TW202012390A - Novel substituted pyrazole derivatives - Google Patents

Abstract

An object of the present disclosure is to provide a novel substituted pyrazole compound or a salt thereof as represented by formula (1) that controls pests: wherein, Q represents an oxygen atom or a sulfur atom, or the like; R represents substituted or unsubstituted aryl, C1-C12 alkyl, or the like; R1 represents hydrogen, substituted or unsubstituted C1-C12 alkylcarbonyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, or the like; R2 and R3 each independently represent hydrogen, substituted or unsubstituted C1-C12 alkyl, or the like; R4 and R5 each independently represent hydrogen, substituted or unsubstituted C1-C12 alkyl, or the like; and X1, X2 and X3 represent C-R8, C-R9 and C-R10, respectively, wherein R8, R9 and R10 each independently represent hydrogen, halogen, methyl, ethyl or the like.

Description

Novel substituted pyrazole derivatives

Field of invention The present disclosure relates to novel pyrazole compounds and processes for preparing these compounds. Furthermore, the present disclosure provides an agricultural and horticultural insecticide and fungicide composition containing the compound of the present disclosure.

Background of the invention In recent years, it has been observed that due to the long-term and large-scale use of conventional insecticides and fungicides, various insects and fungi have acquired resistance to this. Therefore, these known pesticides (pesticides) cannot now effectively control these pests. To overcome this situation, there is an ongoing need to develop new insecticides that can control various chemical-sensitive and chemical-resistant insects and fungi.

Various compounds with pest control activity have been previously developed. For example, WO 2007/088978 (Patent Literature (PTL) 1) discloses quinoline derivatives having fungicidal activity, but there is no description about insecticidal activity. Furthermore, WO 2006/013896 (Patent Literature (PTL) 2), JP 2008-110953 (Patent Literature (PTL) 3), JP 2633377 (Patent Literature (PTL) 4) and US 4168311 (Patent Literature (PTL) 5) A quinoline derivative with an insecticidal activity is revealed.

其中， Z代表一氧原子、一硫原子、SO、SO₂ 、CO或Q等等， 其中Q是一C_1-4 烷撐基團(C_1-4 alkylene group)(該C_1-4 烷撐基團可被取代以一鹵素原子或一氰基基團)； R₁ 、R₂ 和R₃ 代表氫、C_1-4 烷基基團、C_1-4 鹵烷基基團、C_1-4 烷基氧基基團、C_1-4 鹵烷氧基基團、烷基氧基羰基基團、硝基基團、氰基基團、甲醯基基團、乙醯基基團、乙醯基乙氧基基團等等； R₂ 和R₃ 一起代表一個(CH₂ )_m ，其中m代表3或4； X₁ 、X₂ 和X₃ 各個獨立地代表一氫原子、一鹵素原子、一可被取代以一鹵素原子的C_1-4 烷基基團或一C_1-4 烷基氧基基團、一C_1-4 烷基氧基羰基基團、一可被取代以一鹵素原子的C_1-4 烷基氧基基團，或一可被取代以一鹵素原子的C_1-4 烷基氧基羰基基團，有條件的是：X₁ 、X₂ 和X₃ 不同時地代表氫原子； W₁ 代表一氮原子或CY₁ ， W₂ 代表一氮原子或CY₂ ，和 W₃ 代表一氮原子或CY₃ ， 有條件的是：當W₁ 代表一氮原子時，W₂ 和W₃ 分別地代表CY₂ 和CY₃ ，當W₂ 代表一氮原子時，W₁ 和W₃ 分別地代表CY₁ 和CY₃ ，以及當W₃ 代表一氮原子時，W₁ 和W₂ 分別地代表CY₁ 和CY₂ ；以及 Y₁ 、Y₂ 和Y₃ 各個獨立地代表一氫原子、A，或 B， 其中A代表一C_1-8 烷基基團、C_1-8 烷基氧基基團、C_2-8 烯基基團、C_2-8 烯基氧基基團、C_1-8 烷基氧基羰基基團、C_2-8 烯基硫基基團、C_1-8 烷基亞磺醯基基團、C_2-8 烯基亞磺醯基基團、C_1-8 烷基磺醯基基團、C_2-8 烯基磺醯基基團、苯基基團，或苯氧基基團，其中所有這些取代基可進一步被取代以各種不同的基團(諸如鹵素、C_1-4 烷基基團等等)，以及 B代表一鹵素原子，或一C_1-4 烷基基團。PTL 1 and PTL 2 reveal the compounds represented by the following chemical formula ( A ):

Wherein, Z represents an oxygen atom, a sulfur atom, SO, SO _2, CO, etc., or Q, wherein Q is a C _1-4 alkylene group (C _1-4 alkylene group) (wherein the C _1-4 alkyl The propylene group may be substituted with a halogen atom or a cyano group); R ₁ , R ₂ and R ₃ represent hydrogen, C _1-4 alkyl group, C _1-4 haloalkyl group, C _{1 -4} alkyloxy group, C _1-4 haloalkoxy group, alkyloxycarbonyl group, nitro group, cyano group, methyl group, acetyl group, Acetyl ethoxy groups, etc.; R ₂ and R ₃ together represent a (CH ₂ ) _m , where m represents 3 or 4; X ₁ , X ₂ and X ₃ each independently represent a hydrogen atom, a halogen Atom, a C _1-4 alkyl group which may be substituted with a halogen atom or a C _1-4 alkyloxy group, a C _1-4 alkyloxycarbonyl group, a a halogen atom C _1-4 alkyl radical, which may be substituted, or a halogen atom to a C _1-4 alkyloxycarbonyl group, the conditions are: X _1, X ₂ and X ₃ Differently represent hydrogen atoms; W ₁ represents a nitrogen atom or CY ₁ , W ₂ represents a nitrogen atom or CY ₂ , and W ₃ represents a nitrogen atom or CY ₃ , conditionally: when W ₁ represents a nitrogen atom , W ₂ and W ₃ represent CY ₂ and CY _{3 respectively} , when W ₂ represents a nitrogen atom, W ₁ and W ₃ represent CY ₁ and CY _{3 respectively} , and when W ₃ represents a nitrogen atom, W ₁ and W ₂ represent CY ₁ and CY _{2 respectively} ; and Y ₁ , Y ₂ and Y ₃ each independently represent a hydrogen atom, A, or B, where A represents a C _1-8 alkyl group, C _{1 -8} alkyloxy group, C _2-8 alkenyl group, C _2-8 alkenyloxy group, C _1-8 alkyloxycarbonyl group, C _2-8 alkenylthio group Group, C _1-8 alkylsulfinyl group, C _2-8 alkenylsulfinyl group, C _1-8 alkylsulfinyl group, C _2-8 alkenylsulfonyl group Group, phenyl group, or phenoxy group, where all of these substituents can be further substituted with various groups (such as halogen, C _1-4 alkyl groups, etc.), and B represents a halogen Atom, or a C _1-4 alkyl group.

These publications also mention that for agricultural and horticultural purposes, the compound represented by the chemical formula ( A ) is useful as a fungicide and insecticide to control pests. However, these publications do not include the compounds of the present disclosure anywhere. Citation List Patent Literature

PTL 1: WO 2007/088978A1 PTL 2: WO 2006/013896A1 PTL 3: JP 2008-110953 PTL 4: JP 2633377 PTL 5: US 4168311

Solution to Problem of the Invention The present disclosure provides novel substituted pyrazole compounds or salts thereof that exhibit high insecticidal and fungicidal activity against drug-resistant insects and fungi and drug-sensitive insects and fungi.

The present disclosure also provides a process for preparing these novel substituted pyrazole compounds or its salts.

The present disclosure further provides a novel agricultural and horticultural composition comprising a substituted pyrazole compound or a salt thereof as an active ingredient, which exhibits a resistance to chemical-resistant and chemical-sensitive insects and fungi Significant insecticidal and fungicidal effects.

In particular, the present inventors conducted extensive research and successfully synthesized a compound represented by the following chemical formula ( 1 ) or a salt thereof which has shown excellent insecticidal and fungicidal activity. The inventors have conducted further studies based on the above findings.

As a result of extensive research, the present inventors have discovered that a compound represented by the following general formula ( 1 ) or a salt thereof exhibits excellent insecticidal and fungicidal activity.

Therefore, the present disclosure relates to novel substituted pyrazole compounds represented by the following general formula ( 1 ) or their salts.

More specifically, the present disclosure includes the following specific examples: Specific example A1:

其中， Q代表一氧原子、一硫原子、CR₆ R₇ 或直接鍵； R₆ 和R₇ 各個獨立地代表氫、鹵素、氰基、C₁ -C₁₂ 烷基、C₁ -C₁₂ 鹵烷基、C₁ -C₁₂ 烷氧基、C₁ -C₁₂ 鹵烷氧基、C₁ -C₁₂ 氰基烷氧基、C₁ -C₁₂ 烷基硫基、C₁ -C₁₂ 鹵烷基硫基、C₁ -C₁₂ 烷氧基、C₁ -C₁₂ 烷基、C₁ -C₁₂ 鹵烷氧基、C₂ -C₁₂ 烯基、C₂ -C₁₂ 鹵烯基、C₂ -C₁₂ 烯基氧基、C₂ -C₁₂ 鹵烯基氧基、C₂ -C₁₂ 炔基、C₂ -C₁₂ 鹵炔基、C₂ -C₁₂ 炔基氧基、C₂ -C₁₂ 鹵炔基氧基、C₁ -C₁₂ 烷基亞磺醯基、C₁ -C₁₂ 烷基磺醯基、C₁ -C₁₂ 鹵烷基亞磺醯基、C₁ -C₁₂ 鹵烷基磺醯基、C₃ -C₁₂ 環烷基、C₁ -C₁₂ 烷基羰基、C₁ -C₁₂ 烷氧基羰基、C₁ -C₁₂ 鹵烷基羰基、C₁ -C₁₂ 鹵烷氧基羰基、C₁ -C₁₂ 烷基羰基胺基、C₁ -C₁₂ 烷基磺醯基氧基、C₁ -C₁₂ 烷基亞磺醯基氧基、經取代的或未經取代的芳基、經取代的或未經取代的雜芳基或者經取代的或未經取代的飽和雜環； R代表經取代的或未經取代的芳基、經取代的或未經取代的雜芳基、經取代的或未經取代的芳基C₁ -C₁₂ 烷基、經取代的或未經取代的雜芳基C₁ -C₁₂ 烷基、C₁ -C₁₂ 烷基、C₁ -C₁₂ 鹵烷基、C₁ -C₁₂ 氰基烷基、C₁ -C₁₂ 烷氧基C₁ -C₁₂ 烷基、C₁ -C₁₂ 烷基硫基C₁ -C₁₂ 烷基、、C₁ -C₁₂ 鹵烷氧基C₁ -C₁₂ 烷基、C₂ -C₁₂ 烯基、C₂ -C₁₂ 炔基、C₂ -C₁₂ 鹵烯基、C₂ -C₁₂ 鹵炔基、C₁ -C₁₂ 烷基亞磺醯基、C₁ -C₁₂ 烷基磺醯基、C₁ -C₁₂ 鹵烷基亞磺醯基、C₁ -C₁₂ 鹵烷基磺醯基、C₁ -C₁₂ 烷基羰基、C₁ -C₁₂ 鹵烷基羰基、C₁ -C₁₂ 烷氧基羰基、C₁ -C₁₂ 鹵烷氧基羰基、C₃ -C₁₂ 環烷基，或者飽和雜環； R₁ 代表氫、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₃ -C₁₂ 環烷基、經取代的或未經取代的芳基C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基羰基、經取代的或未經取代的C₁ -C₁₂ 鹵烷氧基羰基、經取代的或未經取代的C₂ -C₁₂ 烯基羰基、經取代的或未經取代的C₂ -C₁₂ 炔基羰基、經取代的或未經取代的C₃ -C₁₂ 環烷基羰基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的芳基氧基羰基、經取代的或未經取代的芳基C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的雜芳基氧基羰基、經取代的或未經取代的雜芳基C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的芳基羰基、經取代的或未經取代的芳基C₁ -C₁₂ 烷基羰基、經取代的或未經取代的雜芳基羰基、經取代的或未經取代的雜芳基C₁ -C₁₂ 烷基羰基、經取代的或未經取代的雜環羰基、經取代的或未經取代的雜環C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₃ -C₁₂ 環烷基C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₁ -C₁₂ 烷基亞磺醯基、經取代的或未經取代的C₁ -C₁₂ 烷基磺醯基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基亞磺醯基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基磺醯基、經取代的或未經取代的芳基亞磺醯基、經取代的或未經取代的雜芳基亞磺醯基、經取代的或未經取代的芳基磺醯基，或者經取代的或未經取代的雜芳基磺醯基； R₂ 代表氫、鹵素、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基，或者經取代的或未經取代的C₁ -C₁₂ 鹵烷氧基； R₃ 代表氫、鹵素、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 鹵烷氧基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₃ -C₁₂ 環烷基、經取代的或未經取代的芳基、經取代的或未經取代的雜芳基，或者經取代的或未經取代的雜環； R₄ 和R₅ 各個獨立地代表氫、鹵素、氰基、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 烷基硫基，或者經取代的或未經取代的芳基； X₁ 代表C-R₈ 或N， X₂ 代表C-R₉ 或N，和 X₃ 代表C-R₁₀ 或N， 有條件的是：當X₁ 代表一氮原子時，X₂ 和X₃ 分別地代表C-R₉ 和C-R₁₀ ，當X₂ 代表一氮原子時，X₁ 和X₃ 分別地代表C-R₈ 和C-R₁₀ ，以及當X₃ 代表一氮原子時，X₁ 和X₂ 分別地代表C-R₈ 和C-R₉ ； R₈ 、R₉ 和R₁₀ 各個獨立地代表氫、鹵素、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 鹵烷氧基、經取代的或未經取代的C₁ -C₁₂ 烷基硫基、經取代的或未經取代的C₁ -C₁₂ 鹵烷基硫基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的C₁ -C₁₂ 鹵烷氧基羰基、氰基、硝基或者經取代的或未經取代的胺基。 具體例A2：A substituted pyrazole compound represented by the following chemical formula ( 1 ), or a salt thereof:

Among them, Q represents an oxygen atom, a sulfur atom, CR ₆ R ₇ or a direct bond; R ₆ and R ₇ each independently represent hydrogen, halogen, cyano, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ halogen Alkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ haloalkoxy, C ₁ -C ₁₂ cyanoalkoxy, C ₁ -C ₁₂ alkylthio, C ₁ -C ₁₂ haloalkane Thio, C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkoxy, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₂ -C ₁₂ alkenyloxy, C ₂ -C ₁₂ haloalkenyloxy, C ₂ -C ₁₂ alkynyl, C ₂ -C ₁₂ haloalkynyl, C ₂ -C ₁₂ alkynyloxy, C ₂ -C ₁₂ haloalkynyloxy, C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ haloalkylsulfinyl, C ₁ -C ₁₂ haloalkane Sulfosulfonyl, C ₃ -C ₁₂ cycloalkyl, C ₁ -C ₁₂ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, C ₁ -C ₁₂ haloalkylcarbonyl, C ₁ -C ₁₂ haloalkane Oxycarbonyl, C ₁ -C ₁₂ alkylcarbonylamino, C ₁ -C ₁₂ alkylsulfonyloxy, C ₁ -C ₁₂ alkylsulfinyloxy, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted saturated heterocycle; R represents substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl Group, substituted or unsubstituted aryl C ₁ -C ₁₂ alkyl, substituted or unsubstituted heteroaryl C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkyl, C _1- C ₁₂ haloalkyl, C ₁ -C ₁₂ cyanoalkyl, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkylthio C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkoxy C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₂ -C ₁₂ haloalkenyl, C ₂ -C ₁₂ haloalkynyl , C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ haloalkylsulfinyl, C ₁ -C ₁₂ haloalkylsulfinyl, C ₁ -C ₁₂ alkylcarbonyl, C ₁ -C ₁₂ haloalkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, C ₁ -C ₁₂ haloalkoxycarbonyl, C ₃ -C ₁₂ cycloalkyl, or saturated Heterocycle; R ₁ represents hydrogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted aryl C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkoxycarbonyl, substituted or unsubstituted C ₂ -C ₁₂ alkenylcarbonyl, substituted Or unsubstituted C ₂ -C ₁₂ alkynylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, Substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted aryl C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted heteroaryloxycarbonyl, Substituted or unsubstituted heteroaryl C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryl C ₁ -C ₁₂ alkylcarbonyl , Substituted or unsubstituted heteroarylcarbonyl, substituted or unsubstituted heteroaryl C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted heterocyclic carbonyl, substituted or Unsubstituted heterocyclic C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkylsulfinyl, Substituted or unsubstituted C ₁ -C ₁₂ haloalkylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted heteroarylsulfinyl , Substituted or unsubstituted arylsulfonyl, or substituted or unsubstituted heteroarylsulfonyl; R ₂ represents hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, or substituted or unsubstituted C _1- C ₁₂ haloalkoxy; R ₃ represents hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkyl, substituted Or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ haloalkoxy, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted Or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted Heteroaryl, or substituted or unsubstituted heterocycle; R ₄ and R ₅ each independently represent hydrogen, halogen, cyano, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted of Or unsubstituted C ₁ -C ₁₂ haloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, or Substituted or unsubstituted aryl; X ₁ represents CR ₈ or N, X ₂ represents CR ₉ or N, and X ₃ represents CR ₁₀ or N, with the proviso that when X ₁ represents a nitrogen atom, X ₂ and X ₃ represent CR ₉ and CR _{10 respectively} , when X ₂ represents a nitrogen atom, X ₁ and X ₃ represent CR ₈ and CR _{10 respectively} , and when X ₃ represents a nitrogen atom, X ₁ and X ₂ represents CR ₈ and CR _{9 respectively} ; R ₈ , R ₉ and R ₁₀ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ haloalkoxy, substituted or unsubstituted Substituted C ₁ -C ₁₂ alkylthio, substituted or unsubstituted C ₁ -C ₁₂ haloalkylthio, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, Substituted or unsubstituted C ₁ -C ₁₂ haloalkoxycarbonyl, cyano, nitro or substituted or unsubstituted amine. Specific example A2:

The substituted pyrazole compound or a salt thereof according to the specific example A1, wherein Q represents an oxygen atom or a sulfur atom. Specific example A3:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 or A2, wherein R represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or C ₁ -C ₁₂ alkyl. Specific example A4:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 to A3, wherein R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or Unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted Or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted arylsulfinyl, or substituted or Unsubstituted arylsulfonyl. Specific example A5:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 to A4, wherein R ₂ represents hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or Substituted or unsubstituted C ₁ -C ₁₂ haloalkyl. Specific example A6:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 to A5, wherein R ₃ represents a substituted or unsubstituted C ₁ -C ₁₂ alkyl group, or a substituted or unsubstituted Substituted C ₁ -C ₁₂ haloalkyl. Specific example A7:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 to A6, wherein R ₄ and R ₅ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or substituted or unsubstituted C ₁ -C ₁₂ haloalkyl. Specific example A8:

A substituted pyrazole compound or a salt thereof according to any one of the specific examples A1 to A7, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , and X ₃ represents CR ₁₀ , where R ₈ and R ₉ And R ₁₀ are independently of each other hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkyl, or substituted or unsubstituted Substituted C ₁ -C ₁₂ alkoxy. Specific example A9:

A pest control agent comprising a substituted pyrazole compound according to any one of Specific Examples A1 to A8 or a salt thereof as an active ingredient. Specific example A10:

A method of using a substituted pyrazole compound or a salt thereof according to any one of Specific Examples A1 to A8 for controlling pests. Specific example A11:

A method for controlling pests, which comprises applying a substituted pyrazole compound or a salt thereof according to any one of Specific Examples A1 to A8 to a plant or its vicinity, or a soil where a plant is cultivated . Specific example A12:

A method for controlling pests, which comprises applying an effective amount of the substituted pyrazole compound according to any one of the specific examples A1 to A8 or a salt thereof to the pest, the pest's habitat, or a Predict where to live. Furthermore, the present disclosure includes the following specific examples: Specific example 1:

其中， Q代表一氧原子、一硫原子、CR₆ R₇ 或直接鍵； R₆ 和R₇ 各個獨立地代表氫、鹵素、氰基、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 烷基硫基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 烯基氧基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₂ -C₁₂ 炔基氧基、經取代的或未經取代的C₁ -C₁₂ 烷基亞磺醯基、經取代的或未經取代的C₁ -C₁₂ 烷基磺醯基、經取代的或未經取代的C₃ -C₁₂ 環烷基、經取代的或未經取代的C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的C₁ -C₁₂ 烷基羰基胺基、經取代的或未經取代的C₁ -C₁₂ 烷基磺醯基氧基、經取代的或未經取代的C₁ -C₁₂ 烷基亞磺醯基氧基、經取代的或未經取代的芳基、經取代的或未經取代的雜芳基或者經取代的或未經取代的飽和雜環； R代表氫、經取代的或未經取代的芳基、經取代的或未經取代的雜芳基、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₁ -C₁₂ 烷基亞磺醯基、經取代的或未經取代的C₁ -C₁₂ 烷基磺醯基、經取代的或未經取代的C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的C₃ -C₁₂ 環烷基，或者經取代的或未經取代的飽和雜環； R₁ 代表氫、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₃ -C₁₂ 環烷基、經取代的或未經取代的C₁ -C₁₂ 烷基羰基、經取代的或未經取代的C₂ -C₁₂ 烯基羰基、經取代的或未經取代的C₂ -C₁₂ 炔基羰基、經取代的或未經取代的C₃ -C₁₂ 環烷基羰基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、經取代的或未經取代的芳基氧基羰基、經取代的或未經取代的雜芳基氧基羰基、經取代的或未經取代的芳基羰基、經取代的或未經取代的雜芳基羰基、經取代的或未經取代的雜環羰基、經取代的或未經取代的C₁ -C₁₂ 烷基亞磺醯基、經取代的或未經取代的C₁ -C₁₂ 烷基磺醯基、經取代的或未經取代的芳基亞磺醯基、經取代的或未經取代的雜芳基亞磺醯基、經取代的或未經取代的芳基磺醯基、經取代的或未經取代的雜芳基磺醯基； R₂ 和R₃ 各個獨立地代表氫、鹵素、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₂ -C₁₂ 烯基、經取代的或未經取代的C₂ -C₁₂ 炔基、經取代的或未經取代的C₃ -C₁₂ 環烷基、經取代的或未經取代的芳基、經取代的或未經取代的雜芳基，或者經取代的或未經取代的雜環； R₄ 和R₅ 各個獨立地代表氫、鹵素、氰基、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 烷基硫基或者經取代的或未經取代的芳基； X₁ 代表C-R₈ 或N， X₂ 代表C-R₉ 或N，和 X₃ 代表C-R₁₀ 或N， 有條件的是：當X₁ 代表一氮原子時，X₂ 和X₃ 分別地代表C-R₉ 和C-R₁₀ ，當X₂ 代表一氮原子時，X₁ 和X₃ 分別地代表C-R₈ 和C-R₁₀ ，和當X₃ 代表一氮原子時，X₁ 和X₂ 分別地代表C-R₈ 和C-R₉ ；以及 R₈ 、R₉ 和R₁₀ 各個獨立地代表氫、鹵素、經取代的或未經取代的C₁ -C₁₂ 烷基、經取代的或未經取代的C₁ -C₁₂ 烷氧基、經取代的或未經取代的C₁ -C₁₂ 烷基硫基、經取代的或未經取代的C₁ -C₁₂ 烷氧基羰基、氰基、硝基，或者經取代的或未經取代的胺基。 具體例1a：A substituted pyrazole compound represented by the following chemical formula ( 1 ), or a salt thereof:

Where Q represents an oxygen atom, a sulfur atom, CR ₆ R ₇ or a direct bond; R ₆ and R ₇ each independently represent hydrogen, halogen, cyano, substituted or unsubstituted C ₁ -C ₁₂ alkane Group, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, substituted or unsubstituted C ₂ -C ₁₂ Alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkenyloxy, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₂ -C ₁₂ Alkynyloxy, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted Substituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or Unsubstituted C ₁ -C ₁₂ alkylcarbonylamino, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyloxy, substituted or unsubstituted C ₁ -C ₁₂ alkyl Sulfenyloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted saturated heterocyclic ring; R represents hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₂ -C ₁₂ alkene Group, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, or substituted or unsubstituted saturated heterocycle; R ₁ represents hydrogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₂ -C ₁₂ alkenylcarbonyl, substituted or unsubstituted C ₂ -C ₁₂ alkynylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted Heteroaryloxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted heteroarylcarbonyl, substituted or unsubstituted heterocyclic carbonyl, Substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted arylsulfinyl Sulfonyl, substituted or unsubstituted heteroarylsulfinyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted heteroarylsulfonyl; R ₂ and R ₃ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted Substituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted Substituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocycle; R ₄ and R ₅ each independently represent hydrogen, halogen, cyano, substituted or unsubstituted Substituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, or substituted or Unsubstituted aryl; X ₁ represents CR ₈ or N, X ₂ represents CR ₉ or N, and X ₃ represents CR ₁₀ or N, conditionally: when X ₁ represents a nitrogen atom, X ₂ and X ₃ represents CR ₉ and CR _{10 respectively} , when X ₂ represents a nitrogen atom, X ₁ and X ₃ represent CR ₈ and CR _{10 respectively} , and when X ₃ represents a nitrogen atom, X ₁ and X ₂ respectively Stands for CR ₈ and CR ₉ ; and R ₈ , R ₉ and R ₁₀ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, cyano, nitro, or Substituted or unsubstituted amine groups. Specific example 1a:

The substituted pyrazole compound or a salt thereof according to the specific example 1, wherein in R ₆ and R ₇ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected from C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl, and C ₁ -C ₁₂ haloalkoxy C ₁ -C ₁₂ alkyl The group consisting of; the substituted or unsubstituted C ₁ -C ₁₂ alkoxy is selected from the group consisting of C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ haloalkoxy, and C _1- C ₁₂ cyanoalkoxy group; the substituted or unsubstituted C ₁ -C ₁₂ alkylthio group is selected from C ₁ -C ₁₂ alkylthio group and C ₁ -C ₁₂ haloalkylthio groups; the substituted or unsubstituted C ₂ -C ₁₂ alkenyl group is selected from the group consisting of C ₂ -C ₁₂ alkenyl and C ₂ -C ₁₂ haloalkenyl The group consisting of; the substituted or unsubstituted C ₂ -C ₁₂ alkenyloxy is selected from the group consisting of C ₂ -C ₁₂ alkenyloxy and C ₂ -C ₁₂ haloalkenyloxy The group of the substituted or unsubstituted C ₂ -C ₁₂ alkynyl is selected from the group consisting of C ₂ -C ₁₂ alkynyl and C ₂ -C ₁₂ haloalkynyl; the substituted Or unsubstituted C ₂ -C ₁₂ alkynyloxy is selected from the group consisting of C ₂ -C ₁₂ alkynyloxy and C ₂ -C ₁₂ haloalkynyloxy; the substituted Or unsubstituted C ₁ -C ₁₂ alkylsulfinyl group is selected from the group consisting of C ₁ -C ₁₂ alkylsulfinyl group and C ₁ -C ₁₂ haloalkylsulfinyl group ; The substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl group is selected from the group consisting of C ₁ -C ₁₂ alkylsulfonyl group and C ₁ -C ₁₂ haloalkylsulfonyl group The group; the substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl is C ₃ -C ₁₂ cycloalkyl; the substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl is selected from In the group consisting of C ₁ -C ₁₂ alkylcarbonyl and C ₁ -C ₁₂ haloalkylcarbonyl; the substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl is selected from the group consisting of ₁ -C ₁₂ alkoxycarbonyl group and C ₁ -C ₁₂ haloalkoxycarbonyl group; the substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonylamino group is C ₁ -C ₁₂ Alkylcarbonylamino; the substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyloxy is C ₁ -C ₁₂ alkylsulfonyloxy; and/or the substituted or unsubstituted The substituted C ₁ -C ₁₂ alkylsulfinyloxy is C ₁ -C ₁₂ alkylsulfinyloxy. Specific example 1b:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein in R, the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected from the group consisting of ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ cyanoalkyl, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkyl sulfur Group C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkoxy C ₁ -C ₁₂ alkyl, substituted or unsubstituted aryl C ₁ -C ₁₂ alkyl, and substituted or unsubstituted Substituted heteroaryl aryl C ₁ -C ₁₂ alkyl group; the substituted or unsubstituted C ₂ -C ₁₂ alkenyl group is selected from C ₂ -C ₁₂ alkenyl and C ₂ -C ₁₂ haloalkenyl group; the substituted or unsubstituted C ₂ -C ₁₂ alkynyl group is selected from C ₂ -C ₁₂ alkynyl and C ₂ -C ₁₂ haloalkyn Group consisting of groups; the substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl group is selected from the group consisting of C ₁ -C ₁₂ alkylsulfinyl group and C ₁ -C ₁₂ halo The group consisting of alkylsulfinyl; the substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl is selected from C ₁ -C ₁₂ alkylsulfonyl and C _1- C ₁₂ haloalkyl sulfonyl group; the substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl group is selected from C ₁ -C ₁₂ alkylcarbonyl C ₁ -C ₁₂ halo The group consisting of alkylcarbonyl; the substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl is selected from the group consisting of C ₁ -C ₁₂ alkoxycarbonyl and C ₁ -C ₁₂ haloalkoxy Group consisting of carbonyl; and/or the substituted or unsubstituted saturated heterocycle is a saturated heterocycle. Specific example 1c:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein, in R ₁ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected from The group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkyl and substituted or unsubstituted aryl C ₁ -C ₁₂ alkyl; the substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl is selected from substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ haloalkylcarbonyl, substituted or Unsubstituted aryl C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted heteroaryl C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted heterocyclic C ₁ -C ₁₂ alkylcarbonyl group and a substituted or unsubstituted C _3- C ₁₂ cycloalkyl C ₁ -C ₁₂ alkylcarbonyl group consisting of; the substituted or unsubstituted C ₁ -C ₁₂ alkyl The oxycarbonyl group is selected from a substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl group, a substituted or unsubstituted aryl C ₁ -C ₁₂ alkoxycarbonyl group, and a substituted Or an unsubstituted heteroaryl C ₁ -C ₁₂ alkoxycarbonyl group; the substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl group is selected from substituted Or unsubstituted C ₁ -C ₁₂ alkylsulfinyl and substituted or unsubstituted C ₁ -C ₁₂ haloalkylsulfinyl; and/or the Substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl is selected from substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl and C ₁ -C ₁₂ haloalkyl Sulfonyl groups; and the groups mentioned as R ₁ can be further substituted by various substituent groups (such as F, Cl, Br, I, CN, NO ₂ , CH ₃ , C(CH ₃ ) ₃ , OCH ₃ , CO ₂ CH ₃ , CO ₂ CH ₂ CH ₃ , SO ₂ CH ₃ , OCH ₂ CF ₃ , CF ₃ , or OCF ₃ ) are replaced. Specific example 1d:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein, in R ₂ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected from A group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkyl, and substituted or unsubstituted C ₁ -C ₁₂ haloalkyl; and/or the substituted or unsubstituted The C ₁ -C ₁₂ alkoxy is selected from the group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkoxy, and substituted or unsubstituted C ₁ -C ₁₂ haloalkoxy Formed group. Specific example 1e:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein, in R ₃ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected from A group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkyl, and substituted or unsubstituted C ₁ -C ₁₂ haloalkyl; and/or the substituted or unsubstituted The C ₁ -C ₁₂ alkoxy is selected from the group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkoxy, and substituted or unsubstituted C ₁ -C ₁₂ haloalkoxy Formed group. Specific example 1f:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein, in R ₄ and R ₅ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl group is selected From the group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkyl, and substituted or unsubstituted C ₁ -C ₁₂ haloalkyl. Specific example 1g:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein, in R ₈ , R ₉ and R ₁₀ , the substituted or unsubstituted C ₁ -C ₁₂ alkyl The group is selected from the group consisting of substituted or unsubstituted C ₁ -C ₁₂ alkyl groups, and substituted or unsubstituted C ₁ -C ₁₂ haloalkyl groups; the substituted or Unsubstituted C ₁ -C ₁₂ alkoxy is selected from substituted or unsubstituted C ₁ -C ₁₂ alkoxy, and substituted or unsubstituted C ₁ -C ₁₂ haloalkanes Oxygen group; the substituted or unsubstituted C ₁ -C ₁₂ alkylthio group is selected from substituted or unsubstituted C ₁ -C ₁₂ alkylthio group, and Substituted or unsubstituted C ₁ -C ₁₂ haloalkylthio group; and/or the substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl group is selected from A group consisting of a substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl group, and a substituted or unsubstituted C ₁ -C ₁₂ haloalkoxycarbonyl group. Specific example 1h:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein Q represents an oxygen atom or a sulfur atom; R represents a substituted or unsubstituted aryl group, substituted or Unsubstituted C ₁ -C ₁₂ alkyl, R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, Substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy Carbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted arylcarbonyl, or substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl; R ₂ Represents hydrogen, or substituted or unsubstituted C ₁ -C ₁₂ alkyl; R ₃ represents substituted or unsubstituted C ₁ -C ₁₂ alkyl; R ₄ and R ₅ each independently represent hydrogen, Substituted or unsubstituted C ₁ -C ₁₂ alkyl; X ₁ represents CR ₈ or N, X ₂ represents CR ₉ , and X ₃ represents CR ₁₀ , conditionally: when X ₁ represents a nitrogen atom , X ₂ and X ₃ represent CR ₉ and CR _{10 respectively} , when X ₂ represents a nitrogen atom, X ₁ and X ₃ represent CR ₈ and CR _{10 respectively} , and when X ₃ represents a nitrogen atom, X ₁ And X ₂ represent CR ₈ and CR _{9 respectively} ; and R ₈ , R ₉ and R ₁₀ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or substituted or Unsubstituted C ₁ -C ₁₂ alkoxy. Specific example 2:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein Q represents an oxygen atom or a sulfur atom. Specific example 3:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or Substituted or unsubstituted C ₁ -C ₁₂ alkyl. Specific example 4:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R represents a substituted or unsubstituted C ₆ -C ₁₀ aryl group, or an unsubstituted C ₁ -C ₁₂ alkyl. Specific example 5:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted Substituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted Substituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C _1- C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted arylsulfinyl, or substituted or unsubstituted Substituted arylsulfonyl. Specific example 6:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, unsubstituted C ₂ -C ₁₂ alkynyl, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted Or unsubstituted C ₆ -C ₁₀ arylcarbonyl, unsubstituted C ₆ -C ₁₀ aryloxycarbonyl, or unsubstituted C ₆ -C ₁₀ arylsulfonyl. Specific example 7:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₂ represents hydrogen, halogen, or a substituted or unsubstituted C ₁ -C ₁₂ alkyl group. Specific example 8:

The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₂ represents hydrogen, or an unsubstituted C ₁ -C ₁₂ alkyl group. Specific example 9:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₃ represents a substituted or unsubstituted C ₁ -C ₁₂ alkyl group. Specific example 10:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₄ and R ₅ each independently represent hydrogen, halogen, or substituted or unsubstituted C ₁ -C ₁₂ alkyl. Specific example 11:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₄ and R ₅ each independently represent hydrogen, or an unsubstituted C ₁ -C ₁₂ alkyl group. Specific example 12:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other are hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or substituted or unsubstituted C ₁ -C ₁₂ alkoxy. Specific example 13:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other are hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or unsubstituted C ₁ -C ₁₂ alkoxy. Specific example 14:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein Q represents an oxygen atom. Specific example 15:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R represents a substituted or unsubstituted C ₆ aryl group. Specific example 16:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₁ represents hydrogen, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C ₁₂ Cycloalkylcarbonyl, unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, or substituted or unsubstituted C ₆ arylcarbonyl. Specific example 17:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₂ represents an unsubstituted C ₁ -C ₆ alkyl group. Specific example 18:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₃ represents an unsubstituted C ₁ -C ₆ alkyl group. Specific example 19:

The substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein R ₄ and R ₅ each independently represent hydrogen, or an unsubstituted C ₁ -C ₆ alkyl group. Specific example 20:

A substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other is hydrogen, halogen, unsubstituted C ₁ -C ₆ alkyl, or unsubstituted C ₁ -C ₆ alkoxy. Specific example 21:

A pest control agent comprising a substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples as an active ingredient. Specific example 22:

A method of using a substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples for controlling pests. Specific example 23:

A method for controlling pests, which comprises applying a substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples to a plant or its vicinity, or a soil where a plant is cultivated. Specific example 24:

A method for controlling pests, which comprises applying an effective amount of a substituted pyrazole compound or a salt thereof according to any one of the foregoing specific examples to a pest, a pest's habitat, or a predicted habitat Location. Beneficial effect of invention

A novel substituted pyrazole compound or a salt thereof according to the present disclosure achieves an excellent insecticidal and fungicidal effect. In addition, the pyrazole compound or a salt thereof according to the present disclosure is useful as a novel insecticide and fungicide, which exhibits excellent insecticidal and fungicidal effects, not only against chemical-sensitive fungi but also against Chemical-resistant fungus.

Detailed Description of the Preferred Embodiments Description of Specific Examples This disclosure is described below. Throughout the entire specification, unless specifically noted otherwise, a singular word should be understood to include concepts in the plural. Therefore, unless otherwise noted, singular articles (for example, in the case of English "一(a)", "一(an)", "the (the)" and similar) should also be understood to include The concept in the plural. Further, unless specifically noted otherwise, the terminology used herein should be understood to be used in the meaning conventionally used in the art. Therefore, unless otherwise defined, all terms and scientific and technical terms used herein have the same meaning as those terms conventionally understood by those skilled in the art of the disclosure of the disclosure. In case of a contradiction, this specification (including definitions) takes precedence. 1. Substituted pyrazole compound or one of its salts

或它的一鹽類(在下文中有時被意指為“本揭示的化合物(1)”或“化合物(1)”)， 其中R、R₁ 、R₂ 、R₃ 、R₄ 、R₅ 、X₁ 、X₂ 、X₃ ，以及Q是如上面所定義的。This disclosure is directed to a compound represented by the following chemical formula (1):

Or a salt thereof (sometimes hereinafter referred to as "compound (1) of the present disclosure" or "compound (1)"), wherein R, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , X ₁ , X ₂ , X ₃ , and Q are as defined above.

Next, the terms in this specification are described below.

In this specification, the number of substituents of a group defined by "substituted" is not particularly limited if it is substitutable, and is one or plural. In addition, unless otherwise indicated, when the group is a part or a substituent on other groups, the description about each group also applies.

"C ₁ -C ₁₂ alkyl" means a linear or branched saturated hydrocarbon group having 1 to 12 carbon atoms. "C ₁ -C ₆ alkyl" or "C ₁ -C ₃ alkyl" means a linear or branched saturated hydrocarbon group having 1 to 6 or 1 to 3 carbon atoms, respectively.

"C ₂ -C ₁₂ alkenyl" means a straight or branched chain unsaturated hydrocarbon group having 2 to 12 carbon atoms and containing 1 to 3 double bonds.

"C ₂ -C ₁₂ alkynyl" means a linear or branched unsaturated hydrocarbon group having 2 to 12 carbon atoms and containing 1 triple bond.

"C ₃ -C ₁₂ cycloalkyl" means a cyclic alkyl group having 3 to 12 carbon atoms, and includes those having a partial bridge structure. "C ₃ -C ₆ cycloalkyl" means a cyclic alkyl group having 3 to 6 carbon atoms.

"C ₁ -C ₁₂ alkoxy" means a "C ₁ -C ₁₂ alkyloxy group", where the "C ₁ -C ₁₂ alkyl" portion is defined as described above for "C ₁ -C _"12 alkyl" is the same.

"Aryl" means a monocyclic or polycyclic aromatic hydrocarbon.

"C ₆ -C ₁₀ aryl" means an aryl group having 6 to 10 carbon atoms as defined herein. "C ₆ aryl" means an aryl group having 6 carbon atoms as defined herein.

"Heterocyclic" means a saturated, unsaturated or aromatic heterocyclic group having at least one of nitrogen, oxygen, phosphorus and/or sulfur atoms in the ring and may be substituted in any The location is bonded. "Heterocycle" may mean "heterocycle" or "heterocyclyl".

"Heteroaryl" means an aromatic heterocyclic group having at least one of nitrogen, oxygen, and/or sulfur atoms in the ring and may be bonded at any substitutable position, wherein the ring of heteroaryl The member atoms include 1, 2, 3, or 4 heteroatoms selected from N, O, and S in addition to carbon atoms.

The following shows specific examples of each group as used in this specification.

Examples of halogen include, but are not particularly limited to, fluorine, chlorine, bromine, iodine, and the like.

Examples of C ₁ -C ₁₂ alkyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl , Isobutyl, secondary-butyl, tertiary-butyl, n-pentyl, isopentyl, neopentyl, 1,1-dimethylprop-1-yl, n-hexyl, 1-ethyl Amylpentyl, 2-ethylhexyl, and the like.

Examples of C ₁ -C ₁₂ haloalkyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkyl groups substituted with 1 to 9, preferably 1 to 8 halogen atoms, such as Fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, 2,2-difluoroethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl , 3,3,3-trifluoropropyl, heptafluoroisopropyl, 4,4,4-trifluorobutyl, heptafluoroisobutyl, and the like.

Examples of C ₁ -C ₁₂ alkoxy groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkoxy groups, such as methoxy, ethoxy, n-propoxy, isopropoxy Group, n-butoxy, isobutoxy, secondary-butoxy, tertiary-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, 1,1- Dimethylprop-1-yloxy, n-hexyloxy, 1-ethylpentyloxy, 2-ethylhexyloxy, and the like.

Examples of C ₁ -C ₁₂ haloalkoxy groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkoxy groups substituted with 1 to 9, preferably 1 to 8 halogen atoms , Such as fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, 2,2-difluoroethoxy, trifluoromethoxy, 2,2,2- Trifluoroethoxy, pentafluoroethoxy, 3,3,3-trifluoropropoxy, heptafluoroisopropoxy, 4,4,4-trifluorobutoxy, heptafluoroisobutoxy, And the like.

Examples of C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl include, but are not particularly limited to, wherein C ₁ -C ₁₂ linear or branched alkyl is substituted with a C ₁ -C ₁₂ linear or Branched-chain alkoxyalkyl groups such as methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, isobutyl Oxymethyl, secondary-butoxymethyl, tertiary-butoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n- Butyl, and the like.

Examples of the C ₁ -C ₁₂ haloalkoxy group C ₁ -C ₁₂ alkyl group include, but are not particularly limited to, linear or branched alkane substituted with 1 to 9, preferably 1 to 8 halogen atoms Oxyalkyl, such as fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, iodomethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 2,2,2-trifluoroethoxymethyl, and the like.

Examples of C ₃ -C ₁₂ cycloalkyl include, but are not particularly limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.

Examples of the C ₃ -C ₁₂ cycloalkylcarbonyl group include, but are not particularly limited to, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, and the like.

Examples of C ₁ -C ₁₂ alkylcarbonyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylcarbonyl groups, such as methylcarbonyl (acetyl), ethylcarbonyl (propyl) ), n-propylcarbonyl (butylamide), isopropylcarbonyl (isobutylamide), n-butylcarbonyl (pentylamide), isobutylcarbonyl (isopentylamide), secondary-butylcarbonyl, Tertiary-butylcarbonyl, n-pentylcarbonyl, isopentylcarbonyl, neopentylcarbonyl, (1,1-dimethylprop-1-yl)carbonyl, (1-ethylpentyl)carbonyl, ( 2-ethylhexyl)carbonyl, and the like.

Examples of C ₁ -C ₁₂ haloalkylcarbonyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylcarbonyl groups substituted with 1 to 9, preferably 1 to 5 halogen atoms , Such as fluoromethylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, iodomethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chlorodifluoromethyl Carbonyl, bromodifluoromethylcarbonyl, dichlorofluoromethylcarbonyl, 2,2,2-trichloroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, pentafluoroethylcarbonyl, and the like Thing.

Examples of C ₁ -C ₁₂ alkoxycarbonyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkoxycarbonyl groups, such as methoxycarbonyl, ethoxycarbonyl, n-propoxy Carbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, secondary-butoxycarbonyl, tertiary-butoxycarbonyl, n-pentyloxycarbonyl, isopentyloxy Carbonyl, neopentyloxycarbonyl, (1,1-dimethylprop-1-yloxy)carbonyl, n-hexyloxycarbonyl, (1-ethylpentyloxy)carbonyl, (2-ethyl Hexyloxy)carbonyl, and the like.

Examples of C ₁ -C ₁₂ haloalkoxycarbonyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkoxy groups substituted with 1 to 9, preferably 1 to 5 halogen atoms Carbonyl, such as fluoromethoxycarbonyl, chloromethoxycarbonyl, bromomethoxycarbonyl, iodomethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, difluoromethoxycarbonyl, tri Fluoromethoxycarbonyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 4,4,4-trifluorobutoxy Carbonyl, heptafluoroisopropoxycarbonyl, and the like.

Examples of C ₁ -C ₁₂ cyanoalkyl include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkyl substituted with a cyano group, such as cyanomethyl, cyanoethyl Group, cyano-n-propyl, cyano-isopropyl, cyano-n-butyl, cyano-isobutyl, cyano-secondary-butyl, cyano-tertiary-butyl, Cyano-n-hexyl, and the like.

Examples of C ₁ -C ₁₂ cyanoalkoxy include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkoxy substituted with a cyano group, such as cyanomethoxy, Cyanoethoxy, cyano-n-propoxy, cyano-isopropoxy, cyano-n-butoxy, cyano-iso-butoxy, cyano-secondary-butoxy , Cyano-tertiary-butoxy, cyano-hexyloxy, and the like.

Examples of C ₂ -C ₁₂ alkenyl groups include, but are not particularly limited to, vinyl, propenyl, 2-butenyl, 3-butenyl, 1-methylpropenyl, and the like.

Examples of C ₂ -C ₁₂ haloalkenyl groups include, but are not particularly limited to, 2,2-dichlorovinyl, 2,2-dibromovinyl, 2,2-difluorovinyl, 3,3-di Fluoro-2-propenyl, 4,4-difluoro-3-butenyl, 4,4,4-trifluoro-2-butenyl, and the like.

Examples of C ₂ -C ₁₂ alkynyl groups include, but are not particularly limited to, ethynyl, 2-propynyl (propargyl), 1-methyl-2-propynyl, 1-butynyl, 2- Butynyl, 3-butynyl, and the like.

Examples of C ₂ -C ₁₂ haloalkynyl groups include, but are not particularly limited to, fluoroethynyl, bromoethynyl, chloroethynyl, iodoethynyl, 3,3,3-trifluoro-1-propynyl, and Something similar.

Examples of C ₁ -C ₁₂ alkylsulfinyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkyl sulfinyl groups, such as methylsulfinyl, ethylsulfinyl Acyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, second-butylsulfinyl, tertiary- Butylsulfinyl, and the like.

Examples of the C ₁ -C ₁₂ haloalkylsulfinyl group include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched chains substituted with 1 to 9, preferably 1 to 5 halogen atoms Alkylsulfinyl, such as fluoromethylsulfinyl, chloromethylsulfinyl, bromomethylsulfinyl, iodomethylsulfinyl, dichloromethylsulfinyl, tris Chloromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, dichlorofluoromethane Sulfenyl, 2,2,2-trichloroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, and the like.

Examples of C ₁ -C ₁₂ alkylsulfonyl groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylsulfonyl groups, such as methylsulfonyl, ethylsulfonyl , N-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, secondary-butylsulfonyl, tertiary-butylsulfonyl, and Something similar.

Examples of the C ₁ -C ₁₂ haloalkylsulfonyl group include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkane substituted with 1 to 9, preferably 1 to 5 halogen atoms Sulfosulfonyl, such as fluoromethylsulfonyl, chloromethylsulfonyl, bromomethylsulfonyl, iodomethylsulfonyl, dichloromethylsulfonyl, trichloromethylsulfonyl, Difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, dichlorofluoromethylsulfonyl, 2,2,2-tris Chloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, and the like.

Examples of C ₁ -C ₁₂ alkylthio groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylthio groups, such as methylthio, ethylthio, n-propylthio Group, isopropylsulfanyl group, n-butylsulfanyl group, isobutylsulfanyl group, secondary-butylsulfanyl group, tertiary-butylsulfanyl group, and the like.

Examples of C ₁ -C ₁₂ haloalkylthio groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkyl groups substituted with 1 to 9, preferably 1 to 5 halogen atoms Thio, such as fluoromethylthio, chloromethylthio, bromomethylthio, iodomethylthio, dichloromethylthio, trichloromethylthio, difluoromethylthio, tri Fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, dichlorofluoromethylthio, 2,2,2-trichloroethylthio, 2,2,2-tri Fluoroethylthio, pentafluoroethylthio, and the like.

Examples of C ₂ -C ₁₂ alkenyloxy include, but are not particularly limited to, vinyloxy, 1-propenyloxy, isopropenyloxy, propenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methylpropenyloxy, and the like.

Examples of C ₂ -C ₁₂ haloalkenyloxy include, but are not particularly limited to, 2,2-dichlorovinyloxy, 2,2-dibromovinyloxy, 2,2-difluorovinyl Oxy, 3,3-difluoro-2-propenyloxy, 4,4-difluoro-3-butenyloxy, 4,4,4-trifluoro-2-butenyloxy, and Something similar.

Examples of C ₂ -C ₁₂ alkynyloxy include, but are not particularly limited to, ethynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1,1-di Methyl-2-propynyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, and the like.

Examples of C ₂ -C ₁₂ haloalkynyloxy include, but are not particularly limited to, fluoroethynyloxy, bromoethynyloxy, chloroethynyloxy, iodoethynyloxy, 3,3,3- Trifluoro-1-propynyloxy, and the like.

Examples of C ₁ -C ₁₂ alkylsulfonyloxy groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylsulfonyl groups, such as methylsulfonyloxy, ethyl Sulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, isobutylsulfonyloxy, secondary-butyl Sulfonyloxy, tertiary-butylsulfonyloxy, and the like.

Examples of C ₁ -C ₁₂ alkylsulfinyloxy groups include, but are not particularly limited to, C ₁ -C ₁₂ linear or branched alkylsulfinyloxy groups, such as methylsulfinyloxy Yloxy, ethylsulfinyloxy, n-propylsulfinyloxy, isopropylsulfinyloxy, n-butylsulfinyloxy, isobutylsulfinyl Acyloxy, secondary-butylsulfinyloxy, tertiary-butylsulfinyloxy, and the like.

Examples of substituted or unsubstituted amine groups include, but are not particularly limited to, amine groups, monoalkylamine groups, dialkylamine groups, monoacylamino groups, and the like. Examples of the alkyl group include the C ₁ -C ₁₂ alkyl group mentioned above, and the like. Examples of the acyl group include the above-mentioned C ₁ -C ₁₂ alkoxycarbonyl group, haloalkoxycarbonyl group, arylcarbonyl group, and the like.

Examples of aryl groups include, but are not particularly limited to, phenyl, 1-naphthyl, 2-naphthyl, and the like.

Examples of aryl C ₁ -C ₁₂ alkyl groups include, but are not particularly limited to, benzyl, phenylethyl, phenyl-n-propyl, and the like. These aryl C ₁ -C ₁₂ alkyl groups may be further substituted in the alkyl portion or the aryl portion or both.

Examples of aryloxy groups include, but are not particularly limited to, phenoxy, 1-naphthyloxy, 2-naphthyloxy, and the like.

Examples of aryl C ₁ -C ₁₂ alkoxy groups include, but are not particularly limited to, benzyloxy, phenylethoxy, phenyl-n-propoxy, phenyl-n-butoxy, 1 -Naphthylmethoxy, 2-naphthylmethoxy, and the like.

Examples of heteroaryloxy groups include, but are not particularly limited to, pyridinyloxy, pyrimidinyloxy, pyrazolyloxy, and the like.

Examples of heteroaryl C ₁ -C ₁₂ alkoxy groups include, but are not particularly limited to, pyridyl methoxy, pyridyl ethoxy, pyrimidinyl ethoxy, pyrazolyl methoxy, and the like .

Examples of arylsulfonyl include, but are not particularly limited to, phenylsulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, and the like.

Examples of arylsulfinyl include, but are not particularly limited to, phenylsulfinyl, 1-naphthylsulfinyl, 2-naphthylsulfinyl, and the like.

Examples of heteroaryl groups include, but are not particularly limited to, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl ), isothiazolyl, isoazolazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl ), pyridyl (pyridyl), pyridazinyl (pyridazinyl), pyrimidinyl (pyrimidinyl), pyrazinyl (pyrazinyl), triazinyl (triazinyl), tetrazinyl (tetrazinyl), indolyl (indolyl), iso Isoindolyl, indazolyl, quinazolinyl, carbazolyl, benzoxazolyl, benzisoxazolyl, benzoxazolyl Benzothiazolyl, benzisothiazolyl, benzimidazolyl, quinolinyl, quinolinyl, isoquinolinyl, pyridoindolyl, cinnoline (pyridoindolyl) cinnolinyl), phthalazinyl, quinoxalinyl, purinyl, purinyl, phenothiazinylfuranyl, benzofuranyl, benzofuranyl ( chromanyl), benzothienyl, and the like.

All the aryl and heteroaryl groups mentioned above can be optionally further substituted. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10, and more preferably 1 to 5).

Examples of a heterocyclic group include, but are not particularly limited to, thienyl, furyl, tetrahydrofuranyl, dioxolanyl, dioxanyl, pyrrolyl, pyrrolinyl , Pyrrolidinyl, pyrazolidinyl, isoazolidinyl, oxazolinyl, oxazolidinyl, isoxazolinyl, thiazolyl, isothiazolyl, thiazole Thiazolinyl, thiazolidinyl, isothiazolinyl, pyrazolyl, pyrazolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, Oxadiazolinyl, oxadiazolinyl, thiadiazolinyl, triazolyl, triazolinyl, triazolidinyl, tetrazolyl, tetrazolyl Tetrazolinyl, pyridyl, dihydropyridyl, tetrahydropyridyl, tetrahydropyridyl, piperidyl, oxazinyl, dihydroxazinyl, morpholin Morpholino, thiazinyl, dihydrothiazinyl, (thiamorpholino), thiazinyl, dihydropyridazinyl, dihydropyridazinyl, tetrahydropyridazinyl, hexahydropyridazinyl Hexahydropyridazinyl, oxadiazinyl, oxadiazinyl, dihydrooxadiazinyl, tetrahydrooxadiazinyl, thiadiazinyl, thiadiazinyl, thiadiazinyl, dihydrothiadiazinyl Dihydrothiadiazinyl, tetrahydrothiadiazinyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, pyrazinyl, dihydropyrazinyl , Tetrahydropyrazinyl (tetrahydropyrazinyl), piperazinyl (piperazinyl), triazinyl, dihydrotriazinyl (dihydrotriazinyl), tetrahydrotriazinyl (tetrahydrotriazinyl) , Hexahydrotriazinyl, tetrazinyl, dihydrotetrazinyl, indolyl, indolinyl, isoindolyl, indazolyl, quinazolinyl, di Dihydroquinazolyl, tetrahydroquinazolyl, carbazolyl, benzoxazolyl, benzoxazolinyl, benzoxazolinyl, benzoisoazolyl, benzoisoazolyl Benzisoxazolinyl, benzthiazolyl, benzisothiazolyl, benzisothiazolinyl, benzimidazolyl, indazolinyl, quinolinyl, dihydroquinolinyl (dihydroquinolinyl), tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, tetrahydroisoquinolinyl, pyridoindolyl, dihydrobenzoxazine (Dihydrobenzoxazinyl), cinnoline, dihydrocinnolinyl, tetrahydrocinnolinyl, tetrahydrocinnolinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl ), quinoline group, dihydroquinoxalinyl group, dihydroquinoxalinyl group, tetrahydroquinoxalinyl group, purine group, dihydrobenzotriazinyl group, dihydrobenzotriazinyl group, dihydrobenzotetrazinyl group ), phenothiazinylfuranyl, benzofuranyl, chromanyl, benzothienyl, and the like.

These heterocyclic groups include those substituted with a pendant oxo or thioketone group at any substitutable position.

All the heterocycles mentioned above can be optionally further substituted. Examples of the number of substituents include, but are not particularly limited to, 1 to 20 (preferably 1 to 10, and more preferably 1 to 5).

Examples of a substituent or substituents that are "substituted" include, but are not particularly limited to, halogen, nitro, cyano, hydroxy, formyl, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ halo Alkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ haloalkoxy, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkoxy C _1- C ₁₂ alkyl, C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₁₂ cycloalkyl C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkylcarbonyl, C ₁ -C ₁₂ haloalkylcarbonyl, aromatic Carbonyl, aryloxycarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, C ₁ -C ₁₂ haloalkoxycarbonyl, C ₁ -C ₁₂ cyanoalkyl, C ₁ -C ₁₂ cyanoalkoxy , C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₂ -C ₁₂ alkynyl, C ₂ -C ₁₂ haloalkynyl, C ₁ -C ₁₂ alkylsulfonyl, C ₁ -C ₁₂ haloalkylsulfonyl, C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ haloalkylsulfinyl, C ₁ -C ₁₂ alkylthio, C ₁ -C ₁₂ halo Thio, C ₃ -C ₁₂ cycloalkylsulfonyl, C ₃ -C ₁₂ cycloalkylsulfinyl, C ₃ -C ₁₂ cycloalkylsulfanyl, C ₃ -C ₁₂₂ cycloalkyl C ₁ -C ₁₂ alkylsulfonyl, C ₃ -C ₁₂ cycloalkyl C ₁ -C ₁₂ alkylsulfinyl, C ₃ -C ₁₂ cycloalkyl C ₁ -C ₁₂ alkylthio, C _1- C ₁₂ alkoxy C ₁ -C ₁₂ alkylsulfonyl, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ alkoxy C ₁ -C ₁₂ alkyl Thio, C ₂ -C ₁₂ alkenyloxy, C ₂ -C ₁₂ haloalkenyloxy, C ₂ -C ₁₂ alkynyloxy, C ₂ -C ₁₂ haloalkynyloxy, C ₁ -C ₁₂ alkylsulfonyloxy, C ₁ -C ₁₂ haloalkylsulfonyloxy, C ₁ -C ₁₂ alkylsulfinyloxy, C ₁ -C ₁₂ haloalkylsulfinyloxy Group, OCN, SCN, SF ₅ , substituted or unsubstituted amine group, aryl group, aryl C ₁ -C ₁₂ alkyl group, aryloxy group, aryl C ₁ -C ₁₂ alkoxy group, aryl Sulfosulfonyl, arylsulfinyl, arylthio, aryl C ₁ -C ₁₂ alkylsulfonyl, aryl C ₁ -C ₁₂ alkylsulfinyl, aryl C ₁ -C ₁₂ alkylthio, heterocyclic, heterocyclic C ₁ -C ₁₂ alkyl, heterocyclic oxy, and the like.

Among these, preferred substituents are halogen, nitro, cyano, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ halo Alkoxy, C ₁ -C ₁₂ alkylsulfonyl, C ₁ -C ₁₂ alkoxycarbonyl, C ₁ -C ₁₂ haloalkylsulfonyl, C ₁ -C ₁₂ alkylsulfinyl, C ₁ -C ₁₂ haloalkylsulfinyl, C ₁ -C ₁₂ alkylthio, C ₁ -C ₁₂ haloalkylthio, substituted or unsubstituted amine, aryl, and heterocyclic , And better substituents are fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, C(CH ₃ ) ₃ , trifluoromethyl, methoxy, ethoxy, trifluoro Methoxy, OCH ₂ CF ₃ , CO ₂ CH ₃ , CO ₂ CH ₂ CH ₃ , or SO ₂ CH ₃ .

Preferred substituted aryl groups are halogen-substituted aryl, dihalogen-substituted aryl, C ₁ -C ₁₂ alkyl-substituted aryl, C ₁ -C ₁₂ haloalkyl-substituted Aryl, halogen and C ₁ -C ₁₂ haloalkyl-substituted aryl, C ₁ -C ₁₂ alkoxy-substituted aryl, C ₁ -C ₁₂ haloalkoxy-substituted aryl, and C ₁ -C ₁₂ alkylthio-substituted aryl. More preferred substituted aryl groups are chloro-substituted aryl, dichloro-substituted aryl, fluoro-substituted aryl, difluoro-substituted aryl, trifluoromethyl-substituted aryl , Methyl-substituted aryl, chloro- and trifluoromethyl-substituted aryl, trifluoromethoxy-substituted aryl, methoxy-substituted aryl, trifluoromethoxy-substituted Aryl, and methylthio-substituted aryl.

Preferred substituted heteroaryl groups are halogen-substituted heteroaryl, C ₁ -C ₁₂ alkyl-substituted heteroaryl, C ₁ -C ₁₂ haloalkyl-substituted heteroaryl, halogen And C ₁ -C ₁₂ haloalkyl-substituted heteroaryl, C ₁ -C ₁₂ alkoxy-substituted heteroaryl, C ₁ -C ₁₂ haloalkoxy-substituted heteroaryl, and C ₁ -C ₁₂ alkylthio-substituted heteroaryl. More preferred substituted heteroaryl groups are chloro-substituted heteroaryl, fluoro-substituted heteroaryl, trifluoromethyl-substituted heteroaryl, chloro- and trifluoromethyl-substituted heteroaryl Aryl, trifluoromethoxy-substituted heteroaryl, and methoxy-substituted heteroaryl, and methylthio-substituted heteroaryl.

Preferred substituted heterocyclic groups are halogen-substituted heterocycles, C ₁ -C ₁₂ alkyl-substituted heterocycles, C ₁ -C ₁₂ alkyl-substituted heterocycles, C ₁ -C ₁₂ Alkoxy-substituted heterocycles, C ₁ -C ₁₂ haloalkoxy-substituted heterocycles, and C ₁ -C ₁₂ alkylthio-substituted heterocycles. More preferred substituted heterocyclic groups are chlorine-substituted heterocycles, fluorine-substituted heterocycles, trifluoromethyl-substituted heterocycles, trifluoromethoxy-substituted heterocycles, methoxy- Substituted heterocycles, and methylthio-substituted heterocycles.

The salts of the compound represented by the chemical formula (1) may be any type of salts as long as they are agriculturally acceptable. Examples of such salts include inorganic acid salts, such as monohydrochloride, monosulfate, mononitrate, and the like; organic acid salts, such as monoacetate, monomethanesulfonate, and the like; Alkali metal salts, such as monosodium, potassium, and the like; alkaline earth metal salts, such as monomagnesium, monocalcium, and the like; quaternary ammonium salts, such as dimethylammonium, triethyl Ammonium, and the like; and similar.

X ₁ represents CR ₈ or N, X ₂ represents CR ₉ or N, and X ₃ represents CR ₁₀ or N. However, when X ₁ represents a nitrogen atom, X ₂ and X ₃ represent CR ₉ and CR _{10 respectively} ; when X ₂ represents a nitrogen atom, X ₁ and X ₃ represent CR ₈ and CR _{10 respectively} ; and when When X ₃ represents a nitrogen atom, X ₁ and X ₂ represent CR ₈ and CR _{9, respectively} .

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which Q represents an oxygen atom or a sulfur atom, and a more preferred compound (1) is a compound in which Q represents an oxygen atom .

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which R ₆ and R ₇ each independently represent hydrogen, halogen, or C ₁ -C ₁₂ alkyl, and a more preferred compound ( 1) is a compound in which R ₆ and R ₇ each independently represent hydrogen, chlorine, or methyl.

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which R represents a substituted or unsubstituted aryl group or a C ₁ -C ₁₂ alkyl group, and a better compound (1 ) Is a compound in which R represents halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy-substituted aryl, unsubstituted aryl or methyl.

Among the compounds (1) of the present disclosure, a preferred compound is one in which R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted aryloxycarbonyl, or substituted or unsubstituted arylcarbonyl compounds, and a better compound (1) is one of them R ₁ represents hydrogen, unsubstituted C ₂ -C ₁₂ alkenyl, unsubstituted C ₂ -C ₁₂ alkynyl, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C Compounds of ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, unsubstituted aryloxycarbonyl, or substituted or unsubstituted arylcarbonyl.

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which R ₂ represents hydrogen, a substituted or unsubstituted C ₁ -C ₁₂ alkyl group, and a better compound (1 ) Is a compound in which R ₂ represents hydrogen, methyl or ethyl.

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which R ₃ represents a substituted or unsubstituted C ₁ -C ₁₂ alkyl group, and a more preferred compound (1) is A compound in which R ₃ represents methyl, ethyl or trifluoromethyl.

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which R ₄ and R ₅ each independently represent hydrogen, a substituted or unsubstituted C ₁ -C ₁₂ alkyl group, and a A more preferable compound (1) is a compound in which R ₄ and R ₅ each independently represent hydrogen or methyl.

Among the compounds (1) of the present disclosure, a preferred compound is a compound in which X ₁ , X ₂ and X ₃ each independently represent CR ₈ , CR ₉ , CR ₁₀ , or N, and a more preferred Compound (1) is a compound in which X ₁ , X ₂ and X ₃ each independently represent CR ₈ , CR ₉ , and CR ₁₀ . However, when X ₁ represents a nitrogen atom, X ₂ and X ₃ respectively represent CR ₉ and CR ₁₀ . When X ₂ represents a nitrogen atom, X ₁ and X ₃ respectively represent CR ₈ and CR ₁₀ . When X ₃ represents a nitrogen atom, X ₁ and X ₂ represent CR ₈ and CR _{9, respectively} .

Among the compounds (1) of the present disclosure, a preferred compound is one in which R ₈ , R ₉ and R ₁₀ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl Compound, and a more preferred compound (1) is a compound in which R ₈ , R ₉ and R ₁₀ independently of each other represent hydrogen, chlorine, methyl or ethyl.

Among these, a better compound of the present disclosure is a compound or a salt thereof, wherein Q represents an oxygen atom; R is halogen-, alkyl-, haloalkyl-, alkoxy- or haloalkane Oxy-substituted aryl; unsubstituted aryl; or methyl; R ₁ is hydrogen, unsubstituted C ₂ -C ₁₂ alkenyl, unsubstituted C ₂ -C ₁₂ alkynyl, unsubstituted Substituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, unsubstituted aryloxy Carbonyl, or substituted or unsubstituted arylcarbonyl; R ₂ is hydrogen, or substituted or unsubstituted C ₁ -C ₁₂ alkyl; R ₃ is substituted or unsubstituted C ₁ -C ₁₂ alkyl; R ₄ is hydrogen, or substituted or unsubstituted C ₁ -C ₁₂ alkyl; R ₅ is hydrogen or methyl; X ₁ represents CR ₈ or N; X ₂ represents CR ₉ ; X ₃ represents CR ₁₀ ; R ₈ is hydrogen, C ₁ -C ₁₂ alkyl or halogen; R ₉ is hydrogen, C ₁ -C ₁₂ alkyl or halogen; R ₁₀ is hydrogen, C ₁ -C ₁₂ alkyl or halogen.

A particularly preferred compound of the present disclosure is a compound or a salt thereof, wherein Q represents an oxygen atom; R ₆ is hydrogen; R ₇ is hydrogen; R is a substituted or unsubstituted aryl group, or C ₁ -C ₁₂ alkyl; R ₁ is hydrogen, unsubstituted C ₂ -C ₁₂ alkenyl, unsubstituted C ₂ -C ₁₂ alkynyl, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, Unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, unsubstituted aryloxycarbonyl, or substituted or unsubstituted Arylcarbonyl; R ₂ is hydrogen, methyl or ethyl; R ₃ is methyl, ethyl or trifluoromethyl; R ₄ is hydrogen or methyl; R ₅ is hydrogen, or substituted or unsubstituted Substituted C ₁ -C ₁₂ alkyl; X ₁ represents CR ₈ or N; X ₂ represents CR ₉ ; X ₃ represents CR ₁₀ ; R ₈ is hydrogen, chlorine, methyl or ethyl; R ₉ is hydrogen, chlorine, Methyl or ethyl; R ₁₀ is hydrogen, chlorine, methyl or ethyl.

Another better compound of the present disclosure is a compound or a salt thereof, wherein Q represents an oxygen atom or a sulfur atom, preferably an oxygen atom; R is substituted with halogen, C ₁ -C ₆ alkyl , C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, and/or C ₁ -C ₆ haloalkylsulfonyl C ₆ aryl; R ₁ is hydrogen, unsubstituted C ₁ -C ₆ alkoxycarbonyl, unsubstituted C ₁ -C ₆ alkylcarbonyl, unsubstituted C ₁ -C ₆ haloalkylcarbonyl, unsubstituted C ₃ -C ₆ cycloalkylcarbonyl, or unsubstituted C ₆ arylcarbonyl, or C ₁ -C ₆ haloalkyl-substituted C ₆ arylcarbonyl; R ₂ is C ₁ -C ₃ alkyl; R ₃ is hydrogen or C ₁ -C ₃ alkyl; R ₄ is hydrogen or C ₁ -C ₃ alkyl; R ₅ is hydrogen or C ₁ -C ₃ alkyl; X ₁ represents CR ₈ ; X ₂ represents CR ₉ ; X ₃ represents CR ₁₀ ; R ₈ is hydrogen, C ₁ -C ₃ alkyl, or fluorine; R ₉ is hydrogen or C ₁ -C ₃ alkyl; R ₁₀ is hydrogen or C ₁ -C ₃ alkyl.

A particularly preferred compound of the present disclosure is a compound or a salt thereof, wherein Q represents an oxygen atom or a sulfur atom, preferably an oxygen atom; R is substituted with fluorine, chlorine, bromine, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, and/or C ₁ -C ₃ haloalkoxy C ₆ aryl; R ₁ is hydrogen, unsubstituted C ₁ -C ₆ alkoxy Carbonyl, unsubstituted C ₁ -C ₆ alkylcarbonyl, unsubstituted C ₁ -C ₆ haloalkylcarbonyl, or unsubstituted cyclopropylcarbonyl; R ₂ is methyl; R ₃ is ethyl R ₄ is hydrogen, methyl, or ethyl; R ₅ is hydrogen, methyl, or ethyl; X ₁ represents CR ₈ ; X ₂ represents CR ₉ ; X ₃ represents CR ₁₀ ; R ₈ is hydrogen, methyl Group, or ethyl; R ₉ is methyl; R ₁₀ is hydrogen.

The present disclosure also incorporates the preparation of these novel substituted pyrazole compounds or their salts as represented by the chemical formula ( 1 ). There are various known synthetic synthetic procedures for preparing the compounds of the present disclosure. In the following, a synthetic procedure for a type of compound used in the present disclosure will be described and shown in Route -1 . However, the preparation of these novel substituted pyrazole compounds or their salts is not limited to this method.

其中R、R₁ 、R₂ 、R₃ 、X₁ 、X₂ 、X₃ 和Q是如上面所定義的，而LG和LG₁ 是已知離去基團的任一者。步驟 1-1 Path -1

Where R, R ₁ , R ₂ , R ₃ , X ₁ , X ₂ , X ₃ and Q are as defined above, and LG and LG ₁ are any of the known leaving groups. Step 1-1

This step provides a method for preparing compound (III) by reacting compound ( I ₀ ) with compound ( II ).

其中，R是如上面所定義的。[Reaction Path 1-1]

Where R is as defined above.

The above reaction is performed in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: fatty acid or alicyclic hydrocarbon-based solvents (alicyclic hydrocarbon-based solvents), such as n -hexane, cyclohexane, n -heptane, and the like; aromatic hydrocarbons- Basic solvents, such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents, such as methylene chloride, 1,2-dichloroethane, chloroform, and carbon tetrachloride, And the like; ester solvents such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane, and the like; amide-based solvents such as acetonitrile; N,N -dimethylformamide Amine ( N,N- dimethylformamide, DMF), N,N -dimethylacetamide, N -methyl-2-pyrrolidone ( N- methyl-2-pyrolidone) and the like; Basic solvents, such as dimethylsulfoxide, sulfolane and the like; tetrahydrofuran, N,N -dimethylformamide; and protic solvents, such as methanol, ethanol, isopropanol, Tertiary - butanol or water, etc. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 0.5 to 20 liters per 1 mole of the compound (I), preferably 0.5 to 10 liters.

The amount of the compound (II) to be used is generally 1.0 to 10.0 moles, preferably 1.0 to 1.5 moles per 1 mole of the compound (I).

The reaction temperature varies depending on the starting compound, reagents, solvents and the like, but it is usually from -40°C to the reflux temperature in the reaction system, preferably from 0 to 100°C.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 60 minutes to 10 hours. Step 1-2

In this step, compound (III) is methylated to produce compound (IV).

其中，R是如上面所定義的。[Reaction pathway 1-2]

Where R is as defined above.

Formulation can be done by any known operating procedures. Some examples of methylation include, but are not limited to, the use of POCl ₃ -DMF system or the use of hexamethylenetetramine. The above reaction is performed in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: halogenated hydrocarbon-based solvents such as methylene chloride, 1,2-dichloroethane, chloroform, carbon tetrachloride, and the like; ether-based solvents such as tetrahydrofuran (THF), 1,4-dioxane, and the like; ester solvents such as methyl acetate, ethyl acetate, and the like; amide-based solvents such as acetonitrile; N,N -di Methylformamide (DMF), N,N -dimethylacetamide, N -methyl-2-pyrrolidone, and the like; and trifluoroacetic acid, dimethylsulfoxide, cyclobutane, etc. . Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 1.0 to 20 liters per 1 mole of the compound (III), preferably 1.0 to 10 liters.

The amount of phosphorous oxychloride to be used is usually 1.0 to 20.0 mol per 1 mol of the compound (III), preferably 1.0 to 10.0 mol. Similarly, the amount of hexamethylenetetramine to be used is generally 1.0 to 10.0 moles per 1 mole of the compound (III), preferably 1.0 to 5.0 moles.

The reaction temperature varies depending on the starting compound, reaction reagents, solvent and the like, but it is usually from -40°C to the reflux temperature in the reaction system, preferably from 50 to 120°C.

The reaction time varies depending on the compound, reaction reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 1 to 10 hours. Step 1-3

This step consists of 2 stages. In the first stage, compound (IV) is treated with a suitable peracid to produce an intermediate. In the second stage, this intermediate is hydrolyzed to produce compound (V).

其中，R和Q是如上面所定義的。[Reaction pathway 1-3]

Among them, R and Q are as defined above.

In the first stage, any known peracid may be used, examples include, but are not limited to, m - chloroperoxybenzoic acid (m -chloroperbenzoic acid), hydrogen peroxide, peracetic acid and the like. The amount of peracid is usually 1.0 to 20.0 moles per 1 mole of the compound (IV), preferably 1.0 to 5.0 moles.

The above reaction is performed in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: halogenated hydrocarbon-based solvents such as methylene chloride, 1,2-dichloroethane, chloroform, and carbon tetrachloride, and the like; ether-based solvents such as Tetrahydrofuran (THF), 1,4-dioxane, and the like; ester solvents such as methyl acetate, ethyl acetate, and the like; amide-based solvents such as acetonitrile; N,N- Dimethylformamide (DMF), N,N -dimethylacetamide, N -methyl-2-pyrrolidone, and the like; and dimethylsulfoxide and cyclobutane. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 1.0 to 20 liters per 1 mole of the compound (IV), preferably 1.0 to 10 liters.

In the second stage, the hydrolysis of the intermediate can be made by any known procedures. Examples include, but are not limited to, the use of an acid in a protic solvent or a base in a suitable solvent. For acidic conditions, any well-known acids (like hydrochloric acid, sulfuric acid, etc.) can be used, while under alkaline conditions, any known bases (such as organic bases like triethylamine or inorganic bases like sodium hydroxide) Can be used.

The amount of acid or base to be used is usually 1.0 to 20.0 mol per 1 mol of the compound (IV), preferably 1.0 to 5.0 mol.

The above reaction is performed in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: halogenated hydrocarbon-based solvents such as methylene chloride, 1,2-dichloroethane, chloroform, and carbon tetrachloride, and the like; ether-based solvents such as Tetrahydrofuran (THF), 1,4-dioxane, and the like; ester solvents such as methyl acetate, ethyl acetate, and the like; amide-based solvents such as acetonitrile; N,N- Dimethylformamide (DMF), N,N -dimethylacetamide, N -methyl-2-pyrrolidone, and the like; dimethylmethylene or cyclobutane; and protic solvents, Like methanol, ethanol, water, etc. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 1.0 to 20 liters per 1 mole of the compound (IV), preferably 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reagents, solvents and the like, but it is usually from -40°C to the reflux temperature in the reaction system, preferably from 0 to 100°C.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 6 hours to 18 hours. Step 1-4

This step consists of a reaction between compound (V) and compound (VI) in the presence of a base and a solvent to produce compound (VII).

其中，R、X₁ 、X₂ 、X₃ 和Q是如上面所定義的。LG代表任何適合的離去基團，諸如鹵素、O-甲磺酸鹽(O-mesylates)、O-磺酸鹽、O-甲苯磺酸鹽(O-tosylates)等等。[Reaction pathway 1-4]

Among them, R, X ₁ , X ₂ , X ₃ and Q are as defined above. LG represents any suitable leaving group such as halogen, O-mesylates, O-sulfonates, O-tosylates, etc.

The base used in the above reaction is not particularly limited. As for the base, any conventionally known base can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, and the like; Alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, and the like; inorganic bases, including alkali metal hydrides, such as sodium hydride and potassium hydride, and the like; alkali metal alkoxides ), such as sodium methoxide (sodium methoxide), sodium ethoxide (sodium ethoxide), three - butoxypotassium (potassium tert -butoxide), and the like of the composition; an organic base, such as pyridine (pyridine), three Ethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisopropylethylamine, 4-dimethylamine pyridine, piperidine (piperidine), and the like Any one of these bases or a combination of two or more types of them can be used.

The amount of the base to be used is usually 1.0 to 5.0 moles per 1 mole of the compound (V), preferably 1.0 to 1.5 moles.

The above reaction is carried out in an appropriate solvent. There is no limit to being placed on the solvent as long as the solvent is inactive for the above reaction. Examples of such a solvent include: halogenated hydrocarbon-based solvents such as methylene chloride, 1,2-dichloroethane, chloroform, and carbon tetrachloride, and the like; amide-based solvents, Such as tetrahydrofuran (THF), 1,4-dioxane; acetonitrile; N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methyl-2-pyrrolidine Ketones and the like; as well as dimethyl sulfonate, ciproin, and protic solvents such as methanol, ethanol, water, etc. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 1.0 to 20 liters per 1 mole of the compound (V), preferably 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reaction reagents, solvent and the like, but it is usually from -40°C to the reflux temperature in the reaction system, preferably from 0 to 100°C.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 60 minutes to 12 hours. Step 1-5

This step involves the reduction of the nitro group (NO ₂ ) present in compound (VII) to produce the amine group (NH ₂ ) of compound (VIII).

其中，R、X₁ 、X₂ 、X₃ 和Q是如上面所定義的。[Reaction pathway 1-5]

Among them, R, X ₁ , X ₂ , X ₃ and Q are as defined above.

Regarding the above reaction, various conventional methods are known and can be widely used. Some examples of such methods include, but are not limited to: Palladium Charcoal (Pd-C) in a protic solvent (like methanol, ethanol) under a hydrogen atmosphere; Raney Nickel (Raney Ni) in Under hydrogen atmosphere in protic solvents (like methanol, ethanol); iron powder in acetic acid; zinc powder (Zinc dust) in acetic acid; sodium sulfide (Na ₂ S) in ethanol; zinc powder, ammonium chloride and solvents (Like THF-MeOH, THF-EtOH) a mixture; stannous chloride (Stannous Chloride) in hydrochloric acid and so on.

The reaction temperature varies depending on the starting compound, reagents, solvents and the like, but it is usually from -40°C to the reflux temperature in the reaction system, preferably from 0 to 90°C.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 5 minutes to 48 hours, preferably from 60 minutes to 6 hours. Step 1-6

This step is a method for preparing compound (X) from the reaction of compound (VIII) and compound (IX) in the presence of a catalyst and a suitable solvent.

其中，R、R₂ 、R₃ 、X₁ 、X₂ 、X₃ 和Q是如上面所定義的。[Reaction pathway 1-6]

Among them, R, R ₂ , R ₃ , X ₁ , X ₂ , X ₃ and Q are as defined above.

The above reaction is carried out in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: benzene, chlorobenzene, toluene, xylene, 1,2-dichloroethane, diphenyl ether, acetonitrile, N,N -dimethylformamide (DMF), N,N -Dimethylacetamide, N -methyl-2-pyrrolidone, polyphosphoric acid. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 0.5 to 20 liters, preferably 0.5 to 10 liters per 1 mole of the compound represented by the chemical formula (VIII).

The above reaction can be performed in the presence of a catalyst. There are various conventional catalysts that can be used in this reaction and some examples of these catalysts include: trifluoroacetic acid; hydrochloric acid; sulfuric acid; p -toluenesulfonic acid; boron trifluoride etherate (BF ₃ -Et) ₂ O); aluminum chloride (AlCl ₃ ); iron chloride (FeCl ₃ ); titanium chloride (TiCl ₄ ); tin chloride (SnCl ₄ ).

The amount of acid to be used is usually 1.0 to 5 moles per 1.5 moles of the compound (VIII), preferably 0.05 moles.

The amount of acetoacetate (IX) to be used is usually 1.0 to 10.0 moles, preferably 1.0 to 5.0 moles of the compound (VIII).

The reaction temperature varies depending on the type of starting compound, reagents and solvent, and is generally from 0°C to 200°C.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 2 hours to 16 hours. Step 1-7

This step produces compound ( 1 ) by treating compound (X) with compound (XI).

其中，R、R₁ 、R₂ 、R₃ 、R₉ 、R₁₀ 、X₁ 、X₂ 、X₃ 和Q是如上面所定義的。LG₁ 代表任何適合的離去基團，諸如鹵素、O -甲磺酸鹽、O -磺酸鹽、O -甲苯磺酸鹽等等。[Reaction pathway 1-7]

Wherein, R, R ₁ , R ₂ , R ₃ , R ₉ , R ₁₀ , X ₁ , X ₂ , X ₃ and Q are as defined above. LG ₁ represents any suitable leaving group, such as halogen, O -methanesulfonate, O -sulfonate, O -toluenesulfonate and the like.

The above reaction is carried out in an appropriate solvent or without any solvent. When the above reaction is carried out in a solvent, there is no limitation to be placed on the solvent as long as the solvent is inactive to the above reaction. Examples of such a solvent include: aromatic hydrocarbon-based solvents such as benzene, chlorobenzene, toluene, xylene, and the like; halogenated hydrocarbon-based solvents such as dichloromethane, 1,2-bis Ethyl chloride, chloroform, and carbon tetrachloride, and the like; ether-based solvents, such as diethyl ether, tetrahydrofuran (THF), 1,4-dioxane, and the like; ester solvents, such as Methyl acetate, ethyl acetate, and the like; amide-based solvents, such as acetonitrile; N,N -dimethylformamide (DMF), N,N -dimethylacetamide, N -Methyl-2-pyrrolidone and the like; and ketone-based solvents such as acetone, methyl ethyl ketone, cyclohexanone, and the like; and dimethyl sulfoxide. Any of these solvents may be used alone or a combination of two or more types thereof may be used when needed.

The amount of the solvent to be used is usually 0.5 to 20 liters per 1 mole of the compound represented by the chemical formula (X), preferably 0.5 to 10 liters.

The base used in the above reaction is not particularly limited. As for the base, a conventionally known base can be widely used, and examples of the base include: alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate, potassium bicarbonate, sodium bicarbonate, and the like; Alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, and the like; inorganic bases, including alkali metal hydrides, such as sodium hydride and potassium hydride, and the like; alkali metal alkoxides, such as methoxy sodium, sodium ethoxide, three - butoxide, and the like of the composition; an organic base, such as pyridine, triethylamine, diethylamine, dimethylamine, methylamine, imidazole, benzimidazole, diisobutyl Propylethylamine, 4-dimethylaminepyridine, piperidine, and the like; and preferably pyridine. Any separate one of these bases or a combination of two or more types thereof may be used.

The amount of the base to be used is usually 1.0 to 5.0 moles per 1 mole of the compound (V), preferably 1.0 to 1.1 moles, and sometimes, when an organic base is used, it can also be used as a Solvent.

The amount of the compound (XI) to be used is usually 1.0 to 5.0 moles, preferably 1.0 to 2.0 moles per 1 mole of the compound (V).

The reaction temperature varies depending on the starting compound, reagents, solvent and the like, but it is generally from -10°C to the boiling point of the solvent.

The reaction time varies depending on the compound, reagents, solvent, reaction temperature and the like, but it is usually from 10 minutes to 48 hours, preferably from 1 hour to 12 hours.

Each compound represented in Route -1 can be easily separated from the reaction mixture after completion of the reaction and by known separation and purification techniques (such as filtration, solvent extraction, distillation, recrystallization, and column chromatography) Method).

The compound (1) of the present disclosure can be used as an active ingredient of a pest control agent. Examples of pest control agents include reagents for controlling all pests, mites, nematode or soil pests that cause problems in the agricultural and horticultural fields (agricultural and horticultural insecticides, miticides) , Nematicides, or soil insecticides); animal-ectoparasite-controlling agents (eg, pulicide, ixodicide, and pedivulicide) ), and the like.

In order to use an active ingredient as a pest-controlling agent, it is possible to use the compound (1) of the present disclosure as it is without additional components. However, it is generally preferred to use the compound by combining it with a solid carrier, liquid carrier or gas carrier (propellant), and optionally with a surfactant and other adjuvant (adjuvant) Pharmaceutical preparations, and the mixtures formed according to the known preparation methods into various forms, such as oil solutions, emulsions, wettable powders, flowable preparations, granules, dusts, aerosols, fumigants ( fumigants), or similar.

The compound (1) of the present disclosure is generally included in these formulations in a ratio of 0.01 to 95 wt%, and preferably 0.1 to 50 wt%.

Examples of solid supports include mineral supports such as pyrophyllite clay, kaolin clay, Silicastone clay, talc, diatomaceous earth, zeolite, Bentonite, acid clay, activated clay, attapulgus clay, vermiculite, perlite, pumice, white carbon (e.g. synthetic silicic acid or Synthetic silicate), titanium dioxide and the like; vegetable carriers such as wood flour, corn stalks, walnut shells, cores, rice husks, sawdust, wheat bran, soybean flour, powdered cellulose, starch, dextrin, sugar And the like; inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and the like; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene- Vinyl acetate copolymers, urea-aldehyde resins and the like.

Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, cyclohexanol, and the like; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, Hexanediol, polyethylene glycol, polypropylene glycol, glycerin, and the like; polyol derivatives, such as propylene type glycol ether and the like; ketones, such as acetone, methyl ethyl ketone , Methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone (isophorone) and the like; ethers, such as diethyl ether, 1,4-dioxane, cellosolve, di Propyl ether, tetrahydrofuran and the like; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil and the like; aromatic hydrocarbons such as Toluene, C ₉ -C ₁₀ alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, high-boiling aromatic hydrocarbons and the like; halogenated hydrocarbons such as 1,2-dichloro Ethane, chloroform, carbon tetrachloride and the like; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, phthalic acid Dioctyl phthalate, dimethyl adipate and the like; lactones such as γ-butyrolactone and the like; amides such as di Methylformamide, diethylformamide, dimethylacetamide, N -alkylpyrrolidone, and the like; nitriles, such as acetonitrile and the like; sulfur compounds, such as dimethylsulfoxide and Analogues; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor oil, and the like; and water.

As for the surfactant, there is no particular limitation. However, the surfactant preferably gels or swells in water. Examples include non-ionic surfactants such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene Fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl benzene Ether-formalin condensate (polyoxyethylene alkylphenyl ether-formalin condensate), polyoxyethylene polyoxypropylene block polymer (polyoxyethylene polyoxypropylene block polymer), alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkyl Amine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid diphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene glycol, polyoxyalkylene-addition acetylene di Alcohol, polyoxyethylene ether type silicon, ester type silicon, fluorosurfactant, polyoxyethylene castor oil, polyoxyethylene hardened castor oil and the like; anionic surfactants such as alkyl sulfate, polyoxyethylene Alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, Naphthalenesulfonate, alkylnaphthalenesulfonate, naphthalenesulfonate-formalin condensate salt, alkylnaphthalenesulfonate-formalin condensate salt, fatty acid salt, polycarboxylate, N -methyl-fatty acid sarcosine Acid salt, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate and the like; cationic surfactants include alkylamine salts, such as laurylamine hydrochloride, stearin Amine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyl trimethyl ammonium chloride, alkyl dimethyl benzalkonium chloride And the like; and amphoteric surfactants, such as betaine type (betaine type) (e.g. dialkyldiaminoethyl betaine or alkyl dimethylbenzyl betaine), amino acid type (e.g. di (Alkylaminoethylglycine or alkyldimethylbenzylglycine) and the like.

As for binders and tackifiers, examples include carboxymethyl cellulose or one of its salts, dextrin, water-soluble starch, xanthane gum, guar gum , Sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, having a molecular weight of 100,000 to 5,000,000 The average molecular weight of polyethylene oxide, and natural phospholipids (such as cephalinic acid (cephalinic acid) or lecithin).

As for the thickening agent, examples include water-soluble polymers, such as three gums, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative Substances, polysaccharides, and the like; and fine inorganic powders, such as high-purity bentonite, white carbon, and the like.

As for the colorant, examples include, inorganic pigments such as iron oxide, titanium oxide, Prussian Blue and the like; and organic dyes such as Alizarine dye, azo dye, metal Metal phthalocyanine dye and the like.

As for the spreader, examples include silicon-based surfactants, cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelating compounds, cross-linked polyvinylpyrrolidine Ketones, maleic acid and styrene, methacrylic acid copolymers, half esters between polyol polymers and dicarboxylic anhydrides, and water-soluble salts of polystyrene sulfonic acid.

As for the adhesive, examples include surfactants (such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, or polyoxyethylene fatty acid ester), paraffin, Terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

As for anti-freeze, examples include polyhydric alcohols (such as ethylene glycol, diethylene glycol, propylene glycol, or glycerin).

As for the curing inhibitor, examples include polysaccharides (for example, starch, alginic acid, mannose, or galactose), polyvinylpyrrolidone, white carbon, ester gum, and petroleum resin.

Regarding disintegrator, examples include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyamino carboxyl Acid chelating compound, sulfonated styrene-isobutylene-maleic anhydride copolymer and starch polyacrylonitrile graft copolymer.

As for decomposition inhibitors, examples include, desiccants such as zeolite, quicklime, magnesium oxide and the like; antioxidants such as phenol type, amine type, sulfur type, phosphoric acid type and the like; and ultraviolet absorbers such as water Salicylic acid type, benzophenone type and the like.

When the present pest control agent contains the above-mentioned additive components, their content (according to quality) is selected in the case of a carrier (such as a solid carrier or a liquid carrier) at a usual 5 to 95%, preferably 20 to 90 Within the range of %, in the case of surfactants, it is usually 0.1 to 30%, preferably 0.5 to 10%, and in the case of other additives, it is usually 0.1 to 30%, preferably 0.5 to 10%.

The pest control agent is used in any formulation selected from the group consisting of powder formulations, powder-granule mixtures, granules, wettable powders, water-soluble concentrates, water-dispersible granules, lozenges, large granules (Jumbo), and Emulsifiable concentrate, oil formula, solution, flowable concentrate, emulsion, microemulsion, suspoemulsion, ultra-low volume formula, microcapsule, smoking agent, aerosol, bait , Paste, etc.

In the actual use of the formula, the formula may be used by itself or after being diluted with a diluent (such as water) at a given concentration. The application of the formulation containing the compound or its diluted product can be carried out by a conventionally used method, such as dispersion (for example, spraying, spraying, atomizing, powder dispersion, particle dispersion, dispersion on water surface, or tank) Inbox dispersion), soil application (such as mixing or wetting), surface application (such as coating, powder coating or covering), immersion, poison bait, smoke and similar methods. In order to prevent the infestation and growth of harmful pests (especially harmful insects in the excrement of livestock), it is also possible to mix the above-mentioned active ingredients with a family animal feed.

The ratio (mass %) of the active ingredient in this pest control agent is appropriately selected to satisfy the need. The active ingredient is appropriately selected, for example, in the following range: In powder formulations, powder-particle mixtures, etc.: 0.01 to 20%, preferably 0.05 to 10%. In particles and the like: 0.1 to 30%, preferably 0.5 to 20%. In wettable powders, water-dispersible particles, etc.: 1 to 70%, preferably 5 to 50%. In water-soluble concentrates, solutions, etc.: 1-95%, preferably 10 to 80%. In emulsifiable concentrates, etc.: 5 to 90%, preferably 10 to 80%. In oil formulations, etc.: 1 to 50%, preferably 5 to 30%. In flowable concentrates, etc.: 5 to 60%, preferably 10 to 50%. In emulsion, microemulsion, suspoemulsion, etc.: 5 to 70%, preferably 10 to 60%. In lozenges, baits, pastes, etc.: 1 to 80%, preferably 5 to 50%. In smoking agents and the like: 0.1 to 50%, preferably 1 to 30%. In aerosols and the like: 0.05 to 20%, preferably 0.1 to 10%.

The formulation is sprayed at an appropriate concentration after dilution, or applied directly.

When the pest control agent is used after being diluted with a diluent, the concentration of the active ingredient is generally 0.1 to 5,000 ppm. When the formulation itself is used, its application amount per unit area is 0.1 to 5,000 g per 1 ha for the active ingredient compound; however, the application amount is not limited to this.

Incidentally, when the present compound is used alone as an active ingredient, the present pest control agent is sufficiently effective. However, the pest control agent may be mixed or used in combination with fertilizers and agricultural chemicals such as insecticides, acaricides, nematicides, synergists, fungicides, antiviral agents, attractants, herbicides if necessary Agents, plant growth-controlling agents and the like. In this example, a higher utility is shown.

The compound (1) of the present disclosure is effectively used as an agricultural and horticultural insecticide, acaricide, nematicide, or a soil insecticide. In particular, the disclosed compound (1) is effective for controlling pests: for example, aphids, such as green peach aphids, cotton aphids, and the like; diamondback moths , Spodoptera litura, cabbage armyworms, common cutworms, codling moths, bollworms, tobacco budworms, and dance moths (gypsy moths), rice leafrollers, smaller tea tortrix moths, Colorado potato beetles, cucurbit leaf beetles, boll weevils ), plant hoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthoyiid flies scarabs (scarabs), black cutworms, cutworms, ants and agricultural pests; gastropods, such as slugs, snails, and the like; sanitary-hazardous insects ( hygiene-harming insects), such as rat mites, cockroaches, house flies, house mosquitoes and the like; stored-grain insects, such as wheat moths (angoumois grain moths), adzuki bean weevil, Red flour beetles, mealworms, and the like; clothes-harming insects and house- and household-harming insects, such as valley nests Casemaking clothes moths, black carpet beetles, subterranean termites, and the like; mites, including plant-parasitic mites, such as Two-spotted spider mite, carmine spider mites, citrus red mites, Kanzawa spider mites, European red mites, tea Broad mites, pink citrus rust mites, bulb mites, and the like, and house dust mites, such as Tyrophagus putrescentiae, American room Dermatophagoides farina, Chelacaropsis moorei, and the like; soil pests, including plant parasitic nematodes, such as root-knot nematodes, cyst nematodes, and root rot nematodes -lesion nematodes, white-tip nematodes, strawberry bud nematodes, pine wood nematodes, and the like, as well as isopods, such as coccidia pill bugs, sow bugs, and the like; and the like.

The compound (1) of the present disclosure is characterized by having a particularly excellent fungicidal activity and a broad-spectrum activity. The compound can be used to control plant diseases attributed to various fungal pathogens or resistant fungal pathogens. Examples of such fungal pathogens include those that cause cucumber gray mold, rice plant blast (Rice plant blast (Pyricularia grisea, millet)), rice plant sheath blight (rice plant sheath blight, apple powdery mildew, apple Alternaria blotch, persimmon powdery mildew, grape powdery mildew, barley powdery mildew , Wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, tomato late blight, tomato powdery mildew, strawberry powdery mildew, and tobacco powdery mildew , And the like. Examples

The present disclosure is described in more detail with reference to the following preparation examples, formulation examples, and test examples. However, the present disclosure is not limited to these embodiments. Preparation Example 1

2,3-dimethyl-6-((1-( p -tolyl)-1 H -pyrazol-3-yl)oxy)quinolin-4-ylmethyl carbonate (2,3-dimethyl- Preparation of 6-((1-( p -tolyl)- 1H -pyrazol-3-yl)oxy)quinolin-4-yl methyl carbonate) ( Compound 1A-156 ) (1) 1-( p -tolyl)- 1H -pyrazole

1,1,3,3-Tetramethoxypropane (24.90 g, 151.84 mmol, 1.2 equiv.) was added to p -tolylhydrazine hydrochloride ( p- tolylhydrazine hydrochloride) (20.0 g, 126.53 mmol) and the reaction mixture was refluxed for 10 h ("h" means hour(s).). All volatiles are removed by distillation. The reaction mixture was diluted with distilled water (100 mL) and extracted with dichloromethane (3 x 100 mL). The combined organic layer was washed with distilled water, dried over sodium sulfate be, filtered and concentrated to provide serve like 1- (p - tolyl) - one as a pale yellow oil under reduced pressure 1H - pyrazole (18.1 g, rough ). This crude product is used for example in the next step without any further purification.

¹ H NMR (CDCl ₃ ): 7.89 (d, J = 2.0 Hz, 1H), 7.71 (s, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.24 (bs, 2H), 6.45 (bs, 1H), 2.38 (s, 3H); MS (M+1) 159.17. (2) 1- (p - tolyl) - 1H - pyrazol-4-carbaldehyde

POCl ₃ (87.29 g, 569.33 mmol, 5.0 equiv.) was slowly added to DMF (41.61 g, 569.33 mmol, 5.0 equiv.) under a nitrogen atmosphere at 0 to 10°C. This was then stirred for 15 minutes. A counterweight in DMF (25 ml) of 1- (p - tolyl) - 1H - pyrazolo (. 18.0 g, 113.86 mmol, 1.0 equiv) solution was slowly added to the mixture and the reaction mixture followed by 0-10 Stirred at ℃ for 30 minutes. The resulting mixture was then at room temperature and heated to 110°C for 10 h. After cooling to room temperature, the reaction mixture was slowly poured into distilled water and the pH of the reaction mixture became alkaline by adding 10% NaOH solution to it. The product was then extracted with ethyl acetate (3 x 100 mL). The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n -hexane as an eluent to provide 1-( p as a pale yellow solid - tolyl) - IH - pyrazole-4-carbaldehyde (16.5 g, 78% yield).

¹ H NMR (CDCl ₃ ): 9.96 (s, 1H), 8.39 (s, 1H), 8.15 (s, 1H), 7.59 (d, J = 8.4 Hz, 2H), 7.30-7.29 (m, 2H), 2.41 (s, 3H); MS (M+1) 187.13. (3) 1- (p - tolyl) - 1H - pyrazol-4-ol

m - chloroperoxybenzoic acid (m -Chloroperbenzoic acid) (. 8.34 g, 48.36 mmol, 0.9 equiv) was added at room temperature under a nitrogen atmosphere to a ligand in chloroform (500 mL) of 1- (p - tolyl ) -1H -pyrazole-4-carbaldehyde (10.0 g, 53.74 mmol, 1.0 equiv.) in solution. The resulting mixture was refluxed for 4h. The reaction mixture was then cooled to room temperature, diluted with DCM (100 mL), washed with sodium bicarbonate solution (3 x 100 mL) followed by distilled water (3 x 100 mL), dried over sodium sulfate, filtered and Concentrate under reduced pressure to provide a crude product. Methanol (50 mL), distilled water (25 mL) and then concentrated HCl (50 mL) were added to the crude product and then the reaction mixture was refluxed for 10 h. After cooling to room temperature, all volatiles were distilled off under reduced pressure. The pH of the reaction mixture was then neutralized by adding sodium bicarbonate solution and extracted with ethyl acetate (3 x 100 mL). The combined organic layer was washed with distilled water, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n -hexane as an eluent to provide 1-( p as a light brown solid - tolyl) - IH - pyrazol-4-ol (7.0 g, 75% yield).

¹ H NMR (CDCl ₃ ): 7.56 (s, 1H), 7.46 (d, J = 8.4 Hz, 2H), 7.41 (s, 1H), 7.22 (d, J = 8.4 Hz, 2H), 4.86 (bs, 1H), 2.36 (s, 3H); MS (M+1) 175.13. (4) 4- (4-nitrophenoxy) -1- (p - tolyl) - 1H - pyrazol

Cesium carbonate (4.21 g, 12.92 mmol, 1.5 equiv.) and 1-fluoro-4-nitrobenzene (1.21 g, 8.61 mmol, 1.0 equiv.) were added sequentially to a mixture at room temperature under a nitrogen atmosphere. DMF (50 mL) of 1- (p - tolyl) - 1H - pyrazol-4-ol (. 1.5 g, 8.61 mmol, 1.0 equiv) was. The resulting mixture was then heated to 70°C for 10 h. The reaction mixture was cooled to room temperature, poured into distilled water (100 mL) and extracted with ethyl acetate (3 x 80 mL). The combined organic layer was washed with distilled water, dried over sodium sulfate and filtered. This was then concentrated under reduced pressure to provide 4-(4-nitrophenoxy)-1-( p -tolyl)-1H-pyrazole (1.65 g, rough) as a yellow solid. This crude product is used for example in the next step without any further purification.

¹ H NMR (CDCl ₃ ): 8.23 (d. J = 9.2 Hz, 2H), 7.86 (s, 1H), 7.61 (s, 1H), 7.55 (d, J = 8.4 Hz, 2H), 7.28 (d, J = 8.4 Hz, 2H), 7.15 (d, J = 9.2 Hz, 2H), 2.40 (s, 3H); MS (M+1) 296.16. (5) 4 - ((1- (p- tolyl) - 1H - pyrazol-4-yl) oxy) aniline

Ammonium chloride (2.72 g, 50.83 mmol, 10.0 equiv.) was added to a mixture of 4-(4-nitrophenoxy) in THF: methanol (1:1, 50 mL) and distilled water (5 mL). To a solution of 1-(p-tolyl)-1H-pyrazole (1.50 g, 5.08 mmol), zinc powder (3.32 g, 50.83 mmol, 10 equiv.) was added in portions at room temperature. The resulting mixture was stirred at room temperature for 2h. The reaction mixture was then diluted with ethyl acetate (100 ml) and filtered through a bed of diatomaceous earth. The filtrate was washed with distilled water, dried over sodium sulfate, and filtered. This then was concentrated under reduced pressure to provide serve like one meter white solid 4 - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) aniline (1.34 g, rough) . This crude product is used for example in the next step without any further purification.

¹ H NMR (CDCl ₃ ): 7.64 (s, 1H), 7.51-7.49 (m, 3H), 7.27 (d, J = 8.4 Hz, 2H), 6.94 (d, J = 8.8 Hz, 2H), 6.66 ( d, J = 8.8 Hz, 2H), 4.63 (bs, 2H), 2.37 (s, 3H); MS (M+1) 266.22. (6) 2,3-dimethyl -6 - ((1- (p - tolyl) - IH - pyrazol-4-yl) oxy) - quinolin -4 (1H) - one

Ethyl 2-methyl-3-oxobutanoate (0.74 g, 5.14 mmol, 1.1 equiv.) and p -toluenesulfonic acid (catalytic amount) are sequentially provided under a nitrogen atmosphere added to a counterweight 4 in xylene (30 mL) is - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) aniline (1.24 g, 4.67 mmol, 1.0 equiv.) In solution. The resulting mixture was refluxed for 16h using a Dean-Stark apparatus. All volatiles were distilled off under reduced pressure to provide a crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of methanol and dichloromethane as an eluent to provide 2,3-dimethyl- as a brown solid 6 - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) quinolin -4 (1H) - one (0.7 g, 43% yield).

¹ H NMR (DMSO- d ₆ ): δ 11.52 (bs, 1H), 8.59 (s, 1H), 7.73-7.71 (m, 3H), 7.54-7.52 (m, 1H), 7.47-7.43 (m, 1H ), 7.31 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 7.6 Hz, 1H), 2.37 (s, 3H), 2.34 (s, 3H), 1.94 (s, 3H); MS (M +1) 346.20. (7) 2,3-dimethyl -6 - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) quinolin-4-yl methyl carbonate (1A-156 )

Tertiary-butoxy potassium (16 mg, 0.14 mmol, 1.0 equiv.) was added to a 2,3-dimethyl-6-((1 - (p - tolyl) - 1H - (1H) pyrazol-4-yl) oxy) quinoline -4-- -one (50 mg, 0.14 mmol) and stirred in for 15 minutes. Methyl chloroformate (13 mg, 0.14 mmol, 1.0 equiv.) was added to this solution and the reaction mixture was then stirred at room temperature for 10 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and the organic layer was washed with sodium bicarbonate solution followed by distilled water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n -hexane as an eluent to provide 2,3-like a beige solid dimethyl -6 - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) methyl-quinolin-4-yl carbonate (40 mg, 68.5% yield).

¹ H NMR (CDCl ₃ ): δ 7.99 (d, J = 9.2 Hz, 1H), 7.81 (s, 1H), 7.62 (s, 1H), 7.55 (d, J = 8.4 Hz, 2H), 7.49-7.46 (dd, J = 9.2, 2.8 Hz, 1H), 7.32 (d, J = 2.4 Hz, 1H), 7.27 (s, 1H), 7.25 (s, 1H), 3.91 (s, 3H), 2.71 (s, 3H), 2.39 (s, 3H), 2.30 (s, 3H); MS (M+1) 404.51. Preparation Example 2

2,3-dimethyl-6-((1-( p -tolyl)-1 H -pyrazol-4-yl)oxy)quinolin-4-ylethyl carbonate (2,3-dimethyl- Preparation of 6-((1-( p -tolyl)- 1H -pyrazol-4-yl)oxy)quinolin-4-yl ethyl carbonate) ( Compound 1A-157 ) Tertiary-butoxy potassium (16 mg, 0.14 . mmol, 1.0 equiv) was added at room temperature under a nitrogen atmosphere to a ligand in THF (10 ml) of 2,3-dimethyl -6 - ((1- (p - tolyl) - 1H - pyrazol -4-yl)oxy)quinolin-4( 1H )-one (50 mg, 0.14 mmol) in a mixture and stirred for 15 minutes. Ethyl chloroformate (15 mg, 0.14 mmol, 1.0 equiv.) was added to this solution and the reaction mixture was then stirred at room temperature for 10 h. The reaction mixture was diluted with ethyl acetate (20 mL) and the organic layer was washed with sodium bicarbonate solution followed by distilled water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to provide a crude product. The crude product thus obtained was purified by column chromatography on silica gel using a mixture of ethyl acetate and n -hexane as an eluent to provide 2,3-like a beige solid dimethyl -6 - ((1- (p - tolyl) - 1H - pyrazol-4-yl) oxy) quinolin-4-yl ethyl carbonate (40 mg, 66.2% yield).

¹ H NMR (CDCl ₃ ): δ 7.99 (d, J = 9.2 Hz, 1H), 7.82 (s, 1H), 7.62 (s, 1H), 7.55 (d, J = 8.4 Hz, 2H), 7.49-7.46 (dd, J = 9.2, 2.8 Hz, 1H), 7.30 (d, J = 2.8 Hz, 1H), 7.27 (s, 1H), 7.25 (s, 1H), 4.33-4.28 (q, J = 7.2 Hz, 2H), 2.71 (s, 3H), 2.39 (s, 3H), 2.30 (s, 3H), 1.32 (t, J = 7.2 Hz, 3H); MS (M+1)418.86.

Representative compounds of the present disclosure is illustrated in the following Tables 1 to 4, but the present disclosure is not limited to these compounds.

The compounds shown in Tables 1 to 4 (not the compounds obtained in Preparation Examples 1 to 2 ) were produced by a method similar to that described in Preparation Examples 1 to 2 or the method described in the specification . The abbreviations in Tables 1 to 4 are indicated as follows:

F: fluorine, Cl: chlorine, Br: bromine, Me: methyl, Et: ethyl, n-Pr: n -propyl, n-Bu: n -butyl, ^t Bu: tertiary - butyl, Ph : Phenyl, C ₆ H ₁₁ : cyclohexyl, CF ₃ : trifluoromethyl, C ₃ F ₇ : heptafluoroisopropyl, OCF ₃ : trifluoromethoxy, OMe: methoxy, COMe: methyl Carbonyl, OPh: phenoxy, CO ₂ Me: methoxycarbonyl, CO ₂ Et: ethoxycarbonyl, CO ₂ Ph: phenoxycarbonyl, Cy-pr: cyclopropyl, Cy-pent: cyclopentyl , F ₂ -Ph: difluorophenyl, Cl ₂ -Ph: dichlorophenyl, Cl ₃ -Ph: trichlorophenyl, SO ₂ Me: methylsulfonyl, SO ₂ Et: ethylsulfonyl , SO ₂ CF ₃ : trifluoromethylsulfonyl, CN: cyano, NO ₂ : nitro.

*這兩者異構物藉由管柱層析法是不可分離的 Table 1:

*The two isomers are inseparable by column chromatography

Table 2 :

*這兩者異構物藉由管柱層析法是不可分離的。 Table 3 :

*The two isomers are inseparable by column chromatography.

配方實施例 1 ：乳劑 Table 4 : Details of ¹ H NMR and LC-MS of the synthesized compounds belonging to the structure (1A, 1B & 1C) of the present disclosure:

Formulation Example 1 : Emulsion

Part 10 of each disclosed compound was dissolved in 45 parts of Solvesso 150 and 35 parts of N -methylpyrrolidone. Part 10 of an emulsifier (trade name: Sorpol 3005X, manufactured by Toho Chemical Industry Co., Ltd.) was added here. The mixture is mixed by stirring to provide a 10% emulsion. Formulation Example 2 : Wettable powder

Part 20 of each compound of the present disclosure is added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignosulfonate, 20 parts of fine powder of synthetic hydrated silica, and 54 parts of clay . The mixture is mixed by blending in a juice mixer to provide a 20% wettable powder. Formulation Example 3 : Granules

2 parts of sodium dodecylbenzenesulfonate, 10 parts of bentonite and 83 parts of clay were added to 5 parts of each compound of the present disclosure, and each mixture was sufficiently mixed by stirring. An appropriate amount of water is added here. The resulting mixture is further stirred and granulated with a granulator. The particles were air dried to provide 5% particles. Formulation Example 4 : Powder

Part 1 of each compound of the present disclosure is dissolved in an appropriate amount of acetone. 5 parts of fine powder of synthetic hydrated silica, 0.3 parts of acidic isopropyl phosphate (PAP) and 93.7 parts of clay were added here. The mixture was mixed by blending in a juice mixer, and acetone was removed by evaporation to provide 1% powder. Formulation Example 5 : Flowable formulation

Part 20 of each compound of the present disclosure was mixed with 20 parts of water containing 3 parts of polyoxyethylene tristyrylphenyl ether phosphate triethanolamine and 0.2 parts of Rhodorsil 426R. The mixture was wet pulverized with a DYNO-Mill and was mixed with 60 parts of water containing 8 parts of propylene glycol and 0.32 parts of Sanxian gum to provide a 20% suspension formulated in water.

試驗實施例 1 ( 棉蚜蟲的殺蚜蟲試驗 ) Some test examples are provided below to prove that the disclosed compounds are useful as an active ingredient for insecticides, acaricides and fungicides. Compound A , Compound B and Flometoquin are representative compounds mentioned in the specification of WO2006/013896A1, WO2007/088978A1.

Test Example 1 ( Aphid-killing test of cotton aphids )

A piece of non-woven fabric (4.5 x 5.5 cm) was suspended in a plastic cup through a cut made in the lid of the plastic cup. After the water is poured into the cup, the cup is covered with a lid. A cucumber leaf (approximately 3.5 x 4.5 cm) was then placed on a fully immersed non-woven fabric. Another cucumber leaf with cotton aphids (about 30 aphids samples) was placed on top of the first leaf, and the fabric and leaves were placed at a temperature of 25±2°C and a humidity of 40% Overnight in the constant temperature room. The next morning, when the aphid population had moved to the lower leaves, the top leaves were removed.

Insecticide formulations containing the disclosed compound (100 ppm) were added by adding an aqueous solution (100 ppm) of Sorpol 355 (manufactured by TOHO Chemical Industry Co., Ltd.) to a methanol solution of the disclosed compound. preparation.

These insecticidal formulas are sprayed on the leaves, and the leaves are air-dried and placed in a constant temperature room (25±2°C and a humidity of 50%). The mortality of cotton aphids was calculated after 3 days. Compounds 1A-10 , 1A-11 , 1A-12 , 1A-18 , 1A-19 , 1A-21 , 1A-100 , 1A-115 , 1A-117 , 1A-156 , 1A-159 , 1A-172 , 1A -180 , 1A-181 , 1A-183 , 1A-252 , 1A-254 , 1A-264 , 1A-266 , 1A-314 , 1B-3 , 1B-35 , 1B-36 , 1B-38 , 1B-46 , 1B-47 , 1B-59 , 1B-62 , 1B-64 , 1B-66, and 1B-69 show 80% or more mortality, while the reference compounds ( Compound A , Compound B, and Flometoquin ) each show 100% mortality rate. Test Example 2 ( Insecticidal test on Spodoptera litura )

Insecticidal formulations containing the compounds of the present disclosure (100 ppm and 20 ppm) were prepared in the same manner as in Test Example 1. These insecticidal formulas were sprayed on castor leaves (4 x 4 cm), and the leaves were air-dried and placed in a plastic cup on wet paper. The 4-day-old Spodoptera larvae (12-15 Nos.) were released, and the cup was closed and placed in a constant temperature room (25±2°C and a humidity of 50%). The death rate of Spodoptera was calculated after 3 days. Compounds 1A-5 , 1A-6 , 1A-7 , 1A-8 , 1A-9 , 1A-10 , 1A-32 , 1A-33 , 1A-81 , 1A-84 , 1A-85 , 1A-86 , 1A -87 , 1A-88 , 1A-91 , 1A-92 , 1A-93 , 1A-94 , 1A-96 , 1A-97 , 1A-134 , 1A-160 , 1A-161 , 1A-175 , 1A-185 , 1A-186 , 1A-188 , 1A-190 , 1A-193 , 1A-194 , 1A-195 , 1A-202 , 1A-240 , 1A-241 , 1A-255 , 1A-258 , 1A-267 , 1A -269 , 1A-292 , 1A-293 , 1A-294 , 1A-295 , 1A-296 , 1A-297 , 1A-298 , 1A-299 , 1A-300 , 1A-301 , 1A-306 , 1A-315 , 1A-321 , 1A-324 , 1A-348 , 1A-349 , 1A-352 , 1A-353 , 1A-360 , 1A-361 , 1A-362 , 1A-363, 1A-364 , 1A-367 , 1A -369 , 1A-370 , 1A-371 , 1A-373 , 1A-374 , 1A-375 , 1A-376 , 1A-377 , 1A-378 , 1A-379 , 1A-383 , 1A-384 , 1A-385 , 1A-386 , 1A-387 , 1A-388 , 1A-389 , 1A-390 , 1A-391 , 1A-392 , 1A-393 , 1A-394 , 1A-395 , 1A-396 , 1A-397 , 1A -398 , 1A-406 , 1A-407 , 1A-408 , 1A-409 , 1A-410 , 1A-411 , 1A-412 , 1A-413 , 1A-414 , 1A-415 , 1A-416 , 1A-417 , 1A-418 , 1A-419 , 1A-420 , 1A-428 , 1A-429 , 1A-430 , 1A-432 , 1A-434 , 1A-435 , 1A-436 , 1A-437 , 1A-449 , 1A -452 , 1A-453 , 1A-454 , 1A-455 , 1A-456 , 1A-457 , 1A-458 , 1A-459 , 1A-460 , 1A-463 , 1A-464 , 1A-465 , 1A-466 , 1A-467 , 1A -468 , 1A-469 , 1A-470 , 1A-471 , 1A-472 , 1A-473 , 1A-477 , 1A-478 , 1A-480 , 1A-481 , 1A-484 , 1A-485 , 1A-486 , 1A-487 , 1A-489 , 1A-490, 1A-491 , 1A-492 , 1B-11 , 1B-48 , 1B-49 , 1B-55 , 1B-57 , 1B-77 , 1B-78 , 1B -80 , 1B-81 , 1B-82 , 1B-83 , 1B-84 , 1B-85 , 1B-86 , 1B-87 , 1B-88 , 1C-4 , 1C-6 , 1C-13 , 1C-34 , 1C-37 , 1C-40 , 1C-41 , 1C-43 , 1C-49, and 1C-50 showed 80% or more mortality at 100 ppm, while Reference Compound A showed 0% death at 100 ppm The rates, as well as the reference compounds B and Flometoquin each showed less than 30% mortality at 500 ppm against Spodoptera litura . Compounds 1A-84 , 1A-85 , 1A-87 , 1A-88 , 1A-91 , 1A-92 , 1A-93 , 1A-94 , 1A-96 , 1A-97 , 1A-175 , 1A-185 , 1A -186 , 1A-188 , 1A-190 , 1A-193 , 1A-194 , 1A-195 , 1A-240 , 1A-241 , 1A-255 , 1A-292 , 1A-293 , 1A-295 , 1A-296 , 1A-297 , 1A-299 , 1A-300 , 1A-301 , 1A-348 , 1A-353 , 1A-361 , 1A-362 , 1A-363 , 1A-364 , 1A-373 , 1A-374 , 1A -376 , 1A-377 , 1A-378 , 1A-379 , 1A-387 , 1A-388 , 1A-389 , 1A-394 , 1A-395 , 1A-396 , 1A-397 , 1A-398 , 1A-406 , 1A-407 , 1A-408 , 1A-409 , 1A-411 , 1A-412 , 1A-414 , 1A-415 , 1A-416 , 1A-417 , 1A-418 , 1A-419 , 1A-420 , 1A -428 , 1A-429 , 1A-430 , 1A-434 , 1A-435 , 1A-436 , 1A-437 , 1A-452 , 1A-453 , 1A-454 , 1A-455 , 1A-456 , 1A-457 , 1A-458 , 1A-459 , 1A-463 , 1A-465 , 1A-466 , 1A-467 , 1A-468 , 1A-469 , 1A-470 , 1A-471 , 1A-472 , 1A-484 , 1A -487 , 1A-490 , 1B-48 , 1B-55 , 1B-80 , 1B-81 , 1B-83 , 1C-4 and 1C-13 showed 80% or more mortality at 20 ppm. Test Example 3 ( Acaricidal test on Tetranychus urticae )

A piece of non-woven fabric (4.5 x 5.5 cm) was suspended in a plastic cup through a cut made in the lid of the plastic cup. After the water is poured into the cup, the cup is covered with a lid. One kidney bean leaf (approximately 3.5 x 4.5 cm) is then placed on a fully-soaked non-woven fabric. Another kidney bean leaf with Tetranychus urticae (about 30 mite samples) was placed on top of the first leaf, and the fabric and leaves were placed at a temperature of 25±2°C and 40% Overnight in a constant temperature room with humidity. The next morning, when the mite population had moved to the lower leaves, the top leaves were removed.

The acaricidal formulation containing the compound of the present disclosure (100 ppm) was prepared in the same manner as in Test Example 1. These acaricidal formulations are sprayed on the leaves, and the leaves are air dried and placed in a constant temperature room (25±2°C and a humidity of 50%). The mortality of Tetranychus urticae was calculated after 2 days. Compounds 1B-25 , 1B-38 , 1B-39 , 1B-41 , 1B-46 , 1B-47 , 1B-61 , 1B-62 , 1B-63 , 1B-64 , 1B-66 , 1B-69 , 1B -73 , 1B-75 , 1B-76 , 1B-78 , 1B-82 , 1B-83, and 1B-89 show 80% or more mortality, while Reference Compound A shows 0% mortality at 100 ppm, And Reference Compound B and Flometoquin each showed less than 30% mortality at 500 ppm against Tetranychus urticae. Test Example 4 ( Eggicide test on Tetranychus urticae )

A piece of non-woven fabric (4.5 x 5.5 cm) was suspended in a plastic cup through a cut made in the lid of the plastic cup. After the water is poured into the cup, the cup is covered with a lid. One kidney bean leaf (approximately 3.5 x 4.5 cm) is then placed on a fully immersed non-woven fabric. 20 female adults of Tetranychus urticae were placed on top of the leaves, and the fabric and leaves were placed in a constant temperature room with a temperature of 25±2°C and a humidity of 40% and 16L8D.

The next day, after the number of female adults was adjusted to 20 again, the acaricidal formula containing the compounds of the present disclosure (500 ppm and 100 ppm) prepared in the same manner as in Test Example 1 was sprayed on the leaves The leaves were dried and placed in a constant temperature room (25±2°C and a humidity of 50%). The egg kill rate of Tetranychus urticae was calculated 6 days after spraying the acaricidal formula. Compounds 1B-38 , 1B-39 , 1B-41 , 1B-46 , 1B-47 , 1B-59 , 1B-61 , 1B-62 , 1B-63 , 1B-64 , 1B-66 , 1B-69 , 1B -70 , 1B-73 , 1B-75 , 1B-78 and 1B-83 showed 80% or more mortality at 100 ppm, while the reference compound Compound A showed 40% mortality at 500 ppm and 100% 0% mortality at ppm, and each of Reference Compound B and Flometoquin showed less than 30% mortality at 500 ppm. Compounds 1B-3 , 1B-6 , 1B-7 , 1B-8 , 1B-10 , 1B-38 , 1B-39 , 1B-41 , 1B-42 , 1B-46 , 1B-47 , 1B-59 , 1B -60 , 1B-61 , 1B-62 , 1B-63 , 1B-64 , 1B-65 , 1B-66 , 1B-69 , 1B-70 , 1B-71 , 1B-73 , 1B-74 , 1B-75 , 1B-76 , 1B-78 , 1B-82 , 1B-83 , 1B-85 , 1B-87 , 1B-88 , 1B-89, and 1B-91 showed 80% or more mortality at 500 ppm. Test Example 5 ( Fungicidal test on P. grisea on chestnut )

The small pieces of Mycelia of Grifola frondosa were taken from the culture tube and aseptically transferred to mathur medium plate. The inoculated plate was kept at 25°C for 7 days. The plate was then incubated at 25°C for 5 days under exposure to black light blue 16L8D. After 5 days, the plates were completely covered with fungal spores. The spores were washed from the plate with 0.01% Tween 20 solution and passed through tissue paper. The filtrate was then diluted with 0.01% Tween 20 solution to obtain 2 x 10 ⁵ cfu spores per ml.

A solution of the disclosed compound (500 ppm) prepared in the same manner as in Test Example 1 was sprayed on fresh and healthy 2-week-old chestnut plants. The plants were air-dried and inoculated with a freshly prepared spore suspension. The inoculated plants were then placed in a dew room (25°C and a humidity of 100%). One day after inoculation, the plants were transferred to a constant temperature room (25°C, a humidity of 80%, and 16L8D). Compared to the control, the percentage of disease control was evaluated from the leaf disease area after 5-7 days. Compounds 1A-276 , 1A-325 , 1B-7, and 1B-33 showed 80% or more control, while reference compounds ( Compound A , Compound B, and Flometoquin ) showed less than 50% and less than 30% at 500 ppm, respectively And less than 30 % control. Test Example 6 (fungicidal test on Sphaerotheca fuliginea of cucumber cocklebur (Sphaerotheca fuliginea) a)

Xanthium monofilaments are cultivated on whole cucumber plants. Infected leaves with spores were washed with 0.01% Tween 20 solution and passed through tissue paper. The filtrate was then diluted with 0.01% Tween 20 solution to obtain 2 x 10 ⁵ cfu spores per ml.

A solution of the compound of the present disclosure (500 ppm) prepared in the same manner as in Test Example 1 was sprayed on fresh and healthy 2-week-old cucumber plants. The plants were air-dried and inoculated with a freshly prepared spore suspension. The inoculated plants were then placed in a greenhouse (25°C, a humidity of 60%, and 16L8D). Compared to the control, the percentage of disease control was assessed from the leaf disease area after 12 days. Compounds 1A-172 , 1A-181 , 1A-254 , 1A-262 , 1A-264 , 1A-266 , 1A-325 , 1A-431 , 1B-33 , 1B-57 , 1B-60 , 1B-66 and 1C -10 80% or more display control, and reference compound a exhibits a strong phytotoxicity so that evaluation is not possible on cucumber, and reference compound B are displayed and Flometoquin less than 100% at 500ppm and at 500ppm 70% control. Industrial availability

The substituted pyrazole compounds of the present disclosure or one of their salts show an excellent control effect against a wide range of pests (such as aphids, budworm, mites, etc.), and are used as an agricultural and horticultural use Of pesticides are useful. (Note)

As described above, the present disclosure is exemplified by preferred specific examples of the present disclosure. However, it will be understood that the scope of the present disclosure should be interpreted only by applying for a patent. It is understood that the patents, patent applications and documents cited herein are incorporated into this case as a reference material as if their contents were specifically described here. This application claims the priority of Indian Patent Application No. 201811024217 filed with the Indian Patent Office (Indian Intellectual Property Rights) on June 29, 2018, and its entire contents are incorporated into this case for reference.

(no)

Claims (24)

A substituted pyrazole compound represented by the following chemical formula ( 1 ), or a salt thereof:

Where Q represents an oxygen atom, a sulfur atom, CR ₆ R ₇ or a direct bond; R ₆ and R ₇ each independently represent hydrogen, halogen, cyano, substituted or unsubstituted C ₁ -C ₁₂ alkane Group, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, substituted or unsubstituted C ₂ -C ₁₂ Alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkenyloxy, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₂ -C ₁₂ Alkynyloxy, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted Substituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or Unsubstituted C ₁ -C ₁₂ alkylcarbonylamino, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyloxy, substituted or unsubstituted C ₁ -C ₁₂ alkyl Sulfenyloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted saturated heterocyclic ring; R represents hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₂ -C ₁₂ alkene Group, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, or substituted or unsubstituted saturated heterocycle; R ₁ represents hydrogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₂ -C ₁₂ alkenylcarbonyl, substituted or unsubstituted C ₂ -C ₁₂ alkynylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted Heteroaryloxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted heteroarylcarbonyl, substituted or unsubstituted heterocyclic carbonyl, Substituted or unsubstituted C ₁ -C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted arylsulfinyl Sulfonyl, substituted or unsubstituted heteroarylsulfinyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted heteroarylsulfonyl; R ₂ and R ₃ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted Substituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkyl, substituted or unsubstituted Substituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heterocycle; R ₄ and R ₅ each independently represent hydrogen, halogen, cyano, substituted or unsubstituted Substituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, or substituted or Unsubstituted aryl; X ₁ represents CR ₈ or N, X ₂ represents CR ₉ or N, and X ₃ represents CR ₁₀ or N, conditionally: when X ₁ represents a nitrogen atom, X ₂ and X ₃ represents CR ₉ and CR _{10 respectively} , when X ₂ represents a nitrogen atom, X ₁ and X ₃ represent CR ₈ and CR _{10 respectively} , and when X ₃ represents a nitrogen atom, X ₁ and X ₂ respectively Stands for CR ₈ and CR ₉ ; and R ₈ , R ₉ and R ₁₀ each independently represent hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, substituted or unsubstituted C ₁ -C ₁₂ alkoxy, substituted or unsubstituted C ₁ -C ₁₂ alkylthio, substituted or unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, cyano, nitro, or Substituted or unsubstituted amine groups. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein Q represents an oxygen atom or a sulfur atom. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or Substituted or unsubstituted C ₁ -C ₁₂ alkyl. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R represents a substituted or unsubstituted C ₆ -C ₁₀ aryl group, or an unsubstituted C ₁ -C ₁₂ alkyl. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, substituted or unsubstituted Substituted C ₂ -C ₁₂ alkynyl, substituted or unsubstituted C ₁ -C ₁₂ alkylcarbonyl, substituted or unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, substituted or unsubstituted Substituted C ₁ -C ₁₂ alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C _1- C ₁₂ alkylsulfinyl, substituted or unsubstituted C ₁ -C ₁₂ alkylsulfonyl, substituted or unsubstituted arylsulfinyl, or substituted or unsubstituted Substituted arylsulfonyl. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₁ represents hydrogen, substituted or unsubstituted C ₂ -C ₁₂ alkenyl, unsubstituted C ₂ -C ₁₂ alkynyl, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C ₁₂ cycloalkylcarbonyl, unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, substituted Or unsubstituted C ₆ -C ₁₀ arylcarbonyl, unsubstituted C ₆ -C ₁₀ aryloxycarbonyl, or unsubstituted C ₆ -C ₁₀ arylsulfonyl. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₂ represents hydrogen, halogen, or a substituted or unsubstituted C ₁ -C ₁₂ alkyl group. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₂ represents hydrogen, or an unsubstituted C ₁ -C ₁₂ alkyl group. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₃ represents a substituted or unsubstituted C ₁ -C ₁₂ alkyl group. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₄ and R ₅ each independently represent hydrogen, halogen, or substituted or unsubstituted C ₁ -C ₁₂ alkyl. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₄ and R ₅ each independently represent hydrogen, or an unsubstituted C ₁ -C ₁₂ alkyl group. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other are hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or substituted or unsubstituted C ₁ -C ₁₂ alkoxy. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other are hydrogen, halogen, substituted or unsubstituted C ₁ -C ₁₂ alkyl, or unsubstituted C ₁ -C ₁₂ alkoxy. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein Q represents an oxygen atom. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R represents a substituted or unsubstituted C ₆ aryl group. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₁ represents hydrogen, unsubstituted C ₁ -C ₁₂ alkylcarbonyl, unsubstituted C ₃ -C ₁₂ Cycloalkylcarbonyl, unsubstituted C ₁ -C ₁₂ alkoxycarbonyl, or substituted or unsubstituted C ₆ arylcarbonyl. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₂ represents an unsubstituted C ₁ -C ₆ alkyl group. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₃ represents an unsubstituted C ₁ -C ₆ alkyl group. The substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein R ₄ and R ₅ each independently represent hydrogen, or an unsubstituted C ₁ -C ₆ alkyl group. A substituted pyrazole compound or a salt thereof according to any one of the preceding claims, wherein X ₁ represents CR ₈ , X ₂ represents CR ₉ , X ₃ represents CR ₁₀ , and R ₈ , R ₉ and R ₁₀ Independent of each other is hydrogen, halogen, unsubstituted C ₁ -C ₆ alkyl, or unsubstituted C ₁ -C ₆ alkoxy. A pest control agent comprising the substituted pyrazole compound according to any one of claims 1 to 20 or a salt thereof as an active ingredient. A method of using the substituted pyrazole compound according to any one of claims 1 to 20 or a salt thereof for controlling pests. A method for controlling pests, which comprises applying a substituted pyrazole compound or a salt thereof according to any one of claims 1 to 20 to a plant or its vicinity, or a soil where a plant is cultivated . A method for controlling pests, which comprises applying an effective amount of the substituted pyrazole compound according to any one of claims 1 to 20 or a salt thereof to the pest, the pest's habitat, or a Predict where to live.