TW201002203A - Novel imidazole derivatives - Google Patents

Abstract

The present invention relates to novel imidazole derivatives of formula I as active ingredients which have microbiocidal activity, in particular fungicidal activity: wherein R1 is halogen, C1-C4alkyl or C1-C4haloalkyl; R2 is an optionally substituted aryl; R3 is halogen or OR7; R4 and R5 are, independently of each other, hydrogen, halogen or OR7; R6 is halogen or C1-C4alkyl; and R7 is hydrogen, C1-C6alkyl, C3-C7cycloalkyl, C3-C10cycloalkylalkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C7cycloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C8dialkylamjnoalkyl, C4-C10 cycloalkylaminoalkyl or C4-C10 heterocyclylalkyl; or an argochemically usable salt form thereof; provided that when R3 is halogen, at least one of R4 or R5 is OR7; or when R3 is OR7, at least one of R4 or R5 is OR7 or halogen.

Description

201002203 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a novel imida derivative which is an active ingredient which has a microbicidal activity, and a surviving activity, particularly a fungicidal activity. The present invention relates to the novel active ingredient of the present invention as a novel heterocyclic derivative for the preparation of intermediates of such active ingredients, the preparation of such new inter-substrate, and the agrochemical composition comprising at least one novel active ingredient. , .V 匕, etc., and the preparation of 5 'and the active knowledge or composition in agricultural or garden crops, cut plants, harvested eater, use of infection. Quan Jia is true [prior art] J. "Contents of the Invention" The present invention relates to a compound of the formula:

(wherein \ is halogen, CVC4 alkyl or Cl_c4 haloalkyl; R is an optionally substituted aryl; R is sulphin or ruthenium R7; ruthenium and R5 are each independently hydrogen, halogen or ruthenium R7; 201002203 R6 Is self- or Cl_C4 alkyl; and R7 is hydrogen 'CVC6 alkyl, c Γ CC ^ · Ρ A r 7 alkyl, C3-C10 cycloalkylalkyl, phenyl, C2-C6 dilute, C2_c alkynyl , c2-c6 haloacetylene, r 3 % alkenyl, C2_C| 6 ® alkynyl 'C2_C6 alkoxy group, C4'-I-aminoamino group 汔 Ganqu 1, soil and C4-Ci 〇 heterocyclic Alkyl group; a salt form available on the sputum; the limiting condition is that when R3 is i, R4 哎 R5 士 E, ^ p3 . at least one of 7 times R is OR7; or widely: when '~ At least - in the case of (four) or a pheromone. The aryl group in the 疋 meaning includes an aromatic hydrocarbon ring, such as phenyl, naphthyl, anthracenyl, non-yl and phenyl. Among them, a stupid group is preferred. Although the 'alkyl, alkenyl and alkynyl moieties may be in a straight or branched form' and the alkenyl moiety, in the formula 5, may be (E)- or (z>configuration.", , vinyl, allyl and propargyl, alkenyl and block moieties The combination may comprise one or more double bonds and/or ginseng bonds. It is to be understood that the propylidene alkyllnyl dilute group (dkyUnyWkenyi) is included in these terms. Among the above ambiguities, C2_c6 alkoxyalkyl groups For example, the total number of anaerobic atoms of two alkyl groups: knives is between "one carbon atom. By way of example, the above ambiguity is also suitable for C3_C8 dialkylaminoalkyl or C4-C1G heterocyclic group. The fused ring, carbocyclic ring, heterocyclic ring and aryl hydrazine mentioned above or below, to be substituted, which means that it may have _ or a plurality of the same or different substituents. In general, there will be no more than three substituents at the same time. Examples of substituents are _  ' 烧, _ alkyl, cycloalkyl, cyclohexyl, dilute 6 201002203, haloalkenyl 'Cycloalkenyl, alkynyl' haloalkynyl, alkyloxy, dentyloxy, cycloalkoxy 'alkenyloxy, dentyloxy, alkynyloxy, alkenyloxy' Substrate sulfur's sulphur-based sulphur, cycloalkyl sulphide, alkenyl sulphide, alkynyl sulphur, alkyl carbonyl 'haloalkyl carbonyl 'cycloalkylcarbonyl 'alkenylcarbonyl, alkynyl carbonyl Alkoxyalkyl, cyano, nitro, hydroxy, thiol, amine, alkylamino, dimeric amine. Typical examples of substituted aryl groups as desired include 2-fluorophenyl ' 3-fluorophenyl' 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-phenylphenyl, 3-bromophenyl, 4-bromophenyl, m-tolyl, p- Tolyl, 3-trifluoromethylphenyl ' 4-trifluoromethylphenyl, 3-methoxyphenyl, 'methoxyphenyl, 3-difluoromethoxyphenyl, 4-trifluoromethyl Oxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 2,4-difluorophenyl, 2,5-di-propylphenyl, 2,6-difluorophenyl, 3,4_ Difluorophenyl ' 2,4-dichlorophenyl ' 2,5-dichlorophenyl, 2,6-dichlorophenyl, -dichlorophenyl, 3,4-dimethylphenyl, 3, 4-dimethoxyphenyl, 2-chloro-4-ylfluorophenyl, 2-lacto-5-fluorophenyl, 2-chloro-6-fluorophenyl, 3-ox-4-fluorophenyl, 3 - gas-6-fluorobenyl, 3-ox-4-methylphenyl] 3_chloro-4-yloxyphenyl, 4-chloro-2-fluorophenyl, 4-ox-3-fluorobenzene Base, 4_chloro-3-ylphenyl, 4_gas_3_methoxyphenyl, 3-fluoro-4-methoxyphenyl, 3·fluoro-4-methylphenyl, 4_ Fluorine_3_methoxybenzene , fluoro-3-methylphenyl ' 3 -methoxy · 4 - methylphenyl, methoxymethoxy 3 - methylphenyl, 2,6-fluoro-4-methylphenyl, 2 , 6-difluoro_4_trifluorodecylphenyl, 2,6-difluoro-4-decyloxyphenyl, 2,6-difluoro-4-pyreneoxyphenyl, 2,6_ Difluoro-4-cyanophenyl, 2,4,6-trifluorophenyl 2,5,6-trifluorophenyl. Among the above definitions, the system is fluorine, gas, bromine or iodine. . The alkyl group, by itself or as part of another substituent, will depend on the number of carbon atoms mentioned, for example, fluorenyl, ethyl, propyl, butyl, pentyl, 201002203 hexyl and its isomers, For example, isobutyl, isopentyl or tertiary-drawing. The base 'secondary-butyl, third stage. The dentate group may contain - or a plurality of phases such as c-Ci2, CCi3, c CH3CF2, CF3CF2 or Ca3Cci2. 3 cp3CH2, cyclohexyl group depending on the number of carbon atoms per se or part of other substituents, see for example the groups mentioned. The % propyl, cyclobutyl, cyclopentyl or cyclohexyl group is determined by itself or by the number of carbon atoms of other substituents, for example, depending on the group to be supported, , propylidene, butyl hydrazine | soil, pentene small group, pentylene _3_ group, pentylene. π 'Methyl block group in itself or as he * carbon number..., for example, as mentioned, di-block, di-propionyl, propanyl-, propan-2-yl, -butyne-2_ Base '丨-methyl-2-butynyl, hexynyl fluorenyl-2-butynyl. The presence of a decynyl 1-yl or i-ethyl character - or a plurality of possible asymmetric carbon atoms means that the dioxin = optical isomerism' indicates enantiomeric or diastereomeric due to the existence of Aliphatic C=C double bond, a few: can: raw cis-trans (8) cleavage isomerism. Atropisomers may occur due to the limitation =^. It is intended to include all such possible equivalents and mixtures thereof. The invention is intended to include all such, "b" isomeric forms of the compounds of formula 1 as well as mixtures thereof. In each case, the formula of the present invention! The compound is in the form of a free form 201002203 or a salt form that can be used in agrochemicals. In a first embodiment, the compound of the formula I of the present invention has R1 which is a halogen or a CVC3 alkyl group. In a first embodiment, the compound of the formula I of the present invention has R2 which is a stupid group which is optionally substituted. In a second embodiment, the compound of formula I of the invention has R3 which is fluorine, gas, desert or OR7. In a fourth specific embodiment, the compound of formula I of the present invention has R4 and R5 independently of each other a chloro ‘halo' fluoro, bromo or hydrazine R7. In a fifth embodiment, the compound of formula I of the invention has R6 which is chloro, fluoro, bromo or CVC3 alkyl. In a sixth embodiment, the compound of formula I of the present invention has R7 which is hydrogen, alkyl, c3-c6 cycloalkyl, C3_C9 cycloalkylalkyl, Ci_C5 haloalkyl, c2-c5 alkenyl, c2-c5 halo Alkenyl, c3_c6 cycloalkenyl, c2_c5 alkynyl, ynkynyl, c2-c5 alkoxyalkyl, c3_c7 dialkylaminoalkyl, C4_C9 cycloalkylaminoalkyl or C4-C9 heterocyclyl base. Preferred subgroups of the compounds of formula I according to the invention are those wherein R1 is a gas 'fluoro or Ci-Cz alkyl; R is 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 'chlorophenyl, 3-bromophenyl, 4-bromophenyl, m-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-cyanophenyl, 4-cyanobenzene Base, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3-chloro-4-ylfluorophenyl, cardiochlorin-3-phenylphenyl, 3-fluoro-4-yloxy , 2-fluorophenyl, 2-phenylphenyl, 2-bromophenyl, 2-methoxyphenyl, o-tolyl or 4-chloro-2-fluorophenyl; 9 201002203 R is gas 'fluorine or 〇r*7 ; R and R5 are each independently hydrogen, sulphur, fluorine or OR7; R6 is chloro or methyl; and r7 is nitrogen 'Cl-C3 alkyl, C3-C6 cycloalkylalkyl, C2-C5 Alkenyl group, c2-c4 alkynyl group, c2-c4 alkoxyalkyl group, c3_C8 dialkylaminoalkyl group, c4_c8 bad alkylamino group or (: 4-c8 heterocyclylalkyl group. The present invention A more preferred subgroup of the compound of formula 1 is that t R1 is a gas, a mercapto group or an ethyl group; R2 is a 4-chlorophenyl group; R3 is fluorine or OR7; R4 is fluorine or OR7; R5 is hydrogen or fluorine; R6 is Chlorine; and R is methyl, ethyl, propargyl, 丨_ Pyrrolidinylethyl, dimethylaminopropyl or CrC5 allenyl. Preferred individual compounds are: 2,4-dichloro-1_(4.chloro-phenyl)_5_(2,6_2 Fluorine_4_methoxy-phenyl)-1 Η-ϋ米. Sit, 4-gas-5-(2,6-difluoro-4-decyloxy-phenyl)_1-(4_曱 oxygen Benzyl-phenylmethyl-1 Η-味σ, 4 gas 1-(4-Ga-phenyl)_5_(2,6-difluoro_4_decyloxy-phenyl)_2-methyl-1 Η -Mimi, soil 2,4·dichloro-1-(4-chloro-phenyl)_5_(2,4_difluorojmethoxy-stupyl)-1 Η -σ米1^坐, 201002203 4 -mur-1-(4- gas-benyl)-5-(4-ethoxy-2,6-diox-phenyl)· 2 -methyl-1 Η -. 米σ坐, 4- Gas-1-(4- gas-benyl)-5-(2,6-di-rhos-4-propoxy-phenyl)-2-indolyl-1 Η-味σ坐, 4 - gas-1 -(4- gas-phenyl)-5-[2,6-diox-4-(2-methoxy-ethoxy)-phenyl]-2-methyl-1H-imidazole, 4-gas -1-(4-Ga-phenyl)-5-(2,6-dioxa-4-propan-2-oxooxy-phenyl)-2-indolyl-1H-imidazole, 4-air- 5 - (2,6-dioxa-4-decyloxy-phenyl)-2-methyl-1-p-tolyl-1 Η - miso sitting, 4-gas- 5-(2,6-difluoro -4-decyloxy-phenyl)-1-(4-oxime -Phenyl)-2_methyl-1H-imidazole, 4-gas-5-(2,6-dioxa-4-methoxy-phenyl)-1-(4-ethylidyl-phenyl) -2-methyl-1H-imidazole, 4-air-5-(2,4-dioxa-6-methoxy-phenyl)-1-(4-ethylidyl-phenyl)-2_methyl -1H-imidazole, 4-chloro-1-(4- gas-phenyl)-5-(2,6-dioxa-4-(di-indolyl-1-yl-ethoxy)-phenyl )-2-mercapto-1H-imidazole, 4- gas-1-(4- gas-phenyl)-5-(2,4-dioxa-6-decyloxy-phenyl)-2·indenyl -1 Η -味σ, 4 - gas-1-(4- gas-phenyl)-5-(2,6-di-gas-4-propan-1,2-di-oxy-phenyl)- 2-methyl-1H-imidazole, 4-air-1-(4- gas-phenyl)-5-(2-ethoxy-4,6-di-phenyl)-2-methyl-1H -imidazole, 11 201002203 difluoro-styl)-1-(4-ethynyl-phenyl)_2_ 4 -gas-5-(2-ethyllacyl-4,6-methyl-1 Η-m σ sitting . EXAMPLES Compounds of formula 1.1 wherein 112 and R7 are as defined for the compound of formula J and R1 is a CrC4 alkyl group can be derived from a compound of the formula (wherein R2 is as defined) and R1 is Ci-C: 4 alkyl) and reagent Na〇R7 reagent (wherein R7 is defined as a compound I).

A compound of the formula L2 (wherein R 2 , R 3 , R 4 and R 5 are as defined for the oxime compound and R 1 is a qc:4 alkyl or Ci_Q haloalkyl group) can be obtained from a compound of the formula (wherein R ' R ' R and R 5 ) A compound of formula j is defined and R1 is alkyl or C^-C4 haloalkyl) is reacted with N-chlorosuccinimide or molecular gas.

A compound of the formula (wherein R 2 ' R 3 ' R 4 and R 5 are as defined in the formula and R 1 is a CrC 4 alkyl group) may be derived from a compound of the IV in the presence of a transition metal catalyst (wherein R 2 , R 3 ' R 4 and R5 is defined as a compound of formula 1) and 1 (RiAl reagent (wherein Ri is a C1-C4 alkyl group, preferably a methyl group). ' 12 201002203

Compounds of formula m wherein r 2 , R 3 , r 4 and r 5 are as defined for the compound of formula i and R is a cvc 4 alkyl or Ci—C 4 halo group are alternatively derived from a strong base such as lithium diisopropylamide, followed by Test (10) Reagent 牟 is a base and a pimple, preferably ":) a compound of formula V (wherein R2'~ and deuteration: conversion of the substance. π σ)

】formula! a compound (the towel R2, R3, R4 and r5 are defined as a U compound)

And 2 R6 is a element, preferably chlorine or a compound which can be obtained from a compound of formula V (wherein R2, R3, R4 and R5 macro A and R is a compound of formula 1) and at least 2 罝N-chlorosuccinimide, N_bromon amber sputum or molecular bromine reaction.

RJ

NCS or NBS or C] 2 or

RJ

Definition of the conversion of the compound of formula I, 舆Ν 琥 醯 13 13 imine 13 201002203

NBS

Compounds of formula VI and VII wherein r2 and R7 are as defined in formula: compounds can be derived from the reaction of a compound of formula vm (wherein + R2 is defined as a compound of formula I) with a reagent of formula NaOR7 wherein R7 is as defined for the compound of formula I.

NaOR7

+

A compound of formula V (wherein R 2 ' R 3 , R 4 and R 5 are as defined for the compound of formula I which may be derived from a compound of formula IX (wherein R 2 , R 3 , R 4 and R 5 are as defined for the compound of formula) and tolsulfonyl decyl isocyanide in the base For example, anhydrous potassium carbonate is reacted under the 'as described in Journal of Medicinal Chemistry 2003, 46, 346.

TosMIC test R5 (v)

H a compound of formula IX (wherein R 2 , R 3 , R 4 and R 5 are as defined for the formula I) may be derived from an aldehyde of the compound of formula X (wherein R 3 , R 4 and R 5 are as defined as a compound of formula I) and an amine of formula XI (wherein R 2 is as defined Reaction of compound I)

Journal of Medicinal Chemistry 2003, 46, 3463.

14 201002203 It is surprising that the new compound of formula i has been found to have very beneficial biological activities for practical purposes with only tropic activity to protect plants against diseases caused by fungi as well as bacteria and viruses. . Formula 1 is administered as an active ingredient to the agricultural sector and related uses to control plant pests or inanimate materials to control spoilage microorganisms or organisms that are potentially harmful to the human body. There are several people who report this novel. The uniqueness of this novel compound is that it has excellent activity at low application rates, and it is well tolerated to plants and safe for the environment. The compound has very useful therapeutic, prophylactic and systemic properties and is useful for protecting a variety of useful plants. formula! Compounds can be used to inhibit or destroy harmful substances that occur on plants or plant organs (such as fruits, leaves, stems, snails, or roots) that occur in different crops of useful plants, while The plant that grows later is resistant to, for example, phytopathogenic microorganisms. It is also possible to use a compound of the formula I as a dressing for the treatment of plant propagation material such as seeds (such as fruits, sorghum or granules) or plant cuttings (for example rice) for protection against fungal infections. The plant pathogens in the soil are really awkward. The propagation material can be applied to the cypress 1 team. The cultivar is treated with a composition containing the compound of the formula ί. The seed can be applied, for example, to be sown. The active ingredient of the present invention can also be applied to the granules (coated) by immersing the seeds in a liquid 5 week formulation or coating them as a solid formulation. The combination is applied to the planting site, for example in planting propagation material (4)... applied to the seed furrow during sowing. The present invention is a propagation material. The method of ten + and the plants treated thereby The compound according to the invention was originally used to control the fungus in the relevant area, for example in the protection of technical materials, including food storage or hygiene management. The related technology produces the following. The present invention protects the vine inanimate material from fungi attack such as wood, wallpaper and paint. The compound of the formula 1 is, for example, a plant pathogenic fungus effective against the following classes: * The compound is, for example, effective against the following plant pathogenic fungi: Uungi imperfeeti (for example, Alternaria spp. (4) spp) ) ' # ^ gm (Basidiomycetes)^] ^ R ^ g ^ {Corticium SPP) 'Cornerium genus (Qing), Rhizoctonia (heart (10) SPP) Melon genus (Γ; 2α犹(四)5 -), Rhizoctonia solani, genus Phytophthora (the price of the heart of the family), genus Puccirtia spp ' 魇 岁 〈 〈 pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha pha 5 zhong), 腥Small genus (Π/ZWa spp), AscomyCetes (such as the genus of Helminthosporium (☆ 绍 · · α), wheat powdery mildew (5 / prespp), powdery mildew (heart less to ~), fork green early sacs C (C Podosphaera spp), hook silk, shell _ 餍 ((Jncinula spp), nucleus genus (Afowz / zma _? outside), sclerotium shoulder (Heart/wzWa), Lelebuga (Colletotrichum spp., Late rot (Glomerella SPP;, Fwarz'wm spp, Gibberella (GAZ) ea//a spp), Snow mold Spp), Phaeosphaeria spp, Mycosphaerella spp., Cercospora spp., S. cerevisiae spp., Rhynchosporium spp., Amylovora [MagnapoRthe spp), Heeumannomyces spp, 16 201002203

Ocw/Zwacw/aj, bells and stalks (and), grape stalks (5οί〇; σίί·ηί·α spp), and sinensis (〇〇mycetes) (eg Phytophthora s ), pythium spp, uniaxial genus CP! asmopara spp, genus Per0n0Sp0ra Spp., pseudo-downy mildew (PieWin (four) sunny spp), genus Panicillium (5remz) .a Ink)). The outstanding activity against powdery mildew (for example, Erysiphe necator) and leaf spot (for example, the genus Glomus) has been observed. In addition, the novel compounds of the formula are effective against phytopathogenic bacteria and pathogens ( For example, Pseudomonas (SPA), Pseud〇m〇nas SPP·, Erwinia my 1 〇vora, and grass mosaic virus (T〇bacc〇m〇) Saic virus)) In the scope of the present invention, useful plants that are generally protected include the following two species: cereals (wheat 'barley, rye, oats, rice, corn, high wood and related species) · beet (edible beets) And forage beet); pear fruit, stone fruit and soft fruit (apple 'pear' plum, peach, almond 'cherry, strawberry, raspberry and black j) 'and plants (ugly, lentils, peas, soybeans); oily plants (Rapeseed, : End 1 H '撖视' to hollyhock, coconut, kenaf oil plant, cocoa bean, # "生)'Squash plant (pumpkin, cucumber, melon); fiber plant (cotton, linen, hemp) Jute); citrus fruit (willow, lemon, Grapefruit, orange); vegetable 蒌 not 'Vancho' asparagus 'cabbage' carrot, onion, tomato, horse 钤 ,,: pepper) '彳早 (Avocado, eucalyptus, camphor) or such as tobacco, stone fruit, coffee Plants such as sorghum, pepper, vine, hops, bananas and natural rubber, as well as horticultural plants. Useful plants and/or target crops according to the invention include conventional and genetically enhanced or engineered species, such as insect-resistant (eg, Bt. and VIP varieties) and anti-disease agents (eg, R〇undUpRea (eg Rb) Jy® and LibertyLink® are trademarks of glyph〇sate and glufosinate maize varieties and nematode resistant varieties. For example, suitable genetically enhanced or engineered crop varieties include Stoneville 5599BR Cotton and Stoneville 4892BR cotton varieties. It should be understood that "useful plants" and or "target crops, the term also includes herbicides or herbicides that are bromnezonitrile (br〇m〇xynil) due to traditional methods of reproduction or genetic engineering. Categories (eg HPPD inhibitors, ALS inhibitors (eg primisulfuron, trifluoropropionin (trif) and trifl〇XySulfuron), EPSPS (5_ enol) -Pyrovyl-pyreate _3_phosphate synthase inhibitor, Gs (glutamine-synthetase) inhibitor or PPO (pro-porphyrinogen-oxidase) tolerance Sexually useful An example of a crop that is resistant to imidazolinones (such as imazamox) by conventional propagation methods (mutation techniques) is Ciarefieid 8 (Canola). Genetically engineered. Examples of crops that are resistant to herbicide or herbicide classes include commercially available anti-Glyphosate and giuf〇sinate corns under the trademarks R〇imdupReady8, HerciUex8 and UbertyLink8. Variety. It should be understood that the term “useful plant” and/or “target crop” also includes, by using, a toxin that can synthesize — or a plurality of selective actions — a bacterium that does not know, for example, a bacterium to produce bacteria, especially The useful DNA of the group DNA technology of those of the genus Neurospora), it should be understood that useful plants, 'and / or, target crops, the term of course also includes borrowing 18 201002203 by using capable of synthesis selective Recombinant DNA technology for effective anti-pathogenic substances (such as, for example, so-called "pathogenic-associated proteins" (PRPs, see eg ΕΡ-Α-0 392 225)) Useful plants for transformation. Examples of such anti-pathogenic substances and transgenic substances capable of synthesizing these anti-pathogenic substances are known, for example, from ΕΡ-Α-0 392 225, WO 95/3381 8 and EP-AO 353 191. Those skilled in the art are known to produce such transgenic plants' and are described, for example, in the above publication. As used herein, the term 'where' is the place where the plant is grown, the place where the plant seed of the plant is propagated, or the plant seed of the plant is placed in the soil. An example of such a location is the site of crop plant growth. It will be understood that the term "plant propagation material" means the reproductive organs of plants, such as seeds, which can be used for the proliferation of the latter, as well as plant materials such as cuttings or blocks, such as potatoes. Mention may be made, for example, of seeds (in strict cases), roots, fruits, tubers, bulbs, rhizomes and plant organs. The test may refer to germinating plants and young plants that are to be transplanted after germination or emergence from the soil. These young plants can be protected by general or sickle treatment before being transplanted. Preferably, 'the plant propagation material is understood to mean that the phantom 1 compound is used in an unmodified form or preferably with an adjuvant used in the formulation technique. In this regard, such It can be easily prepared by conventional, 、, § emulsified! 0 Pan, + #... Liquid, can be applied to paste, can be directly sprayed or diluted to dissolve two liquids, dilute emulsion 'wet powder' It can dissolve powders, dusts, granules, and encapsulates in, for example, polymeric materials. The composition type, application side 19 201002203 method such as spray, atomization, dusting, scattering, and the environment in which it is laid, according to the desired agent, such as stabilizer, 枋烟步3 has auxiliary, anti-I bubble Agent, viscosity modifier, binder red hang machine and fertilizer, micro-technics | # Μ ~ j Θ Θ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ - The carrier and adjuvant can be solid or liquid and the substance is used, for example, 夭妒7 s ^ 戈 is used in formulating agents, tackifiers, 擗葙 擗葙 人 人 人 、 、 、 、 、 、 、 、 、 Binder or fertilizer. These WO 97/33890. The temple carrier is described, for example, in the form of a composition, and is applied simultaneously or sequentially with other s objects, a main crop & field or a plant to be treated. The & compound can be, for example, a fertilizer or micronutrient donor or other formulation that can grow (4). They may also be selected from the group consisting of herbicides, 戋非#w曰, ν Κ Μ * 曰 曰 α Α 非 非 non-selective weeding # and heart, fungicides, bactericidal nematodes, agents or several Mixtures of such formulations, if desired, may be combined with a body, a surfactant, or a reinforced adjuvant that is conventionally used in formulating techniques. The compounds of the formula I are generally used in the form of fungicidal compositions for control or protection against phytopathogenic microorganisms, which comprise as active ingredient I--a compound of the formula I which is in a free form or agrochemically A useful salt form, and at least one of the above adjuvants. ^ The fungicidal composition for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of the formula or at least one preferred individual compound as described above, which is in the form of a free form or Agrochemically useful salt forms, as well as at least one of the above-mentioned adjuvants, which may be combined with other fungicides, and in some cases, have an unexpected synergistic 20 201002203 activity. The best ingredients for the mixable ingredients are: azole, such as azaconazole, BAY 14120, bitertanol ' > bromuconazole, Cyproconazole ), difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole 'flutriafol ), hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, mycolobutanil > pefurazoate ), penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, simeconazole 'tebuconazole, four Tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, oral carbinole, such as ridicule. Ancymidol, fenarimol, nuarimol; 2-amino-based cleavage class [eg bupirimate, dimethirimol, erimo (ethirimol); morphines such as: dodemorph, fenpropidine, fenpr〇pimorph, spiroxamine, tridemorph; Stupid amines are called, such as Cypr〇dinil, mepanipyrim, pyrimethanil; 21 201002203 Debbie, such as fenpiclonil, (fludioxonil); stupid amides such as benaxyl, furalaxyl 'metaiaXyi', R-enda, bite amide (〇furace) (oxadixyl); Ben imi σ sit, such as benomyl, carbendazim 'debacarb, fuberidazole, thiabendazole; Amines, such as chlozolinate, dichlozolinate, iprodione, myclozoline 'procymidone, vinclozoline; carboxy-branched amines such as boscalid, carboxin, fenfuram, flutolanil, extinction Mepronil '〇 Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Car Imino (iminoctadine); s tr ob i lur in es, such as azoxystrobin, dimoxystrobin, enestroburin ' fluoro π bacterium vinegar ( Fluoxastrobin), kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin. Picoxystrobin, pyraclostrobin; dithiocarbamate, such as ferbam, zinc | mancozeb 'maneb,' is not bad (metiram) , 曱 锌 乃 prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop prop Captafol' capata, dichlofluanid, fluoromides, folpet, tolyfluanid; copper-compounds such as Bordeaux (Bordeaux) mixture, copper hydroxide, mouse copper oxide 'copper sulfate' cuprous oxide, mancopper (manCOpper); stone xiaoji discretion--derivatives such as dinocap, nitrothal-isopropyl Organic-dish-derivatives, such as edifenphos, iprobenphos 'iSOpr〇thi〇lane, phosdiphen, pyrazophos, dextrosone (tolclofos-methyl); a three-degree sitting that is conventionally prepared and can be prepared by WO 98/46607 . a bite derivative such as 5-chloro-7-(4-mercapto-piperidin-1yl)-6-(2,4,6-trifluoro-phenyl)-[1,2,4]triazole [l,5-a]pyrimidine (formula;

r.H

A chitosan derivative such as 3-difluoroindolyl "-mercapto-1H-pyrazole-4-carboxylic acid (9-isopropyl-1), which is known from WO 04/035589 and WO 06/37632, 2,3,4_tetrahydro-1,4-methylene (methano)-naphthalen-5-yl)-nonanimide (formula U · 1); or 23 201002203

Base_1H_° is more than sal-4-carboxyguanamine (compound F-13). Is a benzamide derivative which is customary and can be prepared by the method described in WO 2004/016088, for example Nb 2_[3_chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2- Trifluoromethylbenzamide, also known as flupirtamine

Various other types' such as acibenz〇iar _S-methyl, anilazine 'benthiavalicarb, blasticidin-S, chinomethionate ), chloroneb, tetrachloroisobenzene (chl〇r〇thai〇nil), cyflufenamid, cym〇xan(1), diphenylquinone (dichi〇ne) , diclomezine, dici〇ran, dietofencab's dimeth〇morph, flium 〇rph, 24 201002203 nitrile sulphur Dithianon), ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, fentin Ferimzone 'fluazinam, flusulfamide, fenhexamid, fosetyl-aluminum, hymexazol, iprovalicarb, Cyazofarnid, kasugamycin 'methasulfocarb, metrafenone' Nicobifen, pencycuron, phthalide 'p〇iy0xins', probenazole, propanocarb, pyroquilon , quinoxyfen, quintozene, sulphur, tiadinil, triaz〇xide, tricyclic saliva, triforine Validarnycin, zoxamide and gamma phosphate. Another aspect of the invention relates to the use of a composition comprising at least one compound of formula I or a compound comprising at least one compound mixed as described above for other fungi Use of a mixture of fungi for controlling or preventing the infestation of plants, harvesting of food crops or inanimate materials by phytopathogenic microorganisms, preferably fungal organisms. Another aspect of the invention relates to the control or prevention of crop plants, Harvesting of food crops or inanimate materials by plant pathogens, microorganisms "has a potential for humans: sexually harmful (especially fungal organisms) infections, including the administration of the active ingredient Compound I is in plants, plant organs or their locus, seeds or any part of inanimate materials. ... 25 201002203 Control or prevention means that crop plants or inanimate materials are reduced by plant pathogens or spoilage microorganisms or potentially harmful to humans (especially fungal organisms) until they are proven to be improved to some extent. A preferred method of controlling or preventing crops from being susceptible to phytopathogenic microorganisms, preferably fungal organisms, comprises administering a compound of formula 1 or an agrochemical composition comprising at least one of the compounds to the foliage of the plant. The frequency of administration and the ratio of administration will depend on the risk of being infected by the corresponding source. However, the compound of formula t may also pass through the root system (four) plants (systemic action), the system 11 of which is to wet the plant area by liquid: the formulation or to incorporate the compound into the plant area in solid form: for example into the soil 'for example with particles ( Soil cast) form. If the crop is a water grain, such particles can be applied to the flooded field. formula! The compound can also be applied to the seed (coating) by coating the liquid composition of the fungicide into the & block or as a solid formulation. Formulations are also included! The compound 'and, if desired, a solid or liquid adjuvant, prepared according to conventional means' typically by intimately mixing and/or grinding the compound with an extender (eg, a solvent or a covalent surfactant (surfactant)) < 1 and as needed... Farming: The compound will usually contain the compound of formula 1 from ο.1 to 99 weight 4 and preferably from 〇.! to 95% by weight, ^% by weight and preferably from 99.8 to 5 by weight. ; = adjuvant is from 99. 9 to "% by weight and preferably from U to 25% and the agent is from 0 to, advantageously the application rate is usually from 5 § to the activity of the knives per hectare (d), preferably from iOgi lkg active ingredient / hectare to _§ active ingredient / hectare. When used as a seed sizing agent: 26 201002203 The agent uses 1 〇mg to 1 g of active substance for the mother kilogram seed. Good products are used to make commercial products into concentrates, and consumers usually use diluted formulations. Plant growth regulators (PGRs) are generally any substance or mixture of substances intended to accelerate or retard growth or maturation; or to alter plants or Development of its products. Plant growth regulators (PG) Rs) affects plant growth and variability. More specifically, various plant growth regulators (pGRs) can, for example, reduce plant height, stimulate seed germination, reduce flowering, darken leaves, alter plant growth rates and improve The present invention also relates to a composition for improving plants, the pot comprising the novel taste of the present invention. A sitting derivative, a type which is generally and hereinafter referred to as "Kang". Possible (4) Advantages 4: Improved plants: 1 · Germination, crop yield, protein content, more development, seed speed, improved nitrogen use efficiency, improved water use efficiency, improved oil 3 summer and / or quality, improved consumption. 卞 厌 厌 厌 厌 、 、 改良 改良 、 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌 厌, anti-light, anti-ultraviolet/water, anti-cold), reduce ethylene (reduced production and / or inhibit the connection of strong points, increase plant height, larger leaves, comparison: degree) less dead seeds ,More Productivity is divided, compared with::: material, need to be cooked, less plant vvefse) (#HM early opening, early grain into () (inverted), increased shoot growth, improved planting 27 201002203 vitality and early Budding. ^ ^ ^ ^ ^ ^? #j ^ Favorable nature, its special tendency 'more planting in the field. For improved plant growth and planting; ^ μ with m good = two force: the leaves More biomass, better roots, reforms ==: substances, more food production, more raw materials, good harvest quality (fatty acid content, # & sales, such as improved Size), modified square = oil, oil, etc.), more locks, better compound extraction), by 'column such as long use of life, the seed of the seed (planted in the season of seed production), or Any other advantages that are familiar to the invention. The object of the present invention is to solve the problem of the present invention. The object of the present invention is to provide an active ingredient for the protection of plants as outlined above, which is invented, in particular, the individual compounds described above. Preferably, the mixture is a mixture of efficacy and a method for improving the health of the plant, and the compound and the mixture are applied to the plant or its locus. Second: the effect of the compound exceeds the conventional fungicidal action. According to the invention;;; the compound 'in particular, the individual (four) preferred compounds described above, exhibit plant health. Objects for plant health include the improvement of various plants, which are not associated with the treasure system. . In a further aspect, the invention relates to a composition comprising at least one formula pharmaceutically acceptable salt as defined in the above 28 201002203, a double diluent on the other hand, or preferably individual Compound way. Or a preferred individual compound and/or at least one to > a pharmaceutically acceptable carrier and/or at least one of the inventions. The invention also relates to a compound of formula 1 as defined above, or a pharmaceutically acceptable compound thereof The salt is used as a medicament. In yet another aspect, the invention also relates to a compound of the formula ί or a preferred individual compound as defined above, which is a salt of the first acceptable salt for the treatment of cancer. In still another aspect, the invention also relates to the use of a compound of formula (4), or a pharmaceutically acceptable salt thereof, as defined above, for the manufacture of a medicament for the treatment of cancer. In a particular aspect, the invention is also directed to a method of treating a diseased cancer in need thereof, which comprises administering to the patient a compound of formula I or a preferred individual compound as hereinbefore defined as being effective in the treatment of the cancer. The present invention further provides a fungicidal or pharmaceutical composition comprising such a mouthwash and/or an agriculturally or pharmaceutically acceptable salt thereof and a suitable carrier. Suitable pharmaceutically acceptable carriers are as described below. According to the formula of the present invention! The imidazole compound, particularly preferably the iridoid compound of formula I as described above, and/or a pharmaceutically acceptable salt thereof, is suitable for use in the treatment, inhibition or control of growth and/or reproduction of tumor cells and diseases associated therewith. . According to the above, the compound is suitable for the treatment of warm-blood vertebrae in cancer, such as mammals and birds, especially humans, but includes other breastfeeding 29 201002203

Animals' special g|| Β Λτ LO (bovine, sheep, mountain and domestic animals, such as dogs, cats, pigs, anti-dancing cranes, guinea fowl, etc.) 'horses and birds, such as chicken, turkey, duck, preferably The compound, particularly as described above, is a cancer that is used in the following organs: or itchy: / or a pharmaceutically acceptable salt thereof is a suitable prostate, a skin ♦... treatment of the disease: lung 'breast' intestine, stomach, Ovary, ^), kidney, bladder, mouth, throat, esophagus, capsules, pancreas, liver and brain. In addition to the present invention, +· T, according to the present invention: the di-salt compound and/or its medicinal connection can be "medically achievable" including: a suitable carrier for the need of oligo. Human i-hearts, the table is not in the scope of sound medical judgment, allergic reactions, „Geqi two-door tissue contact without excessive toxicity, compound within the thorn rate,: Γ complications, in a reasonable benefit/hazard ratio Dosage and/or dosage form. The palpitations, carriers, and excipients are used in combination with pharmaceutical formulations, as described below. /, the dry method is the individual administration type and the "medical receiving material, the composition or the Portuguese sister, the carrier" means the pharmaceutically acceptable excipient, the solvent or the encapsulating material, such as a liquid or Solid filler, thinner' or transport target to other - write 2, and self-g or a part of the body containing other components of the body phase / or body - part of the body. Each - containing the band must be available Examples of acceptable and non-injurious to the patient include: 一些 Some materials that are pharmaceutically acceptable carriers 30 201002203 Sugars such as lactose, starch, such as corn cellulose and its derivatives and Cellulose acetate; Glucose and sucrose; Powder and horse mash potato starch; 'For example, decyl fluorenyl cellulose sodium ethyl fiber powdery yellow gum; Malt; gelatin; talc; safflower seed oil, sesame oil, type Agents such as cocoa butter and suppository wax oils, such as coconut oil, cottonseed oil, corn oil and soybean oil; an alcohol such as propylene glycol; mannitol and polyethylene glycol; polyterpene alcohol, such as glycerin, mountain Sugar alcohol esters, such as ethyl oleate and ethyl laurate; Lingzhi; buffers, such as oxidized water and gas oxidation; alginic acid; pyrogen-free water; isotonic saline; Ringer's solution Ethanol; phosphate buffer solution, and other non-toxic compatible substances used in pharmaceutical formulations. Formula compounds according to the invention, especially those as described above (active compounds) Can be administered in a conventional manner, 乂 31 201002203 for example in oral, intravenous, intramuscular or subcutaneous manner. For oral administration, the activated humanized sigma can be mixed with, for example, an inert diluent or with an edible carrier; The pots can be used to remove the hard shells or soft gelatin capsules, which can be compressed into tablets or they can be mixed directly with the food/feed. The active compound can be combined with the occupational type 丨丨 巧 巧 i μ this σ and can not be digested tablets, mouth containing agents, containing tablets, 筚 、, earn Lu County, Λ y, 憋 液, liquid , syrup and the like. Such preparations should contain at least 1% active compound. The composition of the preparation may of course vary. It is usually included from 2 to 60% by weight of the active compound, based on the total weight of the preparation (dosage unit) of the copolymer. Yang According to the present invention, the imidazole compound, particularly the individual mice as described above, are preferred. The sitting compound 'includes from 1 〇 to ι mg of active compound per oral dosage unit. The σ lozenge, lozenge, pill, and the like may further comprise the following ingredients: a binding agent such as an amine gum, gum arabic, corn starch or gelatin, a formulation d such as dicalcium phosphate, a disintegrant such as corn starch, Potato starch, seaweed I and analogs, glidants such as magnesium stearate, sweeteners such as sucrose, lactose or saccharin, and/or flavoring agents such as mint, vanilla and the like. The capsule may further comprise a liquid carrier. Other substances of the modified dosage form unit nature can also be used. For example, lozenges, pills and capsules can be coated with shellac, sugar or mixtures thereof. In addition to the active compound, the syrup or emulsion may also include a sugar (or other sweetener), a methyl- or propyl-hydroxy hydroxyformate as a preservative, a dosageing agent and/or a flavoring agent. 32 201002203 The ingredients of the active compound preparation may of course be pharmaceutically pure and non-toxic in the amounts used. Further, the active compound can be formulated into a preparation having a controlled release active compound, such as a delayed release preparation. The active compound can also be administered parenterally or intraperitoneally. A solution or suspension of the active compound or a salt thereof can be prepared in water using a suitable wetting agent such as hydroxypropylcellulose. It is also possible to prepare a dispersion in oil using glycerin, liquid polyethylene glycol and mixtures thereof. The practitioner&apos;s such preparations may further comprise a preservative to prevent the growth of microorganisms. Preparations intended for injection include sterile aqueous solutions and dispersions and for the preparation of disinfecting solutions and dispersion disinfecting powders. The preparation must be sufficiently liquid for injection. It must be stable under the conditions of manufacture and storage and must be protected against microbial contamination. The carrier can be a solvent or dispersion medium such as water &apos;ethanol, polyol (e.g., glycerol@-alcohol or liquid polyethylene glycol), mixtures thereof and/or vegetable oils. Pharmaceutical compositions of the present invention suitable for parenteral administration include incorporation of aqueous or non-aqueous solutions, dispersions or emulsifications in accordance with the present invention in combination with or in combination with a plurality of pharmaceutically acceptable disinfectants. a liquid, or a sterilizing powder, which may be reconstituted into a sterile injectable solution or a liquid prior to use: it may contain antioxidants, buffers, bactericides, and penetration of the blood of the formulation of the intended recipient. Solute, or suspension or thickener. ' 33 201002203 Examples of pharmaceutical compositions which can be used in the present invention include water, ethanol, 彡% β aqueous carrier, such as glycerol, C- and the like, and a suitable propylene-ol 1 Ethylene glycol '' ί M yk rn 4, from, for example, eucalyptus oil and Zhuang shot organic esters, such as ethyl oleate. Covering materials such as lecithin plus /, can be maintained by using the size of the coating and by using an interface-active sword. 2. Adjuvants such as preservatives, Zhan, Temple. The 4 composition can also function by including various political figures. Prevention of micro-biochemical vinegar, chlorobutanol...antifungal agents such as p-hydroxyl phenol sorbic acid and the like are allowed to include 4 n # desire to include iso-permeability, ^ 伃 to ensure. It is also possible. In addition, i w and the like in combination with aluminum to achieve an inhalable absorption of the form of injectable medical yttrium, such as early stearic acid. The pharmaceutical compositions of the present invention can be administered by any suitable oral, parenteral, monthly, or topical means, including by transdermal or transrectal, which is suitable for each ecchymosis. The pharmaceutical composition is of course administered as a tablet or capsule:;: the formation of a diameter. For example, the pharmaceutical composition is a monthly, an expectorant, by means of, a main and an eye liquid, a soft and local fish, which is administered by inhalation or inhalation; by a lotion or ointment with a preferred plant 4 by a suppository Rectal administration. Partial or non-oral injection is carried out: System: The invention described above is exemplified in more detail. _ ϋ This example is exemplified by 4-gas-1_(4_gas|the-虱-4-methoxy_<虱-yl)-5-(preparative group of 2,6·)·2-曱Base_1H-flavored saliva (Compound No. Lb.006) Benzo)-[1-(2,4,6-trifluoro-phenyl)-(£) methine]-amine 34 201002203 (4-Chloro- Preparation of phenyl)-[l-(2,4,6-trifluoro-phenyl)- meth-(E)- ylidene]-amine) 4-Gas-aniline (20.36g) and 2,4,6-trifluoro - The phenylhydrazine chain (2555 §) is soluble in toluene (780 ml). This mixture was then refluxed for 4 days in a Dean-Stark apparatus. The reaction mixture was evaporated under reduced pressure to give 43.84 g (4.

Gas-phenyl)-[1-(2,4,6-trifluoro-phenyl)-(e) decyl]-amine. Ijj NMR (300Mhz, CDC13) 8.49ppm, 1H, s; 7.28ppm, 2H, d, J = 8.65Hz; 7.08ppm, 2H, d, J=8.6Hz; 6.77ppm, 2H, t, J = 8.7Hz ° b) Preparation of 1-(4- gas-phenyl)-5-(2,4,6-trifluoro-phenyl)_1H-imidine 33.6 g (4- gas-phenyl)-[l-(2 4,6-Trifluoro-phenyl)-(e)-indenyl]-amine was dissolved in 456 ml of hydrazine, hydrazine-dimethyl decylamine and 375 ml of 1,2-dimethoxyethane. 36.49 g of toluenesulfonium methyl isocyanide and 34.44 g of anhydrous potassium carbonate were added, and the resulting reaction mixture was heated at 1 ° C for 1 20 minutes. After cooling, the mixture was filtered and the solvent was evaporated. The obtained solid was adsorbed on Isolute® HM-N and a mixture of heptane/tertiary butyl methyl ether was used as a continuous extract of 3:1 and 2:1 as a continuous extract. Purification by chromatography gave 9 94 g of 1-(4-chloro-phenyl)-5-(2,4,6-trifluoro-phenyl)-lH-m. 1HNMR (300Mhz, CDC13) 7.72ppm, 1H, s; 7.28ppm, 2H, d, J=8.6Hz; 7.22ppm, 1H,s; 7.02ppm, 2H, d, J=8.7Hz; 6.59ppm, 2H, t , J = 7.3 Hz. c) Preparation of 2-bromo-1-(4-chloro-phenyl)-5-(2,4,6-trifluoro-phenyl)-lH-imidazole 2 g of 1-(4-chloro-phenyl A mixture of -5-(2,4,6-trifluoro-phenyl)-1 oxime-imidazole 1.21 g of η-bromosuccinimide and 21 ml of a gas-like mixture was heated for 4 hours to 80 °C. Next, the mixture was cooled to room temperature, and is〇iute® 35 201002203 HM-N was added to the reaction mixture, and the gas was evaporated. This crude mixture was purified by chromatography on a silica gel using a mixture of hexane/ethyl acetate (1. 1 ) to give 1.96 g of bromo- s. -(2,4,6-Difluoro-phenyl)-lH-imidazole. lHNMR (300 Mhz, CDCI3) 7.29 ppm, 2H, d, J = 8.6 Hz; Ί 1 Η, s; 7.05 ppm, 2H, d, J = 8.5 Hz; 6.55 ppm, 2H, t, J = 7.2 Hz. d) Preparation of 1-(4-chloro-phenyl)-2-indenyl-5-(2,4,6-trifluoromethyl)1H imidazole 2-Bromo-1-(4-chloro-phenyl) -5-(2,4,6-Trifluoro-phenyl)-111-imidazole (3.1 g) was dissolved in 162 ml of tetrahydrofuran. To the solution was added 0.13 g of tetrakis(triphenylphosphine)palladium before refluxing the resulting mixture for 1 minute. After that, the oil bath was removed, and a 2 M solution of 12 ml of (trimethyl)aluminum in toluene was added slowly. This reaction mixture was refluxed for 7 hours before being cooled to 〇 °C. 5 ml of decyl alcohol (gas generation) was added dropwise, and Is〇lute® HM-N was added after 5 minutes, and the solvent was removed under reduced pressure. This residue was purified by chromatography on EtOAc: EtOAc (EtOAc:EtOAc) -Methyl-5-(2,4,6-trifluoro-indenyl)-1 Η-mi. 1Η NMR (300Mhz, CDC13) 7.28ppm, 2H, d, J-8.6Hz; 7.13ppm, 1H, s; 7.07ppm, 2H, d, J = 8.5Hz; 6.56ppm, 2H, t, J = 7.4Hz; 2.3 lppm, 3H, s. e) Preparation of 4-gas-1-(4-gas-phenyl)-2-mercapto-5-(2,4,6-trifluoro-phenyl)-1Η-imidazole 1.61 g of b (4- Gas-phenyl)-2-methyl-5-(2,4,6-trifluoro-methyl)-1 Η-m' 0.83 g of N-chloroammonium imine and 32 ml of chloroform mixed 36 201002203 The material is heated for 16 hours to 80 °C. Then, the mixture was cooled to room temperature, and Isolute® ΗM-N was added to the reaction mixture to evaporate chloroform. This crude mixture was purified by chromatography on a mixture of 4·1 of heptane/acetic acid ethyl acetate as a solvent to obtain 1 _01 g of 4-gas-1 as a white solid (4-gas- Phenyl)-2-methyl-: 5-(2,4,6-trifluoro-phenyl)-lH-imidazole. 1HNMR (300Mhz, CDC13) 7.36ppm, 2H, d, J=8.6Hz; 7.07ppm, 2H, d, J=8.5Hz; 6.63ppm, 2H, t, J=7.3Hz; 2.30ppm, 3H, s. f) 4-Ace-1-(4-chloro-phenyl)-5-(2,6-difluoro-4-methoxy-phenyl)_2-methyl-1Η-feeding. Sitting (Compound No. I. b. 0 0 6) 0.4 g of 4-chloro-1-(4-chloro-phenyl)_2-fluorenyl-5-(2,4,6-trifluoro-phenyl)-1Η A mixture of imidazole, 0.48 ml of sodium decoxide solution (0 l 8 M in methanol) and 5 ml of methanol was stirred at room temperature for 16 hours. This reaction mixture was then poured into ice-cold acidified water. The aqueous solution was extracted twice with ethyl acetate. The combined organic layers were washed with brine then dried over sodium sulfate, filtered and evaporated -5-(2,6-Difluoro-4-methoxy-styl)_2-methyl-1H-imidazole (Compound No. Ib006). (H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.7Hz; 7.07ppm, 2H, d, J=8.58Hz; 6.38ppm, 2H, ^ J = 9.06Hz; 3.76ppm, 3H, s; 2.29 ppm, 3H, s. Example 2: This example is exemplified by 2, 驭dichlorochloro-phenyl)-5-(2,4-dienyl-6-fluorenyl-phenyl)_2-fluorenyl Preparation of ^Mazole (Compound No. I.d_005) a) Preparation of 1-(4-chloro-phenyl)-5-(2,4-difluoro-t-methoxy-phenyl)_ih-flavor 37 201002203 0.4克 1-(4-Gas-propenyl)_5_(2,46-trifluoro-phenyl)imidine. Sit, ο&quot; A mixture of pen-sodium methoxide solution (〇·18Μ in methanol) and 5 ml of methanol was mixed for 16 hours. This reaction mixture was then poured into ice-cold acidified water. The aqueous solution was extracted twice with EtOAc. EtOAc (EtOAc)EtOAc. This crude mixture was purified by chromatography on a silica gel using a mixture of 6:4 heptane/ethyl acetate as a solvent to give 〇〇87 g ι_(4_chloro-phenyl)-5-(2,4- Difluoro-6-decyloxy-phenyl)_lH-mipropene. 1HNMR (300Mhz, CDC13) 7.77ppm, 1H, s; 7.31ppm, 2H, d, J=8.7Hz; 7.2ppm, 1H, s; 7.06ppm, 2H,d, J = 8.6Hz; 6.47ppm,1H, dt , J = 2.42 and 8.95 Hz, 6.35 ppm, 1H, td, J = 1.84 and 9.6 Hz; 3.51 ppm, 3H s. b) 2,4-I--1-(4-chloro-phenyl)-5-(2,4-dii-6-nonyloxy-phenyl)-2-methyl-1H-imidazole (compound number Preparation of ldO〇5) 0.087 g of 1-(4-chloro-phenyl)-5-(2,4-difluoro-6-methoxy-phenyl)_ιη·m. A mixture of 0.074 g of sputum-chlorosulphonimine and 1.7 ml of chloroform was heated for 16 hours to 80 °C. Next, the mixture was cooled to room temperature, and Isolute® HM-N was added to the reaction mixture and evaporated to dryness. This crude mixture was purified by chromatography using a 9:1 Gengxu/Ethyl acetate mixture as a solvent; 0.077 g of 2,4-digas-1 - (4_gas- Phenyl)_5_(2,4-difluoro-6-decyloxy-phenyl)-2-mercapto-1H-imidazole (Compound No. Id005).咜NMR (3〇〇Mhz, CDC13) 7 3 8ppm, π, d, J=8.07Hz; 7.12ppm, 2H, d, J = 8.68Hz; 6.47ppm, 1H, dt, J = 2.41 and 9.01Hz; 6.35 Ppm, 1H, td, J = i 84 an(j 4hz; 3.5 1 ppm, 3H, s. 38 201002203 Table 1 below illustrates examples of the compounds of the formula i of the present invention. Table 1: Individuals of the formula I of the present invention Compound Compound No. R1 R2 R6 001 ch3 3-Fluorophenyl C1 002 ch3 4-Fluorophenyl C1 003 ch3 3-Phenylphenyl C1 004 ch3 4-Phenylphenyl ch3 005 Cl 4-Nitrophenyl Cl 006 ch3 4- Phenyl phenyl Cl 007 ch3 3-bromophenyl Cl 008 ch3 4-bromophenyl Cl 009 ch3 m-tolyl Cl 010 ch3 p-nonylphenyl Cl 011 ch3 3-decyloxyphenyl Cl 012 ch3 4-曱Oxyphenylphenyl 013 ch3 3-cyanophenyl Cl 014 ch3 4-cyanophenyl Cl 015 ch3 3,4-difluorophenyl Cl 016 ch3 3,4-diphenylphenyl Cl 017 ch3 3-gas 4- gas phenyl Cl 018 ch3 4-gas-3-gas phenyl Cl 019 ch3 3-fluoro-4-methoxyphenyl Cl 020 ch3 2-fluorophenyl Cl 021 ch3 2-gas phenyl Cl 022 Ch3 2-bromophenyl Cl 023 ch3 2-decyloxyphenyl Cl 024 ch3 o-quinolyl Cl 025 ch3 4-chloro-2-fluorophenyl Cl 026 CH2CH3 4-chlorophenyl Cl 39 201002203 where a) 26 compounds of formula (I.a):

b) 26 compounds of formula (I.b):

Wherein R1, R2 and R6 are defined in Table 1. c) 26 compounds of formula (I.c):

R° 〇, (I.c) wherein R1, R2 and R6 are as defined in Table 1. d) 26 compounds of formula (I.d):

(Ι-d) wherein R1, R2 and R6 are as defined in Table 1. e) 26 compounds of formula (I.e): 40 201002203 cr

f) 26 compounds of formula (I.f):

Wherein R1, R2 and R6 are defined in Table 1. g) 26 compounds of formula (I.g):

(i-g) ru wherein R1, R2 and R6 are defined in Table 1. h) 26 compounds of formula (I.h):

(l-h) wherein R1, R2 and R6 are as defined in Table 1. i) 26 compounds of formula (I.i):

41 201002203 wherein R1, R2 and R6 are defined in Table 1. j) 26 compounds of formula (I.j):

Wherein R1, R2 and R6 are defined in Table 1. k) 26 formula (I.k) compounds··

(I.k) wherein R1, R2 and R6 are as defined in Table 1. 1) 26 compounds of formula (1.1):

w wherein R1, R2 and R6 are defined in Table 1. m) 2 6 compounds of the formula (I _ m):

(l.m) wherein R1, R2 and R6 are as defined in Table 1. η) 26 compounds of formula (I.η): 42 201002203

〇) 26 formulas (Ι·ο) compounds

p) 26 compounds of the formula (Lp):

R

q) 26 compounds of formula (I.q):

〇

Wherein R1, R2 and R6 are defined in Table 1. r) 26 compounds of formula (I_r): 43 201002203

R

s) 26 compounds of formula (I.s):

Wherein R1, R2 and R6 are defined in Table 1. In the full text, the temperature is expressed in degrees Celsius, "mp" means melting point, "NMR" means nuclear magnetic resonance spectrum; and "" means weight percentage unless otherwise specified. The following abbreviations are: mp ^ melting point br = wide s = single peak dd = : double doublet d two doublet · dt = : double triplet t two triplet q = : four peaks m two peaks · Ppm = per cent parts Table 2 shows the compounds of Table 1 The NMR data were selected (unless otherwise stated, the characteristic data of all cases are not listed). 44 201002203 Table 2: NMR data selected for the compounds of Table 1 Compound Description ^-NMR data (ppm/H number/multiplicity) Ia 006 NMR (300Mhz, CDC13) 7.26ppm, 2H, d, J=8.8Hz; 7.07ppm, 1H, t, J=8.5Hz; 6.97ppm, 2H, d, J=8.5Hz; 6.59ppm, 1H, dd, J=2.4 and 8.7 Hz; 6.42 ppm, 1H, dd, J=2.5 and 11.5 Hz; 3.70 ppm, 3H, s; 2.22 ppm, 3H, s. Ib〇〇4 Ή NMR (300Mhz, CDC13) 7.24ppm, 2H , d, J = 8.6 Hz; 6.97 ppm, 2H, d, J = 8.57 Hz; 6.30 ppm, 2H, d, J = 9.11 Hz; 3.69 ppm, 3H, s; 2.22 ppm, 3H, s; 2.06, 3H, s. IbO〇5 *H NMR (300Mhz, CDC13) 7.36ppm, 2H, d, J = 8.63 Hz; 7.12 ppm, 2H, d, J = 8.55 Hz; 6.41 ppm, 2H, d, J = 9.03 Hz; 3.78 ppm, 3H, s. Ib006 NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J = 8.7 Hz; 7.07 ppm, 2H, d, J = 8.58 Hz; 6.38 ppm, 2H, d, J = 9.06 Hz; 3.76 ppm, 3H, s; 2.29 ppm, 3H, s. Ib012 NMR (300Mhz, CDC13 6.98ppm, 2H, d, J=8.9Hz; 6.78ppm, 2H, d, J=8.9Hz; 6.31ppm, 2H, d, J=9.1Hz; 3.73ppm, 3H, s; 3.68ppm, 3H, s 2.19ppm, 3H, s. Id005 NMR (300Mhz, CDC13) 7.38ppm, 2H, d, J=8.07Hz; 7.12ppm, 2H, d, J=8.68Hz; 6.47ppm, 1H, dt, J=2.41 And 9.01Hz; 6.35ppm, 1H, td, J=1.84 and 10.4Hz; 3.51ppm, 3H, s. Ig〇〇6 NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.65Hz; 7.07ppm, 2H, d, J=8.61Hz; 6.36ppm, 2H, d, J=9.17Hz; 3.96ppm, 2H, q, J=6.99Hz; 2.28ppm, 3H, s; 1.39ppm, 3H, t, J=6.98 Hz. Ih006 *Η NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.67Hz; 7.07ppm, 2H, d, J=8.6Hz; 6.49ppm, 2H, d, J=8.81Hz; 4.64ppm , 2H, d, J = 2.44 Hz; 2.57 ppm, 1H, t, J = 2.36 Hz; 2.29 ppm, 3H, s. Ii006 *H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz ; 7.06ppm, 2H, d, J=8.6Hz; 6.42ppm, 2H, d, J=9.03Hz; 4.04ppm, 2H, dd, J=4.54 and 5.98Hz; 3.71ppm, 2H, dd, J=3.34 and 4.65Hz; 3.42ppm, 3H, s; 2.29ppm, 3H, s. Ij006 lU NMR (300Mhz, CDC13 7.34ppm, 2H, d, J=8.6Hz; 7.07ppm, 2H, d, J=8.62Hz; 6.41ppm, 2H, d, J=9.09Hz; 3.99ppm, 2H, t, J=5.61Hz; 2.71 Ppm, 2H, t, J = 5.64 Hz; 2.32 ppm, 6H, s; 2.29 ppm, 3H, s. Ik005 1H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz; 7.05ppm, 2H , d, J = 8.6 Hz; 6.34 ppm, 2H, d, J = 9.12 Hz; 3.89 ppm, 2H, t, J = 6.4 Hz; 2.33 ppm, 2H, t, J = 7.1 Hz; 2.16 ppm, 6H, s ; 1.97ppm, quintet, 2H, J=7Hz. 45 201002203 Compound No. ^-NMR data (ppm/H number/multiplicity) Ik006 1H NMR (300Mhz, CDC13) 7.29ppm, 2H, d, J=8.63Hz; 7.07ppm, 2H, d, J=8.6Hz; 6.39ppm, 2H, d, J=9.14Hz; 3.95ppm, 2H, t, J=6.36Hz; 2.41ppm, 2H, t, J=7.17Hz; 2.28ppm , 3H, s; 2.23ppm, 6H, s; 1.92ppm, quintet, 2H, J=7.04Hz 1.1.006 1H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz; 7.07ppm, 2H, d, J = 8.6 Hz; 6.38 ppm, 2H, d, J = 9.16 Hz; 3.73 ppm, 2H, d, J = 6.97 Hz; 2.28 ppm, 3H, s; 1.25 ppm, 1H, m; 0.65 ppm, 2H, q, J^Sppm, 2H, q, J=4.78Hz. Im006 1H NMR (300Mhz, D6-DMSO) 10.71ppm, 1H, bs; 7.51ppm, 2H, d, J=8.63Hz; 7.26ppm, 2H, d, J=8.6Hz; 6.45ppm, 2H, d, J =9.43 Hz; 2.21 ppm, 3H, s. In006 1H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz; 7.07ppm, 2H, d, J=8.6Hz; 6.40ppm, 2H, d , J = 9.1 Hz; 4.03 ppm, 2H, t, J = 5.84 Hz; 2.87 ppm, 2H, t, J = 5.82 Hz; 2.6 ppm, 4H, m; 2.28 ppm, 3H, s; 1.80 ppm, 4H, m IO006 'H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz; 7.08ppm, 2H, d, J=8.6Hz; 6.34ppm, 2H, d, J=9.31Hz; 4.44ppm, 1H, hept, J=6.4Hz; 2.28ppm, 3H, s; 1.32ppm, 6H, d, J=6.01Hz. Ip006 rH NMR (300Mhz, CDC13) 7.35ppm, 2H, d, J=8.7Hz; 7.07ppm, 2H, d, J=8.6Hz; 6.71ppm, 1H, t, J=5.88Hz; 6.56ppm, 2H, d, J=8.47Hz; 5.48ppm, 2H, d, J=5.92Hz; 2.29ppm , 3H, s. Iq006 'H NMR (300Mhz, CDC13) 7.34ppm, 2H, d, J=8.6Hz; 7.07ppm, 2H, d, J=8.6Hz; 6.39ppm, 2H, d, J=9.12Hz 3.95ppm, 2H, t, J=6.31Hz; 2.47ppm, 10H, m; 2.29ppm, 3H, s; 2.28ppm, 3H, s; 1.93ppm, 2H, quintet, J=7.18Hz. Ie006 rH NMR (300Mhz, CDC13) 7.23ppm, 2H, d, J=8.68Hz; 6.97ppm, 2H, d, J=8.6H z; 6.13ppm, 1H, d, J = 10.8Hz; 6.06ppm, 1H, s; 3.69ppm, 3H, s; 3.52ppm, 3H, s; 2.22ppm, 3H, s. Is006 lH NMR (300Mhz, CDC13 7.2ppm, 2H, d, J=8.7Hz; 6.94ppm, 2H, d, J=8.67Hz; 5.93ppm, 2H, s; 3.71ppm, 3H, s; 3.56ppm, 6H, s; 2.22ppm, 3H , s. Id006 nH NMR (300Mhz, CDC13) 7.25ppm, 2H, d, J=8.7Hz; 6.97ppm, 2H, d, J=8.6Hz; 6.35ppm, 1H, dt, J=2.3, 8.91Hz; 6.26ppm, 1H, dt, J=2, 10.48Hz; 3.56ppm, 3H, s; 2.22ppm, 3H, s. Ib026 ίΗ NMR (300Mhz, CDC13) 7.27ppm, 2H, d, J=8.67Hz; 7.01 Ppm, 2H, d, J = 8.67 Hz; 6.31 ppm, 2H, d, J = 9.08 Hz; 3.69 ppm, 3H, s; 2.49 ppm, 2H, q, J = 7.56 Hz; 1.18 ppm, 3H, t, 7.55 Hz. 46 201002203 The above reaction scheme is defined by the definition of a variable as in the above formula (I) The compound according to the invention can be defined according to the 'in this case, unless otherwise stated. Buckle/tomato/prevention (early blight versus tomato Biological example Annual caries i Altefnaria) The 4-week tomato plant cv. R〇ter Gnom was treated with a formulated test compound in a spray booth. In the application of De-壬, Yanshan (10) "+ &lt; one day, inoculated with tomato plants by spraying the spore suspension on the test plants. At 22. 〇 / ΜΙ (day / night) and 95 / 〇 Inoculated test plants were grown in a greenhouse at relative humidity, and the percentage of leaf area covered by the disease was evaluated (after 5 to 7 days of administration) when an untreated test plant showed an appropriate amount of disease. 200 ppm of this test according to the present invention Compound ja 〇〇6, 丨b 〇〇5, Ib.〇〇6, Ib012, Id006, Ig〇〇65 Ih006, Ii〇〇6, Ik005, Ik006, 1.1.006, In006, I .p_〇〇6 and Iq〇〇6 inhibited at least 80% of fungal infections in this test, and under the same conditions, untreated control plants were infected with phytopathogenic fungi by more than 8%. Botryotinia Fuckeliana K 5 heart;;.../tomato/prevention (effect of gray mold on tomato) 4 weeks old tomato plant cv. R0ter Gnom was treated with the formulated test compound in the spray chamber. Two days after application, by spore The suspension is sprinkled on the test plant and inoculated into the tomato plant. Two days later, the tomato plants were inoculated by spraying the spore suspension on the test plants. The inoculated test plants were grown in a greenhouse at 2 ° C and 95% relative humidity, and the plants tested without the treatment of 47 201002203 appeared. In the case of disease, 'evaluate the percentage of the area covered by the disease (after 5 to 6 days). In this test, 200 ppm of the compound ja 〇〇6, j, I6, Ib012, Id006, according to the present invention, Ig006, Ii006, ΙΛ·005, I k 〇〇6, Lp 〇〇6 In this test, at least 80% of fungal infections were inhibited, while under the same conditions, untreated control plants were infected with phytopathogenic fungi. More than 8 %. Erysiphe ( wec plus r) / grape / prevention (effect of powdery mildew on grapes) 5 weeks old grape seedlings cv treated with formulated test compounds in the spray chamber Gutedel. Inoculated on grape plants by shaking the plants infected with the above-mentioned grape powdery mildew one day after application. Inoculated test plants were grown in a greenhouse at 24/22 ° C (day/night) and 70% relative humidity. When untreated detection When a moderate amount of disease occurs, the percentage of leaf area covered by the disease is evaluated (after 7 to 9 days of administration). In this test, 200 ppm of the compound according to the present invention ja 〇〇6, j upper 〇〇5, Ib-006, Ib012 , Ib026, Id006, Ig〇〇6, Ih006, Ii〇〇6, Gongxiao_, Ik006, 1.1.006, Im006, Ip〇〇6 and 1 bucket 006 are here. In the test, at least 8O〇/〇 fungal infection was inhibited, and under the same conditions, the untreated control group plants were infected by phytopathogenic fungi by more than 8%. Cercospora. Heart d "Cercospora arachidicola") /筅±/treatment was inoculated by spraying a spore suspension on the lower leaf surface of a 3-week-old peanut plant ev Qe〇rge. After culturing for 2 days at 23. (and 1003⁄4 relative humidity), the inoculated plants were treated in a spray chamber with a test compound 48 201002203. Under the plastic cover of 23: (with 100% relative humidity), another day was incubated. Afterwards, the test plants were kept in a greenhouse at 23〇c /2 (rc (day/night) and 7〇% relative humidity. When the untreated test plants showed an appropriate amount of disease, the percentage of the leaf area covered by the disease was assessed. (After 1 to 12 days). In this test, 200 ppm of compounds jb 〇〇 5, jb 〇〇 6, Ib01 2, 1.1.006 and lj 〇〇 6 according to the invention inhibit at least 8 在 in this test. % fungal infection, and under the same conditions, the untreated control group plants were infected by phytopathogenic fungi more than 80%. Mycosphaerella graminicola (Epipuerella graminicola) / eve / wheat / prevention (leaf leaf spot) (Sept〇Ha leaf sp〇t) to small Effect) The 2-week-old wheat plant cv. Riband was treated with the formulated test compound in a spray chamber. One day after application, the spore suspension was sprayed onto the test plants to inoculate the wheat plants. : /2丨t (day/night) and 95% relative humidity after one day of incubation, the test plants were kept in a greenhouse at 22 C /2 1 C and 70% relative humidity. When untreated plants were tested When a moderate amount of disease occurs, the percentage of leaf area covered by the disease is evaluated (after 16 to 19 days). In this test, 200 ppm of compound jb 〇〇5, j according to the present invention, 〇〇6, 1.1.006, Ij 006, Ik005 and In006 inhibited at least 8% fungal infection in this test', and under the same conditions, the untreated control group plants were infected by phytopathogenic fungi more than 8%. Wheat leaves were recorded (10) Mountain/)/Wheat/Prevention (Brown rust (effect on wheat) 49 201002203 Two-week-old wheat plant cv·Arina was treated with a formulated test compound in a spray chamber. One day after application, by spore suspension Spraying on test plants Inoculated on wheat plants. After 2 days of incubation at 2 (TC and 95% relative humidity), the test plants were kept in a greenhouse at 2 (rc/18ec (day/night) and 60% relative humidity. When the untreated test plants showed an appropriate amount of disease, the percentage of the leaf area covered by the disease was evaluated (after 2 to 4 days of administration) * 200 ppm of the compound according to the present invention in this test! a 〇〇6, ! b 〇〇5, Ib006, Ib012, Ig006, Ih006, Ij〇〇6, Il〇〇6, Im〇〇6, Ip006 and Iq〇〇6 inhibit at least 8% fungal infection in this test Under the same conditions, the untreated control group plants were infected by phytopathogenic fungi by more than 80%. Pyrenoph〇ra teres (helminth〇sporium iere) / barley/prevention (anti-barley reticular effect) Treatment of 1 week old barley plant cv in a spray chamber with formulated test compound Regina. Two days after the application, the barley plants were inoculated by spraying the spore suspension on the test plants. The inoculated test plants were grown in a greenhouse at 2% and 95% relative humidity, and the percentage of leaf area covered by the disease was evaluated (after 5 to 7 days of administration) when an untreated test plant showed an appropriate amount of disease. 200 ppm of the compound i.b.006, h 〇()6 1.1.006, I.j.〇〇6, I k 〇〇5, I k 〇〇6, 11〇〇6, j n 〇〇6 and Μ according to the present invention in this test. % In this test, at least 8% of fungal infections were inhibited, while under the same conditions, untreated control plants were infected with phytopathogenic fungi by more than 8%. 50 201002203 [Simple description of the diagram] Benefits [Main component symbol description] None 51

Claims (1)

201002203 VII. Patent application scope: 1. A compound of formula I, Wherein R1 is halogen, CVC4 alkyl or haloalkyl; R2 is optionally substituted aryl; 'R3 is halogen or OR7; R4 and R5 are independently of each other hydrogen, halogen or OR7; R6 is halogen or CkQ alkyl And R7 is hydrogen, CVC6 alkyl, C3-C7 cycloalkyl, C3-C1G cycloalkylalkyl, Ci_C6-alkyl, C2-C6 dilute, C2-C6 halo, C3-C7 'C2-C6 alkynyl, c2-c6 haloalkynyl, c2-c6 alkoxyalkyl, c3-c8 dialkylaminoalkyl, c4-c1()cycloalkylaminoalkyl or C4-C1G a heterocyclic alkyl group; or an agrochemically usable salt form thereof; wherein, when R3 is a halogen, at least one of R4 or R5 is OR7; or when R3 is OR7, at least one of R4 or R5 is OR7 or halogen. 2. A compound according to claim 1 wherein R1 is halogen or CVC3 alkyl. 3. A compound according to claim 1 or 2 wherein R2 is a phenyl group which is optionally substituted. 4. According to the compound of claim 1 or 2, where R3 is 52 201002203 « 敦 ' 气 ' bromine or OR7. The compound according to claim 1 or 2, wherein R4 and R5 are independently of each other hydrogen, chlorine, fluorine, desert or OR7. 6. A compound according to claim 1 or 2, wherein R6 is chloro 'qi' bromine or (VC3 alkyl; and 7. a compound according to claim 1 or 2, wherein R7 is wind 1 ' Cl-C5 Hyun•基' C3-C6 cycloalkyl, C3-C9 cycloalkyl, C-C5 i-burning&gt;-based c2-c5 alkenyl c2_c5 haloalkenyl, c3_c6 cycloalkenyl, c2_c5 fast radical, CVC5 consists of alkynyl 'c2_c5 alkoxyalkyl, c3-c7 dialkylaminoalkylalkyl-C4_C9 cycloalkylaminoalkyl or c4-c9 heterocyclylalkyl. a compound of 2, wherein R is a gas 'fluoro or κ2 alkyl; R is 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 4_ Bromophenyl, m-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 3,4-difluoro Phenyl, 3,4-dichlorophenyl '3- gas' 4-fluorophenyl, 4-ox-3-fluorophenyl, 3-fluoro-4-methoxyphenyl, 2-fluorophenyl, 2-oxophenyl, 2-bromophenyl, 2-methoxyphenyl, o-tolyl or 4-chloro-2-fluorophenyl; R3 is gas, fluorine or OR7; R4 and R5 are independently of each other hydrogen, Chlorine, fluorine or hydrazine R7; R6 is chloro or methyl; and R7 is hydrogen 'C,-C3 alkyl, c3_c6 cycloalkylalkyl, c2_c5 alkenyl, C2-C4 alkynyl' C2-C4 alkoxyalkylene a compound, a c3_c6 dialkylaminoalkyl group, a c4_c8 cycloalkylaminoalkyl group or a C4-C8 heterocyclic group. 53 201002203 9. The compound according to claim 1 or 2, wherein R1 is chlorine, Methyl or ethyl; R2 is 4-chlorophenyl; R3 is fluorine or OR7; R4 is fluorine or OR7; R5 is hydrogen or fluorine; R6 is chlorine; and R7 is fluorenyl, ethyl, propargyl, 1 a pyrrolidinylethyl, dimethylaminopropyl or C3-C5 allenyl group. A compound selected from the group consisting of 2.4-dichloro-1-(4-chloro-phenyl)- 5-(2,6-difluoro-4-methoxy-phenyl)-1Η-imidazole, 4-gas-5-(2,6-difluoro-4-methoxy-phenyl)-1- (4-methoxy-phenyl)-2indolyl-1H-imidazole, 4-chloro-1-(4-chloro-phenyl)-5-(2,6-difluoro-4-decyloxy- Phenyl)-2-mercapto-1 H-flavor a sitting, 2.4-diqi-1-(4-chloro-phenyl)-5-(2,4-difluoro-6-methoxy-phenyl -1Η-imidazole, 4-chloro-1-(4-carb-phenyl)-5-(4-ethoxy-2,6-difluoro-phenyl)-2-mercapto-1 Η - Rice α, 4-chloro-1-(4-chloro-phenyl)-5-(2,6-difluoro-4-propoxy-phenyl)-2-methyl-1 Η - ° m °Sit, 4-chloro-1-(4-chloro-phenyl)-5-[2,6-diox-4-(2-methoxy-ethoxy)-phenyl]-2-methyl -1H-imidazole, 54 201002203 4-Chloro-1-(4-chloro-phenyl)-5-(2,6-difluoro-4-propan-2-freeoxy-phenyl)-2-indenyl -1H-imidazole, 4-chloro-5-(2,6-difluoro-4-methoxy-phenyl)-2-mercapto-1-p-phenylene-1 Η-味σ, 4 - Gas - 5-(2,6-difluoro-4-decyloxy-phenyl)-1-(4-methoxy-phenyl)-2-methyl-1H-imidazole, 4-gas-5- 2,6-disorder-4-methoxy-phenyl)-1-(4-ethylidyl-phenyl)-2_methyl-1H-imidazole, 4-chloro-5-(2,4·2 Fluor-6-methoxy-phenyl)-1-(4-ethynyl-phenyl)-2·indolyl-1H-imidazole, 4-gas-1-(4-chloro-phenyl)-5- (2,6-Difluoro-4-(2-indolyl-1-yl-ethoxyphenyl)-2-mercapto-1H-imidazole, 4-air-1-(4-niole-phenyl) -5-(2,4-dioxa-6-methoxy-phenyl)-2-methyl-1 Η-. Rice σ sitting, 4-gas-1-(4-gas-phenyl)-5-(2,6-dioxa-4-propan-1,2-di-dioxy-phenyl)_2-methyl- 1H_imidazole, 4-air-1-(4- gas-phenyl)-5-(2-ethoxy-4,6·di-n-phenyl)-2-methyl-1Η-flavor, 4 - gas - 5-(2-ethyllactyl-4,6-di-I-phenyl)-1-(4.ethylhexyl-phenyl)-2_indolyl-1H-imidazole. 11. A method of preparing a compound of formula 1.1, 55 201002203 wherein R 2 and R 7 are as defined in the formula I, and R 1 is CVC 4 alkyl or Ci-q haloalkyl, the process comprising bringing a compound of formula II, Wherein R2 is as defined in the formula I, and R1 is CVC4 alkyl or CVC4 haloalkyl, reacted with a reagent of the formula NaOR7 wherein R7 is as defined in formula I. 12. A method of preparing a compound of formula 1.2, Wherein R 2 , R 3 , R 4 and R 5 are as defined in the formula I, and R 1 is C/C 4 alkyl or (^-(: 4 haloalkyl), the process comprising making a compound of formula III, Wherein R2, R3, R4 and R5 are as defined for the compound of formula I, and R1 is CVC4 alkyl or CVC4 haloalkyl, reacted with N-chlorosuccinimide or molecular chlorine. 13. A method of preparing a compound of formula III, 56 201002203 1 Wherein R 2 , R 3 , R 4 and R 5 are as defined in the formula I, and Ri is (VC 4 alkyl, the process comprising making a compound of the formula Iv, Wherein R 2 , R 3 , R 4 and R 5 are as defined in the formula I, and are reacted with a formula (R'Al reagent (wherein Ri is a Cl-C 4 alkyl group) in the presence of a transition metal catalyst. A fungicidal composition against a phytopathogenic microorganism, which comprises, as an active ingredient, at least one compound according to any one of claims 1 to 10, which is in a free form or a salt which can be used in agrochemicals. Form, and at least one adjuvant. 1 5. The composition according to claim 14 of the patent application, comprising at least one additional fungicidal active compound, preferably selected from the group consisting of: saliva, feeding Carbine (carbin〇les), 2_amine-based biting morpholines, aniline, pyrrole, phenyl decylamine, benzimidazoles, di-ornimines, slow-acting amines Classes of 'strobilurines, dithiocarbamates, N-dentylmethylthiotetrahydro-phthalimidoimides, copper-chemical substances, nitrophenols, Organic _phosphorus-derivatives, sorghum, triazole pyrimidines, chitosan or styrene. Or the prevention of plants, 16. The use of a compound according to any of items i to 1 of the scope of the patent application to harvest food crops, seeds or inanimate materials for use in the infection of pathogens. 2010 2: Control or prevention Crop plants, harvested and eaten (4) (iv) The application of mn i 1 , which is a spoilage microorganism or a potential harm to humans, as an active ingredient, according to the patent application, in the plant, plant part or its location, seed or inanimate matter Any part. 1 8. According to the patent application van 筮 7 7 Μ Μ 丄 丄 mu mu mu mu mu 第 ' ' ' ' 其中 其中 其中 其中 其中 其中 其中 其中 其中 其中 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 The compound of the first and third patents of the patent range '5, β and/or at least one of its pharmaceutically acceptable ^ to 〉, a pharmaceutically acceptable carrier and/or a diluent. A compound or a pharmaceutically acceptable salt thereof according to any one of the claims 1 to 1G of the patent application, which is a medicinal and/or at least one medicinally acceptable one. A compound according to any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, for use in the treatment of cancer. 22. According to the scope of the patent application, the first to the omega- A drug that is a combination of any of the 10 items. &lt; Its use in the preparation of a cancer for the treatment of cancer A-species in need of treatment of cancer. The individual is effectively treated, Luzhi County ΑΑ 1 匕 匕 phase ^ And the compound according to any one of the patent applications of the U 10th item.