A phenylpyrazoline derivative or its salt, composition and use thereof

Abstract

The present invention belongs to the field of pesticides and specifically relates to a substituted phenylpyrazoline derivative or a pesticide-acceptable salt thereof, a composition, and uses thereof. The compound has the structure of Formula (I): #imgabs0#, wherein the definitions of the various groups in the formula are as provided in the specification. The compounds of the present invention are based on the structure of a phenylpyrazoline derivative and incorporate a substituted pyrazole group, resulting in a class of compounds useful as herbicides and / or fungicides, exhibiting outstanding biological activity and crop safety.

Description

Technical Field

[0001] The present invention belongs to the technical field of pesticides, and in particular relates to a phenylpyrazoline derivative or a salt thereof, and a composition thereof, and relates to the use of the compound or the salt thereof, and the composition as a herbicide. Background Art

[0002] Along with the raising of agricultural production level, people are more and more aware of the important role of medicines such as herbicides, insecticides, fungicides, generally adopt chemical weeding, pest control or sterilization at present, as often use medicines such as herbicides, insecticides, fungicides in the planting process of crops such as corn, soybean, cotton, wheat and rice.Although the herbicides, insecticides, fungicides used in current agricultural production process are of a great variety, due to the continuous emergence of problems such as the resistance problem of plant diseases, insect pests and weeds, the efficiency of medicine and the use cost, still need to study continuously for the high efficiency, cost, residual problems of medicines such as insecticides, fungicides, herbicides.Wherein, for the bioactive compound with phenylpyrazoline structure, being described in the patent that publication number is CN1292791A, CN1355806A, but its weeding activity after plant emergence may not be quite satisfactory, and all can not have the activity of sterilization, weeding concurrently simultaneously. Summary of the Invention

[0003] To address the aforementioned problems existing in the prior art, the present invention provides a substituted phenylpyrazoline derivative or salt thereof, composition, and use thereof. Through extensive research on phenylpyrazoline derivatives, the applicant introduced a substituted pyrazole group based on the structure of phenylpyrazoline derivatives, resulting in a class of herbicides and / or fungicides with outstanding biological activity and crop safety.

[0004] The technical solution adopted by the present invention to achieve the above-mentioned purpose is: a phenylpyrazoline derivative or a salt thereof, whose structural formula is as follows:

[0005] Where,

[0006] R1, R2, and R3 are each independently selected from H, C1-C6 alkyl, halosubstituted C1-C6 alkyl, C1-C6 alkoxy, halosubstituted C1-C6 alkoxy, C1-C6 alkylthio, halosubstituted C1-C6 alkylthio, C1-C6 alkylamino, halosubstituted C1-C6 alkylamino, C3-C6 cycloalkyl, halosubstituted C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C4 alkynyl, C1-C6 alkoxy-substituted C1-C6 alkyl, C1-C6 alkylthio-substituted C1-C6 alkyl, C1-C6 alkoxy-substituted C1-C6 alkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkylsulfonyl, halogen, CN, NO2, hydroxyl, sulfhydryl, carboxyl, aldehyde, or amino;

[0007] R4 and R5 are the same or different and are independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio or halogenated C1-C6 alkylthio;

[0008] Alternatively, R4 and R5 together form a group -(CH2) m -, m means 1-6;

[0009] R6 represents H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C4 alkynyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkyl substituted with a C1-C6 alkoxy group, C1-C6 alkoxy substituted with a C1-C6 alkoxy group, C3-C6 cycloalkyloxycarbonyl, C3-C6 cycloalkylaminocarbonyl, C3-C6 heterocyclyl, C3-C6 heterocyclyloxy, C3-C6 heterocyclyloxycarbonyl, C3-C6 heterocyclylaminocarbonyl, C3-C6 heterocyclyl substituted with a C1-C6 alkyl group, C1-C6 alkyl substituted with an aminocarbonyl group, CN, halogen, NO2, COOR1, CONR1R2, thiol, carboxyl, aldehyde, hydroxyl or amino;

[0010] Further, in formula (I), R1 and R2 are the same or different and are independently selected from H, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkylthio, halo-C1-C6 alkylthio, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C4 alkynyl, C1-C6 alkoxy-substituted C1-C6 alkyl, C1-C6 alkoxy-substituted C1-C6 alkoxy, C1-C6 alkylthio-substituted C1-C6 alkyl, halogen, CN or amino;

[0011] R3 is selected from H, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C2-C6 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, halogen, CN or amino;

[0012] R4 and R5 are the same or different and are independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

[0013] Or R4 and R5 together form a group -(CH2) m -, m means 2-6;

[0014] R6 represents H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C4 alkynyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylamino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C4 alkynyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylamino, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C4 alkynyl, aminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkoxy-substituted C1-C6 alkyl, C1-C6 alkoxy-substituted C1-C6 alkoxy, C3-C6 cycloalkyloxycarbonyl, C3-C6 cycloalkylaminocarbonyl, C3-C6 heterocyclyl, aminocarbonyl-substituted C1-C6 alkyl, CN, halogen, NO2, COOR1, CONR1R2, thiol, carboxyl, aldehyde, hydroxyl or amino;

[0015] Furthermore, in formula (I), R1 and R2 are the same or different and are independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C2-C6 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl or halogenated C3-C6 cycloalkyl;

[0016] R3 is selected from H, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C4 alkynyl, halogen or CN;

[0017] R4 and R5 are the same or different and are independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

[0018] Or R4 and R5 together form a group -(CH2) m -, m means 2-5;

[0019] R6 represents H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkenyloxy, C2-C6 alkenylthio, C2-C4 alkynyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkoxy-substituted C1-C6 alkyl, C1-C6 alkoxy-substituted C1-C6 alkoxy, aminocarbonyl-substituted C1-C6 alkyl, CN, halogen, NO2, COOR1, sulfhydryl, carboxyl, aldehyde, hydroxyl or amino;

[0020] Further, in formula (I), R6 represents H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C3-C6 cycloalkyl, C2-C6 alkenyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-substituted C1-C6 alkyl, aminocarbonyl-substituted C1-C6 alkyl, CN, halogen, thiol, carboxyl, hydroxyl or amino;

[0021] Furthermore, in formula (I), R1 and R2 are the same and are independently selected from H, C1-C6 alkyl, C1-C6 alkoxy or C2-C6 alkenyl;

[0022] R3 is selected from H, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, halogen or CN;

[0023] R4 and R5 together form a group -(CH2) m -, m means 3-5;

[0024] R6 is selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxyl or amino;

[0025] Further, in formula (I), R1 and R2 are both the same C1-C4 alkyl group;

[0026] R3 is a C1-C4 alkyl group;

[0027] R4 and R5 together form a group -(CH2)3- or -(CH2)4-;

[0028] R6 is selected from H, C1-C4 alkyl, C1-C4 alkoxy, halogen, hydroxyl or amino;

[0029] Further, R1 and R2 are both the same methyl or ethyl group, R3 is methyl or ethyl group, R4 and R5 together form a group -(CH2)3- or -(CH2)4-, and R6 is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, fluorine, chlorine, bromine, hydroxyl or amino;

[0030] Further, R1 and R2 are both the same methyl or ethyl group, R3 is methyl or ethyl group, R4 and R5 together form a group -(CH2)3- or -(CH2)4-, and R6 is selected from H, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, fluorine, chlorine, bromine, hydroxyl or amino group;

[0031] Furthermore, the structure of formula (I) is any one of the following:

[0032]

[0033]

[0034]

[0035] In the definition of the above compound structural formula, the professional terms used have the following meanings:

[0036] C1-C6 alkyl: a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl or tert-butyl.

[0037] Halogen or halogen: refers to fluorine, chlorine, bromine and iodine.

[0038] Halogenated C1-C6 alkyl: a straight-chain or branched alkyl group having 1 to 6 carbon atoms, in which the hydrogen atoms may be partially or completely replaced by halogen, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.

[0039] C1-C6 alkoxy: a straight-chain or branched alkyl group with 1 to 6 carbon atoms, connected to the structure through an oxygen atom bond, for example, methoxy, ethoxy, etc.

[0040] Halogenated C1-C6 alkoxy: a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, in which the hydrogen atoms may be partially or completely replaced by halogen, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.

[0041] C1-C6 alkylthio: a straight-chain or branched alkyl group with 1 to 6 carbon atoms, connected to the structure through a sulfur atom bond, such as methylthio, ethylthio, etc.

[0042] Halogenated C1-C6 alkylthio: a straight-chain or branched alkylthio group having 1 to 6 carbon atoms, in which the hydrogen atoms may be partially or completely replaced by halogen atoms, for example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc.

[0043] C2-C6 alkenyl: a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl.

[0044] C2-C4 alkynyl: a straight-chain or branched alkynyl group having 2 to 4 carbon atoms, such as ethynyl.

[0045] C1-C6 alkylamino: a straight-chain or branched alkyl group with 1 to 6 carbon atoms, connected to the structure via a nitrogen atom bond, such as methylamino, ethylamino, etc.

[0046] Halogenated C1-C6 alkylamino: a straight-chain or branched alkylamino group having 1 to 6 carbon atoms, wherein the hydrogen atoms in these alkylamino groups may be partially or completely replaced by halogen, for example, chloromethylamino, dichloromethylamino, trichloromethylamino, fluoromethylamino, difluoromethylamino, trifluoromethylamino, chlorofluoromethylamino, trifluoroethylamino, etc.

[0047] C1-C6 alkoxy-substituted C1-C6 alkyl group: a group in which an alkyl group having 1 to 6 carbon atoms is substituted with an alkoxy group having 1 to 6 carbon atoms as a substituent.

[0048] C1-C6 alkyl group substituted by C1-C6 alkylthio group: a group in which an alkyl group having 1 to 6 carbon atoms is substituted by an alkylthio group having 1 to 6 carbon atoms.

[0049] C1-C6 alkoxy-substituted C1-C6 alkoxy group: a group in which an alkoxy group having 1 to 6 carbon atoms is substituted with an alkoxy group having 1 to 6 carbon atoms as a substituent.

[0050] C1-C6 alkylcarbonyl: a group formed by linking an alkyl group having 1 to 6 carbon atoms to a carbonyl group.

[0051] C1-C6 alkoxycarbonyl: a group formed by linking an alkoxy group having 1 to 6 carbon atoms to a carbonyl group.

[0052] C1-C6 alkylaminocarbonyl: a group formed by linking an alkylamino group having 1 to 6 carbon atoms to a carbonyl group.

[0053] C1-C6 alkylsulfonyl group: a group formed by linking an alkyl group having 1 to 6 carbon atoms to a sulfonyl group.

[0054] C3-C6 cycloalkyl: a cycloalkyl group having 3 to 6 carbon atoms.

[0055] Halogenated C3-C6 cycloalkyl: a cycloalkyl group having 3 to 6 carbon atoms, in which the hydrogen atoms may be partially or completely replaced by halogen atoms.

[0056] Aminocarbonyl-substituted C1-C6 alkyl: a group formed by sequentially linking an amino group and a carbonyl group as a substituent for an alkyl group having 1 to 6 carbon atoms, for example, -CH2-CO-NH2.

[0057] C3-C6 cycloalkyloxycarbonyl: a group formed by sequentially connecting a cycloalkyl group having 3 to 6 carbon atoms to an oxygen atom and a carbonyl group.

[0058] C3-C6 heterocyclic group: a group formed by inserting O, S or N into a cycloalkyl group having 3 to 6 carbon atoms.

[0059] C3-C6 heterocyclyloxy: A group formed by inserting O, S or N into a cycloalkyl group having 3 to 6 carbon atoms is connected to the structure via an oxygen atom bond.

[0060] C3-C6 heterocyclyloxycarbonyl: a group formed by sequentially linking a heterocyclyl having 3 to 6 carbon atoms to an oxygen atom and a carbonyl group.

[0061] The salt is a pesticide-acceptable salt, specifically a salt obtained by reacting the phenylpyrazoline derivative of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid may be an inorganic acid (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid, etc.) or an organic acid (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the pesticide-acceptable salt may also be a salt obtained by reacting the phenylpyrazoline derivative of the present invention with a chemically acceptable base, wherein the chemically acceptable base may be an inorganic base (such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or an organic base (such as trimethylamine, triethylamine, etc.);

[0062] Furthermore, the pesticide-acceptable salt may be a potassium salt, a sodium salt, an ammonium salt, a calcium salt, a pyridinium salt or a choline salt.

[0063] The present invention also discloses a herbicidal composition, comprising at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof; preferably, further comprising a formulation carrier or a formulation adjuvant.

[0064] The present invention also discloses a method for controlling unwanted plant and / or crop diseases, comprising applying an effective amount of at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof or the above-mentioned fungicidal and / or herbicidal composition to the unwanted plants and / or crops; preferably, the crops may be crops that develop or do not develop diseases.

[0065] The present invention also discloses the use of at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof or the above-mentioned herbicidal and / or herbicidal composition for controlling and / or preventing unwanted plant and / or crop diseases.

[0066] The present invention also discloses a herbicidal composition, comprising a herbicidally effective amount of at least one of the phenylpyrazoline derivatives or salts thereof as described above; preferably, the composition further comprises a formulation carrier or a formulation adjuvant.

[0067] The present invention also discloses a bactericidal composition, comprising a bactericidal effective amount of at least one of the phenylpyrazoline derivatives or salts thereof as described above; preferably, the composition further comprises a formulation carrier or a formulation auxiliary agent.

[0068] The present invention also discloses a method for controlling unwanted plants, comprising applying a herbicidally effective amount of at least one of the phenylpyrazoline derivatives or salts thereof or the herbicidal composition described above to the unwanted plants.

[0069] The present invention also discloses a method for controlling crop diseases, comprising applying an effective amount of at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof or the above-mentioned fungicide composition to crops; preferably, the crops may be disease-infected or disease-free crops.

[0070] The present invention also discloses use of at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof or the above-mentioned herbicidal composition for controlling unwanted plants.

[0071] The present invention also discloses the use of at least one of the above-mentioned phenylpyrazoline derivatives or salts thereof or the above-mentioned fungicide composition in controlling crop diseases.

[0072] The compound of formula I can be obtained by reacting an intermediate compound represented by formula (II) with an intermediate compound represented by formula (III) to obtain a product (in the following chemical formulas, unless otherwise defined, the substituents and symbols have the same meanings as the substituents and symbols defined in general formula I):

[0073]

[0074] To facilitate the reaction, an alkaline agent may be used as an acid-binding agent in the reaction process shown above. Preferably, the acid-binding agent is an organic alkaline agent, such as triethylamine. The solvent may be selected from one or more solvents selected from acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, dichloroethane, and ethyl acetate.

[0075] Formula II compound is known or can be prepared similarly to known methods. For example, the method according to patent CN99803747.8 can be synthesized, and formula III compound can be prepared by pyrazole acid with corresponding structure. The preparation of pyrazole acid with corresponding structure can be synthesized according to the method provided in the patent of patent CN1161965A or CN102224149A according to publication number, wherein the conversion for amino group includes but is not limited to using concentrated hydrochloric acid to carry out nucleophilic substitution reaction, amino group is replaced by chloro group, and then using Mg / THF to generate Grignard reagent and then passing into carbonic acid gas, then adding acidic reagent to hydrolyze and then using SOCl2 to react and amino group can be converted to acyl chloride group.

[0076] The compounds of formula I of the present invention have outstanding herbicidal activity against many annual monocotyledonous and dicotyledonous unwanted plants. The active substances of the present invention are also effective against perennial weeds that grow from rhizomes, rootstocks, or other perennial organs. As for the timing of use of the active substances of the present invention, it can be before sowing, before germination, or after germination. In particular, representative examples of monocotyledonous and dicotyledonous weed groups that can be controlled by the compounds of the present invention are mentioned. Representative examples of weed species on which the active substances of the present invention can play an effective role include monocotyledonous plants: annual Avena, Lolium, Alopecurus, Echinochloa, Digitaria, Setaria, and Cyperus, and perennial Agropyron, Cyperus, Imperata, and Sorghum, as well as perennial Cyperus.

[0077] With respect to dicotyledonous weed species, its activity extends to species such as annual Galium, Viola, Veronica, Sesame, Chickweed, Amaranth, Sinapis, Ipomoea, Rhizoma Coptidis, Matricaria, and Abutilon, as well as perennial weeds such as Convolvulus, Thistle, Rumex, and Artemisia. Even under the specific conditions of rice sowing, the active ingredients of the present invention are effective in controlling unwanted plants such as Echinochloa, Sagittaria, Alisma, Eriobotrya, Saccharum, and Cyperus. If applied to the soil surface before germination, the compounds of the present invention can completely prevent weed seedlings from emerging, or arrest weed growth as soon as cotyledons emerge, ultimately killing them completely after three to four weeks. While the compounds of the present invention exhibit excellent herbicidal activity against both monocotyledonous and dicotyledonous weeds, they cause little or no damage to economically important crops such as wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. Therefore, the compounds of the present invention are well-suited for selectively controlling unwanted vegetation in agricultural crops or ornamental plants. Furthermore, the compounds of the present invention can significantly regulate the growth of crop plants. By modulating plant metabolism, these compounds can be used to target plant components and promote harvest, for example by causing plant desiccation and dwarfing. Furthermore, they are suitable for regulating and inhibiting undesirable plant growth without disrupting crop growth. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops because it can reduce or completely prevent lodging.

[0078] The compound of the present invention can be applied using general formulations, including wettable powders, soluble powders, emulsifiable concentrates, aqueous emulsions, suspensions, dispersible oil suspensions, dusts, microcapsule suspensions, water-dispersible granules, water-soluble granules, and the like. Thus, the present invention also provides herbicidal compositions comprising a compound of formula I. According to common biological and / or chemical physical parameters, the compound of formula I can be formulated in a variety of ways. Suitable formulation selection examples include wettable powders (WP), wettable liquids (SL), soluble powders (SP), dispersible liquids (DC), aqueous solutions (AS), microemulsions (ME), emulsifiable concentrates (EC), aqueous emulsions (EW), sprayable solutions, suspensions (SC), dispersible oil suspensions (OD), dusts (DP), microcapsule suspensions (CS), water-dispersible granules (WG), water-soluble granules (SG), large granules (GG), granules for broadcasting and soil application (GR), aerosols (AE), ultra-low volume agents (ULV), and wax products. Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives.

[0079] In mixed formulations or tank-mixed formulations, suitable active substances that can be mixed with the active substance of the present invention are, for example, known substances listed in the "World Pesticide New Variety Technology Encyclopedia" (China Agricultural Science and Technology Press, September 2010). For example, the following herbicide active substances can be mixed with the compounds of formula I: acetochlor, butachlor, alachlor, isopropyl metolachlor, isopropyl metolachlor, S-isopropyl metolachlor, pretilachlor, acetochlor, acetochlor, naphthiachlor, R-(L-) naphthiachlor, propanil, mefenacet, bisbencarb, fluazifop, flufenacet, bromobutachlor, dimethachlor, high-efficiency dimethachlor, ethoxybencarb, flufenacet, methoxyfenacet, metazachlor, isopropyl metolachlor, high-efficiency wheat grass fluorine methyl ester, high-efficiency wheat grass fluorine propyl ester, propanil, pethamide, butachlor, cyproconazole, flusulfamide, heptamiprole, isobutachlor, propargyl chlor, terbutachlor, dimethylbenzene, dimethylbenzene, chlorpyrifos, chlorpyrifos, trimethoprim-5-carboxamide, chlorpyrifos ... Atrazine, Metsulfuron, Licorice, Cyanuric acid, Indaziflam, Chlorsulfuron, Metsulfuron-methyl, Bensulfuron-methyl, Chlorsulfuron-methyl, Bensulfuron-methyl, Thisulfuron-methyl, Pyrazosulfuron-methyl, Methiosulfuron-methyl, Iodosulfuron-methyl sodium, Formamidosulfuron-methyl, Ethylsulfuron-methyl, Bensulfuron-methyl, Methiosulfuron-methyl, Nicosulfuron, Ethamidosulfuron-methyl, Acesulfuron-methyl, Ethoxysulfuron-methyl, Cyprosulfuron-methyl, Sulfonsulfuron-methyl, Tetrazosulfuron-methyl, Fentazocrine, Monosulfuron-methyl, Monosulfuron, Fluazuron-methyl, Fluazuron-methyl, Flupyrazosulfuron-methyl, Epoxysulfuron-methyl, Azosulfuron-methyl, Primosulfuron-methyl, Propyrazosulfuron-methyl, Trifloxysulfuron-methyl, Sulfosulphonyl, Trifloxysulfuron-methyl, Trifloxysulfuron-methyl, Metsulfuron-methyl sodium, Fluazuron-methyl, Methylsulfuron Acesulfame-2, Propyrisulfuron (Propyrisulfuron), Acesulfame-2, Propyrisulfuron, Acesulfame-2, Propyrisulfuron (Propyrisulfuron), Acesulfame-2, Propyrisulfuron, Acifluorfen, Fomesulfuron, Lactofenol, Fluazifop-butyl, Oxyfluorfen, Cyclohexan, Cyclohexan, Cyclohexan ethyl, Cyclohexan, Trifluoperazine, Methoxyfen, Trifluoperazine, Fluorinated herbicide-butyl, Fluorofensulfuron, Herbicide-butyl, Acesulfame-2, Dimethoate, Fluoxetine, Halosafen, Chlorotoluron, Isoproturon, Linuron, Diuron, Saprophon, Fluorofensulfuron, Benthiocarb, Methylbenthiocarb, Benthiocarb, Sulfathiocarb, Isoxuron, Terbuthiuron, Clodinafomyl, Chlorbromothiocarb, Methylthiocarb, Acyril, Methoxyfenuron, Bromothiocarb,Methoxycarb, Chlorvalon, Monuron, Cyclomefuron, Nonuron, Flusulfuron, Cyclomefuron, Cyclomefuron, Thiofuron, Buthiuron, Cyclomefuron, Parafluron, Methiathiazolin, Lonethoron, Trimethylisourea, Oxazolidinone, Monisouron, Anisuron, Methiuron, Chloreturon, Tetrafluoroborate, Betaine, Betaine-ethyl Ester, Betaine, Sulfur-butyl, Terclomefur, Avenaglucoside, Afenamide, Chlorpropamide, Dichlorobenzyl, Meclomefur, Chlorprophoxydim, Carboxazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Buthiuron, Cyclomefuron, Cyclomefuron, Wild Isopolinate, Methiobencarb, 2,4-D butyl ester, 2,4-D isooctyl ester, 2,4-D sodium salt, 2,4-D dimethylamine salt, 2,4-D ethylthioester, 2,4-D chlorothioester, 2,4-D propionic acid, high 2,4-D propionate, 2,4-D butyric acid, 2,4-D chloropropionic acid, 2,4-D chloropropionic acid salt, 2,4-D chlorobutyric acid, 2,4,5-T, 2,4,5-T propionic acid, 2,4,5-T butyric acid, 2,4,5-T butyric acid, 2,4-D chloroamine salt, dicamba, cypermethrin, cypermethrin, cypermethrin, trichlorobenzoic acid, ammonia dichloride Chlorobenzoic acid, methoxy-triclosan, diclofenac, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, high-efficiency fluazifop-butyl, quizalofop-butyl, quizalofop-butyl, oxadiazol-butyl, oxadiazol-butyl, cyhalofop-butyl, oxadiazol-butyl, cyhalofop-butyl, oxadiazol-butyl, cyhalofop-butyl, oxadiazol-butyl, clodinafop-butyl, thiazolinone, clodinafop-butyl, chlorfenapyr, trifloxystrobin, isocyanate, paraquat, diquat, oryzalin, ethylbutylfluanid, isopropylcarbamate, sulfuron, cyprodinil, aminopropylfluanid, ethylbutylfluanid, chloroethylfluanid, aminoethylfluanid, diclofenac, dichloroethylfluanid, methalpropalin, propanol, glyphosate, phosphamidon, glufosinate, methylaminophosphine, glufosinate, piperphosphine, bialaphos, dimethoate, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, phosphamidon, Imazapyr, Imazanic acid, Imazaquin, Metoclopramide, Metoclopramide ammonium, Imazapyr, Imazapyr-butyl, Cloflupyr, Cloflupyr 2-ethylhexyl, Clopyralid, Amiclopyralid, Triclopyr, Dithiopyr, Halofop-Cyclopyr, Triclopyralid, Cyclodim, Cyclopyralid, Cyclopyralid, Butoxyethyl Triclopyr, Cliodinate, Sethoxydim, Clethodim, Cyclodixon, Cyclofenac, Butoxydim, Buthidazole, Methiazolin, Cyclozin, Metamitron, Ethiazolin, Ametridione, Amibuzin, Bromoxynil, Bromoxynil Octanoyl, Ioxyl Octanoyl, Ioxyl, Dichlobenil, Diphenylacetonitrile,Bispyribac, Hydroxydichlorvos, Iodobonil, Sulfuramide, Bispyribac, Penoxsulam, Sulfuramide, Chloroacetyl, Bispyribac, Pyramide, Furoxen, Bispyribac-butyl, Pyrimidinesulfonyl, Cyclopyralid, Pyrimidinesulfonyl, Pyramide, Bispyribac-butyl, Mesotrione, Sulfotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, Isoxaflutole, Isoxachlorone, Fenoxasulfone, Methiozolin, Isopropylpyraclostrobin, Pyramide-butyl, Pyrazole, Wild Yankui, Benpyraclostrobin, Metamid, Pyrasulfotole, Pyroxasulfone, Mefenacet, Fluamidazole, Methiazolin, Amitriptyline, Azopyrazone, Fluamidazole, Sulfonamide, Bencarbazone, Bifenacet, Fluamidazole, Herbicide, Cyclopyralid, Cyclopyralid, Flupropacil, Flupropacil, Flufenacet-butyl, Fluoxetine, Flumioxamid, Cyclopyralid, Phthalobenzyl, Flumezin, Pentachlorophenol (sodium), Dinitrophenol, Dinitrophenol, Dioxin, Dioxet, Propylene Oxadiazole, oxadiazole, cyclopentadiazole, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, herbicide-resistant, bromomycin, dimethylpyridazone, pyridafol ... Benzocyclopentane, Avena sativa, Thiadiazole, Cottonamine, Hydrochloride, Methoxybenzone, Bensulfuron, Chlorpheniramine, Trichloropropionic acid, Alorac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazonemethyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, Methylsulfuron, Cambendichlor, Cyprodinil, Halocopirox, Halocopirox.

[0080] For example, the following fungicidal substances can be mixed with the compounds of formula I: bensulfuron, bensulfuron-M, ethoxysulfonate, chiralaxyl, clozylacon, dimethylpyrimidine, ethoxysulfonate, furalaxyl, oxamexyl, metalaxyl, metalaxyl, ofurace, oxalaxyl, quinclorac, benomyl, carbendazim, diethofencarb, malathion, pencycuron, thiabendazole, thiophanate-methyl, zoxamide, fluoxazolidinone, bixafen, boscalid, carboxin, fluopicolide, flutolanil, furoxam, mefenamic acid, oxycarboxin, penthiopyrad, bromopyralid, N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4- Carboxamide, indazolesulfamide, azoxystrobin, cyazolin, kasoxam-butyl, fenoxam-butyl, oxathiocarb, fenamid, fluoxastrobin, kresoxim-butyl, fenoxystrobin, pyraclostrobin, pyribencarb, picoxystrobin, trifloxystrobin, diclofenac, fluazinam, triphenyltin acetate, triphenyltin chloride, tin thiocarb, amine extinguisher, blasticidin, cyprodinil, kasugamycin, kasugamycin-hydrate hydrochloride, pyraclostrobin, pyrimethanil, fenpiclonil, fludioxonil, phenoxyquin, acetobacter, iprodione, procymidone, vinclozolin, aminophosphonic acid, aminophosphonate potassium, dichlorvos, isoprofen, blastifoglu, pyraclofos-methyl, tolclofos-methyl, propamocarb, propamocarb hydrochloride, fenhexamid, oxepiconazole, bisbenzimidazole, oxadiazol, benzyltriazole Alcohol, difenoconazole, diniconazole, R-diniconazole, ethoconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furoconazole, hexaconazole, imidazole, picroconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, silifazole, spiroxamine, tebuconazole, triadimefon, triamcinol, trichlorfon, uniconazole, voriconazole, imazalil, imacandil, oximidazole, chlorfenapyr, flufenapyr, flufenapyr, pyrimidine, trifonazole, triamcinol, pyrimidine, trifonazole, triamcinol, pyrimidine, trifonazole, aldimorph, dodecanone, dodecanone acetate, fenpropimorph, trimorph, fenpropimorph, spiroxamine, naftifine, barnyardgrass, terbinafine, benzthiopyrad, bialaphos, dimethomorph, flumorph, isopropanil, polyoxin, polyoxy ampicillin, validamycin A, cyclopropane, diclocymet, cyanamide, tetrachlorophthalide, pyroquilon, tricyclazole, benzothiadiazole, thiabendazole, thiazolamide, captafol, captan, chlorothalonil, copper salts such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, quinoline copper and Bordeaux mixture, diflubenzuron, dicyanoanthraquinone, dodine, dodine free base, ferbam, folpet, flufolpet, guanidine salt, guanidine acetate, guanidine octylamine, guanidine octylamine alkylbenzenesulfonate, guanidine octylamine acetate, mancozeb, maneb, maneb, maneb, maneb zinc, propineb, sulfur and sulfur preparations including calcium polysulfide, thiram, tolylfluanid, maneb, ziram, amibromdol,Benzenethiocyanate, pyraclostrobin, carbamicin, carvone, mite-killing agent, chloropicrin, thiophene, cyfluanid, cymoxanil, dazomethanil, imidacloprid, pyraclostrobin, dichlorophen, chlornitril, bendiquinone, diphenylamine, ethaboxam, pyrimidine, flutolanil, sulfaquinoxaline, flutolanil, flutolanil, phosphine-aluminum, hexachlorobenzene, 8-hydroxyquinoline, iprodione, isothiocyanate, sulfaquinoxaline, mefenacet, cyanamide, midomycin, domycin, nickel-magnesium, phthalostrobin, octhiophene, oxamocarb, oxyfenthiin, pentachlorophenol and its salts, 2-phenylphenol and its salts, chloranil, propanosine-sodium, proquinazid, nitropyrrolidone, pentachloronitrobenzene, chloranil, tetrachloronitrobenzene, imidazobactam, salicylate, cyanamide.

[0081] In summary, due to the adoption of the above technical solution, the beneficial effects of the present invention are:

[0082] By chemically modifying and molecularly designing phenylpyrazoline derivatives and introducing substituted pyrazolyl structures, a series of more efficient, selective and safe compounds with herbicidal and / or fungicidal activities that can be used for agricultural or forestry weed control and / or crop disease prevention and control are obtained. They have particularly good activity and selectivity against common weeds in paddy fields and have excellent control effects on cucumber downy mildew. DETAILED DESCRIPTION

[0083] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0084] Through comprehensive consideration of the economic efficiency, diversity, and biological activity of the synthesized compounds, some compounds were selected and listed in the table below. The specific compound structures are shown in Table 1, and the specific compound physical properties are shown in Table 2. The compounds in Tables 1 and 2 are intended to better illustrate the present invention and are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0085]

[0086] Table 1 Structure of compounds of formula I

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] Table 2 1 H NMR data

[0093]

[0094]

[0095]

[0096]

[0097] The methods for preparing the compounds of the present invention are described in the following technical schemes and examples. The raw materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. These modifications or variations of the preparation methods of the present invention that result in various isomers of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0098] Example 1

[0099] Synthesis of compound 10:

[0100]

[0101]

[0102] Intermediate 1 (3.16 g, 10 mmol) and acetonitrile (30 ml) were added to a reaction flask, and intermediate 2 (1.98 g, 10 mmol) was added with stirring at 10°C. Triethylamine (2 eq) was added to the mixture under stirring at 10°C, and the reaction was monitored by TLC (ethyl acetate:petroleum ether=1:1, GF254, UV color development). After the reaction was complete, the solvent was removed and the compound was purified by column chromatography to obtain the target compound 10 as a white solid powder with a melting point of 126-128°C. 1H-NMR(CDCl3-d6,500MHz)δ:6.88(s,2H),4.31-4.28(m,2H),4.05-4.00(t,2H),3.96-3.93(t,2H),3.92-3.89(m,4H),2.78-2 .73(t,2H),2.59-2.52(m,2H),2.48-2.43(m,2H),2.29-2.25(s,6H),1.99-1.93(s,2H),1.79-1.74(s,2H),1.13-1.08(m,6H).

[0103] Example 2

[0104] Synthesis of compound 11:

[0105]

[0106] Intermediate 1 (3.16 g, 10 mmol) and acetonitrile (30 ml) were added to a reaction flask, and intermediate 3 (2.52 g, 10 mmol) was added with stirring at 10°C. Triethylamine (2 eq) was added to the mixture under stirring at 10°C, and the reaction was monitored by TLC (ethyl acetate:petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the solvent was removed and the compound was purified by column chromatography to obtain the target compound 11 as a white solid powder with a melting point of 138-141°C. 1 H-NMR(CDCl3-d6,500MHz)δ:6.87(s,2H),4.33-4.30(t,2H),4.06-4.02(t,2H),3.95-3.92(t,2H),3.67-3.63(m,4H ),2.72-2.68(t,2H),2.67-2.63(m,4H),2.53-2.49(s,3H),1.97-1.93(m,2H),1.77-1.74(m,2H),1.15-1.11(m,6H).

[0107] Example 3

[0108] Synthesis of compound 12:

[0109]

[0110] Intermediate 1 (3.16 g, 10 mmol) and acetonitrile (30 ml) were added to a reaction flask, and intermediate 4 (2.40 g, 10 mmol) was added with stirring at 10°C. Triethylamine (2 eq) was added to the mixture under stirring at 10°C, and the reaction was monitored by TLC (ethyl acetate:petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the solvent was removed and the compound was purified by column chromatography to obtain the target compound 12 as a light yellow solid powder with a melting point of 133-136°C. 1 H-NMR(CDCl3-d6,500MHz)δ:6.88(s,2H),4.35-4.31(t,2H),4.05-4.01(t,2H),3.93-3.90(t,2H),3.68-3.64(m,4H),2.73-2 .69(t,2H),2.67-2.63(m,4H),2.54-2.50(s,3H),1.98-1.93(m,2H),1.78-1.74(m,2H),1.26-1.22(s,9H),1.16-1.11(m,6H).

[0111] Example 4

[0112] Synthesis of compound 66:

[0113]

[0114] Intermediate 1 (3.16 g, 10 mmol) and acetonitrile (30 ml) were added to a reaction flask, and intermediate 5 (1.84 g, 10 mmol) was added with stirring at 10°C. Triethylamine (2 eq) was added to the mixture under stirring at 10°C, and the reaction was monitored by TLC (ethyl acetate:petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the solvent was removed and the compound was purified by column chromatography to obtain the target compound 66 as a yellow solid powder with a melting point of 128-131°C. 1 H-NMR(CDCl3-d6,500MHz)δ:6.88(s,2H),4.38-4.31(t,2H),4.09-4.04(t,2H),3.97-3.95(t,2H),3.96-3.90(m,4H ),2.83-2.79(m,2H),2.59-2.52(m,4H),2.49-2.43(m,2H),2.35-2.32(s,3H),2.30-2.27(s,3H),1.13-1.08(m,6H).

[0115] Example 5

[0116] Synthesis of compound 120:

[0117]

[0118] Intermediate 1 (3.16 g, 10 mmol) and acetonitrile (30 ml) were added to a reaction flask, and intermediate 120 (2.15 g, 10 mmol) was added with stirring at 10°C. Triethylamine (2 eq) was added to the mixture under stirring at 10°C, and the reaction was monitored by TLC (ethyl acetate:petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the solvent was removed and the compound was purified by column chromatography to obtain the target compound 120 as a light yellow solid powder with a melting point of 121-123°C. 1 H-NMR(CDCl3-d6,500MHz)δ:6.86(s,2H),4.26(s,3H),4.14-4.10(m,4H),3.75-3.72(m,4H),2.66 (m,2H),2.66-2.60(m,4H),2.42-2.38(s,3H),1.17-1.10(m,9H),2.13(m,2H),1.05-1.02(m,3H).

[0119] Example 6

[0120] Evaluation of herbicidal activity (post-emergence):

[0121] The test compound was dissolved in DMF to prepare a 2.5% stock solution, which was then diluted with water containing 0.1% Tween-80 for later use. The target seeds were sown in a plastic pot with a height of 9 cm and a diameter of 10 cm. After sowing, the soil was covered with 0.5-1 cm of soil. After the bottom was absorbed by water, the seeds were placed in a greenhouse for cultivation. When the seeds grew to the two-leaf stage, they were sprayed with the stems and leaves using a spray tower according to the designed dosage. The experiment was repeated 3 times. After the liquid on the soil surface was naturally air-dried, the soil was treated and the bottom was absorbed by water to 60%, then moved into a greenhouse and cultivated according to conventional methods. The growth and development of the test materials were observed regularly. According to the fourth part of the pesticide indoor bioassay test guidelines NY / T 1155.4-2006, and based on actual conditions, the control effect of the test agent on weeds was regularly investigated by visual inspection after treatment. Control effect grading standard:

[0122] Level 9: Equivalent to 67.6-100% of the weeds in the blank control area;

[0123] Level 8: Equivalent to 35.1-67.5% of the weeds in the blank control area;

[0124] Level 7: Equivalent to 25.1-35% of the weeds in the blank control area;

[0125] Level 6: Equivalent to 15.1-25% of the weeds in the blank control area;

[0126] Level 5: Equivalent to 10.1-15% of the weeds in the blank control area;

[0127] Level 4: Equivalent to 5.1-10% of the weeds in the blank control area;

[0128] Level 3: Equivalent to 2.6-5% of weeds in the blank control area;

[0129] Level 2: Equivalent to 0-2.5% of weeds in the blank control area;

[0130] Level 1: All dead.

[0131] According to the above method, some compounds were selected and compared with the control group (95% pinoxaden TC, commercially available) for parallel determination of herbicidal activity. The herbicidal activity experimental results are shown in the following table:

[0132] Table 3 Prevention level

[0133]

[0134]

[0135] Through the above experiments, it can be found that the compounds protected by the present invention have excellent biological activity, especially against multiflora ryegrass and bluegrass, have good weed control effects, and have good commercial application prospects.

[0136] Example 7

[0137] Crop safety assessment:

[0138] Prepare nutrient soil and fill it into a 10 cm diameter and 9 cm high paper cup. Sow a certain amount of crop seeds into the paper cup and cover with 1.5 cm of soil after sowing. After pressing and watering, incubate in a greenhouse for 2 weeks. Then, dilute the acetone solution containing the test compound technical with water containing 0.1% Tween 80 to the desired concentration. Spray the stems and leaves using a spray tower according to the designed experimental dosage (three replicates per treatment). Then, place the plant in the greenhouse and manage it according to conventional methods. Regularly observe the growth and development of the test material. According to Part 8 of the Guidelines for Indoor Pesticide Bioassays and based on actual conditions, regularly observe the effects of the test agent on the crop by visual inspection after treatment. At the same time, describe the symptoms of pesticide damage. The main symptoms are:

[0139] 1) Color change (yellowing, bleaching, purple, etc.);

[0140] 2) morphological changes (new leaves are deformed, twisted, etc.);

[0141] 3) Growth changes (dehydration, wilting, dwarfing, clustering, etc.).

[0142] Phytotoxicity evaluation grading:

[0143] Grade a: no phytotoxicity;

[0144] Grade B: The degree of phytotoxicity is 1-10%, with no obvious phytotoxicity;

[0145] Grade C: The degree of phytotoxicity is 11-30%, which is slight phytotoxicity;

[0146] Grade d: The degree of phytotoxicity is 31-50%, which is moderate phytotoxicity;

[0147] Grade E: The degree of pesticide damage is 51-100%, which is severe pesticide damage.

[0148] Following the above method, a number of compounds (Compound Nos. 10-13, Compound 16, Compound 19, Compound 66, Compounds 69-70, and Compound 73) were selected for parallel testing of crop safety with pinoxaden. The results of the crop safety test three weeks after application are shown in the following table:

[0149] Table 4 Crop safety test

[0150]

[0151]

[0152] It can be seen that at the current dosage, the compounds protected by the present invention have essentially no phytotoxicity or no obvious phytotoxicity to wheat or barley as observed by visual inspection. Therefore, at a suitable dosage, they have good safety for crops, especially wheat or barley.

[0153] Example 8

[0154] Evaluation of bactericidal biological activity:

[0155] A certain amount of compound sample was weighed and dissolved in acetone to prepare a stock solution for later use. During the experiment, the compound sample and a control agent (95% fluopyram TC, 10% fluthiazolinone OD, and 95% pinoxaden TC, all commercially available) were prepared in water containing 0.1% Tween 80 to form a series of concentration gradient solutions (test compound and control agent concentration: 400 mg / L) for in vivo screening. Potted cucumber seedlings (Xintai Mici) with uniform growth, one leaf and one heart, were selected as the test host plants for cucumber downy mildew (Pseudoperonospora cubensis). A bioassay spray tower was used, spraying 30 ml of solution per treatment and allowing the solution to dry naturally. After 24 hours, the pathogen was inoculated, and a blank control was set up. A spore suspension of cucumber downy mildew was sprayed onto the cucumber seedlings using an inoculator. The inoculated cucumber seedlings were bagged in black plastic bags to maintain moisture for 12 hours, then unbagged and cultured in a greenhouse (22°C, RH = 50, no light). After 4-10 days, when the seedlings have 4-6 true leaves, the fungicidal activity of the compounds is assessed. Results are expressed using a scale of 100 to 0, with 100 representing no disease and 0 representing the most severe disease, according to the American Society of Plant Pathology's "A Manual of Assessment Keys for Plant Diseases."

[0156] Table 5 Test results on cucumber downy mildew

[0157]

[0158]

[0159]

[0160] Through the above experiments, it can be found that the compounds protected by the present invention have excellent fungicidal biological activity, especially for cucumber downy mildew, have excellent prevention and control effects, and have good commercial application prospects.

[0161] The above embodiments are intended only to illustrate the technical concepts and features of the present invention. Their purpose is to enable those skilled in the art to understand the contents of the present invention and implement them accordingly. They are not intended to limit the scope of protection of the present invention. Any equivalent changes or modifications made based on the essence of the present invention are intended to be covered by the scope of protection of the present invention.

Claims

1. A pyrazoline derivative or a salt thereof, having the structural formula as follows: Where, In formula (I), R1 and R2 are the same and are independently selected from H, C1-C6 alkyl, C1-C6 alkoxy or C2-C6 alkenyl; R3 is selected from H, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, halogen or CN; R4 and R5 together form a group -(CH2) m -, m means 3-4; R6 is selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxyl or amino; When R1 is ethyl, R2 is ethyl, R3 is methyl, R4 and R5 together form a group -(CH2) m -, m represents 4, R6 is not methyl; and when R1 is ethyl, R2 is ethyl, R3 is methyl, R4 and R5 together form a group -(CH2) m When - and m represents 4, R6 is not a trifluoromethyl group.

2. A pyrazoline derivative or a salt thereof according to claim 1, characterized in that In formula (I), R1 and R2 are both the same C1-C4 alkyl group; R3 is a C1-C4 alkyl group; R4 and R5 together form a group -(CH2)3- or -(CH2)4-; R6 is selected from H, C1-C4 alkyl, C1-C4 alkoxy, halogen, hydroxyl or amino.

3. A pyrazoline derivative or a salt thereof according to claim 2, characterized in that The structure of formula (I) is any one of the following:

4. A fungicidal and / or herbicidal composition, characterized in that: The method comprises at least one of the pyrazoline derivatives or salts thereof according to any one of claims 1 to 3.

5. A pyrazoline derivative or a salt thereof according to claim 4, further comprising a formulation carrier or a formulation auxiliary agent.

6. A method for controlling unwanted plant and / or crop diseases, characterized in that The method comprises applying an effective amount of at least one of the pyrazoline derivatives or salts thereof according to any one of claims 1 to 3 or the fungicidal and / or herbicidal composition according to any one of claims 4 to 5 to unwanted plants and / or crops, wherein the crop disease is a fungal disease.

7. A pyrazoline derivative or a salt thereof according to claim 6, wherein the crop is a crop that produces or does not produce a disease.

8. Use of at least one of the pyrazoline derivatives or salts thereof according to any one of claims 1 to 3 or the fungicidal and / or herbicidal composition according to any one of claims 4 to 5 for controlling and / or preventing unwanted plant and / or crop diseases, wherein the crop diseases are fungal diseases.

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