CN1188764A

CN1188764A - Pyrazole compounds used as agricultrial germicide and insecticide and acaricide and its preparation

Info

Publication number: CN1188764A
Application number: CN 97105050
Authority: CN
Inventors: 刘长令; 刘晓楠; 张弘; 雷新; 刘武成; 张立新; 李斌; 满瀛; 胡性之; 李宗成
Original assignee: Shenyang Research Institute of Chemical Industry Co Ltd
Current assignee: Shenyang Research Institute of Chemical Industry Co Ltd
Priority date: 1997-01-23
Filing date: 1997-01-23
Publication date: 1998-07-29
Anticipated expiration: 2017-01-23
Also published as: CN1072211C

Abstract

The present invention relates to a kind of pyrazoline-type compounds and their preparation, which can be used as agricultural miticide, disinfactant and insecticide as they have associated activities.

Description

Pyrazole compounds and preparations thereof as agricultural fungicides and insecticides and acaricides

本发明涉及新的吡唑类化合物、它们的制备方法以及它们作为农药的应用。The present invention relates to novel pyrazole compounds, their preparation and their use as pesticides.

众所周知，许多含吡唑的化合物具有良好的杀虫杀螨活性。如CN86-108691A报道的如下通式的化合物，在此通式中，R₃为H，C₁～C₄烷基或苯基。此类化合物并不是十全十美，仍需研制新的更好的化合物。

本发明涉及如下通式的新的吡唑类化合物作为农用杀菌剂及杀虫杀螨剂

通式I通式(I)中：It is well known that many pyrazole-containing compounds have good insecticidal and acaricidal activities. As reported in CN86-108691A, the compound of the following general formula, in this general formula, R ₃ is H, C ₁ -C ₄ alkyl or phenyl. Such compounds are not perfect, and new and better compounds still need to be developed.

The present invention relates to the novel pyrazole compounds of the following general formula as agricultural fungicides and insecticides and acaricides

General formula I In general formula (I):

R1，R2为H、卤素、C1～C6烷基、C2～C16烯基、炔基、C3～C6环烷基、C1～C6卤代烷基(C2～C6烯基、C2～C6炔基、C3～C6环烷基)，R1，R2可相同或不同。R1, R2 are H, halogen, C1~C6 alkyl, C2~C16 alkenyl, alkynyl, C3~C6 cycloalkyl, C1~C6 haloalkyl (C2~C6 alkenyl, C2~C6 alkynyl, C3~ C6 cycloalkyl), R1, R2 can be the same or different.

R3为氢、卤素、(卤代)C1～C6烷基、(卤代)C2～C6烯基、(卤代)C2～C6炔基、(卤代)C3～C6环烷基、(卤代)C3～C6环烯基，NR5R6[R5为H，卤代)C1～C6烷基，(卤代)C2～C6烯基、(卤代)C2～C6炔基、(卤代)C3～C6环烷基、(卤代)C3～C6环烯基，R6为R5、(取代)芳基、(取代)杂芳基]、(取代)芳基、(取代)杂芳基。R3 is hydrogen, halogen, (halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2～C6 alkynyl, (halogenated) C3～C6 cycloalkyl, (halogenated) )C3～C6 cycloalkenyl, NR5R6[R5 is H, halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2～C6 alkynyl, (halogenated) C3～C6 Cycloalkyl, (halogenated) C3-C6 cycloalkenyl, R6 is R5, (substituted) aryl, (substituted) heteroaryl], (substituted) aryl, (substituted) heteroaryl.

R4为H、C1～C6烷基、卤素、NR5R7[R7为R5、(取代)芳基、(取代)杂芳基]，CN、(取代)苄基、(取代)芳基、(取代)杂芳基、CO-Z1～R8(Z1为键，O，S，NR5R7；R8为H、(卤代)C1～C6烷基、(卤代)C2～C6烯基、(卤代)C2～C6炔基、(卤代)C3～C6环烷基、(卤代)C3～C6环烯基、(取代)芳基、CH2CO-Z1-R7、CH2CN)、PX1(X2R9)X3R10(X1为O，S；X2，X3为O，S，NH；X1，X2，X3可相同或不同；R9，R10为R8，可相同或不同。R4 is H, C1～C6 alkyl, halogen, NR5R7 [R7 is R5, (substituted) aryl, (substituted) heteroaryl], CN, (substituted) benzyl, (substituted) aryl, (substituted) hetero Aryl, CO-Z1～R8 (Z1 is a bond, O, S, NR5R7; R8 is H, (halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2～C6 Alkynyl, (halogenated) C3～C6 cycloalkyl, (halogenated) C3～C6 cycloalkenyl, (substituted) aryl, CH2CO-Z1-R7, CH2CN), PX1(X2R9)X3R10 (X1 is O, S; X2, X3 are O, S, NH; X1, X2, X3 can be the same or different; R9, R10 are R8, which can be the same or different.

X为键，O，S，NR11(R11为H，R8)。X is a bond, O, S, NR11 (R11 is H, R8).

Y为键，O，NR11，CH2。Y is a bond, O, NR11, CH2.

Z为键，H，CO、S(O)n，CHR12[R12为H，(卤代)C1～C6烷基]。Z is a bond, H, CO, S(O)n, CHR12 [R12 is H, (halogenated) C1-C6 alkyl].

R4和Z还可组成环[饱和的或不饱和的任意取代的五圆或六圆环：咪唑、二氢咪唑、三唑、恶(二)唑、恶唑啉(酮)、噻(二)唑、噻唑啉(酮)、嘧啶、二(四)氢嘧啶(啉酮)、(三氢)恶嗪]。R4 and Z can also form a ring [saturated or unsaturated arbitrarily substituted five or six rings: imidazole, dihydroimidazole, triazole, oxazoline (two) azole, oxazoline (ketone), thiazoline (two) oxazole, thiazoline (ketone), pyrimidine, di(tetra)hydropyrimidine (ketone), (trihydro)oxazine].

Q为H、R3、CH2R3、OR3、CO-Z1-R8、OR7、S(O)nR8、CN、PX1(X2R9)X3R10。Q is H, R3, CH2R3, OR3, CO-Z1-R8, OR7, S(O)nR8, CN, PX1(X2R9)X3R10.

当Q为(取代)芳基时，可为(取代)苯基，取代基可为H，C1～C6烷基、C2～C6烯基、C2～C6炔基、C3～C6环烷基、C3～C6环烯基，C1～C6卤代烷基(C2～C6烯基、C2～C6炔基、C3～C6环烷基、C3～C6环烯基)，OR8，CO-Z1-R8，CH2CO-Z1-R8，CH2CN，NR5R8，S(O)nR8，SiR12R13R14[R12～R14为(卤代)C1～C6烷基，可相同或不同]，COSiR12R13R14，OSiR12R13R14，CR12R13CN，CR12R13CC13，SF5，When Q is (substituted) aryl, it can be (substituted) phenyl, and the substituent can be H, C1~C6 alkyl, C2~C6 alkenyl, C2~C6 alkynyl, C3~C6 cycloalkyl, C3 ～C6 cycloalkenyl, C1～C6 haloalkyl (C2～C6 alkenyl, C2～C6 alkynyl, C3～C6 cycloalkyl, C3～C6 cycloalkenyl), OR8, CO-Z1-R8, CH2CO-Z1 -R8, CH2CN, NR5R8, S(O)nR8, SiR12R13R14 [R12~R14 are (halogenated) C1~C6 alkyl groups, the same or different], COSiR12R13R14, OSiR12R13R14, CR12R13CN, CR12R13CC13, SF5,

m＝0～1； n＝0～2。m=0~1; n=0~2.

在本申请中所用的名词“烷基，烯基，炔基”分别是指支链或直链的烷基，烯基，炔基。“卤素”指氟，氯，溴，碘。“卤代烷基(烯基、炔基、环烷基、环烯基)”指被1个或更多个相同或不同的卤原子取代了的烷基(烯基、炔基、环烷基、环烯基)，(取代)芳基，(取代)杂芳基，取代基可为H，C1～C6烷基、烯基、炔基、环烷基、环烯基，C1～C6卤代(烷基、烯基、炔基、环烷基)环烯基，OR7，CO-Z1-R7，NR5R6，S(O)nR7，SiR12R13R14，COSiR12R13R14，OSiR12R13R14，CR15R16CN，CR15R16CC13，SF5、取代基可在芳基和杂芳基的任意位置；芳基，杂芳基指苯基，萘基，呋喃基，噻吩基，吡啶基，吡唑基，咪唑基，咪唑并吡啶，三唑基，三唑并嘧啶，噻(二)唑基，恶(二)唑基，嘧啶基，The terms "alkyl, alkenyl and alkynyl" used in this application refer to branched or straight chain alkyl, alkenyl and alkynyl, respectively. "Halogen" means fluorine, chlorine, bromine, iodine. "Haloalkyl (alkenyl, alkynyl, cycloalkyl, cycloalkenyl)" means an alkyl (alkenyl, alkynyl, cycloalkyl, cycloalkenyl) substituted by one or more identical or different halogen atoms Alkenyl), (substituted) aryl, (substituted) heteroaryl, substituents can be H, C1～C6 alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, C1～C6 halogenated (alk Base, alkenyl, alkynyl, cycloalkyl) cycloalkenyl, OR7, CO-Z1-R7, NR5R6, S(O)nR7, SiR12R13R14, COSiR12R13R14, OSiR12R13R14, CR15R16CN, CR15R16CC13, SF5, substituents can be in aryl and any position of heteroaryl; aryl, heteroaryl refers to phenyl, naphthyl, furyl, thienyl, pyridyl, pyrazolyl, imidazolyl, imidazopyridine, triazolyl, triazolopyrimidine, Thia(two)azolyl, oxa(two)azolyl, pyrimidinyl,

在通式(I)中，R1通常在吡唑的1位，其他基团可分别在吡唑的3，4，5任意位置，In the general formula (I), R1 is usually at the 1 position of pyrazole, and other groups can be at any position of 3, 4, and 5 of pyrazole respectively,

当R4＝OH时，通式(I)可为其互变异构体：

When R4=OH, general formula (I) can be its tautomer:

通式(I)所表示的化合物对于属于同翅目的昆虫如飞虱、粉虱、叶蝉和蚜虫等以及螨类有特效。此外，对于蔬菜、果树和观赏植物等的病害如霜霉病，白粉病，锈病等具有优良的杀菌作用。The compound represented by the general formula (I) has specific effects on insects belonging to the order Homoptera, such as planthoppers, whiteflies, leafhoppers, aphids, etc., and mites. In addition, it has excellent bactericidal effect on diseases of vegetables, fruit trees and ornamental plants, such as downy mildew, powdery mildew and rust.

通式(I)所示的化合物的合成方法如下。The synthesis method of the compound represented by general formula (I) is as follows.

方法A(当Y＝O时)： Method A (when Y=O):

其中R1，R2，R3，R4，Z和Qm与前面定义相同。Hal表示卤原子如Cl或Br。wherein R1, R2, R3, R4, Z and Qm are the same as defined above. Hal represents a halogen atom such as Cl or Br.

在上述反应中所用的溶剂可以是任何不妨碍该反应的溶剂，它们包括卤代烃类(如二氯甲烷，二氯乙烷，氯仿，四氯化碳、四氯乙烷)，醇类(如丁醇、异丙醇，乙醇、乙二醇)，醚类(如四氢呋喃、二氧六环、乙二醇双(甲)乙醚、乙醚、异丙醚)，酮类(如丙酮、丁酮、环己酮)，芳香烃类(如苯、甲苯、氯苯、硝基苯)，酯类(如乙酸乙醇、乙酸甲酯)，腈类(如乙腈)，二甲亚砜、二甲基甲酰胺和水。这些溶剂可单独使用也可混合使用。当混合使用这些溶剂进行量相反应时，可使用相转移催化剂，例如四丁基溴化铵、氯化三乙基苯甲基铵等。The solvent used in the above reaction can be any solvent that does not hinder the reaction, and they include halogenated hydrocarbons (such as methylene dichloride, ethylene dichloride, chloroform, carbon tetrachloride, tetrachloroethane), alcohols ( Such as butanol, isopropanol, ethanol, ethylene glycol), ethers (such as tetrahydrofuran, dioxane, ethylene glycol bis (methyl) ether, diethyl ether, isopropyl ether), ketones (such as acetone, butanone , cyclohexanone), aromatic hydrocarbons (such as benzene, toluene, chlorobenzene, nitrobenzene), esters (such as ethanol acetate, methyl acetate), nitriles (such as acetonitrile), dimethyl sulfoxide, dimethyl formamide and water. These solvents may be used alone or in combination. When these solvents are used in combination for a quantitative phase reaction, a phase transfer catalyst such as tetrabutylammonium bromide, triethylbenzylammonium chloride, or the like can be used.

在上述反应中所用的碱为无机碱或有机碱。无机碱包括如碱或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙、碳酸氢钠等，碱或碱土金属的氢氧化物如氢氧化钠、氢氧化钾、氢氧化钙和碱金属的氢化物如氢化锂、氢化钠等。The base used in the above reaction is an inorganic base or an organic base. Inorganic bases include carbonates of alkali or alkaline earth metals such as sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, etc., hydroxides of alkali or alkaline earth metals such as sodium hydroxide, potassium hydroxide, calcium hydroxide and alkali metal Hydrides such as lithium hydride, sodium hydride, etc.

有机碱类包括三乙胺，吡啶、4-二甲氨基吡啶等。碱的用量，使用与通式(II)表示的化合物等摩尔或超量。Organic bases include triethylamine, pyridine, 4-dimethylaminopyridine and the like. The amount of the base used is equimolar or excess to that of the compound represented by the general formula (II).

在反应中，如使用固碱，出现固液两相时，可使用例如聚乙二醇400、600、900等相转移催化剂。In the reaction, if a solid base is used, when a solid-liquid two-phase occurs, a phase transfer catalyst such as polyethylene glycol 400, 600, 900, etc. can be used.

化合物(II)可用下列方法制得：

Compound (II) can be prepared by the following methods:

在上述反应中，所用的溶剂通常是醇类(如甲醇、乙醇，异丙醇等)和水，温度通常是室温至回流，时间是30分钟至6小时。In the above reaction, the solvent used is usually alcohols (such as methanol, ethanol, isopropanol, etc.) and water, the temperature is usually room temperature to reflux, and the time is 30 minutes to 6 hours.

化合物(IV)可由已知方法合成。Compound (IV) can be synthesized by a known method.

化合物(II)也可用下列方法制得： Compound (II) can also be prepared by the following method:

在上述反应中，(V)与氯化剂如氯气，氯化砜，NCS等于惰性溶剂如乙酸乙酯，二氯甲烷、二氯乙烷，二氧六环中在-15～70℃下反应30分钟至6小时得到(VI)；(VI)与HR4在碱(如无机碱包括碱或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙、碳酸氢钠等，碱或碱土金属的氢氧化物如氢氧化钠、氢氧化钾、氢氧化钙和碱金属的氢化物如氢化锂、氢化钠等；有机碱类包括三乙胺，吡啶、4-二甲氨基吡啶等)和惰性溶剂存在下反应制得(II)。In the above reaction, (V) reacts with a chlorinating agent such as chlorine, sulfone chloride, NCS or an inert solvent such as ethyl acetate, dichloromethane, dichloroethane, and dioxane at -15 to 70°C Obtain (VI) in 30 minutes to 6 hours; (VI) and HR4 in alkali (such as inorganic base comprises the carbonate of alkali or alkaline earth metal such as sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate etc., alkali or alkaline earth metal Hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide and alkali metal hydrides such as lithium hydride, sodium hydride, etc.; organic bases include triethylamine, pyridine, 4-dimethylaminopyridine, etc.) and inert solvents Reaction in the presence of (II).

方法B(Y＝NR11，Z＝CR12时)在上述反应中，所用的溶剂通常是醇类(如甲醇、乙醇，异丙醇等)和水，温度通常是室温至回流，时间是30分钟至10小时。Method B (when Y=NR11, Z=CR12) In the above reaction, the solvent used is usually alcohols (such as methanol, ethanol, isopropanol, etc.) and water, the temperature is usually room temperature to reflux, and the time is 30 minutes to 10 hours.

方法C(当R4＝NR5R7时)：

Method C (when R4=NR5R7):

在上述反应中，(IA)同烷基化试剂、酰化试剂等在碱(如无机碱包括碱或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙、碳酸氢钠等，碱或碱土金属的氢氧化物如氢氧化钠。氢氧化钾、氢氧化钙和碱金属的氢化物如氢化锂、氢化钠等；有机碱类包括三乙胺，吡啶、4-二甲氨基吡啶等)和惰性溶剂存在下，于-15℃～150℃反应30分钟至24小时制得(IB)。In the above-mentioned reaction, (IA) is mixed with alkylating reagent, acylating reagent etc. in alkali (as inorganic base comprises the carbonate of alkali or alkaline earth metal such as sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate etc., alkali or Alkaline earth metal hydroxides such as sodium hydroxide. Potassium hydroxide, calcium hydroxide and alkali metal hydrides such as lithium hydride, sodium hydride, etc.; organic bases include triethylamine, pyridine, 4-dimethylaminopyridine, etc.) In the presence of an inert solvent, react at -15°C to 150°C for 30 minutes to 24 hours to prepare (IB).

方法D(当R4＝NR5R7时)：

Method D (when R4=NR5R7):

中间体(VIII)与NR5R6在碱(如无机碱包括碱或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙、碳酸氢钠等，碱或碱土金属的氢氧化物如氢氧化钠、氢氧化钾、氢氧化钙和碱金属的氢化物如氢化锂、氢化钠等；有机碱类包括三乙胺，吡啶、4-二甲氨基吡啶等)和惰性溶剂存在下反应制得(II)，温度是-20～150℃，时间是30分钟至24小时。Intermediate (VIII) and NR5R6 in alkali (such as inorganic bases include carbonates of alkali or alkaline earth metals such as sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, etc., hydroxides of alkali or alkaline earth metals such as sodium hydroxide, Potassium hydroxide, calcium hydroxide and alkali metal hydrides such as lithium hydride, sodium hydride, etc.; organic bases include triethylamine, pyridine, 4-dimethylaminopyridine, etc.) and inert solvents to prepare (II) , the temperature is -20 to 150°C, and the time is 30 minutes to 24 hours.

方法E(当Y＝O或NR10，R4＝NH，Z＝CO，R4和Z组成环时)：

Method E (when Y=O or NR10, R4=NH, Z=CO, R4 and Z form a ring):

在上述反应中，溶剂通常为甲苯、苯、二氧六环，反应温度为室温至回流，反应时间通常为30分钟至48小时，在有或无碱存在下进行。In the above reaction, the solvent is usually toluene, benzene, dioxane, the reaction temperature is from room temperature to reflux, and the reaction time is usually 30 minutes to 48 hours, with or without the presence of a base.

方法F(当Y＝NH，R4＝NH2，Z＝CO，R4和Z组成环时)

Method F (when Y=NH, R4=NH2, Z=CO, R4 and Z form a ring)

在上述反应中，中间体(XI)和(XII)在溶剂如苯类、醇类(甲醇、乙醇、异丙醇)或其对应的醇钠存在下，于室温至回流温度反应30分钟～24小时制得(I)，In the above reaction, intermediates (XI) and (XII) are reacted at room temperature to reflux temperature for 30 minutes to 24 minutes in the presence of solvents such as benzene, alcohols (methanol, ethanol, isopropanol) or their corresponding sodium alkoxides. Hours made (I),

方法G

方法H

方法G和H的操作同方法E。方法I Method G

Method H

The operation of method G and H is the same as that of method E. Method I

在上述反应中所用的溶剂可以是任何不妨碍该反应的溶剂，它们包括卤代烃类(如二氯甲烷，二氯乙烷，氯仿，四氯化碳，四氯乙烷)、醇类(如丁醇，异丙醇，乙醇，乙二醇)、醚类(如四氢呋喃，二氧六环，乙二醇双(甲)乙醚，乙醚，异丙醚)、芳香烃类(如苯，甲苯，氯苯，硝基苯)、酯类(如乙酸乙酯、乙酸甲酯)、腈类(如乙腈)、二甲亚砜、二甲基甲酰胺和水。这些溶剂可单独使用也可混合使用。当混合使用这些溶剂进行量相反应时，可使用相转移催化剂，例如四丁基溴化铵、氯化三乙基苯甲基铵等。The solvent used in the above reaction can be any solvent that does not hinder the reaction, and they include halogenated hydrocarbons (such as methylene dichloride, ethylene dichloride, chloroform, carbon tetrachloride, tetrachloroethane), alcohols ( Such as butanol, isopropanol, ethanol, ethylene glycol), ethers (such as tetrahydrofuran, dioxane, ethylene glycol bis (methyl) ether, diethyl ether, isopropyl ether), aromatic hydrocarbons (such as benzene, toluene , chlorobenzene, nitrobenzene), esters (such as ethyl acetate, methyl acetate), nitriles (such as acetonitrile), dimethylsulfoxide, dimethylformamide and water. These solvents may be used alone or in combination. When these solvents are used in combination for a quantitative phase reaction, a phase transfer catalyst such as tetrabutylammonium bromide, triethylbenzylammonium chloride, or the like can be used.

在上述反应中所用的碱为无机碱或有机碱。无机碱包括如碱或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙、碳酸氢钠等，碱或碱土金属的氢氧化物如氢氧化钠、氢氧化钾、氢氧化钙和碱金属的氢化物如氢化锂，氢化钠等。The base used in the above reaction is an inorganic base or an organic base. Inorganic bases include carbonates of alkali or alkaline earth metals such as sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, etc., hydroxides of alkali or alkaline earth metals such as sodium hydroxide, potassium hydroxide, calcium hydroxide and alkali metal Hydrides such as lithium hydride, sodium hydride, etc.

有机碱类包括三乙胺。吡啶，4-二甲氨基吡啶等。Organic bases include triethylamine. Pyridine, 4-dimethylaminopyridine, etc.

通式(I)所示的化合物可以制成如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、膏剂、可溶性粉剂、颗粒剂、浸渍了活性化合物的天然材料及包入聚合物材料中的微细胶囊。The compound represented by general formula (I) can be prepared as solution, emulsion, wettable powder, suspension, powder, paste, soluble powder, granule, natural material impregnated with active compound and microfine capsule.

这些配方是用已知方法生产的、例如将活性化合物与填充剂即液体溶剂和/或固体载体混合，任选的使用表面活性剂即乳化剂和/或分散剂。These formulations are produced by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and/or solid carriers, optionally using surfactants, ie emulsifiers and/or dispersants.

在使用水作为填充剂的情况下，有机溶剂等也可以用作助溶剂。作为液体溶剂，适用的主要有：芳烃如二甲苯、甲苯、或烷基萘，氯代芳烃或氯代脂肪烃如氯苯、氯乙烯或二氯甲烷，脂肪烃如环己烷或链烷烃如石油馏分、矿物油和植物油，醇类如丁醇或二醇，及其醚类和酯类，酮类如丙酮、丁酮、甲基异丁基酮或环己酮，强极性溶剂如二甲基甲酰胺和二甲基亚砜，以及水等。In the case of using water as an extender, an organic solvent or the like can also be used as a co-solvent. As liquid solvents, the main suitable ones are: aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalene, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as Petroleum distillates, mineral and vegetable oils, alcohols such as butanol or diols, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as di Methylformamide and dimethyl sulfoxide, and water, etc.

作为固体载体，适用的有：铵盐和研磨的天然无机物如高岭土、粘土、滑石、白垩、石英、美国活性白土、蒙脱土，及研磨的合成无机物如高分散的二氧化硅、氧化铝和硅酸盐；作为颗粒剂的固体载体，适用的有：粉碎的天然岩石如方解石，大理石、浮石、海泡石和白云石，以及无机和有机粉末的合成颗粒，和有机材料如锯末、椰子壳、玉米芯和烟草杆的颗粒。As solid carriers, suitable are: ammonium salts and ground natural inorganic substances such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and ground synthetic inorganic substances such as highly disperse silica, oxide Aluminum and silicates; as solid carriers for granules, suitable are: crushed natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of inorganic and organic powders, and organic materials such as sawdust, coconut Particles of husks, corn cobs and tobacco rods.

作为乳化剂，适用的有：非离子型和阴离子型乳化剂如聚氧乙烯脂肪酸酯、聚氧化乙烯脂肪醇醚，烷芳基聚二醇醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及白蛋白水解产物；作为分散剂，适用的有：木质素亚硫酸盐和甲基纤维素。As emulsifiers, suitable are: nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, Aryl sulfonates and albumin hydrolysates; as dispersants suitable: lignin sulfites and methylcellulose.

在这些配方中可以使用粘合剂如羧甲基纤维素及粉末、颗粒或乳胶等形成的天然与合成聚合物如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯，以及天然磷脂如脑磷脂、卵磷脂和合成磷脂。进一步可能的添加剂是矿物油和植物油。Binders such as carboxymethyl cellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate in the form of powders, granules or latex, as well as natural phospholipids such as cephalin, lecithin, can be used in these formulations and synthetic phospholipids. Further possible additives are mineral and vegetable oils.

这些配方一般含有0.1％～95％(重量)活性化合物即通式(I)所示的化合物，较好的为0.5％～95％。These formulations generally contain 0.1% to 95% (weight) of the active compound, that is, the compound represented by the general formula (I), preferably 0.5% to 95%.

本发明的活性化合物可单独配成制剂使用，也可与已知的杀菌剂和杀虫杀螨剂混合使用。The active compounds of the present invention can be formulated into preparations alone or mixed with known fungicides and insecticides and acaricides.

可以同本发明的化合物混用的杀菌剂如下：The fungicides that can be mixed with the compounds of the present invention are as follows:

福美铁、福美双、福美锌、代森锰、代森锌、代森锰锌、多菌灵、苯菌灵、异菌脲、三唑酮、环唑醇(cyproconazole)、己唑醇(bexaconazole)、烯唑醇(diniconazole)、粉唑醇(tlutriafol)、苄氯三唑醇(diclobutrazol)、双苯三唑醇(bitertanol)、戊唑醇(tebuconazole)、氟菌唑(triflumizole)、呋菌唑(furconazole)、腈菌唑(myclobutanil)、唑菌腈(propanenitrile)、糠菌唑(bromuconazole)、丙环唑(propiconazole)、呋醚唑(furconazole-cis)、氟硅唑(flusilazolle)、酰胺唑(imibenconazole)、噁醚唑(difenconazole)、氟醚唑(tetraconazole)、氟苯嘧啶醇(nuarimol)、烯酰吗啉(dimethomorph)、甲霜灵、呋霜灵、苯霜灵、噁酰胺(oxadixyl)、咪鲜胺(prochloraz)、霜脲氰(DPX-3217)、霜霉威(propamocarb)、乙磷铝、乙霉威(diethofencarb)、吡咯类化合物拌种咯(fenpiclonil)、拌种强(CGA173506)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、啶斑肟(pyrifenox)、戊菌隆(pencycuron)、嘧菌腙(ferimzone)、唑菌嗪(triazoxide)、噻菌腈(thicyofen)、氟啶胺(fluazinam)、嘧菌胺、pyrimethanil、cyprodinil、fluquinconazole、BAS480F、BAS490F、CGA245704、CGA 329531、DE-795、DPX-JE874、ICIA0858、ICIA0054、KNF-S474，KTU 3616、KWG4168、LY214352、Mon 24000，XRD563、SSF126、SSF129(以上试验代号的化合物可以从英国植物保护会议论文集等中查到)。Furbam, thiram, thiram, maneb, zinc, mancozeb, carbendazim, benomyl, iprodione, triadimefon, cyproconazole, bexaconazole ), diniconazole, tlutriafol, diclobutrazol, bitertanol, tebuconazole, triflumizole, Furconazole, myclobutanil, propanenitrile, bromuconazole, propiconazole, furconazole-cis, flusilazolle, amides imibenconazole, difenconazole, tetraconazole, nuarimol, dimethomorph, metalaxyl, furalaxyl, benalaxyl, oxamide ( oxadixyl), prochloraz, cymoxanil (DPX-3217), propamocarb, fosmoaluminum, diethofencarb, fenpiclonil, and strong seed dressing (CGA173506), fenpropimorph, fenpropidin, pyrifenox, pencycuron, ferimzone, triazoxide, thiabendonil (thicyofen), fluazinam, azoxystrobin, pyrimethanil, cyprodinil, fluquinconazole, BAS480F, BAS490F, CGA245704, CGA 329531, DE-795, DPX-JE874, ICIA0858, ICIA0054, KNF-S474, KTU 3616, KWG4 .

可以同本发明的化合物混用的杀虫杀螨剂如下：The insecticides and acaricides that can be mixed with the compounds of the present invention are as follows:

拟除虫菊酯类化合物：如氟酯菊酯(acrinathrin)，甲氰菊酯(fenpropathrin)，顺式氯氰菊酯(alphamethrin)，氟氯菊酯(bifenthrin)，乙氰菊酯(cycloprothrin)，氟氯氰菊酯(beta-cyfluthrin)，氯氟氰菊酯(cyhalothrin，PP563)，氯氰菊酯(cypermcthrin)，甲体氯氰菊酯(alpha-cypermethrin)，乙体氯氰菊酯(beta-cypermethrin)，高氰戊菊酯(esfenvalerate)，醚菊酯(etofenprox)，吡氯氰菊酯(fenpirithrin)，氟氰戊菊酯(flucythrinate)，氟胺氰菊酯(fluvalinate)，氯氟氰菊酯(lambda-cyhalothrin，PP321)，七氟菊酯(tefluthrin)，四溴菊酯(tralomethrin)，溴氟菊酯，brofenprox，Cis-resmethrin，clocythrin，deltamethrin，ICIA5682，MTI-732，pyresmethrin，Silafluofen，silafluofen(Hoe498)，SSI-126，zetamethrin。Pyrethroid compounds: such as acrithrin, fenpropathrin, alphamethrin, bifenthrin, cycloprothrin, beta cyfluthrin -cyfluthrin), cyhalothrin (cyhalothrin, PP563), cypermethrin (cypermcthrin), alpha-cypermethrin (alpha-cypermethrin), beta-cypermethrin (beta-cypermethrin), esfenvalerate (esfenvalerate), etofenprox (etofenprox), fenpirithrin, flucythrin (flucythrinate), fluvalinate (fluvalinate), cyhalothrin (lambda-cyhalothrin, PP321), tefluthrin (tefluthrin), four Delmethrin, deltamethrin, brofenprox, Cis-resmethrin, clocythrin, deltamethrin, ICIA5682, MTI-732, pyresmethrin, silafluofen, silafluofen (Hoe498), SSI-126, zetamethrin.

氨基甲酸酯类化合物：如克百威，丁硫克百威、内硫克百威、灭多威、硫双灭多威、棉铃威、苯硫威。Carbamate compounds: such as carbofuran, carbosulfan, carbosulfan, methomyl, thiodicarb, fenthiocarb, and carbofuran.

有机磷类化合物：如丙虫磷、丙硫磷、甲丙硫磷、内溴磷、氯唑磷、特丁磷、甲基吡恶磷、丁苯硫磷、噻唑硫磷、吡唑硫磷、毒死蜱、甲基毒死蜱、辛硫磷、地亚农、Dowco429，MAT-7484。Organophosphorous compounds: such as trifenfos, prothion, methionon, endobrom, chlorazophos, terbufos, methyl pyroxaphos, fenfenfos, thiazofos, pyrazophos , Chlorpyrifos, chlorpyrifos-methyl, phoxim, Diananon, Dowco429, MAT-7484.

苯甲酰脲类化合物：如氟铃脲、伏虫隆、定虫隆、氟虫脲、PH-7023、GR-572、CGA157419、CGA184699。Benzoylurea compounds: such as hexaflumuron, chlorfluron, diflubenuron, flubenzuron, PH-7023, GR-572, CGA157419, CGA184699.

吡啶甲胺类化合物：如吡虫啉、NI-25、TIA-304。Pyridylamine compounds: such as imidacloprid, NI-25, TIA-304.

吡唑类化合物：如NNI850、MK-239、Fipronil。Pyrazole compounds: such as NNI850, MK-239, Fipronil.

哒嗪酮类化合物：如NC-129、NC-170、NC-184、NC-194、NC-196、Pyridazinone compounds: such as NC-129, NC-170, NC-184, NC-194, NC-196,

天然产物：如abamectin、amitrazin、avermectin、azadirachtin。Natural products: such as abamectin, amitrazin, avermectin, azadirachtin.

其他杂环化合物：如杀螨隆、喹螨醚、四螨嗪、AC303630、SU8801、YI-5301、SZI121、CGA 59205、D2341、DPX-MP062、MP-599、PFR-97、RH-5992、RH-2485、RH-0345(以上试验代号的化合物可以从英国植物保护会议论文集等中查到)。Other heterocyclic compounds: such as difenuron, fenazafen, tetrafenazine, AC303630, SU8801, YI-5301, SZI121, CGA 59205, D2341, DPX-MP062, MP-599, PFR-97, RH-5992, RH -2485, RH-0345 (the compounds of the above test codes can be found from the Proceedings of the British Plant Protection Conference, etc.).

实例1：可湿性粉剂Example 1: wettable powder

本发明化合物50份，分别与3份木质素磺酸钙，2份十二烷基硫酸钠和45份合成水合氧化硅混合。混合物均匀地磨碎和混合，得到50％的可湿性粉剂。50 parts of the compound of the present invention are respectively mixed with 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrated silicon oxide. The mixture is uniformly ground and blended to obtain a 50% wettable powder.

实例2：悬浮剂Example 2: Suspending agent

化合物25份，分别与3份聚氧亚乙基脱水山梨醇单油酸酯和72份水混合。混合物被湿磨至需要的25％的悬浮剂。25 parts of the compound were mixed with 3 parts of polyoxyethylene sorbitan monooleate and 72 parts of water respectively. The mixture was wet milled to the required 25% suspending agent.

实例3：粉剂Example 3: powder

本发明化合物2份，分别与88份高岭土和10份滑石混合。混合物被充分地磨碎，得到2％的粉剂。2 parts of the compound of the present invention are mixed with 88 parts of kaolin and 10 parts of talc respectively. The mixture was finely ground to obtain a 2% powder.

实例4：乳油Example 4: EC

本发明化合物20份，分别与14份聚氧亚乙基苯乙烯基苯基醚，6份十二烷基苯磺酸钙和60份二甲苯混合。混合物被充分地混合，得到20％的乳油。20 parts of the compound of the present invention are respectively mixed with 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 60 parts of xylene. The mixture was mixed well to obtain a 20% cream.

实例5：颗粒剂Example 5: Granules

本发明化合物2份，分别与1份合成水合氧化硅。2份木素磺酸钙，30份膨润土和65份高岭上混合。混合物充分磨碎和混合后。加水，均匀捏合、成粒，干燥，得到2％的颗粒剂。2 parts of the compound of the present invention, respectively and 1 part to synthesize hydrated silicon oxide. 2 parts calcium lignosulfonate, 30 parts bentonite and 65 parts kaolin are mixed together. After the mixture is well ground and blended. Add water, knead evenly, granulate, and dry to obtain 2% granules.

实例6：水基悬浮液Example 6: Water-Based Suspension

本发明化合物20份，分别与1.5份脱水山梨醇三油酸酯和28.5份含2份聚乙烯醇的水溶液混合，用砂磨机将混合物磨成粒径不大于3的细粉。每种混合物再与含0.05份黄原胶和0.1份硅酸铝镁的40份水溶液混合，然后，再与10份丙二醇混合，得到20％的水基悬浮液。20 parts of the compound of the present invention were mixed with 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol respectively, and the mixture was ground into a fine powder with a particle size of not more than 3 with a sand mill. Each mixture was mixed with 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 part of magnesium aluminum silicate, and then with 10 parts of propylene glycol to obtain a 20% aqueous suspension.

实例7：油溶液Example 7: Oil solution

本发明化合物0.1份，分别溶解于5份二甲苯和5份三氯乙烷中，所得溶液与89.9份脱臭煤油混合，得到0.1％的油溶液。0.1 part of the compound of the present invention was respectively dissolved in 5 parts of xylene and 5 parts of trichloroethane, and the resulting solution was mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution.

实例8(化合物79)反应式：

Example 8 (compound 79) reaction formula:

(1)1，3-二甲基-5-苯氧基-4-吡唑甲腈的合成(1) Synthesis of 1,3-dimethyl-5-phenoxy-4-pyrazolecarbonitrile

1，3-二甲基-5-苯氧基-4-吡唑甲醛肟21.3克与100毫升乙酸酐回流反应2小时，回收部分乙酸酐及乙酸后，冷却并加水100毫升搅拌，即得固体，过滤、水洗、干燥得20.5克无色结晶体。熔点73～75℃。21.3 g of 1,3-dimethyl-5-phenoxy-4-pyrazole formaldehyde oxime was reacted with 100 ml of acetic anhydride under reflux for 2 hours, after recovering part of acetic anhydride and acetic acid, cooling and adding 100 ml of water and stirring to obtain a solid , filtered, washed with water, and dried to obtain 20.5 g of colorless crystals. The melting point is 73-75°C.

(2)1.3-二甲基-5-苯氧基-4-吡唑酰胺肟的合成(2) Synthesis of 1.3-dimethyl-5-phenoxy-4-pyrazole amidoxime

1，3-二甲基-5-苯氧基-4-吡唑甲腈(8.5克)，碳酸钾(8.0克)，盐酸羟胺(4.0克)于50毫升甲醇中，回流过夜，回收大部分甲醇后，加水搅拌，过滤，干燥即得所需物9.8克。熔点：157～160℃。1,3-Dimethyl-5-phenoxy-4-pyrazolecarbonitrile (8.5 grams), potassium carbonate (8.0 grams), hydroxylamine hydrochloride (4.0 grams) in 50 milliliters of methanol, reflux overnight, recover most After methanol, add water, stir, filter, and dry to obtain 9.8 g of the desired compound. Melting point: 157～160℃.

(3)目的物的合成(3) Synthesis of the target object

上步中间体(1.5克)，对溴甲基苯甲酸叔丁酯(1.8克)，氢氧化钠(0.3克)于30毫升丁酮中，回流反应反应8小时，脱溶后冷却、加水，乙酸乙酯萃取，干燥，脱溶，柱层析得目的物2.0克，熔点：84～86℃。Intermediate (1.5 grams) of the previous step, tert-butyl p-bromomethylbenzoate (1.8 grams), sodium hydroxide (0.3 grams) in 30 milliliters of butanone, reflux reaction for 8 hours, cooling after precipitation, adding water, Extraction with ethyl acetate, drying, precipitation, and column chromatography yielded 2.0 g of the target product, melting point: 84-86°C.

HNMR(CDCl₃，TMS)ppm：7.84～7.98(d，2H)，7.11～7.49(m，5H)，6.82～7.00(d，2H)，5.06(s，2H)，4.77(bs，2H)，3.58(s，3H)，2.37(s，3H)，1.62(s，9H)。HNMR (CDCl ₃ , TMS) ppm: 7.84～7.98(d, 2H), 7.11～7.49(m, 5H), 6.82～7.00(d, 2H), 5.06(s, 2H), 4.77(bs, 2H), 3.58(s, 3H), 2.37(s, 3H), 1.62(s, 9H).

实例9(化合物306)反应式： Example 9 (compound 306) reaction formula:

将1，3-二甲基-5-苯氧基-4-吡唑甲醛肟2.3克、氯甲基三唑盐酸盐(1.5克)、碳酸钾(3.0克)于30毫升丙酮中的混合液加热回流反应8小时，回收大部分溶剂后，加水20毫升，乙酸乙酯萃取，干燥、脱溶得油状物(2.8克)即目的物。Mix 2.3 grams of 1,3-dimethyl-5-phenoxy-4-pyrazole formaldehyde oxime, chloromethyltriazole hydrochloride (1.5 grams), potassium carbonate (3.0 grams) in 30 milliliters of acetone The solution was heated under reflux for 8 hours. After recovering most of the solvent, 20 ml of water was added, extracted with ethyl acetate, dried and precipitated to obtain an oily substance (2.8 g), which was the target product.

实例10(化合物309)反应式： Example 10 (compound 309) reaction formula:

将1，3-二甲基-5-苯氧基-4-吡唑甲醛肟(1.0克)溶于10毫升四氢呋喃中，加入对三氟甲基苯基异氰酸酯(1.0克)及1滴三乙胺，搅拌反应2小时后，过滤即得目的物(1.8克)，熔点110～112℃。Dissolve 1,3-dimethyl-5-phenoxy-4-pyrazole formaldehyde oxime (1.0 g) in 10 ml of tetrahydrofuran, add p-trifluoromethylphenyl isocyanate (1.0 g) and 1 drop of triethyl The amine was stirred and reacted for 2 hours, and the target product (1.8 g) was obtained by filtration, with a melting point of 110-112°C.

HNMR(DMCO，TMS)ppm：8.71(bs，1H)，8.09(s，1H)，7.64(s.4H)，7.45(m，2H)，7.27(m，1H)，3.64(s，3H)，2.41(s，3H)。HNMR (DMCO, TMS) ppm: 8.71 (bs, 1H), 8.09 (s, 1H), 7.64 (s.4H), 7.45 (m, 2H), 7.27 (m, 1H), 3.64 (s, 3H), 2.41(s, 3H).

实例11(化合物231)反应式：

Example 11 (compound 231) reaction formula:

将1，3-二甲基-5-苯氧基-4-吡唑甲醛(0.5克)与2，6-二氯-4-三氟甲基苯肼(0.53克)及1滴冰醋酸溶于20毫升甲醇中，加热回流反应5小时，冷却，乙酸乙酯萃取，水洗，脱溶得油状物。放置得固体(0.95克)。熔点：70～74℃。Dissolve 1,3-dimethyl-5-phenoxy-4-pyrazole formaldehyde (0.5 g) in 2,6-dichloro-4-trifluoromethylphenylhydrazine (0.53 g) and 1 drop of glacial acetic acid In 20 ml of methanol, heat to reflux for 5 hours, cool, extract with ethyl acetate, wash with water, and remove the solvent to obtain an oily substance. Settled to a solid (0.95 g). Melting point: 70-74°C.

HNMR(CDCl₃，TMS)ppm：6.84～7.67(7H)，3.62(s，3H)，2.49(s，3H).HNMR (CDCl ₃ , TMS) ppm: 6.84～7.67(7H), 3.62(s, 3H), 2.49(s, 3H).

实例12(化合物145)反应式： Example 12 (compound 145) reaction formula:

将1，3-二甲基-5-氯-4-吡唑甲酰氯(3.0克)溶于20毫升乙醚中，滴加4-三氟甲基苄胺(2.8克)，室温搅拌1小时，过滤并用乙醚洗即得目的物4.8克，熔点：201～203℃。1,3-Dimethyl-5-chloro-4-pyrazolecarbonyl chloride (3.0 g) was dissolved in 20 ml of ether, 4-trifluoromethylbenzylamine (2.8 g) was added dropwise, and stirred at room temperature for 1 hour, Filter and wash with ether to obtain 4.8 g of the target compound, melting point: 201-203°C.

HNMR(CDC₃，TMS)PPM：7.87(bs，1H)，7.42～7.55(d，2H)，6.84～7.06(d，2H)，6.49(bs，1H)，3.86(s，3H)，2.46(s，3H).HNMR (CDC ₃ , TMS) PPM: 7.87 (bs, 1H), 7.42 ~ 7.55 (d, 2H), 6.84 ~ 7.06 (d, 2H), 6.49 (bs, 1H), 3.86 (s, 3H), 2.46 ( s, 3H).

实例13(化合物315)反应式：将1，3-二甲基-5-苯氧基-4-吡唑甲醛4.0克与水合肼(10毫升)于10毫升甲醇中反应过夜，加水50毫升，搅拌即析出固体腙3.0克。取此腙0.5克溶于10毫升乙醚中同0.45克的对三氟j甲氧基苯基异氰酸酯反应，立即析出沉淀，过滤，乙醚洗得产品0.85克，熔点：119～120℃。Example 13 (compound 315) reaction formula: React 4.0 g of 1,3-dimethyl-5-phenoxy-4-pyrazole carboxaldehyde with hydrazine hydrate (10 ml) in 10 ml of methanol overnight, add 50 ml of water, and stir to precipitate 3.0 g of solid hydrazone. Take 0.5 g of this hydrazone and dissolve it in 10 ml of diethyl ether to react with 0.45 g of p-trifluoroj-methoxyphenyl isocyanate. A precipitate is precipitated immediately, filtered, and washed with diethyl ether to obtain 0.85 g of the product, melting point: 119-120°C.

HNMR(DMSO，TMS)ppm：10.51(s，1H)，8.11(1H)，7.72(1H)，6.94～7.60(m，9H)，3.57(s，3H)，2.39(s，3H)。HNMR (DMSO, TMS) ppm: 10.51 (s, 1H), 8.11 (1H), 7.72 (1H), 6.94-7.60 (m, 9H), 3.57 (s, 3H), 2.39 (s, 3H).

实例14(化合物389)反应式：

Example 14 (compound 389) reaction formula:

将0.8克1.3-二甲基-5-苯氧基-4-吡唑酰胺肟和0.7克2，6-二氟苯甲酰氯溶于20毫升的甲苯中，回流反应8小时，脱溶。柱层析提纯得产品0.9克。熔点：106～108℃。0.8 g of 1.3-dimethyl-5-phenoxy-4-pyrazoleamide oxime and 0.7 g of 2,6-difluorobenzoyl chloride were dissolved in 20 ml of toluene, and refluxed for 8 hours to remove the solvent. Purified by column chromatography to obtain 0.9 g of the product. Melting point: 106-108°C.

HNMR(CDCl₃，TMS)ppm：6.82～7.45(m，8H)，3.68(s，3H)，2.58(s，3H)。HNMR (CDCl ₃ , TMS) ppm: 6.82-7.45 (m, 8H), 3.68 (s, 3H), 2.58 (s, 3H).

实例15(化合物87)反应式： Example 15 (compound 87) reaction formula:

(1)1，3-二甲基-5-苯氧基-4-α-氯吡唑甲醛肟的制备(1) Preparation of 1,3-dimethyl-5-phenoxy-4-α-chloropyrazole formaldehyde oxime

将15克1，3-二甲基-5-苯氧基-4-吡唑甲醛肟溶于100毫升氯仿中，10℃以下通入稍过量的氯气，过滤，氯仿洗，得产品8.8g，熔点：138～152℃。Dissolve 15 grams of 1,3-dimethyl-5-phenoxy-4-pyrazole formaldehyde oxime in 100 milliliters of chloroform, feed a little excess chlorine gas below 10°C, filter, and wash with chloroform to obtain 8.8 g of the product, Melting point: 138-152°C.

HNMR(DMCO，TMS)ppm：6.82～714(m，5H)，3.58(s，3H)，2.27(s，3H)。HNMR (DMCO, TMS) ppm: 6.82-714 (m, 5H), 3.58 (s, 3H), 2.27 (s, 3H).

(2)1，3-二甲基-5-苯氧基-4-α-(1，2，4-三唑)吡唑甲醛肟的制备(2) Preparation of 1,3-dimethyl-5-phenoxy-4-α-(1,2,4-triazole)pyrazole formaldehyde oxime

1，3-二甲基-5-苯氧基-4-α-氯吡唑甲醛肟(6克)，1，2，4-三唑(3.2克)，碳酸钾(4.7克)与60毫升DMF混合加热至回流，反应8小时，冷却，乙酸乙酯萃取，有机层酸洗，水洗，饱和食盐水洗，无水硫酸镁干燥，脱溶，即得产品3克，熔点：150～153℃。1,3-Dimethyl-5-phenoxy-4-α-chloropyrazole formaldehyde oxime (6 grams), 1,2,4-triazole (3.2 grams), potassium carbonate (4.7 grams) and 60 ml DMF was mixed and heated to reflux, reacted for 8 hours, cooled, extracted with ethyl acetate, the organic layer was acid-washed, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, and dissolved to obtain 3 g of the product, melting point: 150-153°C.

HNMR(DMSO，TMS)ppm：8.64(s，1H)，8.00(s，1H)，7.00～7.40(m，3H)，6.67～6.89(m，2H)，3.53(s，3H)，1.96(s，3H).HNMR (DMSO, TMS) ppm: 8.64(s, 1H), 8.00(s, 1H), 7.00～7.40(m, 3H), 6.67～6.89(m, 2H), 3.53(s, 3H), 1.96(s , 3H).

(3)目的物的制备(3) Preparation of target object

1，3-二甲基-5-苯氧基-4-α-1，2，4-三唑吡唑甲醛肟1克，氢化钠1克与20毫升丁酮混合，室温搅拌0.5小时后，加入对苯甲酸叔丁基酯苄溴1克，回流4小时，加水，乙酸乙酯萃取，有机层酸洗，水洗，无水硫酸镁干燥，脱溶，柱层析提纯得产品，为油状物1.2克，1,3-dimethyl-5-phenoxy-4-α-1,2,4-triazole pyrazole formaldehyde oxime 1 g, sodium hydride 1 g mixed with 20 ml methyl ethyl ketone, stirred at room temperature for 0.5 hours, Add 1 g of tert-butyl benzyl bromide terephthalate, reflux for 4 hours, add water, extract with ethyl acetate, pickle the organic layer, wash with water, dry over anhydrous magnesium sulfate, remove the solvent, and purify by column chromatography to obtain the product as an oily substance 1.2 grams,

HNMR(CDCl₃，TMS)ppm：8.42(s，1H)，7.99(s，1H)，7.84～7.99(m，2H)，7.00～7.38(m，3H)、6.67～6.84(m，2H)，5.11(s，2H)，3.67(s，3H)，2.09(s，3H)，1.65(s，9H)。HNMR (CDCl ₃ , TMS) ppm: 8.42 (s, 1H), 7.99 (s, 1H), 7.84-7.99 (m, 2H), 7.00-7.38 (m, 3H), 6.67-6.84 (m, 2H), 5.11 (s, 2H), 3.67 (s, 3H), 2.09 (s, 3H), 1.65 (s, 9H).

用类似的方法可制备表1～7所示的其它化合物：Other compounds shown in Tables 1 to 7 can be prepared in a similar manner:

表1

化合物编号 X R3 R4 R1 O C6H5 CI C4H9t2 O C6H5 NH2 C4H9t3 O C6H5 NHCH3 C4H9t4 O C6H5 NHCO2CH3 C4H9t5 O C6H5 NHCOCH3 C4H9t6 O C6H5 N(Me)2 C4H9t7 O C6H5 NHSO2CH3 C4H9t8 O C6H6 OCH3 C4H9t9 O C6H5 SCH3 C4H9t10 O C6H5 1，2，4-三唑-1-基 C4H9t11 O C6H5 咪唑-1-基 C4H9t12 S C6H5 CI C4H9t13 S C6H5 NH2 C4H9t14 S C6H5 NHCH3 C4H9t15 S C6H5 NHCO2CH3 C4H9t16 S C6H6 NHCOCH3 C4H9t17 S C6H5 N(Me)2 C4H9t18 S C6H5 NHSO2CH3 C4H9t19 S C6H5 OCH3 C4H9t20 S C6H5 SCH3 C4H9t21 S C6H5 1，2，4-三唑-1-基 C4H9t22 S C6H5 咪唑-1-基 C4H9t23 S C10H7 CI C4H9t24 S C10H7 NH2 C4H9t25 S C10H7 NHCH3 C4H9t26 S C10H7 NHCO2CH3 C4H9t27 S C10H7 NHCOCH3 C4H9t28 S C10H7 N(Me)2 C4H9t29 S C10H7 NHSO2CH3 C4H9t30 S C10H7 OCH3 C4H9t31 S C10H7 SCH3 C4H9t32 S C10H7 1，2，4-三唑-1-基 C4H9t33 S C10H7 咪唑-1-基 C4H9t34 O C10H7 CI C4H9t35 O C10H7 NH2 C4H9t36 O C10H7 NHCH3 C4H9t37 O C10H7 NHCO2CH3 C4H9t38 O C10H7 NHCOCH3 C4H9t39 O C10H7 N(Me)2 C4H9t40 O C10H7 NHSO2CH3 C4H9t41 O C10H7 OCH3 C4H9t42 O C10H7 SCH3 C4H9t43 O C10H7 1，2，4-三唑-1-基 C4H9t44 O C10H7 咪唑-1-基 C4H9t45 O C10H7 CI CO2C4H9t46 O C10H7 NH2 CO2C4H9t47 O C10H7 NHCH3 CO2C4H9t48 O C10H7 NHCO2CH3 CO2C4H9t49 O C10H7 NHCOCH3 CO2C4H9t50 O C10H7 N(Me)2 CO2C4H9t51 O C10H7 NHSO2CH3 CO2C4H9t52 O C10H7 OCH3 CO2C4H9t53 O C10H7 SCH3 CO2C4H9t54 O C10H7 1，2，4-三唑-1-基 CO2C4H9t55 O C10H7 咪唑-1-基 CO2C4H9t56 S C10H7 CI CO2C4H9t57 S C10H7 NH2 CO2C4H9t58 S C10H7 NHCH3 CO2C4H9t59 S C10H7 NHCO2CH3 CO2C4H9t60 S C10H7 NHCOCH3 CO2C4H9t61 S C10H7 N(Me)2 CO2C4H9t62 S C10H7 NHSO2CH3 CO2C4H9t63 S C10H7 OCH3 CO2C4H9t64 S C10H7 SCH3 CO2C4H9t65 S C10H7 1，2，4-三唑-1-基 CO2C4H9t66 S C10H7 咪唑-1-基 CO2C4H9t67 S C6H5 CI CO2C4H9t68 S C6H5 NH2 CO2C4H9t69 S C6H5 NHCH3 CO2C4H9t70 S C6H5 NHCO2CH3 CO2C4H9t71 S C6H5 NHCOCH3 CO2C4H9t72 S C6H5 N(Me)2 CO2C4H9t73 S C6H5 NHSO2CH3 CO2C4H9t74 S C6H6 OCH3 CO2C4H9t75 S C6H5 SCH3 CO2C4H9t76 S C6H5 1，2，4-三唑-1-基 CO2C4H9t77 S C6H5 咪唑-1-基 CO2C4H9t78 O C6H5 CI CO2C4H9t79 O C6H5 NH2 CO2C4H9t80 O C6H5 NHCH3 CO2C4H9t81 O C6H5 NHCO2CH3 CO2C4H9t82 O C6H6 NHCOCH3 CO2C4H9t83 O C6H5 N(Me)2 CO2C4H9t84 O C6H5 NHSO2CH3 CO2C4H9t85 O C6H5 OCH3 CO2C4H9t86 O C6H5 SCH3 CO2C4H9t87 O C6H5 1，2，4-三唑-1-基 CO2C4H9t88 O C6H5 咪唑-1-基 CO2C4H9t89 O C6H6 CN CO2C4H9t90 O C6H6 CN C4H9t91 O C6H6 NHCH2CO2CH3 C4H9t92 O C6H6 NHCH2CO2CH3 CO2C4H9t93 O C6H5 H CO2C(Me)2CN94 O C6H5 H CO2C(Me)2CCI395 O C6H5 CI CO2C(Me)2CN96 O C6H5 CI CO2C(Me)2CCI3

表2

化合物编号 X R3 R4 R97 O C6H5 CI C4H9t98 O C6H5 NH2 C4H9t99 O C6H5 NHCH3 C4H9t100 O C6H5 NHCO2CH3 C4H9t101 O C6H5 NHCOCH3 C4H9t102 O C6H5 N(Me)2 C4H9t103 O C6H5 NHSO2CH3 C4H9t104 O C6H6 OCH3 C4H9t105 O C6H5 SCH3 C4H9t106 O C6H5 1，2，4-三唑-1-基 C4H9t107 O C6H5 咪唑-1-基 C4H9t108 S C6H5 CI C4H9t109 S C6H5 NH2 C4H9t110 S C6H5 NHCH3 C4H9t111 S C6H5 NHCO2CH3 C4H9t112 S C6H6 NHCOCH3 C4H9t113 S C6H5 N(Me)2 C4H9t114 S C6H5 NHSO2CH3 C4H9t115 S C6H5 OCH3 C4H9t116 S C6H5 SCH3 C4H9t117 S C6H5 1，2，4-三唑-1-基 C4H9t118 S C6H5 咪唑-1-基 C4H9t119 S C6H5 CI CO2C4H9t120 S C6H5 NH2 CO2C4H9t121 S C6H5 NHCH3 CO2C4H9t122 S C6H5 NHCO2CH3 CO2C4H9t123 S C6H5 NHCOCH3 CO2C4H9t124 S C6H5 N(Me)2 CO2C4H9t125 S C6H5 NHSO2CH3 CO2C4H9t126 S C6H6 OCH3 CO2C4H9t127 S C6H5 SCH3 CO2C4H9t128 S C6H5 1，2，4-三唑-1-基 CO2C4H9t129 S C6H5 咪唑-1-基 CO2C4H9t130 O C6H5 CI CO2C4H9t131 O C6H5 NH2 CO2C4H9t132 O C6H5 NHCH3 CO2C4H9t133 O C6H5 NHCO2CH3 CO2C4H9t134 O C6H6 NHCOCH3 CO2C4H9t135 O C6H5 N(Me)2 CO2C4H9t136 O C6H5 NHSO2CH3 CO2C4H9t137 O C6H5 OCH3 CO2C4H9t138 O C6H5 SCH3 CO2C4H9t139 O C6H5 1，2，4-三唑-1-基 CO2C4H9t140 O C6H5 咪唑-1-基 CO2C4H9t141 O C6H5 H CO2C(Me)2CN142 O C6H5 H CO2C(Me)2CC3143 O C6H5 CI CO2C(Me)2CN144 O C6H5 CI CO2C(Me)2CCI3表3

化合物编号 XR3 R1 Z Q145 CI CH3 - CH2C6H4-4-CF3146 CI CH3 - CH2C6H4-4-C4H9t147 CI CH3 - CH2C6H4-4-CI148 CI CH3 - CH2C6H4-4-OCF3149 OPh CH3 - CH2C6H4-4-OCF3150 CI CH3 - NHC6H4-4-CF3151 CI CH3 - NHC6H4-4-C4H9t152 CI CH3 - NHC6H4-4-CI153 CI CH3 - NHC6H4-4-OCF3154 CI CH3 - NHC6H4-4-OC2HF4155 CI CH3 - C6H4-3-OCH(CH3)2156 CI CH3 O CH2C6H4-4-But157 OPh CH3 O CH2C6H4-4-CO2But158 CI CH3 - NH2C6H3-2，6-(Me)2159 CI CH3 - NHC6H4-4-NO2160 CI CH3 - NHC6H5161 CI CH3 O CH2C6H4-4-OCF3162 CI CH3 O CH2-1-(1，2，4-三唑)163 CI CH3 - C6H4-4-F164 CI CI - C6H4-4-CF3165 CI CI - C6H4-4-C4H9t166 CI CI - C6H4-4-CI167 CI CI - C6H4-4-OCF3168 CI CI - C6H4-3-OCH(CH3)2169 CI CI - C6H4-4-F170 CI CI - CH2C6H4-4-CF3171 CI CI - CH2C6H4-4-C4H9t172 CI CI - CH2C6H4-4-CI173 CI CI - CH2C6H4-4-OCF3174 CI CI - CH2C6H4-4-OC2HF4175 CI CI - NHC6H4-4-CF3176 CI CI - NHC6H4-4-C4H9t177 CI CI - NHC6H4-4-CI178 CI CI - NHC6H4-4-OCF3179 CI CI - NHC6H4-4-OC2HF4180 OPh CH3 - C6H4-3-OCH(CH3)2181 CI CI - NHC6H2-2，6-CI2-4-CF3182 CI CH3 - NHC6H2-2，6-CI2-4CF3183 CI CI - CH2C6H2-2，6-CI2-4-CF3184 CI CH3 - CH2C6H2-2，6-CI2-4-CF3185 CI CF3 - CH2-2-噻酚-4-CO2CH3186 CI CF3 - CH2-3-C5H3N-6-CI187 CI CF3 - 3-C5H3N-6-CI(吡啶)188 CI CF3 - CH2-2-C4H3O(呋喃189 CI CF3 - NHC6H4-4-CF3190 CF3 CI - CH2-2-噻酚-4-CO2CH3191 CF3 CI - CH2-3-C5H3N-6-CI192 CF3 CI - 3-C5H3N-6-CI193 CF3 CI - CH2C6H4-4-CF3194 CF3 CI - NHC6H4-4-CF3195 CI CH3 -

196 CI CF3 - C6H2-2，6-(Br)2-4-OCF3197 OPh CF3 - NHC6H4-4-CF3198 OPh CF3 - NHC6H4-4-NO2199 CI CF3 - NHC6H4-4-CN200 CI CF3 - C6H2-2，6-(Br)2-4-OCF3表4

化合物编号 XR3 R4 YR201 CI NH2 CH2C6H4-4-CF3202 CI NH2 CH2C6H4-4-C4H9t203 CI NH2 CH2C6H4-4-CI204 CI NH2 CH2C6H4-4-OCF3205 CI NH2 CH2C6H4-4-OC2HF4206 CI NH2 NHC6H4-4-CF3207 CI NH2 NHC6H4-4-C4H9t208 CI NH2 NHC6H4-4-CI209 CI NH2 NHC6H4-4-OCF3210 CI NH2 NHC6H4-4-OC2HF4211 CI NH2 C6H4-3-OCH(CH3)2212 CI NH2 NHC6H2-2，6-CI2-4-CF3213 CI NH2 CH2C6H2-2，6-CI2-4-CF3214 CI NH2 C6H4-4-CF3215 CI NH2 C6H4-4-C4H9t216 CI NH2 C6H4-4-CI217 CI NH2 C6H4-4-OCF3218 CI NH2 C6H4-4-OC2HF4219 CI NH2 C6H4-4-F220 OPh H CH2C6H4-4-CF3221 OPh H CH2C6H4-4-C4H9t222 OPh H CH2C6H4-4-CI223 OPh H CH2C6H4-4-OCF3224 OPh H CH2C6H4-4-OC2HF4225 OPh H NHC6H4-4-CF3226 OPh H NHC6H4-4-C4H9t227 OPh H NHC6H4-4-CI228 OPh H NHC6H4-4-OCF3229 OPh H NHC6H4-4-OC2HF4230 OPh H C6H4-3-OCH(CH3)2231 OPh H NHC6H2-26-CI2-4-CF3232 OPh H CH2C6H2-2，6-CI2-4-CF3233 OPh H C6H4-4-CF3234 OPh H C6H4-4-C4H9t235 OPh H C6H4-4-CI236 OPh H C6H4-4-OCF3237 OPh H C6H4-4-OC2HF4238 OPh H C6H4-4-F239 OPh CI CH2C6H4-4-CF3240 OPh CI CH2C6H4-4-C4H9t241 OPh CI CH2C6H4-4-CI242 OPh CI CH2C6H4-4-OCF3243 OPh CI CH2C6H4-4-OC2HF4244 OPh CI NHC6H4-4-CF3245 OPh CI NHC6H4-4-C4H9t246 OPh CI NHC6H4-4-CI247 OPh CI NHC6H4-4-OCF3248 OPh CI NHC6H4-4-OC2HF4249 OPh CI C6H4-3-OCH(CH3)2250 OPh CI NHC6H2-2，6-CI2-4-CF3251 OPh CI CH2C6H2-2，6-CI2-4-CF3252 OPh CI C6H4-4-CF3253 OPh CI C6H4-4-C4H9t254 OPh CI C6H4-4-CI255 OPh CI C6H4-4-OCF3256 OPh CI C6H4-4-OC2HF4257 OPh CI C6H4-4-F258 CI CI CH2C6H4-4-CF3259 CI CI CH2C6H4-4-C4H9t260 CI CI CH2C6H4-4-CI261 CI CI CH2C6H4-4-OCF3262 CI CI CH2C6H4-4-OC2HF4263 CI CI NHC6H4-4-CF3264 CI CI NHC6H4-4-C4H9t265 CI CI NHC6H4-4-CI266 CI CI NHC6H4-4-OCF3267 CI CI NHC6H4-4-OC2HF4268 CI CI C6H4-3-OCH(CH3)2269 CI CI NHC6H2-2，6-CI2-4-CF3270 CI CI CH2C6H2-2，6-CI2-4-CF3271 CI CI C6H4-4-CF3272 CI CI C6H4-4-C4H9t273 CI CI C6H4-4-CI274 CI CI C6H4-4-OCF3275 CI CI C6H4-4-OC2HF4276 CI CI C6H4-4-F277 CI H OCH2CO2C2H5278 CI H OCH(Mc)CO2C2H5279 CI H OCH2-1-(1，2，4-三唑)280 CI H OCONHCH3281 CI H OCONHC6H4-4-CI282 CI H OCONHC6H4-4-CF3283 CI H OCONHC6H4-4-OCF3284 CI H OCONHC6H3-3，4-CI2285 CI H NHCONHC6H4-4-CI286 CI H N(CH3)CONHC6H4-4-CI287 CI H NHCONHC6H4-4-CF3288 CI H NHCONHC6H4-4-OCF3289 CI H NHCONHC6H3-3，4-CI2290 CI H OCOC6H4-4-F291 CI H OCOC6H4-4-CI292 CI H OCOC6H3-2，6-F2293 CI H NHCOC6H4-4-F294 CI H NHCOC6H4-4-CI295 CI H NHCOC6H3-2，6-F2296 CI H OCONHCOC6H3-2，6-F2297 CI H OCONHCOC6H4-2-F298 CI H OCONHCOC6H3-2，6-CI2299 CI H OCONHCOC6H4-2-CI300 CI H NHCONHCOC6H3-2，6-F2301 CI H NHCONHCOC6H4-2-F302 CI H NHCONHCOC6H3-2，6-I2303 CI H NHCONHCOC6H4-2-CI304 OPh H OCH2CO2C2H5305 OPh H OCH(Me)CO2C2H5306 OPh H OCH2-1-(1，2，4-三唑)307 OPh H OCONHCH3308 OPh H OCONHC6H4-4-CI309 OPh H OCONHC6H4-4-CF3310 OPh H OCONHC6H4-4-OCF3311 OPh H OCONHC6H3-3，4-CI2312 OPh H NHCONHC6H4-4CI313 OPh H N(CH3)CONHC6H4-4CI314 OPh H NHCONHC6H4-4-CF3315 OPh H NHCONHC6H4-4-OCF3316 OPh H NHCONHC6H3-3，4-CI2317 OPh H OCOC6H4-4-F318 OPh H OCOC6H4-4-CI319 OPh H OCO6H3-2，6-F2320 OPh H NHCOC6H4-4-F321 OPh H NHCOC6H4-4-CI322 OPh H NHCOC6H3-2，6-F2323 OPh H OCONHCOC6H3-2，6-F2324 OPh H OCONHCOC6H4-2-F325 OPh H OCONHCOC6H3-2，6-CI2326 OPh H OCONHCOC6H4-2-CI327 OPh H NHCONHCOC6H3-2，6-F2328 OPh H NHCONHCOC6H4-2-F329 OPh H NHCONHCOC6H3-2，6-CI2330 OPh H NHCONHCOC6H4-2-CI331 CI H OCH2C6H4-4-C4H9t332 CI H OCH2C6H4-4-CO2C4H9t333 CI H NHCH2C6H4-4-C4H9t334 CI H NHCH2C6H4-4-CO2C4H9t335 OPh H OCH2C6H4-4-C4H9t336 OPh H OCH2C6H4-4-CO2C4H9t337 OPh H NHCH2C6H4-4-C4H9t338 OPh H NHCH2C6H4-4-CO2C4H9t339 OPh H OCH2P(S)(OC2H5)2340 OPh H OCH2P(O)OC2H5(SC3H7)341 OPh H P(S)(OC2H5)2342 OPh H P(O)OC2H5(SC3H7)343 OPh H OCH2-3-C6H3N-6-CI344 OPh NH2 OCH2-3-C6H3N-6-CI345 OPh CN OCONHCH₃346 OPh CO₂CH₃ OCH₃347 OPh H OCOCH2CH2CO2H348 OPh H OCOCH＝CHCO2CH3349 OPh

表5

化合物编号 R1 XR3 Y R350 CH3 CI O CH2C6H4-4-CI351 CH3 CI O CH2C6H4-4-F352 CH3 CI O CH2C6H4-4-C4H9t353 CH3 CI O CH2C6H4-4-CO2CH3354 CH3 CI O CH2C6H4-4-CO2C4H9t355 CH3 CI O CH2-5-C5H3N-2-CI356 CH3 CI O CH2-3-C5H3N-2-CI357 CH3 CI O C6H3-2，6-F2358 CH3 CI O C6H4-3-CI359 CH3 CI O C6H4-4-CI360 CH3 CI O C6H4-4-F361 CH3 CI O C6H4-4-C4H9t362 CH3 CI O C6H4-4-CO2CH3363 CH3 CI O C6H4-4-CO2C4H9t364 CH3 CI O 5-C5H3N-2-CI365 CH3 CI O 3-C5H3N-2-CI366 CH3 CI NCH3 CH2C6H4-4-CI367 CH3 CI NCH3 CH2C6H4-4-F368 CH3 CI NCH3 CH2C6H4-4-C4H9t369 CH3 CI NCH3 CH2C6H4-4-CO2CH3370 CH3 CI NCH3 CH2C6H4-4-CO2C4H9t371 CH3 CI NCH3 CH2-5-C5H3N-2-CI372 CH3 CI NCH3 CH2-3-C5H3N-2-CI373 CH3 CI NCH3 C6H4-4-CI374 CH3 CI NCH3 C6H4-4-F375 CH3 CI NCH3 C6H4-4-C4H9t376 CH3 CI NCH3 C6H4-4-CO2CH3377 CH3 CI NCH3 C6H4-4-CO2C4H9t378 CH3 CI NCH3 5-C5H3N-2-CI379 CH3 CI NCH3 3-C5H3N-2-CI380 CH3 CI NCH3 C6H3-2，6-F2381 CH3 CI NCH3 C6H4-3-CI382 CH3 OPh O CH2C6H4-4-CI383 CH3 OPh O CH2C6H4-4-F384 CH3 OPh O CH2C6H4-4-C4H9t385 CH3 OPh O CH2C6H4-4-CO2CH3386 CH3 OPh O CH2C6H4-4-CO2C4H9t387 CH3 OPh O CH2-5-C5H3N-2-CI388 CH3 OPh O CH2-3-C5H3N-2-CI389 CH3 OPh O C6H3-2，6-F2390 CH3 OPh O C6H4-3-CI391 CH3 OPh O C6H4-4-CI392 CH3 OPh O C6H4-4-F393 CH3 OPh O C6H4-4-C4H9t394 CH3 OPh O C6H4-4-CO2CH3395 CH3 OPh O C6H4-4-CO2C4H9t396 CH3 OPh O 5-C5H3N-2-CI397 CH3 OPh O 3-C5H3N-2-CI398 CH3 OPh NCH3 CH2C6H44-CI399 CH3 OPh NCH3 CH2C6H4-4-F400 CH3 OPh NCH3 CH2C6H4-4-C4H9t401 CH3 OPh NCH3 CH2C6H4-4-CO2CH3402 CH3 OPh NCH3 CH2C6H4-4-CO2C4H9t403 CH3 OPh NCH3 CH2-5-C5H3N-2-CI404 CH3 OPh NCH3 CH2-3-C5H3N-2-CI405 CH3 OPh NCH3 C6H4-4-CI406 CH3 OPh NCH3 C6H4-4-F407 CH3 OPh NCH3 C6H4-4-C4H9t408 CH3 OPh NCH3 C6H4-4-CO2CH3409 CH3 OPh NCH3 C6H4-4-CO2C4H9t410 CH3 OPh NCH3 5-C5H3N-2-CI411 CH3 OPh NCH3 3-C5H3N-2-CI412 CH3 OPh NCH3 C6H3-2，6-F2413 CH3 OPh NCH3 C6H4-3-CI414 CI OPh NCH3 C6H4-4-CI415 CI OPh NCH3 C6H4-4-F416 CI OPh NCH3 C6H4-4-C4H9t417 CI OPh NCH3 C6H4-4-CO2CH3418 CI CI O C6H4-4-CI419 CI CI O C6H4-4-F420 CI CI O C6H4-4-C4H9t421 CI CI O C6H4-4-CO2CH3表6R1和XR3的位置可在吡唑的3位、4或5位。R1 XR3 R2 QCH3 CI CH3 CH2C6H4-4-CICH3 CI CH3 CH2C6H4-4-FCH3 CI CH3 CH2C6H4-4-C4H9tCH3 CI CH3 CH2C6H4-4-CO2CH3CH3 CI CH3 CH2C6H4-4-CO2C4H9tCH3 OPh CH3 CH2-3-C5H3N-6-CICH3 CI CH3 CH2-3-C5H3N-2-CICH3 CI CH3 C6H3-2，6-F2CH3 CI CH3 C6H4-3-CICH3 CI CH3 C6H4-4-CICH3 CI CH3 C6H4-4-FCH3 CI CH3 C6H4-4-C4H9tCH3 CI CH3 C6H4-4-CO2CH3CH3 CI CH3 C6H4-4-CO2C4H9tCH3 CI CH3 5-C5H3N-2-CICH3 OPh CH3 3-C5H3N-2-CICH3 CI CH3 NHC6H5CH3 CI CH3 NH-3-C5H3N-6-CICH3 F CH3 CH2C6H4-4-CICH3 F CH3 CH2C6H4-4-FCH3 F CH3 CH2C6H4-4-C4H9tCH3 F CH3 CH2C6H4-4-CO2CH3CH3 F CH3 CH2C6H4-4-CO2C4H9tCH3 F CH3 CH2-3-C5H3N-6-CICH3 F CH3 CH2-3-C5H3N-2-CIH H Ph C6H3-2，6-F2CH3 F CH3 C6H4-3-CICH3 F CH3 C6H4-4-CICH3 F CH3 C6H4-4-FCH3 F CH3 C6H4-4-C4H9tCH3 F CH3 C6H4-4-CO2CH3CH3 F CH3 C6H4-4-CO2C4H9tCH3 F CH3 5-C5H3N-2-CICH3 F CH3 3-C5H3N-2-CICH3 F CH3 NHC6H5CH3 F CH3 NH-5-C5H3N-2-CIF F CH3 CH2C6H4-4-CIF F CH3 CH2C6H4-4-FF F CH3 CH2C6H4-4-C4H9tF F CH3 CH2C6H4-4-CO2CH3F F CH3 CH2C6H4-4-CO2C4H9tF F CH3 CH2-3-C5H3N-6-CIF F CH3 CH2-3-C5H3N-2-CIF F CH3 C6H3-2，6-F2F F CH3 C6H4-3-CIF F CH3 C6H4-4-CIF F CH3 C6H4-4-FF F CH3 C6H4-4-C4H9tF F CH3 C6H4-4-CO2CH3F F CH3 C6H4-4-CO2C4H9tF F CH3 5-C5H3N-2-CIF F CH3 3-C5H3N-2-CIF F CH3 NHC6H5CF3 H CH3 C6H4-3-CF3CF3 H C2H5 C6H4-4-C4H9tF CH3 F C6H3-2-OC2H5-4-C4H9tF F CH3 NH-5-C5H3N-2-CI表7R1 R2 R3 ZQCH3 CH3 H OCH2C6H4-4-C4H9tCH3 CH3 H OCH2C6H4-4-CO2C4H9tCH3 CH3 H OCH2C6H4-4-CO2CH3CH3 CH3 H OCH2C6H4-4-CICH3 C2H5 H OCH2C6H4-4-CNCH3 CH3 H OCH2C6H4-4-CF3CH3 CH3 H OCH2C6H4-4-OCF3CH3 CH3 H OCH2C6H4-4-NO2CH3 CH3 H OCH2-3-吡啶-6-CICH3 CH3 H OCH2-2-呋喃CH3 CH3 H OCH2-2-噻酚CH3 CH3 H OCH2-1-1，2，4-三唑CH3 CH3 H OCH2-1-吡唑CH3 CH3 H OCH2-2-嘧啶CH3 CH3 H C6H4-3-OCH(CH3)CH3 CH3 CI OCH2C6H4-4-C4H9tCH3 CH3 CI OCH2C6H4-4-CO2C4H9tCH3 CH3 CI OCH2C6H4-4-CO2CH3CH3 CH3 CI OCH2C6H4-4-CICH3 C2H5 CI OCH2C6H4-4-CNCH3 CH3 CI OCH2C6H4-4-CF3CH3 CH3 CI OCH2C6H4-4-OCF3CH3 CH3 CI OCH2C6H4-4-NO2CH3 CH3 CI OCH2-3-吡啶-6-CICH3 CH3 CI OCH2-2-呋喃CH3 CH3 CI OCH2-2-噻酚CH3 CH3 CI OCH2-1-1，2，4-三唑CH3 CH3 CI OCH2-1-吡唑CH3 CH3 CI OCH2-2-嘧啶CH3 CH3 CI C6H4-3-OCH(CH3)2C4H9t CH3 H OCH2C6H4-4-C4H9tC4H9t CH3 H OCH2C6H4-4-CO2C4H9tC4H9t CH3 H OCH2C6H4-4-CO2CH3C4H9t CH3 H OCH2C6H4-4-CIC4H9t CH3 H OCH2C6H4-4-CNC4H9t CH3 H OCH2C6H4-4-CF3C4H9t CH3 H OCH2C6H4-4-OCF3C4H9t CH3 H OCH2C6H4-4-NO2C4H9t CH3 H OCH2-3-吡啶-6-CIC4H9t CH3 H OCH2-2-呋喃C4H9t CH3 H OCH2-2-噻酚C4H9t CH3 H OCH2-1-1，2，4-三唑C4H9t CH3 H OCH2-1-吡唑C4H9t CH3 H OCH2-2-嘧啶C4H9t CH3 H C6H4-3-OCH(CH3)C4H9t CH3 CI OCH2C6H4-4-C4H9tC4H9t CH3 CI OCH2C6H4-4-CO2C4H9tC4H9t CH3 CI OCH2C6H4-4-CO2CH3C4H9t CH3 CI OCH2C6H4-4-CIC4H9t CH3 CI OCH2C6H4-4-CNC4H9t CH3 CI OCH2C6H4-4-CF3C4H9t CH3 CI OCH2C6H4-4-OCF3C4H9t CH3 CI OCH2C6H4-4-NO2C4H9t CH3 CI OCH2-3-吡啶-6-CIC4H9t CH3 CI OCH2-2-呋喃C4H9t CH3 CI OCH2-2-噻酚C4H9t CH3 CI OCH2-1-1，2，4-三唑C4H9t CH3 CI OCH2-1-吡唑C4H9t CH3 CI OCH2-2-嘧啶C4H9t CH3 CI C6H4-3-OCH(CH3)2C2H5 CH3 H OCH2C6H4-4-C4H9tC2H5 CH3 H OCH2C6H4-4-CO2C4H9tC2H5 CH3 H OCH2C6H4-4-CO2CH3C2H5 CH3 H OCH2C6H4-4-CIC2H5 CH3 H OCH2C6H4-4-CNC2H5 CH3 H OCH2C6H4-4-CF3C2H5 CH3 H OCH2C6H4-4-OCF3C2H5 CH3 H OCH2C6H4-4-NO2C2H5 CH3 H OCH2-3-吡啶-6-CIC2H5 CH3 H OCH2-2-呋喃C2H5 CH3 H OCH2-2-噻酚C2H5 CH3 H OCH2-1-1，2，4-三唑C2H5 CH3 H OCH2-1-吡唑C2H5 CH3 H OCH2-2-嘧啶C2H5 CH3 H C6H4-3-OCH(CH3)C2H5 CH3 CI OCH2C6H4-4-C4H9tC2H5 CH3 CI OCH2C6H4-4-CO2C4H9tC2H5 CH3 CI OCH2C6H4-4-CO2CH3C2H5 CH3 CI OCH2C6H4-4-CIC2H5 CH3 CI OCH2C6H4-4-CNC2H5 CH3 CI OCH2C6H4-4-CF3C2H5 CH3 CI OCH2C6H4-4-OCF3C2H5 CH3 CI OCH2C6H4-4-NO2C2H5 CH3 CI OCH2-3-吡啶-6-CIC2H5 CH3 CI OCH2-2-呋喃C2H5 CH3 CI OCH2-2-噻酚C2H5 CH3 CI OCH2-1-1，2，4-三唑C2H5 CH3 CI OCH2-1-吡唑C2H5 CH3 CI OCH2-2-嘧啶C2H5 CH3 CI C6H4-3-OCH(CH3)2CH3 CH3 CI NHC6H4-4-C4H9tCH3 CH3 CI NHC6H4-4-CO2C4H9tCH3 CH3 CI NHC6H4-4-CO2CH3CH3 CH3 CI NHC6H4-4-CICH3 CH3 CI NHC6H4-4-CNCH3 CH3 CI NHC6H4-4-CF3CH3 CH3 CI NHC6H4-4-OCF3CH3 CH3 CI NHC6H4-4-NO2CH3 CH3 CI NHCH2-3-吡啶-6-CICH3 CH3 CI NHCH2-2-呋喃CH3 CH3 CI NHCH2-2-噻酚CH3 CH3 CI NHCH2-1-1，2，4-三唑CH3 CH3 CI NHCH2-1-吡唑CH3 CH3 CI NHCH2-2-嘧啶CH3 CH3 CI NHCH2C6H4-4-OCH(CH3)CH3 CH3 CI NHCH2C6H4-4-C4H9tCH3 CH3 CI NHCH2C6H4-4-CO2C4H9tCH3 CH3 CI NHCH2C6H4-4-CO2CH3CH3 CH3 CI NHCH2C6H4-4-CICH3 CH3 CI NHCH2C6H4-4-CNCH3 CH3 CI NHCH2C6H4-4-CF3CH3 CH3 CI NHCH2C6H2-2，6-CI2-4-OCF3CH3 CH3 CI NHCH2C6H4-4-NO2CH3 CH3 CI NH-3-吡啶-6-CICH3 CH3 CI NH-2-呋喃CH3 CH3 CI NH-2-噻酚CH3 CH3 CI NH-1-1，2，4-三唑CH3 CH3 CI NH-2-嘧啶CH3 CH3 CI NH-2-嘧啶-4，6-(OMe)2CH3 CH3 CI NH-2-嘧啶-4，6-(Me)2CH3 CH3 H NHC6H4-4-C4H9tCH3 CH3 H NHC6H4-4-CO2C4H9tCH3 CH3 H NHC6H4-4-CO2CH3CH3 CH3 H NHC6H4-4-CICH3 CH3 H NHC6H4-4-CNCH3 CH3 H NHC6H4-4-CF3CH3 CH3 H NHC6H4-4-OCF3CH3 CH3 H NHC6H4-4-NO2CH3 CH3 H NHCH2-3-吡啶-6-CICH3 CH3 H NHCH2-2-呋喃CH3 CH3 H NHCH2-2-噻酚CH3 CH3 H NHCH2-1-1，2，4-三唑CH3 CH3 H NHCH2-1-吡唑CH3 CH3 H NHCH2-2-嘧啶CH3 CH3 H NHCH2C6H4-4-OCH(CH3)CH3 CH3 H NHCH2C6H4-4-C4H9tCH3 CH3 H NHCH2C6H4-4-CO2C4H9tCH3 CH3 H NHCH2C6H4-4-CO2CH3CH3 CH3 H NHCH2C6H4-4-CICH3 CH3 H NHCH2C6H4-4-CNCH3 CH3 H NHCH2C6H4-4-CF3CH3 CH3 H NHCH2C6H2-2，6-CI2-4-OCF3CH3 CH3 H NHCH2C6H4-4-NO2CH3 CH3 H NH-3-吡啶-6-CICH3 CH3 H NH-2-呋喃CH3 CH3 H NH-2-噻酚CH3 CH3 H NH-1-1，2，4-三唑CH3 CH3 H NH-2-嘧啶CH3 CH3 H NH-2-嘧啶-4，6-(Me)2CF3 CH3 H OCH2C6H4-4-C4H9tCF3 CH3 H OCH2C6H4-4-CO2C4H9tCF3 CH3 H OCH2C6H4-4-CO2CH3CF3 CH3 H OCH2C6H4-4-CICF3 CH3 H OCH2C6H4-4-CNCF3 CH3 H OCH2C6H4-4-CF3CF3 CH3 H OCH2C6H4-4-OCF3CF3 CH3 H OCH2C6H4-4-NO2CF3 CH3 H OCH2-3-吡啶-6-CICF3 CH3 H OCH2-2-呋喃CF3 CH3 H OCH2-2-噻酚CF3 CH3 H OCH2-1-1，2，4-三唑CF3 CH3 H OCH2-1-吡唑CF3 CH3 H OCH2-2-嘧啶CF3 CH3 H C6H4-3-OCH(CH3)2CF3 CH3 H NHC6H4-4-C4H9tCF3 CH3 H NHC6H4-4-CO2C4H9tCF3 CH3 H NHC6H4-4-CO2CH3CF3 CH3 H NHC6H4-4-CICF3 CH3 H NHC6H4-4-CNCF3 CH3 H NHC6H4-4-CF3CF3 CH3 H NHC6H4-4-OCF3CF3 CH3 H NHC6H4-4-NO2CF3 CH3 H NHCH2-3-吡啶-6-CICF3 CH3 H NHCH2-2-呋喃CF3 CH3 H NHCH2-2-噻酚CF3 CH3 H NHCH2-1-1，2，4-三唑CF3 CH3 H NHCH2-1-吡唑CF3 CH3 H NHCH2-2-嘧啶CF3 CH3 H NHCH2C6H4-4-OCH(CH3)CF3 CH3 H NHCH2C6H4-4-C4H9tCF3 CH3 H NHCH2C6H4-4-CO2C4H9tCF3 CH3 H NHCH2C6H4-4-CO2CH3CF3 CH3 H NHCH2C6H4-4-CICF3 CH3 H NHCH2C6H4-4-CNCF3 CH3 H NHCH2C6H4-4-CF3CF3 CH3 H NHCH2C6H2-2，6-CI2-4-OCF3CF3 CH3 H NHCH2C6H4-4-NO2CF3 CH3 H NH-3-吡啶-6-CICF3 CH3 H NH-2-呋喃CF3 CH3 H NH-2-噻酚CF3 CH3 H NH-1-1，2，4-三唑CF3 CH3 H NH-2-嘧啶CF3 CH3 H NH-2-嘧啶-4，6-(Me)2CF3 CH3 CI NHC6H4-4-C4H9tCF3 CH3 CI NHC6H4-4-CO2C4H9tCF3 CH3 CI NHC6H4-4-CO2CH3CF3 CH3 CI NHC6H4-4-CICF3 CH3 CI NHC6H4-4-CNCF3 CH3 CI NHC6H4-4-CF3CF3 CH3 CI NHC6H4-4-OCF3CF3 CH3 CI NHC6H4-4-NO2CF3 CH3 CI NHCH2-3-吡啶-6-CICF3 CH3 CI NHCH2-2-呋喃CF3 CH3 CI NHCH2-2-噻酚CF3 CH3 CI NHCH2-1-1，2，4-三唑CF3 CH3 CI NHCH2-1-吡唑CF3 CH3 CI NHCH2-2-嘧啶CF3 CH3 CI NHCH2C6H4-4-OCH(CH3)CF3 CH3 CI NHCH2C6H4-4-C4H9tCF3 CH3 CI NHCH2C6H4-4-CO2C4H9tCF3 CH3 CI NHCH2C6H4-4-CO2CH3CF3 CH3 CI NHCH2C6H4-4-CICF3 CH3 CI NHCH2C6H4-4-NCF3 CH3 CI NHCH2C6H4-4-CF3CF3 CH3 CI NHCH2C6H2-2，6-CI2-4-OCF3CF3 CH3 CI NHCH2C6H4-4-NO2CF3 CH3 CI NH-3-吡啶-6-CICF3 CH3 CI NH-2-呋喃CF3 CH3 CI NH-2-噻酚CF3 CH3 CI NH-1-1，2，4-三唑CF3 CH3 CI NH-2-嘧啶CF3 CH3 CI NH-2-嘧啶-4，6-(OMe)2CF3 CH3 CI NH-2-嘧啶-4，6-(Me)2Table 1

化合物编号X R3 R4 R1 O C6H5 CI C4H9t2 O C6H5 NH2 C4H9t3 O C6H5 NHCH3 C4H9t4 O C6H5 NHCO2CH3 C4H9t5 O C6H5 NHCOCH3 C4H9t6 O C6H5 N(Me)2 C4H9t7 O C6H5 NHSO2CH3 C4H9t8 O C6H6 OCH3 C4H9t9 O C6H5 SCH3 C4H9t10 O C6H5 1， 2,4-triazol-1-yl C4H9t11 O C6H5 imidazol-1-yl C4H9t12 S C6H5 CI C4H9t13 S C6H5 NH2 C4H9t14 S C6H5 NHCH3 C4H9t15 S C6H5 NHCO2CH3 C4H9t16 S C6H6 NHCOCH3 C4H9t17 S C6H4 CH2CH3 N(Me) C4H9t19 S C6H5 OCH3 C4H9t20 S C6H5 SCH3 C4H9t21 S C6H5 1，2，4-三唑-1-基C4H9t22 S C6H5 咪唑-1-基C4H9t23 S C10H7 CI C4H9t24 S C10H7 NH2 C4H9t25 S C10H7 NHCH3 C4H9t26 S C10H7 NHCO2CH3 C4H9t27 S C10H7 NHCOCH3 C4H9t28 S C10H7 N(Me)2 C4H9t29 S C10H7 NHSO2CH3 C4H9t30 S C10H7 OCH3 C4H9t31 S C10H7 SCH3 C4H9t32 S C10H7 1,2,4-Triazol-1-yl C4H9t33 S C10H7 Imidazol-1-yl CI C10H94 C4H9t3 C10H7 NH2 C4H9t36 O C10H7 NHCH3 C4H9t37 O C10H7 NHCO2CH3 C4H9t38 O C10H7 NHCOCH3 C4H9t39 O C10H7 N(Me)2 C4H9t40 O C10H7 NHSO2CH3 C4H9t41 O C10H7 OCH3 C4H9t42 O C10H7 SCH3 C4H9t43 O C10H7 1，2，4-三唑-1-基C4H9t44 O C10H7 咪唑-1-基C4H9t45 O C10H7 CI CO2C4H9t46 O C10H7 NH2 CO2C4H9t47 O C10H7 NHCH3 CO2C4H9t48 O C10H7 NHCO2CH3 CO2C4H9t49 O C10H7 NHCOCH3 CO2C4H9t50 O C10H7 N(Me)2 CO2C4H9t51 O C10H7 NHSO2CH3 CO2C4H9t52 O C10H7 OCH3 CO2C4H9t53 O C10H7 SCH3 CO2C4H9t54 O C10H7 1，2，4-三唑-1-基CO2C4H9t55 O C10H7 咪唑-1-基CO2C4H9t56 S C10H7 CI CO2C4H9t57 S C10H7 NH2 CO2C4H9t58 S C10H7 NHCH3 CO2C4H9t59 S C10H7 NHCO2CH3 CO2C4H9t60 S C10H7 NHCOCH3 CO2C4H9t61 S C10H7 N(Me)2 CO2C4H9t62 S C10H7 NHSO2CH3 CO2C4H9t63 S C10H7 OCH3 CO2C4H9t64 S C10H7 SCH3 CO2C4H9t65 S C10H7 1，2，4-三唑-1-基CO2C4H9t66 S C10H7 咪唑-1-基CO2C4H9t67 S C6H5 CI CO2C4H9t68 S C6H5 NH2 CO2C4H9t69 S C6H5 NHCH3 CO2C4H9t70 S C6H5 NHCO2CH3 CO2C4H9t71 S C6H5 NHCOCH3 CO2C4H9t72 S C6H5 N(Me)2 CO2C4H9t73 S C6H5 NHSO2CH3 CO2C4H9t74 S C6H6 OCH3 CO2C4H9t75 S C6H5 SCH3 CO2C4H9t76 S C6H5 1，2，4-三唑-1-基CO2C4H9t77 S C6H5 咪唑-1-基CO2C4H9t78 O C6H5 CI CO2C4H9t79 O C6H5 NH2 CO2C4H9t80 O C6H5 NHCH3 CO2C4H9t81 O C6H5 NHCO2CH3 CO2C4H9t82 O C6H6 NHCOCH3 CO2C4H9t83 O C6H5 N(Me)2 CO2C4H9t84 O C6H5 NHSO2CH3 CO2C4H9t85 O C6H5 OCH3 CO2C4H9t86 O C6H5 SCH3 CO2C4H9t87 O C6H5 1，2，4-三唑-1-基CO2C4H9t88 O C6H5 咪唑-1-基CO2C4H9t89 O C6H6 CN CO2C4H9t90 O C6H6 CN C4H9t91 O C6H6 NHCH2CO2CH3 C4H9t92 O C6H6 NHCH2CO2CH3 CO2C4H9t93 O C6H5 H CO2C(Me)2CN94 O C6H5 H CO2C(Me)2CCI395 O C6H5 CI CO2C(Me)2CN96 O C6H5 CI CO2C(Me)2CCI3

Table 2

化合物编号X R3 R4 R97 O C6H5 CI C4H9t98 O C6H5 NH2 C4H9t99 O C6H5 NHCH3 C4H9t100 O C6H5 NHCO2CH3 C4H9t101 O C6H5 NHCOCH3 C4H9t102 O C6H5 N(Me)2 C4H9t103 O C6H5 NHSO2CH3 C4H9t104 O C6H6 OCH3 C4H9t105 O C6H5 SCH3 C4H9t106 O C6H5 1， 2，4-三唑-1-基C4H9t107 O C6H5 咪唑-1-基C4H9t108 S C6H5 CI C4H9t109 S C6H5 NH2 C4H9t110 S C6H5 NHCH3 C4H9t111 S C6H5 NHCO2CH3 C4H9t112 S C6H6 NHCOCH3 C4H9t113 S C6H5 N(Me)2 C4H9t114 S C6H5 NHSO2CH3 C4H9t115 S C6H5 OCH3 C4H9t116 S C6H5 SCH3 C4H9t117 S C6H5 1，2，4-三唑-1-基C4H9t118 S C6H5 咪唑-1-基C4H9t119 S C6H5 CI CO2C4H9t120 S C6H5 NH2 CO2C4H9t121 S C6H5 NHCH3 CO2C4H9t122 S C6H5 NHCO2CH3 CO2C4H9t123 S C6H5 NHCOCH3 CO2C4H9t124 S C6H5 N(Me)2 CO2C4H9t125 S C6H5 NHSO2CH3 CO2C4H9t126 S C6H6 OCH3 CO2C4H9t127 S C6H5 SCH3 CO2C4H9t128 S C6H5 1，2，4-三唑-1-基CO2C4H9t129 S C6H5 咪唑-1-基CO2C4H9t130 O C6H5 CI CO2C4H9t131 O C6H5 NH2 CO2C4H9t132 O C6H5 NHCH3 CO2C4H9t133 O C6H5 NHCO2CH3 CO2C4H9t134 O C6H6 NHCOCH3 CO2C4H9t135 O C6H5 N(Me)2 CO2C4H9t136 O C6H5 NHSO2CH3 CO2C4H9t137 O C6H5 OCH3 CO2C4H9t138 O C6H5 SCH3 CO2C4H9t139 O C6H5 1，2，4-三唑-1-基CO2C4H9t140 O C6H5 imidazol-1-yl CO2C4H9t141 O C6H5 H CO2C(Me)2CN142 O C6H5 H CO2C(Me)2CC3143 O C6H5 CI CO2C(Me)2CN144 O C6H5 CI CO2C(Me)2CCI3 Table 3

Compound No. XR3 R1 Z Q145 CI CH3 - CH2C6H4-4-CF3146 CI CH3 - CH2C6H4-4-C4H9t147 CI CH3 - CH2C6H4-4-CI148 CI CH3 - CH2C6H4-4-OCF3149 OPh CH3 - CH2C6H4-4-OCF3150 - NHC 6H CI 4 -4-CF3151 CI CH3 - NHC6H4-4-C4H9t152 CI CH3 - NHC6H4-4-CI153 CI CH3 - NHC6H4-4-OCF3154 CI CH3 - NHC6H4-4-OC2HF4155 CI CH3 - C6H4-3-OCH(CH3)2156 CI CH3 O CH2C6H4-4-But157 OPh CH3 O CH2C6H4-4-CO2But158 CI CH3 - NH2C6H3-2,6-(Me)2159 CI CH3 - NHC6H4-4-NO2160 CI CH3 - NHC6H5161 CI CH3 O CH2C6H4-4-OCF3162 CI CH3 O CH2-1-(1,2,4-triazole)163 CI CH3 - C6H4-4-F164 CI CI - C6H4-4-CF3165 CI CI - C6H4-4-C4H9t166 CI CI - C6H4-4-CI167 CI CI - C6H4-4-OCF3168 CI CI - C6H4-3-OCH(CH3)2169 CI CI - C6H4-4-F170 CI CI - CH2C6H4-4-CF3171 CI CI - CH2C6H4-4-C4H9t172 CI CI - CH2C6H4-4-CI173 CI CI - CH2C6H4-4-OCF3174 CI CI - CH2C6H4-4-OC2HF4175 CI CI - NHC6H4-4-CF3176 CI CI - NHC6H4-4-C4H9t177 CI CI - NHC6H4-4-CI178 CI CI - NHC6H4-4-OCF3179 CI CI - NHC6H4-4-OC2HF4180 OPh CH3 - C6H4-3-OCH(CH3)2181 CI CI - NHC6H2-2, 6-CI2-4-CF3182 CI CH3 - NHC6H2-2, 6-CI2-4CF3183 CI CI - CH2C6H2-2, 6-CI2-4-CF3184 CI CH3 - CH2C6H2-2, 6-CI2-4-CF3185 CI CF3 - CH2-2-thiophene-4-CO2CH3186 CI CF3 - CH2-3-C5H3N-6-CI187 CI CF3 - 3 -C5H3N-6-CI(pyridine)188 CI CF3 - CH2-2-C4H3O(furan 189 CI CF3 - NHC6H4-4-CF3190 CF3 CI - CH2-2-thiophene-4-CO2CH3191 CF3 CI - CH2-3-C5H3N -6-CI192 CF3 CI - 3-C5H3N-6-CI193 CF3 CI - CH2C6H4-4-CF3194 CF3 CI - NHC6H4-4-CF3195 CI CH3 -

196 CI CF3 - C6H2-2, 6-(Br)2-4-OCF3197 OPh CF3 - NHC6H4-4-CF3198 OPh CF3 - NHC6H4-4-NO2199 CI CF3 - NHC6H4-4-CN200 CI CF3 - C6H2-2, 6 -(Br)2-4-OCF3 Table 4

Compound No. XR3 R4 YR201 CI NH2 CH2C6H4-4-CF3202 CI NH2 CH2C6H4-4-C4H9t203 CI NH2 CH2C6H4-4-CI204 CI NH2 CH2C6H4-4-OCF3205 CI NH2 CH2C6H4-4-OC2HHF4206 CI N404 N6HC -4-C4H9t208 CI NH2 NHC6H4-4-CI209 CI NH2 NHC6H4-4-OCF3210 CI NH2 NHC6H4-4-OC2HF4211 CI NH2 C6H4-3-OCH(CH3)2212 CI NH2 NHC6H2-2, 6-CI2-4-CF3213 CI NH2 CH2C6H2-2, 6-CI2-4-CF3214 CI NH2 C6H4-4-CF3215 CI NH2 C6H4-4-C4H9t216 CI NH2 C6H4-4-CI217 CI NH2 C6H4-4-OCF3218 CI NH2 C6H4-4-OC2HF4219 CI NH2 C6H4 -4-F220 OPh H CH2C6H4-4-CF3221 OPh H CH2C6H4-4-C4H9t222 OPh H CH2C6H4-4-CI223 OPh H CH2C6H4-4-OCF3224 OPh H CH2C6H4-4-OC2HF4225 OPh H NHC6H4-4-CF3226 OPh H NHC6H 4-C4H9t227 OPh H NHC6H4-4-CI228 OPh H NHC6H4-4-OCF3229 OPh H NHC6H4-4-OC2HF4230 OPh H C6H4-3-OCH(CH3)2231 OPh H NHC6H2-26-CI2-4-CF3232 OPh H CH2C6H2- 2, 6-CI2-4-CF3233 OPh H C6H4-4-CF3234 OPh H C6H4-4-C4H9t235 OPh H C6H4-4-CI236 OPh H C6H4-4-OCF3237 OPh H C6H4-4-OC2HF4238 OPh H C6H4-4- F239 OPh CI CH2C6H4-4-CF3240 OPh CI CH2C6H4-4-C4H9t241 OPh CI CH2C6H4-4-CI242 OPh CI CH2C6H4-4-OCF3243 OPh CI CH2C6H4-4-OC2HF4244 OPh CI NHC6H4-4-CF3245 OPh4CI N OPh CI NHC6H4-4-CI247 OPh CI NHC6H4-4-OCF3248 OPh CI NHC6H4-4-OC2HF4249 OPh CI C6H4-3-OCH(CH3)2250 OPh CI NHC6H2-2, 6-CI2-4-CF3251 OPh CI CH2C6H2-2 , 6-CI2-4-CF3252 OPh CI C6H4-4-CF3253 OPh CI C6H4-4-C4H9t254 OPh CI C6H4-4-CI255 OPh CI C6H4-4-OCF3256 OPh CI C6H4-4-OC2HF4257 OPh CI C6H4-4-F258 CI CI CH2C6H4-4-CF3259 CI CI CH2C6H4-4-C4H9t260 CI CI CH2C6H4-4-CI261 CI CI CH2C6H4-4-OCF3262 CI CI CH2C6H4-4-OC2HF4263 CI CI NHC6H4-4-CF3264 CI 4 CI NHC6H5 CI NHC6H4-4-CI266 CI CI NHC6H4-4-OCF3267 CI CI NHC6H4-4-OC2HF4268 CI CI C6H4-3-OCH(CH3)2269 CI CI NHC6H2-2, 6-CI2-4-CF3270 CI CI CH2C6H2-2, 6-CI2-4-CF3271 CI CI C6H4-4-CF3272 CI CI C6H4-4-C4H9t273 CI CI C6H4-4-CI274 CI CI C6H4-4-OCF3275 CI CI C6H4-4-OC2HF4276 CI CI C6H4-4-F277 CI H OCH2CO2C2H5278 CI H OCH(Mc)CO2C2H5279 CI H OCH2-1-(1,2,4-triazole)280 CI H OCONHCH3281 CI H OCONHC6H4-4-CI282 CI H OCONHC6H4-4-CF3283 CI H OCONHC6H4-4-OCF3284 CI H OCONHC6H3-3,4-CI2285 CI H NHCONHC6H4-4-CI286 CI H N(CH3)CONHC6H4-4-CI287 CI H NHCONHC6H4-4-CF3288 CI H NHCONHC6H4-4-OCF3289 CI H NHCONHC6H3-3,4-CI2290 CI H OCOC6H4-4-F291 CI H OCOC6H4-4-CI292 CI H OCOC6H3-2, 6-F2293 CI H NHCOC6H4-4-F294 CI H NHCOC6H4-4-CI295 CI H NHCOC6H3-2, 6-F2296 CI H OCONHCOC6H3-2 , 6-F2297 CI H OCONHCOC6H4-2-F298 CI H OCONHCOC6H3-2, 6-CI2299 CI H OCONHCOC6H4-2-CI300 CI H NHCONHCOC6H3-2, 6-F2301 CI H NHCONHCOC6H4-2-F302 CI H NHCONHCOC6H3-2, 6 -I2303 CI H NHCONHCOC6H4-2-CI304 OPh H OCH2CO2C2H5305 OPh H OCH(Me)CO2C2H5306 OPh H OCH2-1-(1,2,4-triazole)307 OPh H OCONHCH3308 OPh H OCONHC6H4-4-CI309 OPh H OCONHC6H4- 4-CF3310 OPh H OCONHC6H4-4-OCF3311 OPh H OCONHC6H3-3, 4-CI2312 OPh H NHCONHC6H4-4CI313 OPh H N(CH3)CONHC6H4-4CI314 OPh H NHCONHC6H4-4-CF3315 OPh H NHCONHC6H4-4-OCF3316 OPh H NHCONHC6H 3,4-CI2317 OPh H OCOC6H4-4-F318 OPh H OCOC6H4-4-CI319 OPh H OCO6H3-2,6-F2320 OPh H NHCOC6H4-4-F321 OPh H NHCOC6H4-4-CI322 OPh H NHCOC6H3-2,6- F2323 OPh H OCONHCOC6H3-2, 6-F2324 OPh H OCONHCOC6H4-2-F325 OPh H OCONHCOC6H3-2, 6-CI2326 OPh H OCONHCOC6H4-2-CI327 OPh H NHCONHCOC6H3-2, 6-F2328 OPh H NHCONHCOC6H4-2-F329 OPh H NHCONHCOC6H3-2, 6-CI2330 OPh H NHCONHCOC6H4-2-CI331 CI H OCH2C6H4-4-C4H9t332 CI H OCH2C6H4-4-CO2C4H9t333 CI H NHCH2C6H4-4-C4H9t334 CI H NHCH2C6H4-4-CO2C3Ht6H4 H9CH4 O9CH2 OPh H OCH2C6H4-4-CO2C4H9t337 OPh H NHCH2C6H4-4-C4H9t338 OPh H NHCH2C6H4-4-CO2C4H9t339 OPh H OCH2P(S)(OC2H5)2340 OPh H OCH2P(O)OC2H5(SC3H7)341 OPh H P(S)(OC2H5) 2342 OPh H P(O)OC2H5(SC3H7)343 OPh H OCH2-3-C6H3N-6-CI344 OPh NH2 OCH2-3-C6H3N-6-CI345 OPh CN OCONHCH ₃ 346 OPh CO ₂ CH ₃ OCH ₃ 347 OPh H OCOCH2CH2CO2H348 OPh HOCOCH＝CHCO2CH3349 OPh

table 5

Compound No. R1 XR3 Y R350 CH3 CI O CH2C6H4-4-CI351 CH3 CI O CH2C6H4-4-F352 CH3 CI O CH2C6H4-4-C4H9t353 CH3 CI O CH2C6H4-4-CO2CH3354 CH3 CI O CH2C6H4-CH4-CO2C4H2CI O355 -5-C5H3N-2-CI356 CH3 CI O CH2-3-C5H3N-2-CI357 CH3 CI O C6H3-2, 6-F2358 CH3 CI O C6H4-3-CI359 CH3 CI O C6H4-4-CI360 CH3 CI O C6H4 -4-F361 CH3 CI O C6H4-4-C4H9t362 CH3 CI O C6H4-4-CO2CH3363 CH3 CI O C6H4-4-CO2C4H9t364 CH3 CI O 5-C5H3N-2-CI365 CH3 CI O 3-C5H3N-2-CI366 CH3 CI NCH3 CH2C6H4-4-CI367 CH3 CI NCH3 CH2C6H4-4-F368 CH3 CI NCH3 CH2C6H4-4-C4H9t369 CH3 CI NCH3 CH2C6H4-4-CO2CH3370 CH3 CI NCH3 CH2C6H4-4-CO2C4H9H5CH371 CH3 CI 252C CH3 CI NCH3 CH2-3-C5H3N-2-CI373 CH3 CI NCH3 C6H4-4-CI374 CH3 CI NCH3 C6H4-4-F375 CH3 CI NCH3 C6H4-4-C4H9t376 CH3 CI NCH3 C6H4-4-CO2CH3377 CH3 CI NCH3 C6H4-4 -CO2C4H9t378 CH3 CI NCH3 5-C5H3N-2-CI379 CH3 CI NCH3 3-C5H3N-2-CI380 CH3 CI NCH3 C6H3-2, 6-F2381 CH3 CI NCH3 C6H4-3-CI382 CH3 OPh O CH2C6H4-4-CI383 CH3 OPh O CH2C6H4-4-F384 CH3 OPh O CH2C6H4-4-C4H9t385 CH3 OPh O CH2C6H4-4-CO2CH3386 CH3 OPh O CH2C6H4-4-CO2C4H9t387 CH3 OPh O CH2-5-C5H3N-2-CI388 CH3 OPh O CH3N3-C5H -2-CI389 CH3 OPh O C6H3-2, 6-F2390 CH3 OPh O C6H4-3-CI391 CH3 OPh O C6H4-4-CI392 CH3 OPh O C6H4-4-F393 CH3 OPh O C6H4-4-C4H9t394 CH3 OPh O C6H4 -4-CO2CH3395 CH3 OPh O C6H4-4-CO2C4H9t396 CH3 OPh O 5-C5H3N-2-CI397 CH3 OPh O 3-C5H3N-2-CI398 CH3 OPh NCH3 CH2C6H44-CI399 CH3 OPh NCH3 CH2C6H4-4-CH400 CH3 OPh2C NCH4 -4-C4H9t401 CH3 OPh NCH3 CH2C6H4-4-CO2CH3402 CH3 OPh NCH3 CH2C6H4-4-CO2C4H9t403 CH3 OPh NCH3 CH2-5-C5H3N-2-CI404 CH3 OPh NCH3 CH2-3-C5H3N-2-CI405 CH3 OPh4 NCH3 C6H -CI406 CH3 OPh NCH3 C6H4-4-F407 CH3 OPh NCH3 C6H4-4-C4H9t408 CH3 OPh NCH3 C6H4-4-CO2CH3409 CH3 OPh NCH3 C6H4-4-CO2C4H9t410 CH3 OPh NCH3 5-C5H3N-2-CI411 CH3 OPhC5NH3 NCH3 -2-CI412 CH3 OPh NCH3 C6H3-2, 6-F2413 CH3 OPh NCH3 C6H4-3-CI414 CI OPh NCH3 C6H4-4-CI415 CI OPh NCH3 C6H4-4-F416 CI OPh NCH3 C6H4-4-C4H9t417 CI OPh NCH3 C6H4 -4-CO2CH3418 CI CI O C6H4-4-CI419 CI CI O C6H4-4-F420 CI CI O C6H4-4-C4H9t421 CI CI O C6H4-4-CO2CH3 Table 6 The positions of R1 and XR3 can be at the 3, 4 or 5 positions of the pyrazole. R1 XR3 R2 QCH3 CI CH3 CH2C6H4-4-CICH3 CI CH3 CH2C6H4-4-FCH3 CI CH3 CH2C6H4-4-C4H9tCH3 CI CH3 CH2C6H4-4-CO2CH3CH3 CI CH3 CH2C6H4-4-CO2C4H9tCH3 OPh CH3 CI3N3-3-6H CI CH3 CH2-3-C5H3N-2-CICH3 CI CH3 C6H3-2,6-F2CH3 CI CH3 C6H4-3-CICH3 CI CH3 C6H4-4-CICH3 CI CH3 C6H4-4-FCH3 CI CH3 C6H4-4-C4H9tCH3 CI CH3 C6H4-4-CO2CH3CH3 CI CH3 C6H4-4-CO2C4H9tCH3 CI CH3 5-C5H3N-2-CICH3 OPh CH3 3-C5H3N-2-CICH3 CI CH3 NHC6H5CH3 CI CH3 NH-3-C5H3N-6-CICH3 F CH3 CH2C6H4-4- CICH3 F CH3 CH2C6H4-4-FCH3 F CH3 CH2C6H4-4-C4H9tCH3 F CH3 CH2C6H4-4-CO2CH3CH3 F CH3 CH2C6H4-4-CO2C4H9tCH3 F CH3 CH2-3-C5H3N-6-CICH3 F CH3 CH2-3-C5H3N-2- CIH H Ph C6H3-2,6-F2CH3 F CH3 C6H4-3-CICH3 F CH3 C6H4-4-CICH3 F CH3 C6H4-4-FCH3 F CH3 C6H4-4-C4H9tCH3 F CH3 C6H4-4-CO2CH3CH3 F CH3 C6H4-4 -CO2C4H9tCH3 F CH3 5-C5H3N-2-CICH3 F CH3 3-C5H3N-2-CICH3 F CH3 NHC6H5CH3 F CH3 NH-5-C5H3N-2-CIF F CH3 CH2C6H4-4-CIF F CH3 CH2C6H4-4-FF F CH3 CH2C6H4-4-C4H9tF CH3 CH2C6H4-4-CO2CH3F CH3 CH2C6H4-4-CO2C4H9tF CH3 CH2-3-C5H3N-6-CIF F CH3 CH2-3-C5H3N-2-CIF F CH3 C6H3-2,6-F2F F CH3 C6H4-3-CIF F CH3 C6H4-4-CIF F CH3 C6H4-4-FF F CH3 C6H4-4-C4H9tF F CH3 C6H4-4-CO2CH3F F CH3 C6H4-4-CO2C4H9tF F CH3 5-C5H3N-2- CIF F CH3 3-C5H3N-2-CIF F CH3 NHC6H5CF3 H CH3 C6H4-3-CF3CF3 H C2H5 C6H4-4-C4H9tF CH3 F C6H3-2-OC2H5-4-C4H9tF F CH3 NH-5-C5H3N-2-CI Table 7 R1 R2 R3 ZQCH3 CH3 H OCH2C6H4-4-C4H9tCH3 CH3 H OCH2C6H4-4-CO2C4H9tCH3 CH3 H OCH2C6H4-4-CO2CH3CH3 CH3 H OCH2C6H4-4-CICH3 C2H5 H OCH2C6H4-4-CNCH3 CH3 H OCH2C6H4-C3-CF H3CH 4-OCF3CH3 CH3 H OCH2C6H4-4-NO2CH3 CH3 H OCH2-3-pyridine-6-CICH3 CH3 H OCH2-2-furan CH3 CH3 H OCH2-2-thiophene CH3 CH3 H OCH2-1-1,2,4- Triazole CH3 CH3 H OCH2-1-pyrazole CH3 CH3 H OCH2-2-pyrimidine CH3 CH3 H C6H4-3-OCH(CH3)CH3 CH3 CI OCH2C6H4-4-C4H9tCH3 CH3 CI OCH2C6H4-4-CO2C4H9tCH3 CH3 CI OCH2C6H4-4 -CO2CH3CH3 CH3 CI OCH2C6H4-4-CICH3 C2H5 CI OCH2C6H4-4-CNCH3 CH3 CI OCH2C6H4-4-CF3CH3 CH3 CI OCH2C6H4-4-OCF3CH3 CH3 CI OCH2C6H4-4-NO2CH3 CH3 CI OCH2-3-pyridine-6-CICH3 CH3 CI OCH2-2-furan CH3 CH3 CI OCH2-2-thiophene CH3 CH3 CI OCH2-1-1,2,4-triazole CH3 CH3 CI OCH2-1-pyrazole CH3 CH3 CI OCH2-2-pyrimidine CH3 CH3 CI C6H4 -3-OCH(CH3)2C4H9t CH3 H OCH2C6H4-4-C4H9tC4H9t CH3 H OCH2C6H4-4-CO2C4H9tC4H9t CH3 H OCH2C6H4-4-CO2CH3C4H9t CH3 H OCH2C6H4-4-CIC4H9t CH3 H OCH2C6H4-4-CNC4H9t CH3 H OCH2C6H4-4-CF3C4H9t CH3 H OCH2C6H4-4-OCF3C4H9t CH3 H OCH2C6H4-4-NO2C4H9t CH3 H OCH2-3-pyridine-6-CIC4H9t CH3 H OCH2-2-furan C4H9t CH3 H OCH2-2-thiophene C4H9t CH3 H OCH2-1-1, 2,4-triazole C4H9t CH3 H OCH2-1-pyrazole C4H9t CH3 H OCH2-2-pyrimidine C4H9t CH3 H C6H4-3-OCH(CH3)C4H9t CH3 CI OCH2C6H4-4-C4H9tC4H9t CH3 CI OCH2C6H4-4-CO2C4H9tC4H9t CH3 CI OCH2C6H4-4-CO2CH3C4H9t CH3 CI OCH2C6H4-4-CIC4H9t CH3 CI OCH2C6H4-4-CNC4H9t CH3 CI OCH2C6H4-4-CF3C4H9t CH3 CI OCH2C6H4-4-OCF3C4H9t CH3 CI OCH2C6H4-CI9tCH2CH3 CI OCH2C6H4-CI9tCH2CH3 -CIC4H9t CH3 CI OCH2-2-furan C4H9t CH3 CI OCH2-2-thiophene C4H9t CH3 CI OCH2-1-1,2,4-triazole C4H9t CH3 CI OCH2-1-pyrazole C4H9t CH3 CI OCH2-2-pyrimidine C4H9t CH3 CI C6H4-3-OCH(CH3)2C2H5 CH3 H OCH2C6H4-4-C4H9tC2H5 CH3 H OCH2C6H4-4-CO2C4H9tC2H5 CH3 H OCH2C6H4-4-CO2CH3C2H5 CH3 H OCH2C6H4-4-CIC2H5CH2CH2CH2CHCN -4-CF3C2H5 CH3 H OCH2C6H4-4-OCF3C2H5 CH3 H OCH2C6H4-4-NO2C2H5 CH3 H OCH2-3-pyridine-6-CIC2H5 CH3 H OCH2-2-furan C2H5 CH3 H OCH2-2-thiophene C2H5 CH3 H OCH2- 1-1,2,4-triazole C2H5 CH3 H OCH2-1-pyrazole C2H5 CH3 H OCH2-2-pyrimidine C2H5 CH3 H C6H4-3-OCH(CH3)C2H5 CH3 CI OCH2C6H4-4-C4H9tC2H5 CH3 CI OCH2C6H4- 4-CO2C4H9tC2H5 CH3 CI OCH2C6H4-4-CO2CH3C2H5 CH3 CI OCH2C6H4-4-CIC2H5 CH3 CI OCH2C6H4-4-CNC2H5 CH3 CI OCH2C6H4-4-CF3C2H5 CH3 CI OCH2C6H4-4-OCF3C2H5 CH3 CI OCH2C6H4-4-NO2C2H5 CH3 CI OCH2-3 -pyridine-6-CIC2H5 CH3 CI OCH2-2-furan C2H5 CH3 CI OCH2-2-thiophene C2H5 CH3 CI OCH2-1-1,2,4-triazole C2H5 CH3 CI OCH2-1-pyrazole C2H5 CH3 CI OCH2 -2-Pyrimidine C2H5 CH3 CI C6H4-3-OCH(CH3)2CH3 CH3 CI NHC6H4-4-C4H9tCH3 CH3 CI NHC6H4-4-CO2C4H9tCH3 CH3 CI NHC6H4-4-CO2CH3CH3 CH3 CI NHC6H4-4-CICH3 CH3 CI NHC6H4-4- CNCH3 CH3 CI NHC6H4-4-CF3CH3 CH3 CI NHC6H4-4-OCF3CH3 CH3 CI NHC6H4-4-NO2CH3 CH3 CI NHCH2-3-pyridine-6-CICH3 CH3 CI NHCH2-2-furan CH3 CH3 CI NHCH2-2-thiophene CH3 CH3 CI NHCH2-1-1,2,4-triazole CH3 CH3 CI NHCH2-1-pyrazole CH3 CH3 CI NHCH2-2-pyrimidine CH3 CH3 CI NHCH2C6H4-4-OCH(CH3)CH3 CH3 CI NHCH2C6H4-4-C4H9tCH3 CH3 CI NHCH2C6H4-4-CO2C4H9tCH3 CH3 CI NHCH2C6H4-4-CO2CH3CH3 CH3 CI NHCH2C6H4-4-CICH3 CH3 CI NHCH2C6H4-4-CNCH3 CH3 CI NHCH2C6H4-4-CF3CH3 CH3 CI NHCH2CH6H2-4-OC3FCH3 NHCH2C6H4-4-NO2CH3 CH3 CI NH-3-pyridine-6-CICH3 CH3 CI NH-2-furan CH3 CH3 CI NH-2-thiophene CH3 CH3 CI NH-1-1,2,4-triazole CH3 CH3 CI NH-2-pyrimidine CH3 CH3 CI NH-2-pyrimidine-4,6-(OMe)2CH3 CH3 CI NH-2-pyrimidine-4,6-(Me)2CH3 CH3 H NHC6H4-4-C4H9tCH3 CH3 H NHC6H4-4 -CO2C4H9tCH3 CH3 H NHC6H4-4-CO2CH3CH3 CH3 H NHC6H4-4-CICH3 CH3 H NHC6H4-4-CNCH3 CH3 H NHC6H4-4-CF3CH3 CH3 H NHC6H4-4-OCF3CH3 CH3 H NHC6H4-4-NO2CH3 CH3 H NHCH2-3- Pyridine-6-CICH3 CH3 H NHCH2-2-furan CH3 CH3 H NHCH2-2-thiophene CH3 CH3 H NHCH2-1-1,2,4-triazole CH3 CH3 H NHCH2-1-pyrazole CH3 CH3 H NHCH2- 2-Pyrimidine CH3 CH3 H NHCH2C6H4-4-OCH(CH3)CH3 CH3 H NHCH2C6H4-4-C4H9tCH3 CH3 H NHCH2C6H4-4-CO2C4H9tCH3 CH3 H NHCH2C6H4-4-CO2CH3CH3 CH3 H NHCH2C6H4-4-CICH3 CH3 H NHCH2C6H CH3 H NHCH2C6H4-4-CF3CH3 CH3 H NHCH2C6H2-2, 6-CI2-4-OCF3CH3 CH3 H NHCH2C6H4-4-NO2CH3 CH3 H NH-3-pyridine-6-CICH3 CH3 H NH-2-furan CH3 CH3 H NH- 2-thiophene CH3 CH3 H NH-1-1,2,4-triazole CH3 CH3 H NH-2-pyrimidine CH3 CH3 H NH-2-pyrimidine-4,6-(Me)2CF3 CH3 HO OCH2C6H4-4- C4H9tCF3 CH3 H OCH2C6H4-4-CO2C4H9tCF3 CH3 H OCH2C6H4-4-CO2CH3CF3 CH3 H OCH2C6H4-4-CICF3 CH3 H OCH2C6H4-4-CNCF3 CH3 H OCH2C6H4-4-CF3CF3 CH3 H OCH2C6H4-4-NOOCF3CF4-CH3H3CF3 CH3H3CF3 CH3H O CH3 H OCH2-3-pyridine-6-CICF3 CH3 H OCH2-2-furan CF3 CH3 H OCH2-2-thiophene CF3 CH3 H OCH2-1-1,2,4-triazole CF3 CH3 H OCH2-1-pyridine Azole CF3 CH3 H OCH2-2-pyrimidine CF3 CH3 H C6H4-3-OCH(CH3)2CF3 CH3 H NHC6H4-4-C4H9tCF3 CH3 H NHC6H4-4-CO2C4H9tCF3 CH3 H NHC6H4-4-CO2CH3CF3 CH3 H NHC6H4-4-CICF3 CH3 H NHC6H4-4-CNCF3 CH3 H NHC6H4-4-CF3CF3 CH3 H NHC6H4-4-OCF3CF3 CH3 H NHC6H4-4-NO2CF3 CH3 H NHCH2-3-pyridine-6-CICF3 CH3 H NHCH2-2-furan CF3 CH3 H NHCH2- 2-thiophene CF3 CH3 H NHCH2-1-1,2,4-triazole CF3 CH3 H NHCH2-1-pyrazole CF3 CH3 H NHCH2-2-pyrimidine CF3 CH3 H NHCH2C6H4-4-OCH(CH3)CF3 CH3 H NHCH2C6H4-4-C4H9tCF3 CH3 H NHCH2C6H4-4-CO2C4H9tCF3 CH3 H NHCH2C6H4-4-CO2CH3CF3 CH3 H NHCH2C6H4-4-CICF3 CH3 H NHCH2C6H4-4-CNCF3 CH3 H NHCH2C6H4-4-CF3CF3 CH36 H NH2CI2-CH2, 4-OCF3CF3 CH3 H NHCH2C6H4-4-NO2CF3 CH3 H NH-3-pyridine-6-CICF3 CH3 H NH-2-furan CF3 CH3 H NH-2-thiophene CF3 CH3 H NH-1-1,2,4- Triazole CF3 CH3 H NH-2-pyrimidine CF3 CH3 H NH-2-pyrimidine-4,6-(Me)2CF3 CH3 CI NHC6H4-4-C4H9tCF3 CH3 CI NHC6H4-4-CO2C4H9tCF3 CH3 CI NHC6H4-4-CO2CH3CF3 CH3 CI NHC6H4-4-CICF3 CH3 CI NHC6H4-4-CNCF3 CH3 CI NHC6H4-4-CF3CF3 CH3 CI NHC6H4-4-OCF3CF3 CH3 CI NHC6H4-4-NO2CF3 CH3 CI NHCH2-3-pyridine-6-CICF3 CH3 CI NHCH2-2- Furan CF3 CH3 CI NHCH2-2-thiophene CF3 CH3 CI NHCH2-1-1,2,4-triazole CF3 CH3 CI NHCH2-1-pyrazole CF3 CH3 CI NHCH2-2-pyrimidine CF3 CH3 CI NHCH2C6H4-4-OCH (CH3)CF3 CH3 CI NHCH2C6H4-4-C4H9tCF3 CH3 CI NHCH2C6H4-4-CO2C4H9tCF3 CH3 CI NHCH2C6H4-4-CO2CH3CF3 CH3 CI NHCH2C6H4-4-CICF3 CH3 CI NHCH2C6H4-4-NCF3 CH2H4CI NH3-3CF3 CH2H4CI NH3-3CF3 CH2H4 CI NHCH4C3CF3 2,6-CI2-4-OCF3CF3 CH3 CI NHCH2C6H4-4-NO2CF3 CH3 CI NH-3-pyridine-6-CICF3 CH3 CI NH-2-furan CF3 CH3 CI NH-2-thiophene CF3 CH3 CI NH-1- 1,2,4-Triazole CF3 CH3 CI NH-2-pyrimidine CF3 CH3 CI NH-2-pyrimidine-4,6-(OMe)2CF3 CH3 CI NH-2-pyrimidine-4,6-(Me)2

部分化合物的物性和核磁(90MHz)数据：Physical and NMR (90MHz) data of some compounds:

2 熔点：98～100℃.2 Melting point: 98～100℃.

10 油状物，HNMR(CDCl3，TMS)ppm：8.42(s，1H)，7.90(s，1H)，6.44～7.44(m，9H)，5.02(s，2H)，3.65(s，3H)，2.01(s，3H)，1.31(s，9H)10 Oil, HNMR (CDCl3, TMS) ppm: 8.42 (s, 1H), 7.90 (s, 1H), 6.44～7.44 (m, 9H), 5.02 (s, 2H), 3.65 (s, 3H), 2.01 (s, 3H), 1.31 (s, 9H)

146 熔点：91～93℃.HNMR(CDCl3，TMS)ppm：7.71(q，4H)，6.40(bs，1H)，4.57(d，2H)，3.78(s，3H)，2.48(s，3H)，1.31(d，6H)146 Melting point: 91～93℃. HNMR (CDCl3, TMS) ppm: 7.71 (q, 4H), 6.40 (bs, 1H), 4.57 (d, 2H), 3.78 (s, 3H), 2.48 (s, 3H) , 1.31(d, 6H)

150 熔点：190～192℃. 152 熔点：210～212℃.150 Melting point: 190～192℃. 152 Melting point: 210～212℃.

155 熔点：90～92℃.HNMR(CDCl3，TMS)ppm：7.78(bs，1H)，6.91～7.40(m，3H)，6.57～6.75(d，2H)，4.58(m，1H)，3.83(s，3H)，2.52(s，3H)，1.31(d，6H)155 Melting point: 90～92℃. HNMR (CDCl3, TMS) ppm: 7.78(bs, 1H), 6.91～7.40(m, 3H), 6.57～6.75(d, 2H), 4.58(m, 1H), 3.83( s, 3H), 2.52 (s, 3H), 1.31 (d, 6H)

159 熔点：200℃(分解). 160 熔点：74～76℃.159 Melting point: 200°C (decomposition). 160 Melting point: 74～76°C.

169 熔点：173～175℃.HNMR(CDCl3，TMS)ppm：8.08(bs，1H)，7.45～7.69(m，2H)，6.88～7.15(m，2H)，3.88(s，3H)169 Melting point: 173～175℃. HNMR (CDCl3, TMS)ppm: 8.08(bs, 1H), 7.45～7.69(m, 2H), 6.88～7.15(m, 2H), 3.88(s, 3H)

170 熔点：135～136℃.HNMR(CDCl3，TMS)ppm：7.53(q，4H)，6.84(bs，1H)，4.69(d，2H)，3.87(s，3H)170 Melting point: 135～136℃. HNMR (CDCl3, TMS) ppm: 7.53 (q, 4H), 6.84 (bs, 1H), 4.69 (d, 2H), 3.87 (s, 3H)

182 熔点：170～172℃.182 Melting point: 170～172℃.

277 熔点：75～78℃.HNMR(CDCl3，TMS)ppm：7.98(s，1H)，4.58(s，2H)，4.15(q，2H)，3.75(s，3H)，2.24(s，3H)，1.22(t，3H)277 Melting point: 75～78℃. HNMR (CDCl3, TMS) ppm: 7.98 (s, 1H), 4.58 (s, 2H), 4.15 (q, 2H), 3.75 (s, 3H), 2.24 (s, 3H) , 1.22(t, 3H)

285 熔点：227～230℃(d)，HNMR(DMSO，TMS)ppm：10.73(bs，1H)，8.53(bs，1H)，7.87(s，1H)，7.64(d，2H)，7.33(d，2H)，3.76(s，3H)，2.41(s，3H)285 Melting point: 227～230°C (d), HNMR (DMSO, TMS) ppm: 10.73 (bs, 1H), 8.53 (bs, 1H), 7.87 (s, 1H), 7.64 (d, 2H), 7.33 (d , 2H), 3.76(s, 3H), 2.41(s, 3H)

286 熔点：175～177℃.HNMR(DMSO，TMS)ppm：8.96(s，1H)，8.84(s，1H)，7.56(s，1H)，7.42(d，2H)，7.31(d，2H)，3.78(s，3H)，3，67(s，3H)，2.41(s，3H)286 Melting point: 175～177°C. HNMR (DMSO, TMS) ppm: 8.96 (s, 1H), 8.84 (s, 1H), 7.56 (s, 1H), 7.42 (d, 2H), 7.31 (d, 2H) , 3.78(s, 3H), 3, 67(s, 3H), 2.41(s, 3H)

287 熔点：231～233℃. 288 熔点：222～224℃。287 Melting point: 231～233℃. 288 Melting point: 222～224℃.

289 熔点：176～178℃. 295 熔点：196～199℃。289 Melting point: 176～178℃. 295 Melting point: 196～199℃.

304 油状物，HNMR(DMCO，TMS)ppm：7.69(s，1H)，6.89(m，2H)，7.47(m，2H)，7.19(m，1H)，4.42(s，2H)，4.15(q，2H)，3.57(s，3H)，2.26(s，3H)，1.20(t，3H)304 oil, HNMR (DMCO, TMS) ppm: 7.69 (s, 1H), 6.89 (m, 2H), 7.47 (m, 2H), 7.19 (m, 1H), 4.42 (s, 2H), 4.15 (q , 2H), 3.57(s, 3H), 2.26(s, 3H), 1.20(t, 3H)

308 熔点：115～118℃.HNMR(CDCl3+DMSO，TMS)ppm：8.32(bs，1H)，8.08(s，1H)，7.36(H，2H)，7.28(m，4H)，7.16(m，1H)，7.07(m，2H)，3.65(s，3H)，2.24(s，3H)308 Melting point: 115～118℃. HNMR (CDCl3+DMSO, TMS) ppm: 8.32 (bs, 1H), 8.08 (s, 1H), 7.36 (H, 2H), 7.28 (m, 4H), 7.16 (m, 1H), 7.07(m, 2H), 3.65(s, 3H), 2.24(s, 3H)

312 熔点：200～203℃.HNMR(DMSO，TMS)ppm：10.48(bs，1H)，8.89(bs，1H)，7.61(s，1H)，7.18～7.55(m，7H)，7.00(d，2H)，3.58(s，3H)，2.39(s，3H)312 Melting point: 200～203℃. HNMR (DMSO, TMS)ppm: 10.48(bs, 1H), 8.89(bs, 1H), 7.61(s, 1H), 7.18～7.55(m, 7H), 7.00(d, 2H), 3.58(s, 3H), 2.39(s, 3H)

318 熔点：113～115℃，HNMR(CDCl3+DMSO，TMS)ppm：8.19(s，1H)，7.97(d，2H)，7.52(d，2H)，6.95～7.50(m，5H)，3.62(s，3H)，2.39(s，3H)318 Melting point: 113～115℃, HNMR (CDCl3+DMSO, TMS) ppm: 8.19(s, 1H), 7.97(d, 2H), 7.52(d, 2H), 6.95～7.50(m, 5H), 3.62( s,3H), 2.39(s,3H)

324 熔点：135～137℃，HNMR(CDCl3，TMS)ppm：9.91(bs，1H)，8.13(m，1H)，8.06(s，1H)，7.61(m，1H)，6.89(m，2H)，7.00～7.55(m，5H)，3.65(s，3H)，2.47(s，3H)324 Melting point: 135～137℃, HNMR (CDCl3, TMS) ppm: 9.91 (bs, 1H), 8.13 (m, 1H), 8.06 (s, 1H), 7.61 (m, 1H), 6.89 (m, 2H) , 7.00～7.55(m, 5H), 3.65(s, 3H), 2.47(s, 3H)

344 熔点：112～114℃，HNMR(CDCl3，TMS)ppm：8.40(s，1H)，7.56～7.78(m，1H)，7.04～7.56(m，5H)，6.77～7.04(d，2H)，5.00(s，2H)，4.80(bs，1H)，3.58(s，3H)，2.37(s，3H)344 Melting point: 112～114℃, HNMR (CDCl3, TMS) ppm: 8.40(s, 1H), 7.56～7.78(m, 1H), 7.04～7.56(m, 5H), 6.77～7.04(d, 2H), 5.00(s, 2H), 4.80(bs, 1H), 3.58(s, 3H), 2.37(s, 3H)

349 油状物 385 熔点：180～182℃。349 Oily substance 385 Melting point: 180～182℃.

本发明的化合物具有很好的杀菌、杀虫和杀螨活性，用于防治多种病原菌引起的病害如：霜霉病、灰霉病、白粉病、纹枯病、稻瘟病、锈病等；也可用于防治鳞翅目昆虫如粘虫、小菜蛾、同翅目昆虫如飞虱、蚜虫等，双翅目昆虫如蚊、蝇等以及螨类如棉红蜘蛛、朱砂叶螨等包括若虫、成虫特别是卵，即对卵有优异的活性。The compound of the present invention has good bactericidal, insecticidal and acaricidal activities, and is used to prevent and treat diseases caused by various pathogenic bacteria such as: downy mildew, gray mold, powdery mildew, sheath blight, rice blast, rust, etc.; It can be used to control Lepidoptera insects such as armyworm, diamondback moth, Homoptera insects such as planthoppers, aphids, etc., Diptera insects such as mosquitoes, flies, etc., and mites such as cotton red spider, cinnabar spider mite, etc., including nymphs and adults In particular, eggs, that is, have excellent activity on eggs.

1、对蚕豆蚜的试验1. Test on broad bean aphid

用本发明的化合物，用药浓度为500ppm，供试蚜虫为3天龄，每次处理试虫50～100头，以清水对照，重复三次，处理后放置20～23℃观察室中，24小时后调查死亡率，部分结果如下：化合物编号死亡率(％)2 10079 100With the compound of the present invention, the drug concentration is 500ppm, and the tested aphids are 3 days old, and 50 to 100 test insects are treated each time, compared with clear water, and repeated three times. Investigate mortality, some results are as follows: Compound No. Mortality (%) 2 10079 100

2、对朱砂叶螨的试验2. Test on Tetranychus cinnabarinus

采用浸液法，本发明的化合物用药浓度为500ppm，将已移接成螨50～70头的2片菜豆苗真叶，放入已配好的药液中浸5秒钟后取出，放置20～25℃观察室中，以清水对照，重复三次，24小时后调查死亡率，部分结果见如下：Adopt the liquid immersion method, the dosage concentration of the compound of the present invention is 500ppm, 2 pieces of bean seedling true leaves that have been grafted with 50-70 heads of adult mites are put into the prepared medicinal liquid and soaked for 5 seconds, then taken out, and placed for 20 In the observation room at ~25°C, water was used as control, repeated three times, and the mortality rate was investigated after 24 hours. Part of the results are as follows:

化合物编号死亡率(％)

2 1002 100

79 10079 100

146 100146 100

3、杀卵活性试验-盆栽法3. Ovicidal activity test - pot method

将健壮朱砂叶螨成螨5头接于二真叶盆栽菜豆苗上，2日后去除成螨，调查螨卵基数，在稀释好的药液中浸渍5秒钟，然后置于室温内培养。处理后6日待空白对照全部孵化完毕调查卵的孵化及孵化出幼螨的存活情况，部分结果如下：5 adult mites of robust Tetranychus cinnabarinus were grafted on the two-true leaf potted bean seedlings. After 2 days, the adult mites were removed, and the base number of mite eggs was investigated. They were immersed in the diluted medicinal solution for 5 seconds, and then cultured at room temperature. 6 days after the treatment, the blank control was completely hatched to investigate the hatching of the eggs and the survival of the hatched larvae. Some results were as follows:

化合物编号浓度(ppm) 卵基数(粒) 活螨数综合效果(％) Compound No. Concentration (ppm) Egg base number (grain) Live mite number Comprehensive effect (%)

2 10 102 0 1002 10 102 0 100

79 10 255 0 10079 10 255 0 100

杀螨隆 10 230 109 46.4

4、杀卵活性试验-叶碟法4. Ovicidal activity test - leaf disc method

将健壮朱砂叶螨成螨5头接于直径为1厘米的菜豆苗叶碟上，于观察室保湿培养、24小时后去陈成螨，调查螨卵基数，在稀释好的药液中浸渍5秒钟，7日待空白对照全部孵化完毕，调查卵的孵化及孵化出幼螨的存活情况，部分结果如下：Connect 5 robust adults of Tetranychus cinnabarinus to a bean seedling leaf dish with a diameter of 1 cm, keep them moisturized in the observation room, remove the mature mites after 24 hours, investigate the base number of mite eggs, immerse in the diluted medicinal solution for 5 seconds, 7 Wait until the hatching of the blank control is completed, and investigate the hatching of the eggs and the survival of the hatched larvae. Some results are as follows:

化合物编号浓度(ppm) 卵基数(粒) 未孵卵数(粒) 抑制率(％) Compound number Concentration (ppm) Egg base number (grain) Unhatched egg number (grain) Inhibition rate (%)

79 125 63 62 98.479 125 63 62 98.4

5、灰霉病试验5. Gray mold test

本发明的化合物用药浓度为1000ppm，喷雾法处理黄瓜苗，24小时后利用灰霉病菌进行人工接种，以清水对照，重复三次，保湿5天后调查发病情况，部分结果如下：The dosage concentration of the compound of the present invention is 1000ppm. The cucumber seedlings are treated by spraying method. After 24 hours, they are artificially inoculated with Botrytis cinerea, compared with clear water, and repeated three times. After moisturizing for 5 days, the incidence of the disease is investigated, and some results are as follows:

化合物编号防效(％) Compound No. Control Efficacy (%)

288 100288 100

6、白粉病试验6. Powdery mildew test

本发明的化合物用药浓度为1000ppm，盆栽小麦长至二叶期，喷雾处理24小时后人工接种白粉病粉孢子，以清水对照，重复三次，保湿7天后调查发病情况，部分结果见如下：The dosage concentration of the compound of the present invention is 1000ppm, the potted wheat grows to the second-leaf stage, after 24 hours of spray treatment, powdery mildew powdery spores are artificially inoculated, compared with clear water, repeated three times, and the incidence is investigated after moisturizing for 7 days. Some results are as follows:

化合物编号防效(％) 化合物编号防效(％) Compound No. Control Efficacy (%) Compound No. Control Efficacy (%)

277 95 305 100277 95 305 100

278 95 331 100278 95 331 100

304 100 343 90304 100 343 90

7、霜霉病试验7. Downy mildew test

本发明的化合物用药浓度为1000ppm，喷雾法处理黄瓜苗，24小时后利用孢子囊悬浮液进行人工接种，以清水对照，重复三次，保湿7天后调查发病情况，部分结果见如下：The dosage concentration of the compound of the present invention is 1000ppm. The cucumber seedlings are treated by spraying method. After 24 hours, the sporangia suspension is used to carry out artificial inoculation. With clear water as contrast, repeat three times, and investigate the disease condition after moisturizing for 7 days. Partial results are as follows:

化合物编号防效(％) Compound No. Control Efficacy (%)

2 952 95

306 95306 95

385 75385 75

8、纹枯病试验8. Sheath blight test

本发明的化合物用药浓度为1000ppm。喷雾法处理水稻苗，24小时后利用纹枯病菌进行人工接种，以清水对照，重复三次，保湿3天后调查发病情况，部分结果如下：The dosage concentration of the compound of the present invention is 1000ppm. The rice seedlings were treated by spraying method, artificially inoculated with sheath blight bacteria 24 hours later, and compared with clean water, repeated three times, and investigated the disease after 3 days of moisturizing. Some results are as follows:

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Claims

1. Pyrazole compounds and preparations thereof as agricultural fungicides and insecticides and acaricides The general formula of the compound (I) of the present invention is: In the formula:

R1 and R2 are H, halogen, C1~C6 alkyl, C2~C16 alkenyl, alkynyl, C3~C6 cycloalkyl, C1~C6 haloalkyl (C2~C6 alkenyl, C2~C6 alkynyl, C3~ C6 cycloalkyl), R1, R2 can be the same or different.

R3 is hydrogen, halogen, (halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2～C6 alkynyl, (halogenated) C3～C6 cycloalkyl, (halogenated) )C3～C6 cycloalkenyl, NR5R6[R5 is H, halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2～C6 alkynyl, (halogenated) C3～C6 Cycloalkyl, (halogenated) C3～C6 cycloalkenyl, R6 is R5, (substituted) aryl, (substituted) heteroaryl], (substituted) aryl, (substituted) heteroaryl,

R4 is H, C1～C6 alkyl, halogen, NR5R7[R7 is R5, (substituted) aryl, (substituted) heteroaryl], CN, (substituted) benzyl, (substituted) aryl, (substituted) hetero Aryl, CO-Z1～R8 (Z1 is a bond, O, S, NR5R7; R8 is a bond, H, (halogenated) C1～C6 alkyl, (halogenated) C2～C6 alkenyl, (halogenated) C2 ~C6 alkynyl, (halogenated) C3~C6 cycloalkyl, (halogenated) C3~C6 cycloalkenyl, (substituted) aryl, CH2CO-Z1-R7, CH2CN), PX1 (X2R9) X3R10 (X1 is O, S: X2, X3 are O, S, NH; X1, X2, X3 can be the same or different; R9, R10 are R8, which can be the same or different.

X is a bond, O, S, NR11 (R11 is H, R8).

Y is a bond, O, NR11, CH2.

Z is a bond, H, CO, S(O)n, CHR12 [R12 is H, (halogenated) C1-C6 alkyl].

R4 and Z can also form a ring [saturated or unsaturated arbitrarily substituted five or six rings: imidazole, dihydroimidazole, triazole, oxazoline (two) azole, oxazoline (ketone), thiazoline (two) oxazole, thiazoline (ketone), pyrimidine, di(tetra)hydropyrimidine (ketone), (trihydro)oxazine].

Q is H, R3, CH2R3, OR3, CO-Z1-R8, OR8, S(O)nR8, CN, PX1(X2R9)X3R10,

When Q is (substituted) aryl, it can be (substituted) phenyl, and the substituent can be H, C1~C6 alkyl, C2~C6 alkenyl, C2~C6 alkynyl, C3~C6 cycloalkyl, C3 ～C6 cycloalkenyl, C1～C6 haloalkyl (C2～C6 alkenyl, C2～C6 alkynyl, C3～C6 cycloalkyl, C3～C6 cycloalkenyl), OR8, CO-Z1-R8, CH2CO-Z1 -R8, CH2CN, NR5R8, S(O)nR8, SiR13R14R15 [R13~R15 are (halogenated) C1~C6 alkyl groups, the same or different], COSiR13R14R15, OSiR13R14R15, CR12R13CN, CR12R13CC13, SF5,

m=0～1; n=0～2,

The terms "alkyl, alkenyl, alkynyl" refer to branched or straight chain alkyl, alkenyl, alkynyl, respectively. "Halogen" means fluorine, chlorine, bromine, iodine. "Haloalkyl (alkenyl, alkynyl, cycloalkyl, cycloalkenyl)" means an alkyl (alkenyl, alkynyl, cycloalkyl, cycloalkenyl) substituted by one or more identical or different halogen atoms Alkenyl), (substituted) aryl, (substituted) heteroaryl, substituents can be H, C1～C6 alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, C1～C6 halogenated (alk group, alkenyl, alkynyl, cycloalkyl) cycloalkenyl, OR7, CO-Z1 R8, NR5R7, S(O)nR8, SiR13R14R15, COSiR13R14R15, OSiR13R14R15, CR1 2R13CN, CR12R13CC13, SF5, substituents can be in aryl and any position of heteroaryl; aryl, heteroaryl refers to phenyl, naphthyl, furyl, thienyl, pyridyl, pyrazolyl, imidazolyl, imidazopyridine, triazolyl, triazolopyrimidine, Thia(di)azolyl, oxa(di)azolyl, pyrimidinyl.

2. The pyrazole compound (1) according to claim 1, characterized in that it can be mixed with any one, two or more of the known fungicides and insecticides and acaricides. Known fungicides such as: ferbam, thiram, ziram, maneb, zinc, mancozeb, carbendazim, benomyl, iprodione, triadimefon, cyclaconazole, hexazole Alcohol, Diniconazole, Fenconazole, Benconazole Triaconazole, Dibenzotriazole, Tebuconazole, Fluconazole, Furconazole, Mycloconazole, Fenconazole, Fuconazole, Propiconazole, Fufeconazole, flusilazole, amide azole, difefeconazole, fluteconazole, flumezolidinol, dimethomorph, metalaxyl, furalaxyl, benalaxyl, oxamide, prochloraz, cymeurea Cyanide, propamocarb, profosmocarb, dimethocarb, seed dressing, seed dressing strong, fenfenmorph, fenpropidin, pyrimandroxime, pentocuron, pyrizazone, pyraclostrobin, thiabendonil , fluazinam, pyrimethanil, pyrimethanil, cyprodinil, fluquinconazole, BAS 480F, BAS490F, CGA245704, CGA 329531, DE-795, DPX-JE874, ICIA0858, ICIA0054, KNF-S474, KTU 3616, KWG4168, LY2142302, , XRD563, SSF126, SSF129. Known insecticides and acaricides such as: bifenthrin, fenpropathrin, cis-cypermethrin, bifenthrin, cypermethrin, cyfluthrin, cyhalothrin, cypermethrin, alpha-cypermethrin, b-cypermethrin Cypermethrin, esfenvalerate, etofenprox, cypermethrin, flucyvalerate, fluvalinate, cyhalothrin, tefluthrin, deltamethrin, deltafluthrin, brofenprox, Cis-resmethrin, clocythrin, deltamethrin, ICIA5682, MTI-732, pyresmethrin, silafluofen, silafluofen (Hoe498), SSI-126, zetamethrin; Dimethomyl, Resincarb, Benthiocarb; Profenfos, Prothion, Meprothion, Profenofos, Chlorazofos, Terbufos, Methylpyrophos, Fenfos, Thiazolesulfur Phosphorus, pyrazofos, chlorpyrifos, chlorpyrifos-methyl, phoxim, Diananon, Dowco429, MAT-7484; hexaflumuron, chlorpyrifos, chlorpyrifos, flubenzuron, PH-7023, GR-572 , CGA157419, CGA184699; imidacloprid, NI-25, TIA-304; NN1850, MK-239, Fipronil: NC-129, NC-170, NC-184, NC-194, NC-196; abamectin, amitrazin, avermectin, azadirachtin ; Fenuron, Fenazafen, Tetrafen, AC303630, SU8801, YI-5301, SZI121, CGA 59205, D2341, DPX-MP062, MP-599, PFR-97, RH-5992, RH-2485, RH- 0345.

3. The mixed preparation according to claim 2, characterized in that the effective content of compound (1) is 0.1% to 95% (by weight), preferably 0.5% to 95%, and the preparations include solutions, emulsions, wettable Dusts, suspensions, powders, elixirs, soluble powders, granules, natural materials impregnated with active compounds and microcapsules enclosed in polymeric materials.

4. The compound (1) of the present invention has good bactericidal, insecticidal and acaricidal activities. It is used to prevent and control diseases caused by various pathogenic bacteria, such as: downy mildew, gray mold, powdery mildew, sheath blight, rice blast, rust, etc.; it can also be used to control Lepidoptera insects such as armyworm, diamondback moth, homoptera Insects such as planthoppers, aphids, etc., dipteran insects such as mosquitoes, flies, etc., and mites such as cotton red spider mite, cinnabar spider mite, etc. include nymphs, adults, especially eggs, that is, they have excellent activity on eggs.