weed seeds are sowed. On the day of sowing, the surface of surface of the soil is uniformly treated with one or more the soil is uniformly treated with one or more crystals selected crystals selected from the group consisting of 1 crystal of from the group consisting of 1 crystal of flumioxazin to 7" flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. 100, or 200 g/ha. After 15 days, cottonseeds are sowed to This potis placed in a greenhouse. The pest control effect and which one or more compounds selected from the group B are crop injuries are examined 15 days after the seeds are sowed. attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is placed in a greenhouse. The pest control effect and crop Example 7 injuries are examined 15 days after the seeds are sowed. 0239. A potis filled with soil and weeds are sowed, and the surface of the soil is uniformly treated with one or more Example 2 crystals selected from the group consisting of 1 crystal of flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, 0234 One or more compounds selected from the group B 100, or 200 g/ha. After 15 days, wheat seeds are sowed to are attached to cotton seeds at a dose of 1, 10, or 100 g/100 kg which one or more compounds selected from the group B are seeds. Next, the seeds are sowed in a cultivated field. Stem attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is leaves of the weed are directly treated with one or more placed in a greenhouse. The pest control effect and crop crystals selected from the group consisting of 1 crystal of injuries are examined 15 days after the seeds are sowed. 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 Example 8 being lignified at a length of 15 cm from the surface of the 0240 A potis filled with soil and weeds are sowed, and the ground 30 days after these seeds are sowed. The pest control surface of the soil is uniformly treated with one or more effect and crop injuries are examined 28 days after the treat crystals selected from the Group consisting of 1 crystal of ment. flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, tomato seeds are sowed to Example 3 which one or more compounds selected from the group B are 0235 A potis filled with soil and weeds are sowed, and the attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is surface of the soil is uniformly treated with one or more placed in a greenhouse. The pest control effect and crop crystals selected from the group consisting of 1 crystal of injuries are examined 15 days after the tomato seeds are flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, Sowed. 100, or 200 g/ha. After 7 days, soybean seeds are sowed to which one or more compounds selected from the group B are Example 9 attached at a dose of 1, 10, or 100/100 kg seeds. This pot is 0241 A potis filled with soil and weeds are sowed, and the placed in a greenhouse. The pest control effect and crop surface of the soil is uniformly treated with one or more injuries are examined 15 days after the seeds are sowed. crystals selected from the group consisting of 1 crystal of flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, Example 4 100, or 200 g/ha. After 15 days, eggplant seeds are sowed to which one or more compounds selected from the group B are 0236. One or more compounds selected from the group B attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is are attached to soybean seeds at a dose of 1, 10, or 100 g/100 placed in a greenhouse. The pest control effect and crop kg seeds. Next, a pot is filled with soil and the soybean seeds injuries are examined 15 days after the eggplant seeds are and weed seeds are sowed. On the day of sawing, the Surface Sowed. of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 crystal of flumiox Example 10 azin to 7" crystal of flumioxazin at a dose of 25, 50, 100, or 0242 A potis filled with soil and weeds are sowed, and the 200 g/ha. This pot is placed in a greenhouse. The pest control surface of the soil is uniformly treated with one or more effect and crop injuries are examined 15 days after the seeds crystals selected from the group consisting of 1 crystal of are sowed. flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. After 15 days, bell pepper seeds are sowed Example 5 to which one or more compounds selected from the group B 0237. A potis filled with soil and weeds are sowed, and the are attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot surface of the soil is uniformly treated with one or more is placed in a greenhouse. The pest control effect and crop crystals selected from the group consisting of 1 crystal of injuries are examined 15 days after the bell pepper seeds are flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, Sowed. 100, or 200 g/ha. After 7 days, corn seeds are sowed to which Example 11 one or more compounds selected from the group B are attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is 0243 A potis filled with soil and weeds are sowed, and the placed in a greenhouse. The pest control effect and crop surface of the soil is uniformly treated with one or more injuries are examined 15 days after the seeds are sowed. crystals selected from the group consisting of 1 crystal of US 2014/0200140 A1 Jul. 17, 2014 flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, This potis placed in a greenhouse. The pest control effect and 100, 200, or 400 g/ha. After 15 days, sugar cane stem frag crop injuries are examined 15 days after the seeds are sowed. ments are planted to which one or more compounds selected from the group B at a dose of 1, 10, or 100 g/100 kg stem Example 17 fragments. This pot is placed in a greenhouse. The peat con 0249. One or more compounds selected from the group B trol effect and crop injuries are examined 15 days after the are attached to common bean seeds at a dose of 1, 10, or 100 Sugar cane stem fragments are planted. g/100 kg seeds. Next, a pot is filled with soil and the common Example 12 bean seeds and weed seeds are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more 0244. A potis filled with soil and weeds are sowed, and the crystals selected from the group consisting of 1 crystal of surface of the soil is uniformly treated with one or more flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, crystals selected from the group consisting of 1 crystal of 100, or 200 g/ha. This pot is placed in a greenhouse. The pest flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, control effect and crop injuries are examined 15 days after the 100, or 200 g/ha. After 15 days, common bean seeds are seeds are sowed. sowed to which one or more compounds selected from the group B are attached at a dose of 1, 10, or 100 g/100 kg seeds. Example 18 This potis placed in agreenhouse. The pest control effect and 0250 One or more compounds selected from the group B crop injuries are examined 15 days after the common bean are attached to pea seeds at a dose of 1, 10, or 100 g/100 kg seeds are Sowed. seeds. Next, apot is filled with sailand the pea seeds and weed Example 13 seeds are sowed. On the day of sowing, the surface of the soil is uniformly treated with one or more crystals selected from 0245. A potis filled with soil and weeds are sowed, and the the group consisting of 1' crystal of flumioxazinto 7" crystal surface of the soil is uniformly treated with one or more of flumioxazin at a dose of 25, 50, 100, or 200/ha. This pot is crystals selected from the group consisting of 1 crystal of placed in a greenhouse. The pest control effect and crop flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, injuries are examined 15 days after the seeds are sowed. 100, or 200/ha. After 15 days, rice seeds are sowed to which one or more compounds selected from the group B are Example 19 attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is 0251 One or more compounds selected from the group B placed in a greenhouse. The pest control effect and crop are attached to sunflower seeds at a dose of 1, 10, or 100 g/100 injuries are examined 15 days after the rice seeds are sowed. kg seeds. Next, a pot is filled with soil and the sunflower seeds Example 14 and weed seeds are sowed. On the day of sowing, the Surface of the soil is uniformly treated with one or more crystals 0246 A potis filled with soil and weeds are sowed, and the selected from the group consisting of 1 crystal of flumiox surface of the soil is uniformly treated with one or more azin to 7" crystal of flumioxazin at a dose of 25, 50, 100, or crystals selected from the group consisting of 1 crystal of 200 g/ha. This pot is placed in a greenhouse. The pest control flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, effect and crop injuries are examined 15 days after the seeds 100, or 200 g/ha. After 15 days, rapeseeds are sowed to which are sowed. one or more compounds selected from the group B are attached at a dose of 1, 10, or 100 g/100 kg seeds. This pot is Example 20 placed in a greenhouse. The pest control effect and crop 0252 One or more compounds selected from the group B injuries are examined 15 days after the rapeseeds are sowed. are attached to Sugar cane stem fragments at a dose of 1, 10. Example 15 or 100 g/100 kg stem fragments. Next, a pot is filled with soil, then weed seeds are sowed and the stem fragments are 0247 One or more compounds selected from the group B planted. On the day of sowing and planting, the Surface of the are attached to Sugar cane stem fragments at a dose of 1, 10. soil is uniformly treated with one or more crystals selected or 100 g/100 kg stem fragments. Then, the stem fragments are from the group consisting of 1 crystal of flumioxazin to 7" planted in a cultivated field. When the plant height of the crystal of flumioxazin at a dose of 25, 50, 100, 200, or 400 Sugarcane becomes 60 cm or higher after the stem fragments g/ha. This pot is placed in a greenhouse. The pest control are planted, stem leaves of the weed are directly treated with effect and crop injuries are examined 15 days after sowing one or more crystals selected from the group consisting of 1 and planting. crystal of flumioxazinto 7" crystal of flumioxazinata dose of 25, 50, 100, 200, or 400 g/ha. The pest control effect and crop Example 21 injuries are examined 28 days after the treatment. 0253) One or more compounds selected from the group B Example 16 are attached to potato tubers at a dose of 1, 10, or 100 g/100kg tubers. Next, a pot is filled with soil, then weed seeds are 0248 One or more compounds selected from the group B Sowed and the tubers are planted. On the day of Sowing and are attached to peanut seeds at a dose of 1, 10, or 100 g/100kg planting, the surface of the soil is uniformly treated with one seeds. Next, a pot is filled with soil and the peanut seeds and or more crystals selected from the group consisting of 1 weed seeds are sowed. On the day of sowing, the surface of crystal offlumioxazinto 7" crystal offlumioxazin at a dose of the soil is uniformly treated with one or more crystals selected 12.5, 25, 50, or 100 g/ha. This pot is placed in a greenhouse. from the group consisting of 1 crystal of flumioxazin to 7" The pest control effect and crop injuries are examined 15 days crystal of flumioxazin at a dose of 25, 50, 100, or 200 g/ha. after Sowing and planting. US 2014/0200140 A1 Jul. 17, 2014

Example 22 100, 200, or 400 g/ha. This pot is placed in a greenhouse. The pest control effect and crop injuries are examined 15 days 0254. One or more compounds selected from the group B after the treatment with one or more crystals selected from the are attached to onion seeds at a dose of 1, 10, or 100 g/100 kg group consisting of 1 crystal of flumioxazinto 7" crystal of seeds. Next, a pot is filled with soil and the onion seeds and weed seeds are Sowed. This pot is placed in a greenhouse. flumioxazin. When the onion grows 2 to 6 leaves, the surface of the soil and Example 27 stem leaves of the weeds are uniformly treated with one or more crystals selected from the group consisting of 1 crystal 0259 Each of combinations of compounds selected from of flumioxazin to 7" crystal of flumioxazin at a dose of 12.5, the combinations shown in Tables 9, 10 and 11 is attached to 25, 50, or 100 g/ha. The pest control effect and crop injuries cotton seeds at a dose of 1, 10, or 100 g/100 kg seeds. Next, a are examined 15 days after the treatment with A-type crystal pot is filled with soil and the cotton seeds and weed seeds are flumioxazin. sowed. The surface of the soil and stem leaves of the weeds are uniformly treated with one or more crystals selected from Example 23 the group consisting of 1 crystal of flumioxazinto 7" crystal of flumioxazin at a dose of 25, 50, 100, 200, or 400 g/ha in the 0255 One or more compounds selected from the group B condition of the cotton main stem being lignified at a length of are attached to garlic bulbs at a dose of 1, 10, or 100/100 kg 15cm from the surface of the ground 30 days after these seeds bulbs. Next, a pot is filled with soil, then weed seeds are are sowed. This potis placed in agreenhouse. The pest control sowed and the bulbs are planted. On the day of sowing and effect and crop injuries are examined 15 days after the treat planting, the surface of the soil is uniformly treated with one or more crystals selected from the group consisting of 1 ment with one or more crystals selected from the group con crystal offlumioxazinto 7" crystal of flumioxazinata dose of sisting of 1 crystal of flumioxazin to 7" crystal of flumiox 50, 100, 200, or 400 g/ha. This pot is placed in a greenhouse. aZ1. The pest control effect and crop injuries are examined 15 days after sowing and planting. TABLE 9 Number of Example 24 combination Combinations of compounds 0256. One or more compounds selected from the group B -1 Clothianidin pconazole -2 Clothianidin Metconazole are attached to sunflower seeds at a dose of 1, 10, or 100 g/100 -3 Clothianidin Diphenoconazole kg seeds. Next, a pot is filled with soil and the sunflower seeds -4 Clothianidin Tebuconazole and weed seeds are sowed. This pot is placed in agreenhouse. -S Clothianidin Prothioconazole When the sunflower grows 2 to 6 leaves, the surface of the soil -6 Clothianidin Fluguinconazole -7 Clothianidin Triticonazole and stem leaves of the weeds are uniformly treated with one -8 Clothianidin mazalil or more crystals selected from the group consisting of 1 -9 Clothianidin Pencycuron crystal offlumioxazinto 7" crystal of flumioxazinata dose of -10 Clothianidin Prochloraz 12.5, 25, 50, or 100 g/ha. The pest control effect and crop -11 Clothianidin Pyraclostrobin -12 Clothianidin AZOxystrobin injuries are examined 15 days after the treatment with one or -13 Clothianidin Trifloxystrobin more crystals selected from the group consisting of 1 crystal -14 Clothianidin Metalaxyl of flumioxazin to 7" crystal of flumioxazin. -15 Clothianidin Metalaxyl-M -16 Clothianidin Fludioxonil -17 Clothianidin Thiram Example 25 -18 Clothianidin Mancozeb -19 Clothianidin Flutolani 0257. One or more compounds selected from the group B -20 Clothianidin Sedaxane are attached to wheat seeds at a dose of 1, 10, or 100 g/100 kg -21 Clothianidin Penflufen seeds. Next, a pot is filled with soil and the wheat seeds and -22 Clothianidin Fluxapyroxad weed seeds are Sowed. This pot is placed in a greenhouse. -23 Clothianidin Bacillus firmus -24 Clothianidin Pasteuria penetrans When the wheatgrows 2 to 6 leaves, the surface of the soil and -2S Clothianidin Abamectin stem leaves of the weeds are uniformly treated with one or -26 Clothianidin Thiodicarb more crystals selected from the group consisting of 1 crystal -27 Clothianidin Tolclophos-methyl of flumioxazin to 7" crystal of flumioxazin at a dose of 12.5, -28 Clothianidin Ethaboxam -29 Clothianidin Compound 4 25, 50, or 100 g/ha. The pest control effect and crop injuries -30 Clothianidin Compound 2 are examined 15 days after the treatment with one or more -31 Clothianidin Compound 3 crystals selected from the group consisting of 1 crystal of -32 Clothianidin Compound 1 flumioxazin to 7" crystal of flumioxazin. -33 Clothianidin Compound 5 -34 Clothianidin Orysastrobin -35 Clothianidin Isotianil Example 26 -36 Clothianidin Probenazole -37 Clothianidin Diclocymet 0258 Each of combinations of compounds selected from -38 Clothianidin Furametpyr the combinations shown in Tables 9, 10 and 11 is attached to -39 Imidacloprid Ipconazole Soybean seeds, corn seeds, or cotton seeds at a dose of 1, 10. -40 Imidacloprid Metconazole -41 Imidacloprid Diphenoconazole or 100 g/100 kg seeds. Next, a pot is filled with soil and the -42 Imidacloprid Tebuconazole crop seeds and weed seeds are sowed. On the day of sowing, -43 Imidacloprid Prothioconazole the surface of the soil is uniformly treated with one or more -44 Imidacloprid Fluguinconazole crystals selected from the group consisting of 1 crystal of -45 Imidacloprid Triticonazole flumioxazin to 7" crystal of flumioxazin at a dose of 25, 50, US 2014/0200140 A1 Jul. 17, 2014 16

TABLE 9-continued TABLE 9-continued

Number of Number of combination Combinations of compounds combination Combinations of compounds -46 midaclopri mazalil -120 Beta-cyfluthrin Fluguinconazole -47 midaclopri Pencycuron -121 Beta-cyfluthrin Triticonazole -48 midaclopri Prochloraz -122 Beta-cyfluthrin Imazalil -49 midaclopri Pyraclostrobin -123 Beta-cyfluthrin Pencycuron -SO midaclopri Azoxystrobin -124 Beta-cyfluthrin Prochloraz -S1 midaclopri Trifloxystrobin -125 Beta-cyfluthrin Pyraclostrobin -52 midaclopri Metalaxyl -126 Beta-cyfluthrin AZOxystrobin -53 midaclopri Metalaxyl-M -127 Beta-cyfluthrin Trifloxystrobin -54 midaclopri Fludioxonil -128 Beta-cyfluthrin Metalaxyl -55 midaclopri Thiram -129 Beta-cyfluthrin Metalaxyl-M -56 midaclopri Mancozeb -130 Beta-cyfluthrin Fludioxonil -57 midaclopri Flutolani -131 Beta-cyfluthrin Thiram -58 midaclopri Sedaxane -132 Beta-cyfluthrin Mancozeb -59 midaclopri Penflufen -133 Beta-cyfluthrin Flutolani -60 midaclopri Fluxapyroxad -134 Beta-cyfluthrin Sedaxane -61 midaclopri Bacilius firmus -13S Beta-cyfluthrin Penflufen -62 midaclopri Pasteuria penetrans -136 Beta-cyfluthrin Fluxapyroxad -63 midaclopri Abamectin -137 Beta-cyfluthrin Bacillus firmus -64 midaclopri Thiodicarb -138 Beta-cyfluthrin Pasteuria penetrans -65 midaclopri Tolclophos-methyl -139 Beta-cyfluthrin Abamectin -66 midaclopri Ethaboxam -140 Beta-cyfluthrin Thiodicarb -67 midaclopri Compound 4 -141 Beta-cyfluthrin Tolclophos-methyl -68 midaclopri Compound 2 -142 Beta-cyfluthrin Ethaboxam -69 midaclopri Compound 3 -143 Beta-cyfluthrin Compound 4 -70 midaclopri Compound 1 -144 Beta-cyfluthrin Compound 2 -71 midaclopri Compound 5 -145 Beta-cyfluthrin Compound 3 -72 midaclopri Orysastrobin -146 Beta-cyfluthrin Compound 1 -73 midaclopri Isotianil -147 Beta-cyfluthrin Compound 5 -74 midaclopri Probenazole -148 Abamectin Ipconazole -75 midaclopri Diclocymet -149 Abamectin Metconazole -76 midaclopri Furametpyr -1SO Abamectin Diphenoconazole -77 Thiamethoxam Ipconazole -151 Abamectin Tebuconazole -78 Thiamethoxam Metconazole -152 Abamectin Prothioconazole -79 Thiamethoxam Diphenoconazole -153 Abamectin Fluguinconazole -80 Thiamethoxam Tebuconazole -154 Abamectin Triticonazole -81 Thiamethoxam Prothioconazole -155 Abamectin Imazalil -82 Thiamethoxam Fluguinconazole -156 Abamectin Pencycuron -83 Thiamethoxam Triticonazole -157 Abamectin Prochloraz -84 Thiamethoxam Imazalil -158 Abamectin Pyraclostrobin -85 Thiamethoxam Pencycuron -159 Abamectin AZOxystrobin -86 Thiamethoxam Prochloraz -160 Abamectin Trifloxystrobin -87 Thiamethoxam Pyraclostrobin -161 Abamectin Metalaxyl -88 Thiamethoxam Azoxystrobin -162 Abamectin Metalaxyl-M -89 Thiamethoxam Trifloxystrobin -163 Abamectin Fludioxonil -90 Thiamethoxam Metalaxyl -164 Abamectin Thiram -91 Thiamethoxam Metalaxyl-M -16S Abamectin Mancozeb -92 Thiamethoxam Fludioxonil -166 Abamectin Flutolani -93 Thiamethoxam Thiram -167 Abamectin Sedaxane -94 Thiamethoxam Mancozeb -168 Abamectin Penflufen -95 Thiamethoxam Flutolani -169 Abamectin Fluxapyroxad -96 Thiamethoxam Sedaxane -170 Abamectin Bacillus firmus -97 Thiamethoxam Penflufen -171 Abamectin Pasteuria penetrans -98 Thiamethoxam Fluxapyroxad -172 Abamectin Thiodicarb -99 Thiamethoxam Bacilius firmus -173 Abamectin Tolclophos-methyl -100 Thiamethoxam Pasteuria penetrans -174 Abamectin Ethaboxam -101 Thiamethoxam Abamectin -175 Abamectin Compound 4 -102 Thiamethoxam Thiodicarb -176 Abamectin Compound 2 -103 Thiamethoxam Tolclophos-methyl -177 Abamectin Compound 3 -104 Thiamethoxam Ethaboxam -1.78 Abamectin Compound 1 -105 Thiamethoxam Compound 4 -179 Abamectin Compound 5 -106 Thiamethoxam Compound 2 -18O Thiodicarb Ipconazole -107 Thiamethoxam Compound 3 -181 Thiodicarb Metconazole -108 Thiamethoxam Compound 1 -182 Thiodicarb Diphenoconazole -109 Thiamethoxam Compound 5 -183 Thiodicarb Tebuconazole -110 Thiamethoxam Orysastrobin -184 Thiodicarb Prothioconazole -111 Thiamethoxam Isotianil -185 Thiodicarb Fluguinconazole -112 Thiamethoxam Probenazole -186 Thiodicarb Triticonazole -113 Thiamethoxam Diclocymet -1.87 Thiodicarb Imazalil -114 Thiamethoxam Furametpyr -188 Thiodicarb Pencycuron -115 Beta-cyfluthrin Ipconazole -1.89 Thiodicarb Prochloraz -116 Beta-cyfluthrin Metconazole -190 Thiodicarb Pyraclostrobin -117 Beta-cyfluthrin Diphenoconazole -191 Thiodicarb AZOxystrobin -118 Beta-cyfluthrin Tebuconazole -192 Thiodicarb Trifloxystrobin -119 Beta-cyfluthrin Prothioconazole -193 Thiodicarb Metalaxyl US 2014/0200140 A1 Jul. 17, 2014 17

TABLE 9-continued TABLE 9-continued

Number of Number of combination Combinations of compounds combination Combinations of compounds -194 Thiodicarb Metalaxyl-M -268 Metalaxyl-M Compound 5 -195 Thiodicarb Fludioxonil -269 Metalaxyl-M Furametpyr -196 Thiodicarb Thiram -270 Fludioxoni pconazole -197 Thiodicarb Mancozeb -271 ioxoni Metconazole -198 Thiodicarb Flutolani -272 ioxoni Diphenoconazole -199 Thiodicarb Sedaxane -273 ioxoni Tebuconazole -2OO Thiodicarb Penflufen -274 ioxoni Prothioconazole -201 Thiodicarb Fluxapyroxad -275 ioxoni Fluguinconazole -2O2 Thiodicarb Bacilius firmus -276 ioxoni -2O3 Thiodicarb Pasteuria penetrans -277 ioxoni -204 Thiodicarb Tolclophos-methyl -278 ioxoni Pencycuron -205 Thiodicarb Ethaboxam -279 ioxoni Prochloraz -2O6 Thiodicarb Compound 4 -280 ioxoni Pyraclostrobin -2O7 Thiodicarb Compound 2 -281 ioxoni AZOxystrobin -208 Thiodicarb Compound 3 -282 ioxoni Trifloxystrobin -209 Thiodicarb Compound 1 -283 ioxoni Thiram -210 Thiodicarb Compound 5 -284 ioxoni Flutolani -211 Thiodicarb Furametpyr -285 ioxoni Sedaxane -212 Metalaxy pconazole -286 ioxoni Penflufen -213 Metalaxy Metconazole -287 ioxoni Fluxapyroxad -214 Metalaxy Diphenoconazole -288 ioxoni Bacillus firmus -215 Metalaxy Tebuconazole -289 ioxoni Pasteuria penetrans -216 Metalaxy Prothioconazole -290 ioxoni Tolclophos-methyl -217 Metalaxy Fluguinconazole -291 ioxoni Ethaboxam -218 Metalaxy Triticonazole -292 ioxoni Compound 4 -219 Metalaxy mazalil -293 ioxoni Compound 2 -22O Metalaxy Pencycuron -294 ioxoni Compound 3 -221 Metalaxy Prochloraz -295 ioxoni Compound 1 -222 Metalaxy Pyraclostrobin -296 ioxoni Compound 5 -223 Metalaxy Azoxystrobin -297 udioxoni Furametpyr -224 Metalaxy Trifloxystrobin -299 CO3ZOIt Pyraclostrobin -225 Metalaxy Fludioxonil -299 CO3ZO AZOxystrobin -226 Metalaxy Thiram -300 CO3ZO Trifloxystrobin -227 Metalaxy Flutolani -301 CO3ZO Thiram -228 Metalaxy Sedaxane -302 CO3ZO Flutolani -229 Metalaxy Penflufen -303 CO3ZO Sedaxane -23O Metalaxy Fluxapyroxad -304 CO3ZO Penflufen -231 Metalaxy Bacilius firmus -30S CO3ZO Fluxapyroxad -232 Metalaxy Pasteuria penetrans -306 CO3ZO Bacillus firmus -233 Metalaxy Tolclophos-methyl -307 CO3ZO Pasteuria penetrans -234 Metalaxy Ethaboxam -3O8 CO3ZO Tolclophos-methyl -235 Metalaxy Compound 4 -309 CO3ZO Ethaboxam -236 Metalaxy Compound 2 -310 CO3ZO Compound 4 -237 Metalaxy Compound 3 -311 CO3ZO Compound 2 -238 Metalaxy Compound 1 -312 CO3ZO Compound 3 -239 Metalaxy Compound 5 -313 CO3ZO Compound 1 -240 Metalaxy Furametpyr -314 CO3ZO Compound 5 -241 Metalaxyl-M pconazole -315 Metconazo Pyraclostrobin -242 Metalaxwl-M Metconazole -316 Metconazo AZOxystrobin -243 Metalaxyl-M Diphenoconazole -317 Metconazo Trifloxystrobin -244 Metalaxyl-M Tebuconazole -318 Metconazo Thiram -245 Metalaxyl-M Prothioconazole -319 Metconazo Flutolani -246 Meta axyl-M Fluguinconazole -320 Metconazo Sedaxane -247 Metalaxyl-M Triticonazole -321 Metconazo Penflufen -248 Metalaxyl-M mazalil -322 Metconazo Fluxapyroxad -249 Metalaxyl-M Pencycuron -323 Metconazo Bacillus firmus -2SO Metalaxyl-M Prochloraz -324 Metconazo Pasteuria penetrans -251 Metalaxyl-M Pyraclostrobin -32S Metconazo Tolclophos-methyl -2S2 Metalaxyl-M Azoxystrobin -326 Metconazo Ethaboxam -2S3 Metalaxyl-M Trifloxystrobin -327 Metconazo Compound 4 -254 Metalaxyl-M Fludioxonil -328 Metconazo Compound 2 -255 Metalaxyl-M Thiram -329 Metconazo Compound 3 -2S6 Metalaxyl-M Flutolani -330 Metconazo Compound 1 - 257 Metalaxyl-M Sedaxane -331 Metconazole Compound 5 -258 Metalaxyl-M Penflufen -332 Diphenoconazole Pyraclostrobin -259 Metalaxyl-M Fluxapyroxad -333 Diphenoconazole AZOxystrobin -260 Metalaxyl-M Bacilius firmus -334 Diphenoconazole Trifloxystrobin -261 Metalaxyl-M Pasteuria penetrans -335 Diphenoconazole Thiram -262 Metalaxyl-M Tolclophos-methyl -3.36 Diphenoconazole Flutolani -263 Metalaxyl-M Ethaboxam -337 Diphenoconazole Sedaxane -264 Metalaxyl-M Compound 4 -338 Diphenoconazole Penflufen -26S 8. axyl-M Compound 2 -339 Diphenoconazole Fluxapyroxad -266 8. axyl-M Compound 3 -340 Diphenoconazole Bacillus firmus -267 8. axyl-M Compound 1 -341 Diphenoconazole Pasteuria penetrans US 2014/0200140 A1 Jul. 17, 2014 18

TABLE 9-continued TABLE 10-continued

Number of Number of combination Combinations of compounds combination Combinations of compounds -342 Diphenoconazole Tolclophos-methyl 2-26 Combination of 1-15 Triticonazole -343 Diphenoconazole Ethaboxam 2-27 Combination of 1-15 Tebuconazole -344 Diphenoconazole Compound 4 2-28 Combination of 1-15 Diphenoconazole -345 Diphenoconazole Compound 2 2-29 Combination of 1-15 Ipconazole -346 Diphenoconazole Compound 3 2-30 Combination of 1-15 Thiophanate-methyl -347 Diphenoconazole Compound 1 2-31 Combination of 1-15 Fludioxonil -348 Diphenoconazole Compound 5 2-32 Combination of 1-15 Tolclophos-methyl -349 Prothioconazole Pyraclostrobin 2-33 Combination of 1-15 Thiran -350 Prothioconazole Azoxystrobin 2-34 Combination of 1-15 Captain -351 Prothioconazole Trifloxystrobin 2-3S Combination of 1-15 Carboxin -352 Prothioconazole Thiram 2-36 Combination of 1-15 Boscalid -353 Prothioconazole Flutolani 2-37 Combination of 1-15 Thiabendazole -354 Prothioconazole Sedaxane 2-38 Combination of 1-15 Ethaboxam -355 Prothioconazole Penflufen 2-39 Combination of 1-18 Pyraclostrobin -356 Prothioconazole Fluxapyroxad 2-40 Combination of 1-18 AZOxystrobin -357 Prothioconazole Bacilius firmus 2-41 Combination of 1-18 Trifloxystrobin -358 Prothioconazole Pasteuria penetrans 2-42 Combination of 1-18 Compound 1 -359 Prothioconazole Tolclophos-methyl 2-43 Combination of 1-18 Metconazole -360 Prothioconazole Ethaboxam 2-44 Combination of 1-18 Prothioconazole -361 Prothioconazole Compound 4 2-45 Combination of 1-18 Triticonazole -362 Prothioconazole Compound 2 2-46 Combination of 1-18 Tebuconazole -363 Prothioconazole Compound 3 2-47 Combination of 1-18 Diphenoconazole -364 Prothioconazole Compound 1 2-48 Combination of 1-18 Ipconazole -36S Prothioconazole Compound 5 2-49 Combination of 1-18 Thiophanate-methyl -366 Fipronil Tefluthrin 2-SO Combination of 1-18 Fludioxonil -367 midacloprid Tefluthrin 2-51 Combination of 1-18 Tolclophos-methyl -368 Carboxin Thiram 2-52 Combination of 1-13 Thiram -369 C yraclostrobin Fluxapyroxad 2-53 Combination of 1-18 Captain -370 Flutolani Mancozeh 2-54 Combination of 1-18 Carboxin -371 Fluauinconazole Prochloraz 2-55 Combination of 1-18 Boscalid 2-56 Combination of 1-18 Thiabendazole 2-57 Combination of 1-28 Boscalid 2-58 Combination of 1-28 Metconazole TABLE 10 2-59 Combination of 1-28 Ipconazole 2-60 Combination of 1-28 Triticonazole Number of 2-61 Combination of 1-28 Tebuconazole combination 2-62 Combination of 1-28 Thiabendazole Combinations of compounds 2-63 Combination of 1-28 Carboxin 2-1 Com bination of 1-14 Pyraclostrobin 2-64 Combination of 1-28 Penflufen 2-2 Com bination of 1-14 Azoxystrobin 2-65 Combination of 1-28 Sedaxane 2-3 Com bination of 1-14 Trifloxystrobin 2-66 Combina ion of 1-28 Fluxapyroxad 2-4 Com bination of 1-14 Compound 1 2-67 Combination of 1-28 Fluopyram 2-5 Com bination of 1-14 Metconazole 2-68 Combination of 1-28 Thiram 2-6 Com bination of 1-14 Prothioconazole 2-69 Combination of 1-233 Metconazole 2-7 Com bination of 1-14 Triticonazole 2-70 Combination of 1-27 pconazole 2-8 Com bination of 1-14 Tebuconazole 2-71 Combination of 1-14 Compound 5 2-9 Com bination of 1-14 Diphenoconazole 2-72 Combination of 1-15 Compound 5 2-10 Com bina ion of 1-14 Ipconazole 2-73 Combination of 1-28 Compound 5 2-11 Com bination or 1- 4 Thlophanate-methyl 2-74 Combination of 1-90 Fludioxonil 2-12 Com bination or 1- 4 Fludioxonil 2-75 Combination of 1-91 Fludioxonil 2-13 Com bination oil- 4 Tolclophos-methyl 2-76 Combination of 1-52 Pyraclostrobin 2-14 Com bination or 1- 4 hiram 2-77 Combination of 1-53 Pyraclostrobin 2-15 Com bination or 1- 4 Captain 2-78 Combination of 1-52 Trifloxystrobin 2-16 Com bination of 1-14 Carboxin 2-79 Combination of 1-53 Trifloxystrobin 2-17 Com bination of 1-14 Boscalid 2-8O Combination of 1-216 Penflufen 2-18 Com bination of 1-14 hiabendazole ill 2-19 Com bination of 1-14 Ethaboxam 2-81 Combina on o -4 Bacillus firmus 2-2O Com bination of 1-15 Pyraclostrobin 2-82 Combination of 1-52 Tebuconazole 2-21 Com bination of 1-15 Azoxystrobin 2-83 Combination of 1-53 Tebuconazole 2-22 Com bination of 1-15 Trifloxystrobin 2-84 Combination of 1-42 Triazoxide 2-23 Com bination of 1-15 Compound 1 2-85 Combination of 1-52 Mycrobutanil 2-24 Com bination of 1-15 Metconazole 2-86 Combination of 1-53 Mycrobutanil 2-2S Com bination of 1-15 Prothioconazole

TABLE 11

Number of combination Combination of compounds 3-1 Combination of 2-57 Pyraclostrobin Compound 1 3-2 Combination of 2-57 Pyraclostrobin Tolclophos-methyl US 2014/0200140 A1 Jul. 17, 2014 19

TABLE 1 1-continued

Number of combination Combination of compounds 3-3 Com bina ion o Pyraclostrobin Metconazole 3-4 Com bina ion o Pyraclostrobin Metalaxyl 3-5 Com bina ion o Pyraclostrobin Metconazole 3-6 Com bina ion o Pyraclostrobin Metconazole 3-7 Com bina ion o Pyraclostrobin Compound 1 3-8 Com bina ion o Pyraclostrobin Compound 1 3-9 Com bina ion o Pyraclostrobin Tolclophos-methyl 3-10 Com bina ion o Pyraclostrobin Tolclophos-methyl 3-11 Com bina ion o Thiram 3-12 Com bina ion o Trifloxystrobin 3-13 Com bina ion o Trifloxystrobin 3-14 Com bina ion o Trifloxystrobin 3-15 Com bina ion o Compound 1 3-16 Com bina ion o AZOxystrobin 3-17 Com bina ion o Thiabendazole 3-18 Com bina ion o Trifloxystrobin 3-19 Com bina ion o AZOxystrobin 3-2O Com bina ion o Thiabendazole 3-21 Com bina ion o Trifloxystrobin Compound 1 3-22 Com bina ion o AZOxystrobin Compound 1 3-23 Com bina ion o Thiram Compound 1 3-24 Com bina ion o Tolclophos-me hyl 3-2S Com bina ion o Ethaboxam Compound 1 3-26 Com bina ion o Compound 1 3-27 Com bina ion o Diphenoconazo 3-28 Com bina ion o Diphenoconazo 3-29 Com bina ion o Diphenoconazo 3-30 Com bina ion o Diphenoconazo 3-31 Com bina ion o Diphenoconazo 3-32 Com bina ion o Diphenoconazo 3-33 Com bina ion o Diphenoconazo 3-34 Com bina ion o Diphenoconazo 3-3S Com bina ion o Diphenoconazo 3-36 Com bina ion o Diphenoconazo 3-37 Com bina ion o Diphenoconazo 3-38 Com bina ion o Diphenoconazo 3-39 Com bina ion o Diphenoconazo 3-40 Com bina ion o Metconazole Diphenoconazole 3-41 Com bina ion o pconazole Diphenoconazole 3-42 Com bina ion o Triticonazole Diphenoconazole 3-43 Com bina ion o Tebuconazole Diphenoconazole 3-44 Com bina ion o Thiabendazole Diphenoconazole 3-45 Com bina ion o Carboxin Diphenoconazole 3-46 Com bina ion o Penflufen Diphenoconazole 3-47 Com bina ion o Sedaxane Diphenoconazole 3-48 Com bina ion o Fluxapyroxad Diphenoconazole 3-49 Com bina ion o Fluopyram Diphenoconazole 3-SO Com bina ion o Thiram Diphenoconazole 3-51 Com bina ion o Pyraclostrobin Ipconazole 3-52 Com bina ion o Pyraclostrobin Ipconazole 3-53 Com bina ion o Pyraclostrobin Ipconazole 3-54 Com bina ion o Trifloxystrobin 3-55 Com bina ion o Trifloxystrobin 3-56 Com bina ion o Trifloxystrobin 3-57 Com bina ion o Ipconazole Trifloxystrobin 3-58 Com bina ion o AZOxystrobin 3-59 Com bina ion o AZOxystrobin 3-60 Com bina ion o Ipconazole AZOxystrobin 3-61 Com bina ion o Compoun Carboxin 3-62 Com bina ion o Compoun Penflufen 3-63 Com bina ion o Compoun Sedaxane 3-64 Com bina ion o Compoun Fluxapyroxad 3-6S Com bina ion o Compoun Fluopyram 3-66 Com bina ion o Compoun Oxycarboxin 3-67 Com bina ion o Compoun Thifluzamide 3-68 Com bina ion o Compoun Flutolani 3-69 Com bina ion o Compoun Pencycuron 3-70 Com bina ion o Compoun Fludioxonil 3-71 Com bina ion o Compoun Metconazole 3-72 Com bina ion o Compoun Tebuconazole 3-73 Com bina ion o Compoun Diphenoconazole 3-74 Com bina ion o Compoun Triticonazole 3-75 Com bina ion o Compoun Imazalil US 2014/0200140 A1 Jul. 17, 2014 20

TABLE 1 1-continued

Number of combination Combination of compounds 3-76 Combination of 2-32 Compoun Triadimenol 3-77 Combination of 2-32 Compoun Fluquinconazole 3-78 Combination of 2-32 Compoun Prochloraz 3-79 Combination of 2-32 Compoun Prothioconazole 3-8O Combination of 2-32 Compoun Diniconazole 3-81 Combination of 2-32 Compoun Diniconazole-M 3-82 Combination of 2-32 Compoun Ipconazole 3-83 Combination of 2-32 Compoun Cyproconazole 3-84 Combination of 2-32 Compoun Tetraconazole 3-85 Combination of 2-32 Compoun Carboxin 3-86 Combination of 2-32 Compoun Penflufen 3-87 Combination of 2-32 Compoun Sedaxane 3-88 Combination of 2-32 Compoun Fluxapyroxad 3-89 Combination of 2-32 Compoun Fluopyrm 3-90 Combination of 2-32 Compoun Oxycarboxin 3-91 Combination of 2-32 Compoun Fludioxonil 3-92 Combination of 2-32 Compoun Thiram 3-93 Combination of 2-32 Compoun Captain 3-94 Combination of 2-32 Compoun Thiophanate-methyl 3-95 Combination of 2-32 Compoun Thiabendazole 3-96 Combination of 2-13 Compoun Metconazole 3-97 Combination of 2-13 Compoun Tebuconazole 3-98 Combination of 2-13 Compoun Diphenoconazole 3-99 Combination of 2-13 Compoun Triticonazole 3-100 Combination of 2-13 Compoun mazalil 3-101 Combination of 2-13 Compoun Triadimenol 3-102 Combination of 2-13 Compoun Fluquinconazole 3-103 Combination of 2-13 Compoun Prochloraz 3-104 Combination of 2-13 Compoun Prothioconazole 3-105 Combination of 2-13 Compoun Diniconazole 3-106 Combination of 2-13 Compoun Diniconazole-M 3-107 Combination of 2-13 Compoun pconazole 3-108 Combination of 2-13 Compoun Cyproconazole 3-109 Combination of 2-13 Compoun Tetraconazole 3-110 Combination of 2-13 Compoun Carboxin 3-111 Combination of 2-13 Compoun Penflufen 3-112 Combination of 2-13 Compoun Sedaxane 3-113 Combination of 2-13 Compoun Fluxapyroxad 3-114 Combination of 2-13 Compoun Fluopyram 3-115 Combination of 2-13 Compoun Oxycarboxin 3-116 Combination of 2-13 Compoun Fludioxonil 3-117 Combination of 2-13 Compoun Thiram 3-118 Combination of 2-13 Compoun Captain 3-119 Combination of 2-13 Compoun Thiophanate-methyl 3-120 Combination of 2-13 Compoun Thiabendazole 3-121 Combination of 2-69 Compoun Oxadixyl 3-122 Combination of 2-69 Compoun Hymexazol 3-123 Combination of 2-69 Compoun Fenamidone 3-124 Combination of 2-69 Compoun Cymoxanil 3-125 Combination of 2-69 Compoun Fluopicolide 3-126 Combination of 2-70 Carboxin 3-127 Combination of 2-10 Tolclophos-methy Carboxin 3-128 Combination of 2-10 Tolclophos-methy Penflufen 3-129 Combination of 2-10 Tolclophos-methy Sedaxane 3-130 Combination of 2-10 Tolclophos-methy Fluxapyroxad 3-131 Combination of 2-10 Tolclophos-methy Fluopyram 3-132 Combination of 2-5 Tolclophos-methy 3-133 Combination of 2-5 Tolclophos-methyl Azoxystrobin 3-134 Combination of 2-5 Tolclophos-methy Fluoxastrobin 3-13S Combination of 2-5 Tolclophos-methy Trifloxystrobin 3-136 Combination of 2-5 Tolclophos-methy Pyraclostrobin 3-137 Combination of 2-5 Tolclophos-methy Orysastrobin 3-138 Combination of 2-5 Tolclophos-methy Carboxin 3-139 Combination of 2-5 Tolclophos-methy Oxycarboxin 3-140 Combination of 2-5 Tolclophos-methy Fludioxonil 3-141 Combination of 2-5 Tolclophos-methy Thiram 3-142 Combination of 2-5 Tolclophos-methy Captain 3-143 Combination of 2-5 Tolclophos-methy Thiophanate-methyl 3-144 Combination of 2-5 Tolclophos-methy Thiabendazole 3-145 Combination of 2-5 Ethaboxam 3-146 Combination of 2-5 Ethaboxam Tolclophos-methyl 3-147 Combination of 2-38 Compound 1 Compound 2 3-148 Combination of 2-19 Compound 1 Compound 2 US 2014/0200140 A1 Jul. 17, 2014 21

TABLE 1 1-continued

Number of combination Combination of compounds 3-149 Com bina ion o Compound 5 Compoun 3-1SO Com bina ion o Compound 5 Compoun 3-151 Com bina ion o Ipconazole Compoun 3-152 Com bina ion o Ipconazole Compoun 3-153 Com bina ion o Metconazole Compoun 3-154 Com bina ion o Metconazole Compoun 3-155 Com bina ion o Tolclophos-methyl Compoun 3-156 Com bina ion o Tolclophos-methyl Compoun 3-157 Com bina ion o Compound 1 Compoun 3-158 Com bina ion o Compound 1 Compoun 3-159 Com bina ion o Compound 1 Compoun 3-160 Com bina ion o Compound 1 Compoun 3-161 Com bina ion o Compound 5 Compoun 3-162 Com bina ion o Fludioxonil Compoun 3-163 Com bina ion o Compound 5 Compoun 3-164 Com bina ion o Tolclophos-methyl Compoun 3-16S Com bina ion o Metconazole Compoun 3-166 Com bina ion o Compound 4 Compoun 3-167 Com bina ion o Compound 4 Compoun 3-168 Com bina ion o Ipconazole Compoun 3-169 Com bina ion o Compound 4 Compoun 3-170 Com bina ion o Boscalid Pyraclostrobin Metconazole 3-171 Com bina ion o Boscalid Pyraclostrobin Ipconazole 3-172 Com bina ion o Boscalid Pyraclostrobin Metconazole 3-173 Com bina ion o Boscalid Pyraclostrobin Compound 1 3-174 Com bina ion o Boscalid Pyraclostrobin Compound 1 3-175 Com bina ion o Boscalid Pyraclostrobin Tolclophos-methyl 3-176 Com bina ion o Boscalid Pyraclostrobin Tolclophos-methyl 3-177 Com bina ion o Compound 1 Metconazo Oxadixyl 3-178 Com bina ion o Compound 1 Metconazo Hymexazol 3-179 Com bina ion o Compound 1 Metconazo Fenamidone 3-18O Com bina ion o Compound 1 Metconazo Cymoxanil 3-181 Com bina ion o Compound 1 Metconazo Fluopicolide 3-182 Com bina ion o Compound 1 Metconazo Oxadixyl 3-183 Com bina ion o Compound 1 Metconazo Hymexazol 3-184 Com bina ion o Compound 1 Metconazo Fenamidone 3-185 Com bina ion o Compound 1 Metconazo Cymoxanil 3-186 Com bina ion o Compound 1 Metconazole Fluopicolide 3-187 Com bina ion o Ethaboxam Tolclophos-methyl AZOxystrobin 3-188 Com bina ion o Ethaboxam Tolclophos-methyl Fluoxastrobin 3-189 Com bina ion o Ethaboxam Tolclophos-methyl Trifloxystrobin 3-190 Com bina ion o Ethaboxam Tolclophos-methyl Pyraclostrobin 3-191 Com bina ion o Ethaboxam Tolclophos-methyl Orysastrobin 3-192 Com bina ion o Ethaboxam Tolclophos-methyl Carboxin 3-193 Com bina ion o Ethaboxam Tolclophos-methyl Penflufen 3-194 Com bina ion o Ethaboxam Tolclophos-methyl Sedaxane 3-195 Com bina ion o Ethaboxam Tolclophos-methyl Fluxapyroxad 3-196 Com bina ion o Ipconazole Compound 2 Fluopyram 3-197 Com bina ion o Ipconazole Compound 2 Oxycarboxin 3-198 Com bina ion o Metconazole Compound 2 Fludioxonil 3-199 Com bina ion o Metconazole Compound 2 Thiram 3-200 Com bina ion o Tolclophos-methyl Compound 2 Captain 3-2O1 Com bina ion o Tolclophos-methyl Compound 2 Thiophanate-methyl 3-2O2 Com bina ion o Compound 1 Compound 2 Thiabendazole 3-2O3 Com bina ion o Metconazole 3-204 Com bina ion o Metconazole 3-2OS Com bina ion o Diphenoconazole 3-2O6 Com bina ion o Triticonazole 3-2O7 Com bina ion o Tebuconazole 3-208 Com bina ion o Thiabendazole 3-209 Com bina ion o Carboxin 3-210 Com bina ion o Thiram 3-211 Com bina ion o Captain 3-212 Com bina ion o Compound 1 3-213 Com bina ion o Compound 1 3-214 Com bina ion o Compound 1 3-215 Com bina ion o Tolclophos-methyl 3-216 Com bina ion o Tolclophos-methyl 3-217 Com bina ion o Captain 3-218 Com bina ion o Captain 3-219 Com bina ion o Ethaboxam Metconazole 3-220 Com bina ion o Ethaboxam Compound 1 3-221 Com bina ion o Ethaboxam Tolclophos-methyl US 2014/0200140 A1 Jul. 17, 2014 22

TABLE 1 1-continued

Number of combination Combination of compounds 3-222 Combination of 2-73 Tolclophos-methyl 3-223 Combination of 2-7 Ethaboxam Ipconazole 3-224 Combination of 2-7 Ethaboxam Diphenoconazole 3-225 Combination of 2-7 Ethaboxam Triticonazole 3-226 Combination of 2-7 Ethaboxam Tebuconazole 3-227 Combination of 2-7 Ethaboxam Thiabendazole 3-228 Combination of 2-7 Ethaboxam Carboxin 3-229 Combination of 2-7 Ethaboxam Thiram 3-230 Combination of 2-7 Ethaboxam Captain 3-231 Combination of 2-73 pconazole 3-232 Combination of 2-7 Fludioxoni AZOxystrobin Prothioconazole 3-233 Combination of 2-7 Fludioxoni Pyraclostrobin Prothioconazole 3-234 Combination of 2-7 Fludioxoni Trifloxystrobin Prothioconazole 3-235 Combination of 2-7 Fludioxoni Fluoxastrobin Prothioconazole 3-236 Combination of 2-7 Fludioxoni AZOxystrobin Triticonazole 3-237 Combination of 2-7 Fludioxoni Pyraclostrobin Triticonazole 3-238 Combination of 2-7 Fludioxoni Trifloxystrobin Triticonazole 3-239 Combination of 2-7 Fludioxoni Fluoxastrobin Triticonazole 3-240 Combination of 2-7 Fludioxoni AZOxystrobin Tebuconazole 3-241 Combination of 2-7 Fludioxoni Pyraclostrobin Tebuconazole 3-242 Combination of 2-7 Fludioxoni Trifloxystrobin Tebuconazole 3-243 Combination of 2-7 Fludioxoni Fluoxastrobin Tebuconazole 3-244 Combination of 2-7 Fludioxoni AZOxystrobin Diphenoconazole 3-245 Combination of 2-7 Fludioxoni Pyraclostrobin Diphenoconazole 3-246 Combination of 2-7 Fludioxoni Trifloxystrobin Diphenoconazole 3-247 Combination of 2-7 Fludioxoni Fluoxastrobin Diphenoconazole 3-248 Combination of 2-72 Fludioxoni AZOxystrobin Prothioconazole 3-249 Combination of 2-72 Fludioxoni Pyraclostrobin Prothioconazole 3-2SO Combination of 2-72 Fludioxoni Trifloxystrobin Prothioconazole 3-251 Combination of 2-72 Fludioxoni Fluoxastrobin Prothioconazole 3-2S2 Combination of 2-72 Fludioxoni AZOxystrobin Triticonazole 3-2S3 Combination of 2-72 Fludioxoni Pyraclostrobin Triticonazole 3-2S4 Combination of 2-72 Fludioxoni Trifloxystrobin Triticonazole 3-255 Combination of 2-72 Fludioxoni Fluoxastrobin Triticonazole 3-2S6 Combination of 2-72 Fludioxoni AZOxystrobin Tebuconazole 3-257 Combination of 2-72 Fludioxoni Pyraclostrobin Tebuconazole 3-258 Combination of 2-72 Fludioxoni Trifloxystrobin Tebuconazole 3-259 Combination of 2-72 Fludioxoni Fluoxastrobin Tebuconazole 3-260 Combination of 2-72 Fludioxoni AZOxystrobin Diphenoconazole 3-261 Combination of 2-72 Fludioxoni Pyraclostrobin Diphenoconazole 3-262 Combination of 2-72 Fludioxoni Trifloxystrobin Diphenoconazole 3-263 Combination of 2-72 Fludioxoni Fluoxastrobin Diphenoconazole 3-264 Combination of 2-7 Compound 1 Compound 2 3-265 Combination of 2-7 Pyraclostrobin Compound 2 3-266 Combination of 2-7 AZOxystrobin Compound 2 3-267 Combination of 2-7 Trifloxystrobin Compound 2 3-268 Combination of 2-7 Metconazole Compound 2 3-269 Combination of 2-7 Prothioconazole Compound 2 3-270 Combination of 2-7 Triticonazole Compound 2 3-271 Combination of 2-7 Tebuconazole Compound 2 3-272 Combination of 2-7 Diphenoconazole Compound 2 3-273 Combination of 2-7 pconazole Compound 2 3-274 Combination of 2-7 Thiophanate-methyl Compound 2 3-275 Combination of 2-7 Fludioxonil Compound 2 3-276 Combination of 2-7 Tolclophos-methyl Compound 2 3-277 Combination of 2-7 Thiuram Compound 2 3-278 Combination of 2-7 Captain Compound 2 3-279 Combination of 2-7 Carboxin Compound 2 3-280 Combination of 2-7 Penflufen Compound 2 3-281 Combination of 2-7 Sedaxane Compound 2 3-282 Combination of 2-7 Fluxapyroxad Compound 2 3-283 Combination of 2-7 Fluopyram Compound 2 3-284 Combination of 2-7 Boscalid Compound 2 3-285 Combination of 2-7 Thiabendazole Compound 2 3-286 Combination of 2-72 Compound 1 Compound 2 3-287 Combination of 2-72 Pyraclostrobin Compound 2 3-288 Combination of 2-72 AZOxystrobin Compound 2 3-289 Combination of 2-72 Trifloxystrobin Compound 2 3-290 Combination of 2-72 Metconazole Compound 2 3-291 Combination of 2-72 Prothioconazole Compound 2 3-292 Combination of 2-72 Triticonazole Compound 2 3-293 Combination of 2-72 Tebuconazole Compound 2 3-294 Combination of 2-72 Diphenoconazole Compound 2 US 2014/0200140 A1 Jul. 17, 2014 23

TABLE 1 1-continued

Number of combination Combination of compounds 3-295 Combination of 2-72 pconazole Compound 2 3-296 Combination of 2-72 Thiophanate-methyl Compound 2 3-297 Combination of 2-72 Fludioxonil Compound 2 3-298 Combination of 2-72 Tolclophos-methyl Compound 2 3-299 Combination of 2-72 Thiuram Compound 2 3-300 Combination of 2-72 Captain Compound 2 3-301 Combination of 2-72 Carboxin Compound 2 3-3O2 Combination of 2-72 Penflufen Compound 2 3-303 Combination of 2-72 Sedaxane Compound 2 3-304 Combination of 2-72 Fluxapyroxad Compound 2 3-30S Combination of 2-72 Fluopyram Compound 2 3-306 Combination of 2-72 Boscalid Compound 2 3-307 Combination of 2-72 Thiabendazole Compound 2 3-3O8 Combination of 2-7 Compound 1 Compound 3 3-309 Combination of 2-7 Pyraclostrobin Compound 3 3-310 Combination of 2-7 AZOxystrobin Compound 3 3-311 Combination of 2-7 Trifloxystrobin Compound 3 3-312 Combination of 2-7 Metconazole Compound 3 3-313 Combination of 2-7 Prothioconazole Compound 3 3-314 Combination of 2-7 Triticonazole Compound 3 3-315 Combination of 2-7 Tebuconazole Compound 3 3-316 Combination of 2-7 Diphenoconazole Compound 3 3-317 Combination of 2-7 pconazole Compound 3 3-318 Combination of 2-7 Thiophanate-methyl Compound 3 3-319 Combination of 2-7 Fludioxonil Compound 3 3-320 Combination of 2-7 Tolclophos-methyl Compound 3 3-321 Combination of 2-7 Thiuram Compound 3 3-322 Combination of 2-7 Captain Compound 3 3-323 Combination of 2-7 Carboxin Compound 3 3-324 Combination of 2-7 Penflufen Compound 3 3-32S Combination of 2-7 Sedaxane Compound 3 3-326 Combination of 2-7 Fluxapyroxad Compound 3 3-327 Combination of 2-7 Fluopyram Compound 3 3-328 Combination of 2-7 Boscalid Compound 3 3-329 Combination of 2-7 Thiabendazole Compound 3 3-330 Combination of 2-72 Compound 1 Compound 3 3-331 Combination of 2-72 Pyraclostrobin Compound 3 3-332 Combination of 2-72 AZOxystrobin Compound 3 3-333 Combination of 2-72 Trifloxystrobin Compound 3 3-334 Combination of 2-72 Metconazole Compound 3 3-335 Combination of 2-72 Prothioconazole Compound 3 3-336 Combination of 2-72 Triticonazole Compound 3 3-337 Combination of 2-72 Tebuconazole Compound 3 3-338 Combination of 2-72 Diphenoconazole Compound 3 3-339 Combination of 2-72 pconazole Compound 3 3-340 Combination of 2-72 Thiophanate-methyl Compound 3 3-341 Combination of 2-72 Fludioxonil Compound 3 3-342 Combination of 2-72 Tolclophos-methyl Compound 3 3-343 Combination of 2-72 Thiuram Compound 3 3-344 Combination of 2-72 Captain Compound 3 3-345 Combination of 2-72 Carboxin Compound 3 3-346 Combination of 2-72 Penflufen Compound 3 3-347 Combination of 2-72 Sedaxane Compound 3 3-348 Combination of 2-72 Fluxapyroxad Compound 3 3-349 Combination of 2-72 Fluopyram Compound 3 3-3SO Combination of 2-72 Boscalid Compound 3 3-351 Combination of 2-72 Thiabendazole Compound 3 3-352 Combination of 2-7 Compound 1 Compound 4 3-353 Combination of 2-7 Pyraclostrobin Compound 4 3-3S4 Combination of 2-7 AZOxystrobin Compound 4 3-355 Combination of 2-7 Trifloxystrobin Compound 4 3-356 Combination of 2-7 Metconazole Compound 4 3-357 Combination of 2-7 Prothioconazole Compound 4 3-358 Combination of 2-7 Triticonazole Compound 4 3-359 Combination of 2-7 Tebuconazole Compound 4 3-360 Combination of 2-7 Diphenoconazole Compound 4 3-361 Combination of 2-7 pconazole Compound 4 3-362 Combination of 2-7 Thiophanate-methyl Compound 4 3-363 Combination of 2-7 Fludioxonil Compound 4 3-364 Combination of 2-7 Tolclophos-methyl Compound 4 3-36S Combination of 2-7 Thiuram Compound 4 3-366 Combination of 2-7 Captain Compound 4 3-367 Combination of 2-7 Carboxin Compound 4 US 2014/0200140 A1 Jul. 17, 2014 24

TABLE 1 1-continued

Number of combination Combination of compounds 3-368 Combination o 2-71 Penflufen Compoun 3-369 Combination o 2-71 Sedaxane Compoun 3-370 Combination o 2-71 Fluxapyroxad Compoun 3-371 Combination o 2-71 Fluopyram Compoun 3-372 Combination o 2-71 Boscalid Compoun 3-373 Combination o 2-71 Thiabendazole Compoun 3-374 Combination o 2-72 Compound 1 Compoun 3-375 Combination o 2-72 Pyraclostrobin Compoun 3-376 Combination o 2-72 AZOxystrobin Compoun 3-377 Combination o 2-72 Trifloxystrobin Compoun 3-378 Combination o 2-72 Metconazole Compoun 3-379 Combination o 2-72 Prothioconazole Compoun 3-380 Combination o 2-72 Triticonazole Compoun 3-381 Combination o 2-72 Tebuconazole Compoun 3-382 Combination o 2-72 Diphenoconazole Compoun 3-383 Combination o 2-72 pconazole Compoun 3-384 Combination o 2-72 Thiophanate-methyl Compoun 3-385 Combination o 2-72 Fludioxonil Compoun 3-386 Combination o 2-72 Tolclophos-methyl Compoun 3-387 Combination o 2-72 Thiuram Compoun 3-388 Combination o 2-72 Captain Compoun 3-389 Combination o 2-72 Carboxin Compoun 3-390 Combination o 2-72 Penflufen Compoun 3-391 Combination o 2-72 Sedaxane Compoun 3-392 Combination o 2-72 Fluxapyroxad Compoun 3-393 Combination o 2-72 Fluopyram Compoun 3-394 Combination o 2-72 Boscalid Compoun 3-395 Combination o 2-72 Thiabendazole Compoun 3-396 Combination o 2-74 AZOxystrobin Abamectin Sedaxane 3-397 Combination o 2-75 Azoxystrobin Abamectin Sedaxane 3-398 Combination o 2-76 Fluxapyroxad 3-399 Combination o 2-77 Fluxapyroxad 3-400 Combination o 2-81 Fluxapyroxad 3-4O1 Combination o 2-78 Penflufen 3-402 Combination o 2-79 Penflufen 3-403 Fipronil Pyraclostrobin Thiophanate-methyl Fluxapyroxad 3-404 Fluoxastrobin Prothioconazole Tebuconazole Triazoxide 3-405 Combination o 3-398 Sedaxane 3-4O6 Combination o 3-399 Sedaxane 3-4O7 Combination o 2-85 Trifloxystrobin Fluxapyroxad Thiodicarb 3-408 Combination o 2-86 Trifloxystrobin Fluxapyroxad Thiodicarb 3-409 Combination o 2-85 Pyraclostrobin Fluxapyroxad Thiodicarb 3-410 Combination o 2-86 Pyraclostrobin Fluxapyroxad Thiodicarb

0260 According to the method of controlling pests of the each of the crystals showing a powder X-Ray diffraction present invention, pests in clop fields can be efficiently con pattern which has diffraction peaks with 20 values () trolled. shown in the corresponding right column of Table 1, 1. A method of controlling weeds in a crop field, the method including treating the crop field with crystal of flu TABLE 1 mioxazin, before sowing or planting, at the same time of Sowing or planting, or after sowing or planting crop seeds or 20 value () Vegetative organs such as tubers, bulbs, or stem fragments which are treated with one or more compounds selected from 1 crystal 7.5 + 0.1, 11.9 + 0.1, 15.3 + 0.1 the following group B; 2” crystal 8.7 + 0.1, 9.4 + 0.1, 14.7 + 0.1, 18.8 0.1 Group B: neonicotinoid type compounds, diamide type 3 crystal 7.7 + 0.1, 10.9 + 0.1, 13.5 + 0.1, compounds, carbamate type compounds, organic phos 14.6+ 0.1, 15.0 + 0.1 phorous type compounds, biological nematicidal com 4 crystal pounds, other insecticidal compounds and nematicidal 7.7 + 0.1, 10.7 + 0.1, 13.4 + 0.1, compounds, azole type compounds, strobilurin type 14.3 + 0.1, 14.8 + 0.1 compounds, metalaxyl type compounds, SDHI com 5th crystal 5.5 + 0.1, 10.3 + 0.1, 10.9 + 0.1, pounds, and other fungicidal compounds and plant 13.20.1 growth regulators, 6 crystal 7.7 + 0.1, 8.6 + 0.1, 11.0 + 0.1, wherein the crystal of flumioxazin is one or more 13.2 + 0.1, 14.7 + 0.1, 15.1 + 0.1, selected from the group consisting of 1 crystal. 2" 7" crystal 14.5 + 0.1, 18.7 + 0.1 crystal, 3 crystal, 4' crystal, 5' crystal, 6' crystal and 7" crystal, US 2014/0200140 A1 Jul. 17, 2014

2. A method of controlling pests in a crop field, the method including the steps of (I) Br treating crop seeds or vegetative organs such as tubers, bulbs, or stem fragments with one or more compounds selected from the group B; O Br Group B: neonicotinoid type compounds, diamide type com pounds, carbamate type compounds, organic phosphorous NH type compounds, biological nematicidal compounds, other insecticidal compounds and nematicidal compounds, azole I / \ C type compounds, strobilurin type compounds, metalaxyl type O compounds, SDHI compounds, and other fungicidal com HN pounds and plant growth regulators; and treating the crop field with crystal of flumioxazin, before sowing or planting, at the same time of sowing or " planting, or after Sowing or planting the crop seeds or Veg B-2. carbamate type compounds: aldicarb, oxamyl. etative organs such as tubers, bulbs, or stem fragments which thiodicarb, carbofuran, carbosulfan, and dimethoate; are treated with the compounds of the group B, B-3, organic phosphorous type compounds: fenami phos, imicyafos, fensulfothion, terbufos, fosthiazate, wherein the crystal of flumioxazin phosphocarb, dichlofenthion, isamidofos, isaZophos, is one or more selected from the group consisting of 1 ethoprophos, cadusafos, chlorpyrifos, heterofos, crystal, 2" crystal, 3' crystal, 4' crystal, 5' crystal, 6' mecarphon, phorate, thionazin, triaZophos, diami crystal and 7" crystal, dafos, fosthietan, and phosphamidon; B-4, biological nematicidal compounds: Harpin Protein, each of the crystals showing a powder X-Ray diffraction Pasteuria nishizawae, Pasteuria penetrans, Myroth pattern which has diffraction peaks with 20 values () ecium verrucaria, Burholderia cepacia, Bacillus chi shown in the corresponding right column of Table 1, tonosporus, Paecilomyces lilacinus, Bacillus amy loliquefaciens, Bacillus firmus, Bacillus subtilis, TABLE 1. Bacillus pumulis, Trichoderma harzianum, Hirsutella rhossiliensis, Hirsutella minnesotensis, Verticillium 20 value () chlamydosporum, and Arthrobotry's dactyloides, B-5, other insecticidal compounds and nematicidal compounds: fipronil, ethiprole, Sulfoxaflor, 1 crystal 7.5 + 0.1, 11.9 + 0.1, 15.3 + 0.1 flupyradifurone, beta-cyfluthrin, tefluthrin, chlorpyri 2” crysta 8.7 + 0.1,9.4 + 0.1, 14.7 + 0.1, fos, abamectin, Spirotetramat, and fluenSulfone; 18.8 0.1 B-6, azole type compounds: azaconazole, bitertanol, 3 crysta 7.7 + 0.1, 10.9 + 0.1, 13.5 + 0.1, bromuconazole, cyproconazole, diphenoconazole, 14.6 + 0.1, 15.0 + 0. diniconazole, epoxyconazole, fenbuconazole, flu 4 crysta 7.7 + 0.1, 10.7 + 0.1, 13.4 + 0.1, quinconazole, flusilaZole, flutriafol, hexaconazole, 14.3 + 0.1, 14.8 + O. imibenconazole, ipconazole, metconazole, mycrobu 5' crysta 5.5 + 0.1, 10.3 + 0.1, 10.9 + 0.1, tanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadime 13.20.1 nol, triticonazole, fenarimol, nuarimol, pyrifenox, 6 crysta 7.7 + 0.1, 8.6 + 0.1, 11.0 + 0.1, imazalil, Oxpoconazole-fumarate, pefurazoate, 13.2 + 0.1, 14.7 + 0.1, 15.1 + 0.1, prochloraz, and triflumizol; 7th crysta 14.5 + 0.1, 18.7 + 0. B-7, strobilurin type compounds: kresoxim-methyl, azoxystrobin, trifloxystrobin, fluoxastrobin, picox yStrobin, pyraclostrobin, dimoxystrobin, pyriben 3. The control method according to claim 1, wherein the carb, metominostrobin, orysastrobin, and N-methyl group B is the following compounds: 2-2-(2,5-dimethylphenoxy)methylphenyl-2- methoxy-acetamide (racemic or enantiomer, group B: containing a mixture of R-enantiomer and S-enanti omer (optional ratio)); B-1, neonicotinoid type compounds: clothianidin, thia B-8, metalaxyl type compounds: metalaxyl and metal methoxam, imidacloprid, dinotefuran, nitenpyram, axyl-M; acetamiprid, and thiacloprid; B-9, SDHI compounds: sedaxane, penflufen, carboxin, boscalid, furametpyr, flutolanil, fluxapyroxad, isopy diamide type compounds: flubendiamide, chlorantranil razam, fluopyram, and thifluZamide; iprole, cyantraniliprole, and compounds represented B-10, other fungicidal compounds: tolclophos-methyl, by the formula (I): thiram, Captan, carbendazim, thiophanate-methyl, US 2014/0200140 A1 Jul. 17, 2014 26

mancozeb, thiabendazole, isotianil, triazoxide, (RS)- rhossiliensis, Hirsutella minnesotensis, Verticillium 2-methoxy-N-methyl-2-O-(2,5-xylyloxy)-o-tolyl chlamydosporum, and Arthrobotry's dactyloides, acetamide, fludioxonil, ethaboxam, 3-chloro-5-phe B-5, other insecticidal compounds and nematicidal nyl-6-methyl-4-(2,6-difluorophenyl)pyridazine, compounds: fipronil, ethiprole, Sulfoxaflor, 3-cyano-5-phenyl-6-methyl-4-(2,6-difluorophenyl) flupyradifurone, beta-cyfluthrin, tefluthrin, chlorpyri pyridazine, and N-(1,1,3-trimethylindan-4-yl)-1-me fos, abamectin, Spirotetramat, and fluenSulfone; thyl-3-difluoromethylpyrazole-4-carboxylic acid B-6, azole type compounds: azaconazole, bitertanol, amide (racemic or enantiomer, containing a mixture bromuconazole, cyproconazole, diphenoconazole, of R-enantiomer and S-enantiomer (optional ratio)); diniconazole, epoxyconazole, fenbuconazole, flu and quinconazole, flusilaZole, flutriafol, hexaconazole, B-11, plant growth inhibitors: ethephon, chlormeduat imibenconazole, ipconazole, metconazole, mycrobu chloride, mepicquat-chloride, and 4-oxo-4-(2-phenyl tanil, penconazole, propiconazole, prothioconazole, ethyl)aminobutyric acid. simeconazole, tebuconazole, tetraconazole, triadime 4. The control method according to claim 1, wherein the nol, triticonazole, fenarimol, nuarimol, pyrifenox, crop is soybean, peanut, common bean, pea, corn, cotton, imazalil, Oxpoconazole-fumarate, pefurazoate, wheat, rice, Sunflower, potato, Sugar cane, or vegetables. prochloraz, and triflumizol; 5. The control method according to claim 2, wherein the B-7, strobilurin type compounds: kresoxim-methyl, pests are weeds and/or arthropods and/or plant pathogens. azoxystrobin, trifloxystrobin, fluoxastrobin, picox 6. The control method according to claim 2, wherein the yStrobin, pyraclostrobin, dimoxystrobin, pyriben pests are weeds. carb, metominostrobin, orysastrobin, and N-methyl 7. The control method according to claim 2, wherein the 2-2-(2,5-dimethylphenoxy)methylphenyl-2- group B is the following compounds: methoxy-acetamide (racemic or enantiomer, containing a mixture of R-enantiomer and S-enanti group B: omer (optional ratio)); B-1, neonicotinoid type compounds: clothianidin, thia B-8, metalaxyl type compounds: metalaxyl and metal methoxam, imidacloprid, dinotefuran, nitenpyram, axyl-M; acetamiprid, and thiacloprid; B-9, SDHI compounds: sedaxane, penflufen, carboxin, diamide type compounds: flubendiamide, chlorantranil boscalid, furametpyr, flutolanil, fluxapyroxad, isopy iprole, cyantraniliprole, and compounds represented razam, fluopyram, and thifluzamide: by the formula (I): B-10, other fungicidal compounds: tolclophos-methyl, thiram, Captan, carbendazim, thiophanate-methyl, mancozeb, thiabendazole, isotianil, triazoxide, (RS)- (I) Br 2-methoxy-N-methyl-2-O-(2,5-xylyloxy)-o-tolyl acetamide, fludioxonil, ethaboxam, 3-chloro-5-phe nyl-6-methyl-4-(2,6-difluorophenyl)pyridazine, N 3-cyano-5-phenyl-6-methyl-4-(2,6-difluorophenyl) o 4 / B r N C l: pyridazine, and N-(1,1,3-trimethylindan-4-yl)-1-me thyl-3-difluoromethylpyrazole-4-carboxylic acid NH amide (racemic or enantiomer, containing a mixture N of R-enantiomer and S-enantiomer (optional ratio)); and B-11, plant growth inhibitors: ethephon, chlormeduat O chloride, mepicquat-chloride, and 4-oxo-4-(2-phenyl C.HN ethyl)aminobutyric acid. 8. The control method according to claim 2, wherein the crop is soybean, peanut, common bean, pea, corn, cotton, wheat, rice, Sunflower, potato, Sugar cane, or vegetables. " 9. The control method according to claim 3, wherein the crop is soybean, peanut, common bean, pea, corn, cotton, B-2, carbamate type compounds: aldicarb, oxamyl, wheat, rice, Sunflower, potato, Sugar cane, or vegetables. thiodicarb, carbofuran, carbosulfan, and dimethoate; 10. The control method according to claim 7, wherein the B-3, organic phosphorous type compounds: fenami crop is soybean, peanut, common bean, pea, corn, cotton, phos, imicyafos, fensulfothion, terbufos, fosthiazate, wheat, rice, Sunflower, potato, Sugar cane, or vegetables. phosphocarb, dichlofenthion, isamidofos, isaZophos, 11. The control method according to claim 3, wherein the ethoprophos, cadusafos, chlorpyrifos, heterofos, pests are weeds and/or arthropods and/or plant pathogens. mecarphon, phorate, thionazin, triaZophos, diami 12. The control method according to claim 4, wherein the dafos, fosthietan, and phosphamidon; pests are weeds and/or arthropods and/or plant pathogens. B-4, biological nematicidal compounds: Harpin Protein, 13. The control method according to claim 7, wherein the Pasteuria nishizawae, Pasteuria penetrans, Myroth pests are weeds and/or arthropods and/or plant pathogens. ecium verrucaria, Burholderia cepacia, Bacillus chi 14. The control method according to claim 8, wherein the tonosporus, Paecilomyces lilacinus, Bacillus amy pests are weeds and/or arthropods and/or plant pathogens. loliquefaciens, Bacillus firmus, Bacillus subtillis, 15. The control method according to claim 9, wherein the Bacillus pumulis, Trichoderma harzianum, Hirsutella pests are weeds and/or arthropods and/or plant pathogens. US 2014/0200140 A1 Jul. 17, 2014 27

16. The control method according to claim 10, wherein the pests are weeds and/or arthropods and/or plant pathogens. 17. The control method according to claim 3, wherein the pests are weeds. 18. The control method according to claim 4, wherein the pests are weeds. 19. The control method according to claim 7, wherein the pests are weeds. 20. The control method according to claim 8, wherein the pests are weeds.