JP2011037817A - Insecticidal, miticidal, nematicidal, molluscicidal, fungicidal, or bactericidal agent composition and pest controlling method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new insecticidal, miticidal, nematicidal, molluscicidal, fungicidal, or bactericidal agent composition and a pest controlling method. <P>SOLUTION: The insecticidal, miticidal, nematicidal, molluscicidal, fungicidal, or bactericidal agent composition contains: one or more substances selected from substituted isoxazoline compounds expressed by formula (1) and their salts; and one or more selected from known active components having pest-controlling activity. In the formula (1), A<SP>1</SP>is C-Y or nitrogen atom; A<SP>2</SP>and A<SP>3</SP>are each C-H or the like; A<SP>4</SP>is C-H or nitrogen atom; G is benzene ring or the like; L is -CH(R<SP>4</SP>)- or the like; X is halogen atom, trifluoromethyl or the like; R<SP>1</SP>is -C(O)R<SP>1a</SP>, -C(O)NHR<SP>1c</SP>or the like; R<SP>2</SP>is hydrogen atom, methyl, ethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl, propargyl or the like; R<SP>3</SP>is trifluoromethyl, chlorodifluoromethyl or the like; and m is integer of 0-5. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention is characterized by mixing a substituted isoxazoline compound or a salt thereof and an active ingredient of a known insecticide, acaricide, nematicide, molluscicide, fungicide or bactericide. It relates to a pest control agent.

  The substituted isoxazoline compound represented by the formula (1) of the present invention or a salt thereof is known and its activity as a pest control agent is known (for example, see Patent Document 1 and Patent Document 2).

  Moreover, the active ingredient group A which has the insecticidal activity, the acaricidal activity, the nematicidal activity, the molluscicidal activity, the bactericidal activity or the bactericidal activity which is the second active ingredient in the present invention, the active ingredient group B, the active ingredient group All the active ingredients described as C and active ingredient group D are also publicly known (for example, refer nonpatent literature 1).

International Publication No. 2007/105814 International Publication No. 2009/035004

The Pesticide Manual, 14th edition, The British Crop Protection Council, 2006

  Today, the development of insecticides, acaricides and fungicides for the control of various pests such as agricultural and horticultural pests, forest pests, and hygiene pests is widely promoted, and a wide variety of drugs are put into practical use. However, in recent years, as a result of the long-term use of such drugs, pests have acquired insecticide resistance, and pathogens have acquired fungicide resistance. As a result, there are increasing situations in which it is difficult to control with conventional drugs. Some of these drugs are highly toxic and some are perturbing the ecosystem by remaining in the environment for a long time. Therefore, development of a novel drug having not only a high pest control effect but also low toxicity and low persistence is always expected.

  On the other hand, considering the diversity of insects and pathogens as a group of organisms, the mode of damage, and the variety of scenes of harm, all these control scenes can be achieved simply by using these new drugs or existing known drugs alone. It is very difficult to control all pests effectively. Therefore, a new method for controlling pests that are difficult to control is also strongly induced by appropriately combining multiple insecticides, acaricides, nematicides, molluscs, bactericides or bactericides to induce higher control efficacy. It has been requested.

  In view of such circumstances, the present inventors have conducted intensive research to develop a pest control agent that exhibits excellent pest control activity and has less adverse effects on non-target organisms such as mammals, fish, natural enemies, and beneficial insects. As a result, the substituted isoxazoline compound represented by the following formula (1) or a salt thereof and a known insecticidal, acaricidal, nematicidal, molluscicidal, active ingredient having bactericidal or bactericidal activity are contained. The present invention has been found to have excellent synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effects that cannot be predicted from the use of each composition alone.

  That is, the present invention relates to the following compositions [1] to [8] (hereinafter referred to as the present composition) and the control methods [9] to [12] (hereinafter referred to as the present method). Is.

  [1] Formula (1):

[Wherein, A ¹ , A ² , A ³ and A ⁴ each independently represents CY or a nitrogen atom,
G represents a benzene ring, a nitrogen-containing 6-membered aromatic heterocycle, a furan ring, a thiophene ring or a 5-membered aromatic heterocycle containing two or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom;
L is -C (R ⁴ ) (R ^4a )-, -C (R ⁴ ) (R ^4a ) CH _2- , -CH ₂ C (R ⁴ ) (R ^4a )-, -N (R ^4b )- Or -C (R ⁴ ) (R ^4a ) N (R ^4b )-
X is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ⁵ , C ₃ -C ₈ cycloalkyl , optionally substituted by R ⁵ _(C 3 ~C ₈₎ cycloalkyl, optionally substituted by _{E-1~E-21, C 2} ~C 6 _{^{alkenyl, R 5 (C 2 ~C 6}} ) alkenyl , C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halocycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted by R ⁵ , —OH, —OR ⁶ , — ^{_{OS (O) 2 R 6,}} -SH, -S (O) r R 6, -N (R 8) R 7, -N = C (R 8a) R 7a, -C (O) R 9, -C (R ⁹ ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , M-3, M-13, M-30, -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , M-23 to M-26, M-28, M _{-29, -S (O) 2 OR} 10, -S (O) ^{N (R 12) R 11,} -Si (R 13a) (R 13b) R 13, phenyl, _{(Z) n1} represents phenyl or D-1 to D-38 substituted by, m is an integer of 2 or more When represented, each X may be the same as or different from each other;
Further, when two Xs are adjacent to each other, the two adjacent Xs are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -CH ₂ CH ₂ N (R ¹⁴ )-, -CH ₂ N (R ¹⁴ ) CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -OCH ₂ CH ₂ S-, -CH ₂ CH = CH-,- OCH = CH-, -SCH = CH-, -N (R ¹⁴ ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹⁴ ) CH = N-, -N (R ¹⁴ By forming N = CH-, -CH = CHCH = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -N = CHCH = N- or -N = CHN = CH- In addition, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by Z Well, moreover, when two or more Z are substituted at the same time, each Z may be the same as or different from each other. At best,
Y is a hydrogen atom, a halogen atom, cyano, nitro, _{azido, -SCN, -SF 5, C 1} ~C 6 alkyl, optionally substituted by R ⁵ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted by R ⁵ , E-1 to E-21, C ₂ -C ₆ alkenyl, optionally substituted by R ⁵ (C ₂ -C ₆₎ alkenyl, C ₂ -C ₆ alkynyl, optionally substituted by R ⁵ _(C 2 _{~C 6)} ^{alkynyl, -OH, -OR 6, -OS (} O) 2 R 6, -SH, -S ( ^{_{O) r R 6, -N (}} R 8) R 7, -N (R 8) C (O) R 9a, -N = C (R 8a) R 7a, -C (O) N (R 12) R ¹¹ , —C (S) N (R ¹² ) R ¹¹ , —Si (R ^13a ) (R ^13b ) R ¹³ , phenyl, phenyl substituted by (Z) _n1 or D-1 to D-38; When two or more Y are present simultaneously, each Y may be the same as or different from each other. Well,
Further, when two Ys are adjacent to each other, the two adjacent Ys are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -SCH ₂ S-, -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH ₂ -,- CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = N-, -SCH = N-, -CH = CHCH = CH- , -CH = CHCH = N-, -CH = CHN = CH-, -CH = NCH = CH- or -N = CHCH = CH- to form a 5-membered ring with the carbon atom to which each Y binds Alternatively, a 6-membered ring may be formed, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with Z, and further substituted with two or more Z at the same time. Each Z may be the same as or different from each other,
R ¹ is a hydrogen atom, —C (O) R ^1a , —C (O) OR ^1b , —C (O) SR ^1b , —C (O) N (R ^1d ) R ^1c , —C (S) R ^{1a, -C (S) oR 1b} , -C (S) SR 1b, -C (S) N (R 1d) R 1c, -S (O) 2 R 1b , or ^{_{-S (O) 2 N (R}} 1d ) ^Represents R ^1c
R ^1a is hydrogen atom, C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted by R ¹⁵ _{(C 3} -C ₁₂₎ cycloalkyl, E-1~E-21, C 2 ~C 12 alkenyl, optionally substituted by R ¹⁵ _(C 2 ~C ₁₂₎ alkenyl, C ₅ -C ₁₂ cycloalkenyl, C ₅ ~ C ₁₂ halocycloalkenyl, C ₂ -C ₁₂ alkynyl, (C ₂ -C ₁₂ ) alkynyl optionally substituted by R ¹⁵ , —C (O) R ⁹ , —C (O) R ^9a , —C (R ⁹ ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , -C (R ⁹ ) = NN (R ¹⁷ ) R ¹⁶ , -C (O) OR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , M-4, phenyl, (Z) _n1 substituted phenyl or D-1 to D-38,
R ^1b is optionally substituted by C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, R ¹⁵ _(C 3 _{~C 12} ) cycloalkyl, E-2~E-5, E -7, E-13, E-14, E-16, C 2 ~C 12 alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, phenyl, (Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D-8~D-10, D-12~D- 19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ^1c is a hydrogen atom, C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted by R ¹⁵ _{(C 3} -C ₁₂₎ cycloalkyl, E-2~E-7, E -13~E-21, C 2 ~C 12 alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ Haloalkynyl, -C (O) R ⁹ , -C (O) R ^9a , -C (R ⁹ ) = NOR ¹⁰ , -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) ^{N (R 12) R 11,} M-7, M-17, -C (S) R 9, -C (S) OR 10, -C (S) SR 10, -C (S) N (R 12) R ¹¹ , M-9, M-19, —OR ¹⁰ , —S (O) ₂ R ¹⁰ , —S (O) ₂ N (R ¹² ) R ¹¹ , —N (R ¹⁷ ) R ¹⁶ , phenyl, ( Z) represents phenyl substituted by _n1 , D-1 to D-25 or D-27 to D-38;
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkylthio _(C 1 _{~C 4)} alkyl, cyano _(C 1 _{~C 6)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, C ₃ -C ₆ alkenyl or _C 3 -C ₆ alkynyl Or R ^1d together with R ^1c forms a C ₂ -C ₆ alkylene chain to form a 3-7 membered ring with the nitrogen atom to which R ^1c and R ^1d are bonded. represents good, this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and C ₁ -C ₆ alkyl group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylaminocarbonyl groups, C -C ₆ haloalkylcarbonyl aminocarbonyl group, di (C ₁ -C ₆ alkyl) aminocarbonyl group, may be optionally substituted by oxo or thioxo group,
R ² is a hydrogen atom, cyano, C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ^15a , C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ ^{haloalkynyl, -C (O) R 9,} -C (O) R 9a, -C (O) OR 10, -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (O) C (O) OR ¹⁰ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ haloalkoxy, —SR ¹⁰ , —S (O) ₂ R ¹⁰ , —SN (R ^17a ) R ^16a , phenyl, (Z) _n1 Represents phenyl or D-32 substituted by R ⁵ , or R ² together with R ¹ forms a C _{4 to} C ₆ alkylene chain, so that 5 together with the nitrogen atom to which R ¹ and R ² are bonded. Represents that a 7-membered ring may be formed. Alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and _C 1 -C ₆ alkyl group, C ₁ -C ₆ alkylidene group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl groups, C ₁ -C ₆ alkylaminocarbonyl group, C ₁ -C ₆ halo alkylaminocarbonyl group, di _{(C 1} -C ₆ alkyl) aminocarbonyl group, a phenyl group, D-32 group, D-34 group may be optionally substituted by oxo or thioxo group,
R ³ represents a halogen atom, cyano, optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ⁵ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ⁵ ( C ₃ -C ₈₎ cycloalkyl, E-1~E-21, C 3 ~C 6 alkenyl, optionally substituted by R ⁵ _(C 2 _{~C 6)} alkenyl, C ₃ -C ₆ alkynyl, R ⁵ (C ₂ -C ₆ ) alkynyl, —OR ⁶ , —S (O) _r R ⁶ , —N (R ¹² ) R ¹¹ , —C (O) R ⁹ , —C (R ⁹ ) optionally substituted by ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , M-3, M-13, M-30, -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , -Si (R ^13a ) (R ^13b ) R ¹³ , -P ( O) (OR ¹⁸ ) ₂ , phenyl, phenyl substituted by (Z) _n1 or D-1 to D-38,
R ⁴ is a hydrogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} -C (S) NH 2, phenyl, (Z) phenyl substituted by _{n1, D-1, D-} 2, D-9, D-10 or D-32 Or when A ¹ or A ⁴ represents CY, R ⁴ together with Y represents —CH ₂ CH ₂ —, —CH ₂ O—, —CH ₂ S (O) _r — , —CH ₂ N (R ⁷ ) —, —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ CH ₂ S (O) _r —, —CH ₂ CH ₂ N (R ⁷ ) -, -CH ₂ OCH _2- , -CH ₂ S (O) _r CH ₂ -or -CH ₂ N (R ⁷ ) CH ₂ -to form a 5-membered ring with atoms to which R ⁴ and Y are bonded Alternatively, a condensed ring may be formed by forming a 6-membered ring, in which case a hydrogen atom bonded to each carbon atom forming the 5-membered or 6-membered ring. May be optionally substituted halogen atom, by C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl group,
R ^4a represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^4a together with R ⁴ forms a C ₂ -C ₅ alkylene chain, thereby binding R ⁴ and R ^4a . Represents that a 3- to 6-membered ring may be formed together with a carbon atom, and this alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a C ₁ -C ₄ alkyl group, —CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkylaminocarbonyl group, C ₁ -C ₄ halo alkylaminocarbonyl group, di _(C 1 -C ₄ alkyl) amino Optionally substituted by a carbonyl group or a phenyl group,
R ^4b is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₃ -C ₆ halocycloalkyl carbonyl, represents C ₁ -C ₆ alkoxycarbonyl or _C 1 -C ₆ haloalkoxycarbonyl,
D-1 to D-38 each represent an aromatic heterocycle represented by the following structural formula;

Z is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfinyl (C ₁ -C ₄ ) Alkyl, C ₁ -C ₄ haloalkylsulfinyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkylsulfonyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, -OH, C ₁ ~C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyloxy, C ₁ -C ₆ haloalkyl sulfonyloxy, C ₁ -C ₆ alkylthio, C ₁ C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, -NH _2, C ₁ ~C ₆ alkyl amino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, —C (O) NH ₂ , C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ haloalkyl aminocarbonyl, di _(C 1 -C ₆ alkyl) _{aminocarbonyl, -C (S) NH 2,} -S (O) 2 NH 2, C 1 ~C 6 alkylaminosulfonyl, di _(C 1 -C ₆ alkyl) Represents aminosulfonyl or phenyl, and when n1, n2, n3 or n4 represents an integer of 2 or more, each Z may be the same as or different from each other;
Further, when two Zs are adjacent, the two adjacent Zs are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O- , —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S—, —OCH ₂ CH ₂ S— or —CH═CH—CH═CH— to form a carbon atom to which each Z is bonded. may form a 5- or 6-membered ring, this time with each a hydrogen atom a halogen atom bonded to the carbon atoms forming the ring, a cyano group, a nitro groups, C ₁ -C ₄ alkyl groups, C ₁ -C ₄ haloalkyl group, may be optionally substituted by C ₁ -C ₄ alkoxy or _C 1 -C ₄ alkylthio group,
E-1 to E-21 each represent a saturated heterocyclic ring represented by the following structural formula,

R ⁵ is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, C _{3 to} C ₈ halocycloalkyl, E-1 to E-21, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , -N (R ⁸ ) R ⁷ , -N (R ⁸ ) C (O) R ^9a , -C (O) OR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -Si (R ^13a ) (R ^13b ) R ¹³ , phenyl, (Z) phenyl substituted by _n1 or D-1 to D-38;
R ⁶ is optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ²² _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ²² _(C 3 _{~C 8} ) cycloalkyl, E-2~E-5, E -7, E-13, E-14, E-16, E-17, E-20, C 2 ~C 6 alkenyl, optionally substituted by R ²² and _(C 2 _{~C 6)} alkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, optionally substituted by R ²² _(C 3 _{~C 6)} alkynyl , C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D-8~D -10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ ^{haloalkynyl, -C (O) R 9,} -C (O) OR 10, -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , -C (O) C (O) R ¹⁰ , —C (O) C (O) OR ¹⁰ , —OH, —S (O) ₂ R ¹⁰ , —S (O) ₂ N (R ¹² ) R ¹¹ , —P (O) ( OR ¹⁸ ) ₂ or -P (S) (OR ¹⁸ ) ₂
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, -CHO, C ₁ -C ₆ alkylcarbonyl, or represents C ₁ -C ₆ haloalkylcarbonyl or _C 1 -C ₆ alkoxycarbonyl, or , R ⁸ together with R ⁷ represents a C _{2 to} C ₆ alkylene chain, thereby forming a 3- to 7-membered ring with the nitrogen atom to which R ⁷ and R ⁸ are bonded; in this case the alkylene chain is an oxygen atom, may contain one sulfur atom or a nitrogen atom, and optionally substituted halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, the oxo group or thioxo group May have been
R ^7a represents C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, phenoxy or phenoxy substituted by (Z) _n1 ;
R ^8a represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, phenyl or phenyl substituted by (Z) _{n 1} , or R ^8a is R ^7a Together with C ₄ -C ₆ alkylene chain to form a 5- to 7-membered ring together with the carbon atoms to which R ^7a and R ^8a are attached. May contain one oxygen or sulfur atom,
R ⁹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- 4~E-7, E13~E-16, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₂ -C ₆ alkynyl or represents _C 2 -C ₆ haloalkynyl,
R ^9a represents phenyl, phenyl substituted by (Z) _n1 , naphthyl or D-1 to D-38;
R ¹⁰ is C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E-2 -E -5, E-7, E- 13, E-14, E-16~E-21, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D- 8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ¹¹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- _{2 to} E-7, E-13 to E-21, C _{2 to} C ₆ alkenyl, C _{2 to} C ₆ haloalkenyl, C _{3 to} C ₆ alkynyl, C _{3 to} C ₆ haloalkynyl, phenyl, (Z) _n1 Represents phenyl, D-1 to D-25 or D-27 to D-38, substituted by
R ¹² is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio _(C 1 _{~C 4)} alkyl, cyano _(C 1 _{~C 4)} alkyl, or represents C ₃ -C ₆ alkenyl or _C 3 -C ₆ alkynyl, or, R ¹² is R ^{11 represents} a C _{2 to} C ₆ alkylene chain to form a 3 to 7 membered ring together with the nitrogen atom to which R ¹¹ and R ¹² are bonded, and this alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group or a C It is optionally substituted by ₁ -C ₄ alkoxycarbonyl group The
R ¹³ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, phenyl or phenyl substituted by (Z) _{n 1} ,
R ^13a and R ^13b each independently represent C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy;
R ¹⁴ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxycarbonyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxycarbonyl (C ₁ -C ₄₎ alkyl, phenyl _(C 1 -C ₄₎ alkyl, _(Z) phenyl substituted by _{n1 (C} 1 -C ₄₎ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₃ ~ C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, phenyl or phenyl substituted by (Z) _n1
Further, when Z is present at the adjacent position to R ¹⁴ is, -CH ₂ and adjacent R ¹⁴ and _{Z CH 2 CH 2 CH 2 -} , -CH = CH-CH = CH-, -N = CH- An atom to which each of R ¹⁴ and Z is bonded by forming CH = CH-, -CH = N-CH = CH-, -CH = CH-N = CH- or -CH = CH-CH = N- may form a 6-membered ring with a substituted this time, a hydrogen atom is a halogen atom attached to each carbon atom forming the ring, optionally by C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl group May have been
R ¹⁵ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, hydroxy (C ₃ -C ₈ ) cycloalkyl, C ₁ -C ₄ alkoxy (C ₃ -C ₈₎ cycloalkyl, E-1~E-21, C 5 ~C 10 cycloalkyl, C ₅ -C ₁₀ halo ^{cycloalkenyl, -OR 23, -N (R 24} ) R 23, -SH, -S (O ) _r R ²⁵ , -S (O) _q (R ²⁵ ) = NR ²⁰ , -C (O) R ²⁶ , -C (R ²⁶ ) = NOH, -C (R ²⁶ ) = NOR ²⁷ , -C (O ) OH, -C (O) OR ²⁷ , -C (O) SR ²⁷ , -C (O) N (R ²⁹ ) R ²⁸ , -C (O) N (R ²⁹ ) OR ²⁷ , -C (O) N (R ²⁹ ) N (R ^28a ) R ²⁸ , -C (O) C (O) OR ²⁷ , -C (S) OR ²⁷ , -C (S) SR ²⁷ , -C (S) N (R ²⁹ ) R ²⁸ , -C (= NR ²⁸ ) OR ²⁷ , -C (= NR ²⁸ ) SR ²⁷ , -C (= NR ²⁹ ) N (R ^28a ) R ²⁸ , -C (= NOR ²⁷ ) N (R ^{29 _{) R 28, -S (O)}} 2 OH, -S (O) 2 OR 27, -S (O) 2 N (R 29) R 28, -Si (R 13 ^{) (R 13b) R 13,} -P (O) (OR 18) 2, -P (S) (OR 18) 2, -P ( _{phenyl) 2,} -P _{(O) (phenyl) 2,} M-1 ~ M-30, phenyl, (Z) phenyl substituted by _n1 , naphthyl or D-1 to D-38;
R ^15a is a halogen atom, cyano, nitro, C _{3 to} C ₈ cycloalkyl, E-4 to E-6, E-13 to E-15, C _{5 to} C ₁₀ cycloalkenyl, —OR ²³ , —N ( ^{R 24) R 23, -S (} O) r R 25, -C (O) R 26, -C (R 26) = NOH, -C (R 26) = NOR 27, M-3, -C (O ) OR ²⁷ , -C (O) SR ²⁷ , -C (O) N (R ²⁹ ) R ²⁸ , M-7, M-17, -C (S) OR ²⁷ , -C (S) SR ²⁷ ,- C (S) N (R ²⁹ ) R ²⁸ , M-9, M-19, -C (O) C (O) OR ²⁷ , -S (O) ₂ N (R ²⁹ ) R ²⁸ , -Si (R ^{13a) (R 13b) R 13} , -P (O) (OR 18) 2, -P (S) (OR 18) 2, phenyl, phenyl substituted by _{(Z) n1, D-1~D} -3 , D-7, D-10, D-11, D-22 or D-32 to D-35,
M-1 to M-30 each represents a partially saturated heterocyclic ring represented by the following structural formula,

R ¹⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- 2~E-7, E-13~E- 21, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ ^{haloalkynyl, -C (O) R 26,} -C (O) OR 27, -C (O) SR 27, -C (O) N (R 29) R 28, -C (S) R ²⁶ , -C (S) OR ²⁷ , -C (S) SR ²⁷ , -C (S) N (R ²⁹ ) R ²⁸ , -S (O) ₂ R ²⁷ , -S (O) ₂ N (R ²⁹ ) R ²⁸ , -P (O) (OR ¹⁸ ) ₂ , -P (S) (OR ¹⁸ ) ₂ , phenyl, phenyl substituted by (Z) _{n 1} , D-1 to D-25 or D-27 to D-38
R ¹⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkylsulfonyl _(C 1 -C ₄₎ alkyl, C ₁ -C ₄ haloalkylsulfonyl _(C 1 -C ₄₎ alkyl, cyano _(C 1 -C ₄₎ alkyl, C ₁ -C ₄ alkoxycarbonyl (C ₁ -C ₄₎ alkyl, phenyl _(C 1 _{~C 4)} alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, or represents C ₃ -C ₆ alkynyl or _C 3 -C ₆ haloalkynyl, Alternatively, R ¹⁷ is to form a _C 2 -C ₆ alkylene chain together with ^{R 16} Ri represents that may form a 3- to 7-membered ring together with the nitrogen atom to which R ¹⁶ and R ¹⁷ are attached, the time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₂ alkoxy _(C 1 -C ₂₎ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group or _{C 1} -C ₄ alkoxy may be optionally substituted by a carbonyl group,
R ^16a is C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy (C ₁ -C ₁₂ ) alkyl, cyano (C ₁ -C ₁₂ ) alkyl, C ₁ -C ₁₂ alkoxycarbonyl _(C 1 _{~C 12)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{n1 (C} 1 _{~C 4)} alkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ halo alkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, C ₁ -C ₁₂ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, -C (O) ON = C (CH 3) SCH 3, -C (O) ON = C (SCH ₃ ) C (O) N (CH ₃ ) ₂ represents phenyl or phenyl substituted by (Z) _n1 ;
R ^17a is C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy (C ₁ -C ₁₂ ) alkyl, cyano (C ₁ -C ₁₂ ) alkyl, C ₁ -C ₁₂ alkoxycarbonyl _(C 1 _{~C 12)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{n1 (C} 1 _{~C 4)} alkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ halo alkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, phenyl or _(Z) or represents phenyl which is substituted by _n1, or, R ^17a together with ^{R 16a} _C 4 _{~C 7} alkylene By forming a chain, it represents that a 5- to 8-membered ring may be formed together with the nitrogen atom to which R ^16a and R ^17a are bonded. At this time, the alkylene chain may contain one oxygen atom or sulfur atom. , and _C 1 _~C May be optionally substituted by alkyl or C ₁ -C ₄ alkoxy group,
R ¹⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁹ is a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, hydroxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxycarbonyl _(C 1 -C ₄₎ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, di _(C 1 -C ₆ alkyl) amino, C ₁ ~ C ₆ alkoxycarbonyl, phenyl or phenyl substituted by (Z) _{n 1} , and when p1 to p8 represent an integer of 2 or more, each R ¹⁹ may be the same as or different from each other. Well, furthermore, when two R ¹⁹ are substituted on the same carbon atom, the two R ¹⁹ together are oxo, thioxo, imino, C ₁ -C ₄ alkylimino, C ₁ -C ₄ alkoxy imino or _C 1 -C ₄ alkylidene It indicates that may form,
R ²⁰ is a hydrogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ haloalkylsulfonyl,
R ²¹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -OH, ^{benzyloxy, -C (O) R 31,} -C (O) OR 32, -C (O) SR 32, -C (O) N (R 34 ) R ³³ , -C (S) N (R ³⁴ ) R ³³ , -S (O) ₂ R ³² , -P (O) (OR ¹⁸ ) ₂ , -P (S) (OR ¹⁸ ) ₂ , phenyl, (Z) represents phenyl or D-3 substituted by _n1 ,
R ²² is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, C _{3 to} C ₈ halocycloalkyl, E-1 to E-21, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylamino, di _(C 1 -C ₆ alkyl) amino, - CHO, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, phenyl, (Z) phenyl substituted by _n1 or D-1 to D-38,
R ²³ is a hydrogen atom, C ₁ -C ₈ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 8)} alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted by R ³⁰ _{(C 3} ˜C ₈ ) cycloalkyl, E-2 to E-7, E-13 to E-21, C _{3 to} C ₈ alkenyl, (C _{3 to} C ₈ ) alkenyl optionally substituted by R ³⁰ , C ₃ to C ₈ alkynyl, (C ₃ -C ₈ ) alkynyl optionally substituted by R ³⁰ , —C (O) R ³¹ , —C (O) OR ³² , —C (O) SR ³² , —C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) R ³² , -C (O) C (O) OR ³² , -C (S) R ³¹ , -C (S) OR ³² , -C (S) SR ³² , -C (S) N (R ³⁴ ) R ³³ , -S (O) ₂ R ³² , -S (O) ₂ N (R ³⁴ ) R ³³ , -Si (R ^13a ) (R ^{13b) R 13, -P (O} ) (OR 18) 2, -P (S) (OR 18) 2, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4 ~ D-6, D-8 ~ D-10, D-12 ~ D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ²⁴ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₄ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ). Alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, cyano (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C _{1 to} C ₆ alkoxy, phenyl or phenyl substituted by (Z) _{n 1} , or R ²⁴ together with R ²³ forms a C _{2 to} C ₅ alkylene chain to form R ²³ and R ²⁴ represents that a 3- to 6-membered ring may be formed together with the nitrogen atom to which ²⁴ is bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C _1- C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ Alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, a phenyl group, optionally substituted by a phenyl group, an oxo group or a thioxo group substituted by (Z) _n1 Often,
R ²⁵ is, C ₁ -C ₈ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 8)} alkyl, optionally substituted by C ₃ -C ₈ cycloalkyl, R ³⁰ _(C 3 _{~C 8} ) cycloalkyl, optionally substituted by E-2~E-5, E- 7, E-13, E-14, E-16, C 3 ~C 8 _{^{alkenyl, R 30 (C 3 ~C 8}} ) alkenyl, C ₃ -C ₈ alkynyl, optionally substituted by R ³⁰ _(C 3 _{~C 8)} ^{alkynyl, -C (O) R 31,} -C (O) OR 32, -C (O) SR 32, -C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) R ³² , -C (O) C (O) OR ³² , -C (S) R ³¹ , -C (S) OR ³² , —C (S) SR ³² , —C (S) N (R ³⁴ ) R ³³ , —SH, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, phenylthio, (Z) _n1 substituted been ^{phenylthio, -P (O) (OR 18} ) 2, -P (S) (OR 18) 2, phenyl, (Z) phenyl substituted by _{n1, D-9, D-} 10 It represents D-12, D-14~D-17, D-30 or D-32~D-35,
R ²⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ). alkyl, C ₁ -C ₆ haloalkoxy _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ alkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ alkylsulfonyl _(C 1 ~C ₄₎ alkyl, C ₁ -C ₆ haloalkylsulfonyl _(C 1 ~C ₄₎ alkyl, phenyl _(C 1 ~C ₄₎ alkyl, phenyl substituted by _{(Z) n1 (C} 1 _{~C 4)} represents alkyl, C ₃ -C ₆ cycloalkyl, phenyl substituted by phenyl or _{(Z) n1,}
R ²⁷ is optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ³⁰ _(C 3 _{~C 8} ) cycloalkyl, optionally substituted by E-2~E-5, E- 7, E-13, E-14, E-16, C 2 ~C 6 _{^{alkenyl, R 30 (C 2 ~C 6}} ) Alkenyl, C ₃ -C ₆ alkynyl, (C ₃ -C ₆ ) alkynyl, phenyl optionally substituted by R ³⁰ , phenyl, (Z) _{n 1} substituted phenyl, D-1, D-2, D-4 D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ²⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted by R ³⁰ _{(C 3} ˜C ₈ ) cycloalkyl, E-1 to E-7, E-13 to E-21, C _{2 to} C ₆ alkenyl, (C _{2 to} C ₆ ) alkenyl optionally substituted by R ³⁰ , C ₃ to C ₈ alkynyl, (C ₃ -C ₆ ) alkynyl optionally substituted by R ³⁰ , phenyl, (Z) phenyl substituted by _{n 1} , D-1 to D-25 or D-27 to D-38 ,
R ^28a represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ²⁹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C Represents ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl or phenyl substituted by (Z) _{n 1} , or R ²⁹ together with R ²⁸ forms a C ₂ -C ₅ alkylene chain. , R ²⁸ and R ²⁹ may form a 3- to 6-membered ring together with the nitrogen atom to which R ²⁸ and R ²⁹ are bonded, and this alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, a phenyl group, substituted by _{(Z) n1} Depending on the phenyl group or oxo group Optionally substituted,
R ³⁰ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E-4, E-5, E-8, E-9, E-11, E- 13, E-14, E- 17, E-18, E-20, -OH, -OR 32, -OC (O) R 31, -OC (O) OR 32, -OC (O) N (R 34 ) R ³³ , -OC (S) N (R ³⁴ ) R ³³ , -SH, -S (O) _r R ³² , -SC (O) R ³¹ , -SC (O) OR ³² , -SC (O) N (R ³⁴ ) R ³³ , -SC (S) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) R ³³ , -N (R ³⁴ ) CHO, -N (R ³⁴ ) C (O) R ³¹ , -N (R ³⁴ ) C (O) OR ³² , -N (R ³⁴ ) C (O) SR ³² , -N (R ³⁴ ) C (O) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) C (S) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) S (O) ₂ R ³² , -C (O) R ³¹ , -C (O) OH, -C (O) OR ³² , -C (O) SR ³² , -C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) OR ³² , -Si (R ^13a ) (R ^13b ) R ¹³ , -P (O ) (substituted by _{^{OR 18) 2, -P (S}} ) (OR 18) 2, -P ( _{phenyl) 2,} -P (O) _{(phenyl) 2,} phenyl, _{(Z) n1} The phenyl or D-1~D-38,
R ³¹ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-4, E-5 , E-13, E-14, C 2 ~C 8 alkenyl, C ₂ -C ₈ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo represents cycloalkenyl, C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl, phenyl, phenyl or D-1 to D-38 substituted by _{(Z) n1,}
R ³² is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, E-4, E-5 , C ₂ -C ₈ represents alkenyl, C ₂ -C ₈ haloalkenyl, a C ₃ -C ₈ alkynyl or phenyl,
R ³³ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, E-4, E-5 _{, E-13, C 2 ~C} 8 alkenyl, C ₂ -C ₈ haloalkenyl, C ₃ -C ₈ alkynyl, phenyl, phenyl substituted by _{(Z) n1, D-1~D} -25 or D-27 ~ Represents D-38,
R ³⁴ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, or R ³⁴ Represents that, together with R ³³ , a C _{2 to} C ₅ alkylene chain may be formed to form a 3 to 6 membered ring together with the nitrogen atom to which R ³³ and R ³⁴ are bonded. alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group , C ₁ -C ₄ alkoxycarbonyl group, may be optionally substituted by a phenyl group substituted by a phenyl group or (Z) _n1,
R ³⁵ is cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-4, E-5, E-13, E-14, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, phenoxy, _{(Z) n1} phenoxy substituted by, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, phenylthio, _(Z) phenylthio substituted by _n1, C ₁ -C ₄ alkylsulfonyl , C ₁ -C ₄ haloalkylsulfonyl, phenylsulfonyl, _(Z) phenylsulfonyl substituted by _{^{n1, -N (R 37) R}} 36, C 1 ~C 6 alkyl carbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ ~ C ₆ alkoxycarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, tri (C ₁ -C ₄ alkyl) silyl, phenyl, phenyl substituted by (Z) _{n 1} , naphthyl or D-1 -D-38 Represents
R ³⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenylcarbonyl or phenyl substituted by (Z) _n1 Represents carbonyl,
R ³⁷ represents a hydrogen atom or C ₁ -C ₆ alkyl,
m represents an integer of 0 to 5;
n1 represents an integer of 1 to 5,
n2 represents an integer of 0 to 4,
n3 represents an integer of 0 to 3,
n4 represents an integer of 0 to 2,
n5 represents an integer of 0 or 1,
p1 represents an integer of 0 to 2,
p2 represents an integer of 0 to 3,
p3 represents an integer of 0 to 4,
p4 represents an integer of 0 to 5;
p5 represents an integer of 0 to 6,
p6 represents an integer of 0 to 7,
p7 represents an integer of 0 to 8,
p8 represents an integer of 0 to 9,
q represents an integer of 0 or 1,
r represents an integer of 0 to 2. ]
Insecticides, acaricides, nematicides, killers containing one or more selected from the substituted isoxazoline compounds represented by the formula (I) and salts thereof and one or more selected from the following active ingredient group A Mollusc, bactericidal or bactericidal composition.

Active ingredient group A: acibenzolar-S-methyl (acibenzolar-S-methyl), acipetacs (acypetacs), aldimorph, allyl alcohol, amisulbrom, amobam, ampropylfos ), Anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil , Benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorf, binapacryl, Biff Nil (biphenyl), bitertanol, bixafen, blasticidin-S, bordeaux mixture, boscalid, bromconazole, bupirimate, butiobate (Buthiobate), butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid ), Carvone, cheshunt mixture, chinomethionat, clobenthiazone, chloraniformethane, chloranil, chlorfenazole, chlorneb ( chloroneb) Chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, basic carbonate, basic hydroxide Copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper Zinc zinc chromate, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazol (Cypendazole), shi Proconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid, dichlofluanid, dichlofluanid dichlone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, diphenoimazole diflunoimazole ), Dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinokat Dinocap, dinocap-4, dinocap-6, dinoton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, disulfiram (Disulfiram), ditalimfos, dithianon, denoic (DNOC), dodemorph, dodine, dorazoxolon, edifenphos, epoxiconazole, Ethaboxam, etaconazole, etem, etemil, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil Fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, phenoxanil, fenpiclonil, fenpropidin, fenpropimorph (Fenpropimorph), fentin, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumetover, flumorph, fluopicolide, fluopyram, fluorimide (Fluoroimide), fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil (Flutolanil), flutianil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furcarbanil , Furconazole, fluconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene ( hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole azole), iminoctadine-albesilate, iminoctadine-triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb, isothianyl, isotianil isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, maneb mebenil), mecarbinzid, mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, meth Metonazole, methasulfocarb, metfuroxam, metiram, metinominostrobin, metrafenone, metsulfovax, milneb, microbutanil myclobutan , Myclozolin, nabam, natamycin, organic nickel (nickel bis (dimethyldithiocarbamate)), nitrostyrene, nitrothal-isopropyl, nuarimol, ofurace ), Orysastrobin, oxadixyl, oxine copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazo Penconazole, pencicuron, pentachlorophenol (PCP), penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picoxystrobin ), Piperalin, polycarbamate, polyoxins, polyoxin-D (polyoxorim), potassium azide, potassium hydrogen carbonate, probenazole, prochloraz , Procymidone, propamocarb hydrochloride, propiconazole, propineb, proquinazid, pyrazophos, pyribencarb-methyl , Pyrifenox, pyrimethanil, pyroquilon, prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin, pyridinitril, oxychlor ), Piroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quintozene, rabenzazole, salicylanilide, and salicylanilide sedaxane), silthiofam, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, Sulfur, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thio Chlorofenhim, thiophanate, thiophanate-methyl, thiram, thiazinil, tioxymid, tolclofos-methyl, tolylfluanid ), Triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide, triclamide (Trichlamide), tricyclazole, tridemorph (triridemorph), trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, vinclozolin , Zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, shiitake fruiting body extract, ZF- 9646 (trial name), aureofungin, benzalkonium chloride, bethoxazin, bithionol, bronopol, formaldehyde, nitrapyrin, octhilinone ) Oxolinic acid, oxytetracycline, ribavirin, streptomycin, tecloftalam, aldoxycarb, cadusafos, DBCP, diclofenthion (dichlofenthion) , DSP, ethoprophos, fenamiphos, fensulfothion (
fensulfothion, fosthiazate, fosthietan, imacyafos, isamifofos, isazofos, methyl bromide, methyl isothiocyanate, oxamyl, oxamyl Sodium azide, thionazin, BYI-1921 (test name), MAI-08015 (test name), acequinocyl, acrinathrin, amidoflumet, amitraz, bifenazate (Bifenazate), bromopropylate, chlorobezilate, clofentezine, cyenopyrafen, cyflumetofen, cyhexatin, dicohol, Dienochlor, etoxazole, fenazaquin, fenbutatin oxide, phenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, formate, formate Halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, spirodiclofen, spiromesifen, fenfenpyrad te Thioquinox, NNI-0711 (test name), abamectin, acephate, acetamiprid, alanica Alanycarb, aldicarb, allethrin, azinphos-ethyl, azinphos-methyl, bacillus thuringiensis, bendiocarb, benfurthrin (Benfluthrin), benfuracarb, bensultap, bifenthrin, bistrifluron, buprofezin, butocarboxim, carbaryl, carbofuran, carbofuran Fan (carbosulfan), cartap, chlorantraniliprole, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlorpyrifos, Chlorpyrifos-methyl, chromafenozide, clothianidin, cyantraniliprole, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin cyhalothrin), gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta Permethrin (zeta-cypermethrin), cyphenothrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorvos, diflubenzuron, Dimethoate, dimethylvinphos, dinotefuran, diofenolan, disulfoton, emamectin-benzoate, empenthrin, endosulfan, alpha-endosulfan (alpha) -endosulfan), EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenfluthrin, fenitrothion, Fenobucarb, fenoxycarb, fenthion, fenvalerate, fipronil, flonicamid, fluaz (Fluazuron), flubendiamide (flubendiamide), flucycloxuron (flucycloxuron), flucythrinate (flufenerim), flufenoxuron (flufenoxuron), flufenprox (flufenprox), flumethrin (flumethrin), Fluvalinate, tau-fluvalinate, fonofos, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, Imidacloprid, imiprothrin, indoxacarb, indoxacarb-MP, indoxacarb-MP, isofenphos, isoprocarb, isoxathion, lepimectin (le pimectin, lufenuron, malathion, metaflumizone, metaldehyde, methacrifos, metamidophos, methidathion, methomyl, methoprene, methoxychlor (Methoxychlor), methoxyfenozide, metofluthrin, monocrotophos, muscalure, nicotine-sulfate, nitenpyram, novaluron, noviflumuron, ometofluuron omethoate, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, permethrin, phenotorin thrin), phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl (Pirimiphos-methyl), profenofos, propaphos, prothiofos, protrifenbute, pymetrozine, pyraclofos, pyrethrins, pyridalylson, pyrifalyl (Pyrifluquinazon), pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spinetram, spinosad, spirotetramate (spirote) tramat), sulfotep, sulfoxaflor, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin (Tetramethrin), d-T-80-phthalthrin (d-tetramethrin), thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad (Tolfenpyrad), tralomethrin, transfluthrin, triazamate, trichlorfon, triflumuron, bamidothion, NM-138 Test name) and ME-5343 (test name).

[2] In formula (1),
A ¹ represents CY or a nitrogen atom,
A ² and A ³ represent CH,
A ⁴ represents CH or a nitrogen atom,
G represents a benzene ring,
L represents —CH (R ⁴ ) —
X represents a halogen atom, cyano, —SF ₅ , C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio, and when m represents 2 or 3, each X is They may be the same or different from each other,
Y is a hydrogen atom, a halogen atom, cyano, nitro, methyl, ethyl, C ₁ -C ₂ haloalkyl, C ₂ -C ₃ alkynyl, C ₁ -C ₂ haloalkoxy, C ₁ -C ₂ haloalkylthio or -C ( S) NH ₂
R ¹ represents —C (O) R ^1a , —C (O) SR ^1b , —C (O) N (R ^1d ) R ^1c or —C (S) R ^1a ,
R ^1a is C ₁ -C ₄ alkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ¹⁵ , C ₃ -C ₄ cycloalkyl, E-4, E-5, C ₂ -C ₄ alkenyl. , C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl, (Z) _n1 substituted phenyl or D-32,
R ^1b represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ^1c represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ^1d represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ² represents a hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₂ ) alkyl substituted by R ^15a , C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ³ represents C ₁ -C ₂ haloalkyl,
R ⁴ represents a hydrogen atom, cyano, methyl, ethynyl or —C (S) NH ₂ , or when A ¹ represents CY, R ⁴ together with Y represents —CH ₂ CH ₂ By forming-or -CH ₂ CH ₂ CH _{2-, a} condensed ring may be formed by forming a 5-membered ring or 6-membered ring with the atoms to which R ⁴ and Y are bonded,
Z represents a halogen atom, cyano, nitro or C ₁ -C ₄ alkylthio, when n1 and n2 represents an integer of 2 or more, each Z may be the even or different from each other the same as each other,
R ¹⁵ is a halogen atom, C ₃ -C ₄ cycloalkyl, methoxy, ethoxy, C ₁ -C ₂ haloalkoxy, —N (R ²⁴ ) R ²³ , —S (O) _r R ²⁵ , —S (O) _q (R ²⁵ ) = NR ²⁰ or —C (O) N (R ²⁹ ) R ²⁸
R ^15a is cyano, C ₃ -C ₄ cycloalkyl, methoxy, ethoxy, C ₁ -C ₂ haloalkoxy, —N (R ²⁴ ) R ²³ , methoxycarbonyl, ethoxycarbonyl, —C (O) N (R ²⁹ ) Represents R ²⁸ or —C (S) NH ₂ ;
R ²⁰ represents a hydrogen atom or C ₁ -C ₂ haloalkylcarbonyl,
R ²³ represents cyano (C ₁ -C ₂ ) alkyl, —C (O) R ³¹ , methoxycarbonyl or ethoxycarbonyl,
R ²⁴ represents a hydrogen atom, methoxycarbonyl or ethoxycarbonyl,
R ²⁵ represents methyl, ethyl, C ₁ -C ₂ haloalkyl or cyanomethyl;
R ²⁸ represents a hydrogen atom, methyl or ethyl,
R ²⁹ represents a hydrogen atom or methyl;
R ³¹ represents methyl, ethyl, C ₁ -C ₂ haloalkyl or cyclopropyl;
m represents an integer of 1 to 3,
n1 represents an integer of 1 to 3,
n2 represents an integer of 0 to 2,
The composition according to [1], wherein p6 represents 0.

[3] In formula (1),
A ¹ represents CY,
A ⁴ represents CH,
X represents a halogen atom or trifluoromethyl, and when m represents 2 or 3, each X may be the same as or different from each other;
Y represents a hydrogen atom, a halogen atom, nitro or methyl,
R ¹ represents —C (O) R ^1a or —C (O) NHR ^1c ;
R ^1a represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl, optionally substituted by R ¹⁵ , cyclopropyl, E-4 or E-5,
R ^1c represents C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, cyclopropyl, allyl or propargyl;
R ² represents a hydrogen atom, methyl, ethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl or propargyl,
R ³ represents trifluoromethyl or chlorodifluoromethyl,
R ⁴ represents a hydrogen atom, cyano or methyl,
R ¹⁵ represents cyclopropyl or —S (O) _r R ²⁵ ;
The composition according to [2] above, wherein R ²⁵ represents methyl, ethyl, or C ₁ -C ₂ haloalkyl.

[4] In formula (1),
R ¹ represents -C (O) R ^1a ;
R ^1a represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, cyclopropylmethyl or cyclopropyl,
R ² represents a hydrogen atom, methyl, ethyl, cyanomethyl or propargyl,
R ³ represents trifluoromethyl,
The composition according to [3] above, wherein R ⁴ represents a hydrogen atom or methyl.

[5] In the formula (1),
R ¹ represents -C (O) R ^1a ;
R ^1a represents methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, ethylthiomethyl, ethylsulfinylmethyl, ethylsulfonylmethyl or bis (methylthio) methyl;
R ² represents a hydrogen atom, methyl, ethyl, cyanomethyl or propargyl,
R ³ represents trifluoromethyl,
The composition according to [3] above, wherein R ⁴ represents a hydrogen atom or methyl.

  [6] One or more selected from the substituted isoxazoline compound represented by the formula (1) described in the above [1] to [5] and a salt thereof, and one selected from the following active ingredient group B Or the insecticide or acaricide composition containing 2 or more types.

  Active ingredient group B: acequinocyl, chlorfenapyr, cyenopyrafen, cyflumetofen, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenbutatin oxide milbemectin), propargite, spirodiclofen and spiromesifen.

  [7] One or more types selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to [5] and salts thereof, and one type selected from the following active ingredient group C Or the insecticide composition containing 2 or more types.

  Active ingredient group C: acephate, acetamiprid (acetamiprid), clothianidin (clothianidin), dinotefuran (ethiprole), flonicamid (flonicamid), imidacloprid (imidacloprid), nitenpyram (inenpyram) Pyridaben, pyrifluquinazon, spirotetramat, sulfoxaflor, thiacloprid, thiamethoxam and tolfenpyrad.

  [8] One or more kinds selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to [5] and salts thereof, and one kind selected from the following active ingredient group D Or the insecticide composition containing 2 or more types.

  Active ingredient group D: abamectin, acephate, bacillus thuringiensis, chlorantraniliprole, chlorfenapyr, chromafenozide, chromatraniprole (cyantraniliprole) , Lambda-cyhalothrin, cypermethrin, deltamethrin, emamectin-benzoate, flubendiamide, flufenoxuron, indoxacarb-MP MP), lepimectin, mesomyl, permethrin, pyridalyl, spinetoram and spinosad.

  [9] From one or more selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to the above [5] and salts thereof and the active ingredient group A described in the above [1]. A pest or disease control method for treating one or two or more selected at the same time or in close proximity.

  [10] From one or more selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to the above [5] and salts thereof, and the active ingredient group B described in the above [6] A method for controlling pests or ticks, wherein one or more selected species are treated simultaneously or in close proximity.

  [11] From one or more selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to the above [5] and salts thereof, and the active ingredient group C described in the above [7]. A method for controlling pests, wherein one or more selected species are treated simultaneously or in close proximity.

  [12] One or more selected from the substituted isoxazoline compounds represented by the formula (1) described in the above [1] to [5] and salts thereof, and the active ingredient group D described in [8] above. A method for controlling pests, wherein one or more selected species are treated simultaneously or in close proximity.

  The composition of the present invention and the method of the present invention exhibit an excellent synergistic control effect against various pests and a sufficient synergistic control effect against pests that have acquired resistance to existing pest control agents. Demonstrate.

  Therefore, the present invention can provide a useful novel pest control composition and an effective control method using them.

  The compound represented by the formula (1) included in the present invention may have an E-isomer and a Z-isomer geometric isomer depending on the kind of the substituent. , Z-form or a mixture containing E-form and Z-form in any proportion. In addition, the compound represented by the formula (1) included in the present invention has an optically active substance resulting from the presence of one or more asymmetric carbon atoms, but the compound represented by the formula (1) of the present invention. The compound represented by the formula includes all optically active substances or racemates.

  Among the compounds represented by the formula (1) included in the present invention, those that can be converted into acid addition salts according to a conventional method are, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide. Hydrohalic acid salts such as acids, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfone Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid A salt of a carboxylic acid such as an acid or a salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds represented by the formula (1) included in the present invention, those that can be converted into a metal salt according to a conventional method are, for example, alkali metal salts such as lithium, sodium, and potassium, calcium, and barium. , An alkaline earth metal salt such as magnesium, or an aluminum salt.

  The substituted isoxazoline compound represented by the formula (1) used as an active ingredient of the pesticidal composition of the present invention includes, for example, International Patent Application Publication (WO 2007/105814), International Patent Application Publication (WO 2009/105). No. 035004)) or the following method can be used.

  Manufacturing method A

In accordance with the method described in International Patent Application Publication (WO 2007/074789), formula (2) [wherein G, X, R ³ and m each represent the same meaning as described above. And a compound represented by formula (3) [wherein A ¹ , A ² , A ³ , A ⁴ , L, R ¹ and R ² each have the same meaning as described above. And a compound represented by the formula (4) obtained by subjecting a compound such as diethylamine or the like to aldol condensation in the presence of a base such as diethylamine, wherein A ¹ , A ² , A ³ , A ⁴ , G, L, X, R ¹ , R ² , R ³ and m each have the same meaning as described above. The compound represented by the formula (5) [wherein A ¹ , A ² , A ³ , A ⁴ , G, G] is dehydrated with thionyl chloride in the presence of a base such as pyridine. L, X, R ¹ , R ² , R ³ and m each have the same meaning as described above. And then reacting with a hydroxylamine salt in the presence of a base such as sodium hydroxide to give a compound of formula (1) [wherein A ¹ , A ² , A ³ , A ⁴ , G , L, X, R ¹ , R ² , R ³ and m each have the same meaning as described above. The substituted isoxazoline compound represented by this can be obtained.

  In the production method A, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated in ice water, or subjected to usual post-treatment such as extraction after extraction with an organic solvent and concentration. The substituted isoxazoline compound represented by (1) can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.

  Some of the compounds represented by the formula (2) used in the production method A are known compounds, and others can be synthesized, for example, as shown in the reaction formulas 1 to 5. .

  Reaction formula 1

Known formula (6) [wherein G, X and m represent the same meaning as described above, and J ¹ represents a bromine atom or an iodine atom. ] Is lithiated using a general method described in the literature, for example, using alkyllithium, then known formula (7) [wherein R ³ represents the same meaning as described above, and J ² represents a halogen atom. atom, a hydroxyl group, a metal salt _{(e.g., -OLi, -ONa), C 1} ~C 4 alkoxy group (e.g., methoxy group, ethoxy group), di _(C 1 -C ₄ alkyl) amino group (e.g., diethylamino group) , C ₁ -C ₄ alkoxy (C ₁ -C ₄ alkyl) amino group (e.g., O, N-dimethyl-hydroxyamino group) or a cyclic amino group (e.g., piperidin-1-yl group, morpholin-4-yl group, 4-methylpiperazin-1-yl group) and the like. Journal of the American Chemical Society [J. Am. Chem. Soc.] 1955, 77, 3657, Tetrahedron Lett. 1980 21, 2129 and 1991, 32, 2003, US Patent Application Publication (US Pat. No. 5,514,816) or the like, or after reacting with magnesium to form a Grignard reactant, the formula (7) Heterocycles 1987, 25, 221; Synth. Commun. 1985, 15, 1291 and 1990, 20, 1469, By reacting according to the method described in the German Patent Application Publication (DE 19727042), etc., the formula (2) [wherein G, X, R ³ and m have the same meaning as described above. ] Can be synthesized.

  Reaction formula 2

Formula (2-1) wherein G is a benzene ring and R ³ is —CF ₂ R ^3a in the formula (2) [wherein X ¹ represents a halogen atom or trifluoromethyl, and X ² represents a hydrogen atom or Represents a halogen atom, provided that when X ¹ represents a halogen atom, X ² represents a halogen atom and R ^3a represents a halogen atom. And 1.0 to 1.5 equivalents of chlorinating agent such as N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin with respect to 1 equivalent of the compound represented by In the presence of 0.1 equivalents of iodine and 1-10 equivalents of a strong acid such as chlorosulfonic acid or sulfuric acid, the reaction is carried out in the temperature range of 0 to 50 ° C. for 1 to 15 hours, or in the formula (2-1) 0.001 to 0.05 equivalents of a Lewis acid catalyst such as aluminum chloride, iron (III) chloride or antimony (V) chloride, and 0.001 to 0.005 equivalents if necessary. In the temperature range of 30 to 110 ° C. in the presence of iodine, the reaction is carried out for 3 to 20 hours while blowing 0.8 to 2.0 equivalents of chlorine gas as a chlorinating agent. , and the equation (2-2) wherein R ³ is _{^{-CF 2 R 3a, X 1,}} X 2 and ^{R 3a} is Serial represent the same meaning as. ] Can be synthesized.

  Some of the compounds represented by the formula (2-1) used here are known compounds, and some of them are commercially available. Others can be easily synthesized according to known methods described in the literature, for example, the method described in Japanese Patent Application Publication (JP 2008/133242) and the like.

  Reaction formula 3

Formula (2-1) wherein G is a benzene ring and R ³ is —CF ₂ R ^3a in formula (2) [wherein X ¹ , X ² and R ^3a represent the same meaning as described above. ], Using 1.0 to 1.5 equivalents of a brominating agent such as N-bromosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin relative to 1 equivalent of the compound represented by The reaction is performed in a temperature range of 0 to 60 ° C. for 1 to 24 hours using a sulfuric acid mixture as a solvent, or dichloromethane, chloroform or trifluoromethane in the presence of 1 to 10 equivalents of a strong acid such as trifluoromethanesulfonic acid or sulfuric acid. In the formula (2), G is a benzene ring and R ³ is —CF ₂ R ^3a by reacting with acetic acid or the like as a solvent in a temperature range of room temperature to 60 ° C. for 0.5 to 48 hours. (2-3) [wherein X ¹ , X ² and R ^3a represent the same meaning as described above. ] Can be synthesized.

  Reaction formula 4

Formula (2-1) wherein G is a benzene ring and R ³ is —CF ₂ R ^3a in formula (2) [wherein X ¹ , X ² and R ^3a represent the same meaning as described above. Trifluoromethanesulfonic acid using 1.0 to 1.5 equivalents of an iodinating agent such as N-iodosuccinimide or 1,3-diiodo-5,5-dimethylhydantoin relative to 1 equivalent of the compound represented by Alternatively, the reaction is performed using a strong acid such as sulfuric acid as a solvent at a temperature range of 0 ° C. to room temperature for 1 to 12 hours, or 1.0 to 1 equivalent of the compound represented by the formula (2-1). Use 2.0 equivalents of iodine as an iodinating agent, add 1.0 to 2.1 equivalents of an oxidizing agent such as sodium iodate or sodium periodate if necessary, and a solvent such as 90% sulfuric acid or fuming sulfuric acid. In the formula (2-4) [Formula (2-4) wherein G is a benzene ring and R ³ is —CF ₂ R ^3a by reacting in the temperature range of 0 to 50 ° C. for 1 to 20 hours. Among them, X ¹ , X ² and R ^3a represent the same meaning as described above. ] Can be synthesized.

  Reaction formula 5

Formula (2-5) in which G is a benzene ring and R ³ is —CF ₂ R ^3a in formula (2) [wherein X ² represents a halogen atom, and R ^3a represents a halogen atom. ] Is reacted with 2.0 to 4.0 equivalents of a halogenating agent using the same conditions as in Reaction Scheme 2 to Reaction Formula 4, whereby G in Formula (2) Formula (2-6), which is a benzene ring and R ³ is —CF ₂ R ^3a [wherein X ² represents a halogen atom, X ³ represents a chlorine atom, a bromine atom or an iodine atom, and R ^3a represents Represents a halogen atom. ] Can be synthesized.

  Some of the compounds represented by the formula (2-5) used here are known compounds, and some of them are available as commercial products. Others are easily synthesized according to known methods described in the literature, for example, the methods described in Synthesis, 1996, page 1093, Japanese Patent Application Publication (JP 2008/133242), etc. be able to.

  Some of the compounds represented by formula (3) used in production method A are known compounds, and others can be synthesized, for example, as shown in Reaction Scheme 6 or Reaction Scheme 7. .

  Reaction formula 6

Formula (8) [wherein A ¹ , A ² , A ³ , A ⁴ , R ¹ and R ² represent the same meaning as described above, and R ⁴ represents a hydrogen atom, methyl, trifluoromethyl, ethynyl, cyano or — C (S) NH ₂ represents, and J ³ represents a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₄ haloalkylsulfonyloxy group (for example, a trifluoromethanesulfonyloxy group) or the like. A compound represented by, for example, palladium or the presence of a transition metal catalyst such as nickel, the formula (9) [wherein, R C ₁ -C ₈ alkyl group, 2- (hydroxy) ethyl group, 2- (C ₁ -C ₄ alkoxy) ethyl, 2- (vinyloxy) ethyl group or 2- represents a [2- (hydroxy) ethoxy] ethyl group or the like. The reaction conditions of a known vinyl ether represented by the general Heck reaction described in the literature, for example, The Journal of Organic Chemistry [J. Org. Chem.] 2001, 66, 4340, etc. In the formula (3), L is —CH (R ⁴ ) —, wherein A ¹ , A ² , A ³ , A ⁴ , R ¹ And R ² represents the same meaning as described above, and R ⁴ represents a hydrogen atom, methyl, trifluoromethyl, ethynyl, cyano, or —C (S) NH ₂ . ] Can be synthesized.

  Reaction formula 7

Formula (10) [wherein A ¹ , A ² , A ³ , A ⁴ , R ¹ and R ² represent the same meaning as described above, and R ⁴ represents a hydrogen atom, methyl, trifluoromethyl, ethynyl, cyano or — It represents a C (S) NH _2. ], For example, in the presence of a Lewis acid catalyst such as aluminum chloride or iron (III) chloride, acetyl chloride or acetic anhydride and a general Friedel-Craft acylation reaction described in the literature, for example, International Patent Application Publication ( In the formula (3), L is —CH (R ⁴ ) — in which the reaction is carried out using the conditions described in WO 99/19301) and the like, wherein A ¹ , A ² , A ³ , A ⁴ , R ¹ and R ² represent the same meaning as described above, and R ⁴ represents a hydrogen atom, methyl, trifluoromethyl, ethynyl, cyano or —C (S) NH ₂ . ] Can be synthesized.

  The compound represented by the formula (8) used in the reaction formula 6 can be synthesized, for example, as shown in the reaction formula 8 to the reaction formula 13.

  Reaction formula 8

Formula (11) [wherein A ¹ , A ² , A ³ , A ⁴ , R ² , R ⁴ and J ³ represent the same meaning as described above. And 1 to 1.1 equivalents of formula (12) [wherein R ^1a represents the same meaning as described above. ], For example, dichloromethane, chloroform, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane and the like, if necessary, 1 to 4 equivalents of sodium carbonate, potassium carbonate In the presence of a base such as triethylamine, pyridine or 4- (dimethylamino) pyridine, a condensing agent 1 such as WSC (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride), CDI (carbonyldiimidazole) By using 4 equivalents and reacting in the temperature range from 0 ° C. to the reflux temperature of the reaction mixture for 10 minutes to 24 hours, in the formula (8), R ¹ is —C (O) R ^1a [Wherein, A ¹ , A ² , A ³ , A ⁴ , R ^1a , R ² , R ⁴ and J ³ represent the same meaning as described above. The compound represented by this can be obtained.

  Some of the carboxylic acids represented by the formula (12) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures relating to known compounds.

  Reaction formula 9

Formula (11) [wherein A ¹ , A ² , A ³ , A ⁴ , R ² , R ⁴ and J ³ represent the same meaning as described above. And 1 to 1.5 equivalents of the formula (13) [wherein R ^1a represents the same meaning as described above, J ⁴ represents a chlorine atom, a bromine atom, and a C _{1 to} C ₄ alkylcarbonyl. oxy group (e.g., pivaloyloxy group), represents a C ₁ -C ₄ alkoxycarbonyloxy group (e.g., iso-butyloxycarbonyl group), or azolyl group (e.g., imidazol-1-yl group). Or a compound represented by formula (14): wherein R ^1a represents the same meaning as described above. ], For example, dichloromethane, chloroform, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4-dioxane, ethyl acetate, acetonitrile or the like as a solvent, and if necessary, 1 to 2 equivalents of carbonic acid. In the presence of a base such as sodium, potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine, the reaction is carried out in the temperature range from 0 ° C. to the reflux temperature of the reaction mixture for 10 minutes to 24 hours to obtain R in formula (8). Formula (8-1) wherein ¹ is -C (O) R ^1a [wherein A ¹ , A ² , A ³ , A ⁴ , R ^1a , R ² , R ⁴ and J ³ have the same meaning as described above. To express. The compound represented by this can be obtained.

  Some of the compound represented by the formula (13) and the compound represented by the formula (14) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to general synthesis methods described in the literature relating to the synthesis of acid halides, mixed acid anhydrides and the like.

  Reaction formula 10

Formula (11) [wherein A ¹ , A ² , A ³ , A ⁴ , R ² , R ⁴ and J ³ represent the same meaning as described above. And a compound represented by formula (15): wherein R ^1b and J ⁴ represent the same meaning as described above. And a compound represented by the formula (8-2) [wherein R ¹ is —C (O) SR ^1b in the formula (8)]: , A ¹ , A ² , A ³ , A ⁴ , R ^1b , R ² , R ⁴ and J ³ represent the same meaning as described above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (15) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to general synthesis methods described in the literature.

  Reaction formula 11

Formula (11) [wherein A ¹ , A ² , A ³ , A ⁴ , R ² , R ⁴ and J ³ represent the same meaning as described above. And a compound represented by formula (16): wherein R ^1c , R ^1d and J ⁴ represent the same meaning as described above. And a compound represented by the formula (8-) wherein R ¹ is —C (O) N (R ^1d ) R ^1c in the formula (8). 3) [wherein A ¹ , A ² , A ³ , A ⁴ , R ^1c , R ^1d , R ² , R ⁴ and J ³ represent the same meaning as described above. The compound represented by this can be obtained.

  Some of the compounds represented by the formula (16) used here are known compounds, and some of them are available as commercial products. Others can be easily synthesized according to general synthesis methods described in the literature.

  Reaction formula 12

Formula (11) [wherein A ¹ , A ² , A ³ , A ⁴ , R ² , R ⁴ and J ³ represent the same meaning as described above. And 1 to 1.2 equivalents of formula (17) [wherein R ^1c represents the same meaning as described above. For example, dichloromethane, 1,2-dichloroethane, methanol, ethanol, tetrahydrofuran, 1,4-dioxane, N, N-dimethylformamide, water, etc. In the presence of 1 to 4 equivalents of a base such as sodium, potassium carbonate, triethylamine, pyridine or 4- (dimethylamino) pyridine, the reaction is carried out in the temperature range from 0 ° C. to the reflux temperature of the reaction mixture for 2 minutes to 24 hours. Formula (8-4) wherein R ¹ is —C (O) NHR ^1c in (8) [wherein A ¹ , A ² , A ³ , A ⁴ , R ^1c , R ² , R ⁴ and J ³ are Represents the same meaning as above. The compound represented by this can be obtained.

  Some of the isocyanates represented by formula (17) used here are known compounds, and some of them are available as commercial products. In addition, other compounds can be easily synthesized according to general synthesis methods described in literatures relating to known compounds.

  Reaction formula 13

Formula (8-1) wherein R ¹ is —C (O) R ^1a in Formula (8) [wherein A ¹ , A ² , A ³ , A ⁴ , R ^1a , R ² , R ⁴ and J ³ Represents the same meaning as described above. And 1 to 10 equivalents of diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis (4-methoxyphenyl)- 1,3,2,4-dithiadiphosphetane = 2,4-disulfide) and the like, if necessary, benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane, tert-butylmethyl Ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or HMPA (hexamethylphosphoric triamide) is used as a solvent, and if necessary, such as sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine or pyridine. Reacting in the presence of 1 to 4 equivalents of base at room temperature to the reflux temperature of the reaction mixture for 10 minutes to 50 hours, or By using a base such as pyridine as a solvent and reacting in a temperature range from 80 ° C. to the reflux temperature of the reaction mixture for 1 to 3 hours, in the formula (8), R ¹ is —C (S) R ^1a -5) [wherein A ¹ , A ² , A ³ , A ⁴ , R ^1a , R ² , R ⁴ and J ³ represent the same meaning as described above. Can be obtained.

  The compound represented by the formula (10) used in the reaction formula 7 can also be synthesized in the same manner as the compound represented by the formula (8).

  Some of the compounds represented by the formula (11) used in the reaction formulas 8 to 12 are known compounds, and some of them are available as commercial products. Others can also be easily synthesized according to a general synthesis method described in the literature on known substituted benzylamines.

  In each of these reactions, each intermediate that is a raw material compound of production method A can be obtained by carrying out a normal post-treatment after completion of the reaction.

  In addition, each intermediate produced by these methods can be used in the next step as it is without isolation and purification.

[Synthesis example]
By specifically disclosing below the synthesis example of the substituted isoxazoline compound represented by the formula (1) used as an active ingredient of the pest control composition of the present invention, the compound represented by the formula (1) Although a manufacturing method is demonstrated in more detail, the manufacturing method of the compound represented by Formula (1) is not limited by these.

Synthesis example 1
N- [2-Chloro-4- [5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenyl] methyl-2 -(Ethylsulfonyl) acetamide (Compound No. 19).

Step 1; Preparation of 2,2,2-trifluoro-1- [3-iodo-5- (trifluoromethyl) phenyl] ethanone 2,2,2-trifluoro-1- [3- (trifluoromethyl) 6% 30% fuming sulfuric acid and 1.90 g of iodine were added to 2.42 g of phenyl] ethanone and stirred at 50 ° C. for 5 hours. After completion of the reaction, the reaction mixture was poured into 10 g of ice and extracted with diethyl ether (20 ml × 1). The organic layer was washed with 10 ml of saturated sodium sulfite aqueous solution, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and reduced pressure. The solvent was distilled off to obtain 2.56 g of the desired product as a pale yellow oily substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.53 (s, 1H), 8.28 (s, 1H), 8.25 (s, 1H).

Step 2: 1- (3-Chloro-4-methylphenyl) -4,4,4-trifluoro-3-hydroxy-3- [3-iodo-5- (trifluoromethyl) phenyl] butan-1-one 1.84 g of 2,2,2-trifluoro-1- [3-iodo-5- (trifluoromethyl) phenyl] ethanone and 0.84 g of 1- (3-chloro-4-methylphenyl) ethanone To 3 ml solution, 1.00 g of triethylamine was added and stirred at 60 ° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into 10 ml of water and extracted with ethyl acetate (20 ml × 1). The organic layer was washed with 10 ml of 2N hydrochloric acid aqueous solution, then dehydrated and dried in the order of saturated saline and then anhydrous sodium sulfate, and reduced pressure. The solvent was distilled off to obtain 1.83 g of a crude target product as a pale yellow resinous substance. This was directly used in the next step without further purification.

Step 3; of 1- (3-Chloro-4-methylphenyl) -4,4,4-trifluoro-3- [3-iodo-5- (trifluoromethyl) phenyl] -2-buten-1-one Preparation 1- (3-Chloro-4-methylphenyl) -4,4,4-trifluoro-3-hydroxy-3- [3-iodo-5- (trifluoromethyl) phenyl] butan-1-one To a solution of 83 g of toluene in 3 ml of toluene, 0.83 g of thionyl chloride and 0.53 g of pyridine were added with stirring at 80 ° C., and stirring was further continued for 2 hours at the same temperature. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of water was added and stirred for 10 minutes. The organic layer was separated, washed with 10 ml of 2N aqueous sodium hydroxide solution, dehydrated in the order of saturated brine and then anhydrous sodium sulfate. -The solvent was distilled off under drying and reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 1.36 g of the desired product as a pale yellow oily substance.

Step 4; Preparation of 3- (3-chloro-4-methylphenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazole 1- 1.36 g of (3-chloro-4-methylphenyl) -4,4,4-trifluoro-3- [3-iodo-5- (trifluoromethyl) phenyl] -2-buten-1-one and tetrabutyl A solution of 0.26 g of ammonium bromide in 7 ml of toluene was added dropwise with stirring with ice cooling, 0.31 g of sodium hydroxide in 1 ml of water and 2 ml of hydroxylamine hydrochloride in 0.25 g of water. The mixture was stirred for 15 hours. After completion of the reaction, 2 ml of concentrated hydrochloric acid was added to the reaction mixture with stirring under ice-cooling and stirred for 5 minutes. The organic layer was separated, washed with 3 ml of 2N aqueous hydrochloric acid and 3 ml of water, saturated brine and then anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, followed by dehydration and drying. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (5:95) to obtain 0.88 g of the desired product as a pale yellow resinous substance.

Step 5; Preparation of 3- (4-Bromomethyl-3-chlorophenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazole under nitrogen atmosphere Of 3- (3-chloro-4-methylphenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazole 0.79 g of 1, To an 8 ml solution of 2-dichloroethane, 0.26 g of N-bromosuccinimide and 0.04 g of α, α′-azobisisobutyronitrile were added, and the mixture was stirred for 2 hours while heating under reflux. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 10 ml of water was added and extracted with chloroform (10 ml × 1), and the organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate. did. The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (5:95) to obtain 0.58 g of the desired product as a pale yellow oily substance.

Step 6; Preparation of 3- (4-aminomethyl-3-chlorophenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazole 3- (4-Bromomethyl-3-chlorophenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazole 0.58 g of N, N-dimethylformamide To a 1 ml solution, 0.17 g of potassium phthalimide was added and stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with diethyl ether (20 ml × 1). The organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate. -[2-Chloro-4- [5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenylmethyl] phthalimide 48 g was obtained.

  The obtained phthalimide was dissolved in 10 ml of ethanol, 0.5 ml of hydrazine monohydrate was added, and the mixture was stirred for 2 hours with heating under reflux. After completion of the reaction, the reaction mixture was cooled to 0 ° C., the precipitated white solid was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate to obtain 0.16 g of the desired product as a pale yellow oil.

Step 7; N- [2-Chloro-4- [5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenyl] Preparation of methyl-2- (ethylthio) acetamide 3- (4-Aminomethyl-3-chlorophenyl) -5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5- To a solution of 0.16 g of dihydroisoxazole and 0.04 g of (ethylthio) acetic acid in 3 ml of dichloromethane was added 0.06 g of 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride and stirred at room temperature for 10 minutes. did. After completion of the reaction, 2 ml of water was added to the reaction mixture, the organic layer was separated, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure through a short-pass column of silica gel. 0.10 g of the product was obtained as white crystals.
Melting point 112.0-115.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.14 (s, 1H), 8.03 (s, 1H), 7.82 (s, 1H), 7.72 (s, 1H), 7.40-7.55 (m, 3H ), 4.58 (d, J = 6.0Hz, 2H), 4.10 (d, J = 17.4Hz, 1H), 3.68 (d, J = 17.4Hz, 1H), 3.27 (s, 2H), 2.53 (q, J = 7.5Hz, 2H), 1.23 (t, J = 7.5Hz, 3H).

Step 8; N- [2-Chloro-4- [5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenyl] Preparation of methyl-2- (ethylsulfonyl) acetamide N- [2-Chloro-4- [5- [3-iodo-5- (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroiso To a solution of oxazol-3-yl] phenyl] methyl-2- (ethylthio) acetamide (0.10 g) in dichloromethane (3 ml) at room temperature was added 0.12 g of 3-chloroperbenzoic acid, and the mixture was stirred at the same temperature for 10 minutes. Stir. After completion of the reaction, 2 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and passed through a silica gel short path column. The solvent was distilled off under reduced pressure to obtain 0.16 g of the desired product as white crystals.
Melting point: 145.0-148.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.13 (s, 1H), 8.02 (s, 1H), 7.81 (s, 1H), 7.71 (s, 1H), 7.45-7.6 (m, 2H ), 6.92 (bs, 1H), 4.60 (d, J = 6.0Hz, 2H), 4.09 (d, J = 17.4Hz, 1H), 3.88 (s, 2H), 3.67 (d, J = 17.4Hz, 1H ), 3.14 (q, J = 7.5Hz, 2H), 1.42 (t, J = 7.5Hz, 3H).

Synthesis example 2
(S) -1- [4- [5- [3,5-Bis (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenyl] -N- ( Isobutyryl) ethylamine (Compound No. 22).

Step 1: Production of N-[(S) -1- (4-bromophenyl) ethyl] isobutyramide
To a solution of 6.0S g of (S) -1- (4-bromophenyl) ethylamine and 5.20 g of pyridine in 15 ml of dichloromethane was added dropwise 15 ml of a solution of 3.50 g of isobutyryl chloride in 15 ml of dichloromethane with stirring under ice cooling. And stirred at room temperature for 1 hour. After completion of the reaction, 90 ml of water was added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted twice with 20 ml of chloroform. The organic layers were combined, washed with 100 ml of water, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.85 g of the desired product as white crystals.
Melting point: 163.0 to 165.0 ° C
[α] _D ^24.0 -129.16 ° (EtOH, c = 1.000)
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 7.45 (d, J = 8.4 Hz, 2H), 7.17 (d, J = 8.4 Hz, 2H), 5.58 (bs, 1H), 5.07 (qui, J = 7.2Hz, 1H), 2.34 (sep, J = 6.9Hz, 1H), 1.47 (d, J = 7.2Hz, 3H), 1.16 and 1.14 (d, J = 6.9Hz, 6H).

Step 2: Preparation of N-[(S) -1- (4-acetylphenyl) ethyl] isobutyramide 6.85 g of N-[(S) -1- (4-bromophenyl) ethyl] isobutyramide, butyl vinyl ether 7 To a solution of .62 g and 4.21 g of potassium carbonate in 20 ml of n-butanol, 0.314 g of 1,3-bis (diphenylphosphino) propane and 0.057 g of palladium (II) acetate were added, and the reaction was performed at 110 ° C. under a nitrogen atmosphere. Stir for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, 20 ml of toluene was added to the residue, and further 14 ml of water and 1.5 ml of concentrated hydrochloric acid were added with stirring under ice cooling. After filtration through Celite, the organic layer was separated, and the aqueous layer was extracted with toluene (10 ml × 2). The organic layers were combined and washed with 10 ml of water, dehydrated and dried in the order of saturated brine and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The remaining solid was washed with 100 ml of diethyl ether to obtain 4.03 g of the desired product as white crystals.
Melting point 137.0-139.0C
[α] _D ^24.0 -165.28 ° (EtOH, c = 1.000)
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.92 (d, J = 8.4 Hz, 2H), 7.38 (d, J = 8.4 Hz, 2H), 5.68 (d, J = 7.2 Hz, 1H) , 5.16 (qui, J = 7.2Hz, 1H), 2.59 (s, 3H), 2.37 (sep, J = 6.9Hz, 1H), 1.49 (d, J = 7.2Hz, 3H), 1.17 and 1.15 (d, J = 6.9Hz, 6H).

Step 3; (S) -1- [4- [3- [3,5-Bis (trifluoromethyl) phenyl] -4,4,4-trifluoro-3- (hydroxy) butyryl] phenyl] -N- Preparation of (isobutyryl) ethylamine 1- [3,5-bis (trifluoromethyl) phenyl] -2,2,2-trifluoroethanone 4.23 g and N-[(S) -1- (4-acetylphenyl) To a solution of 2.50 g of ethyl] isobutyramide in 2.5 ml of ethyl acetate was added 0.235 g of diethylamine, and the mixture was stirred at 45 ° C. for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was eluted with ethyl acetate-hexane (1: 5 to 1: 1 gradient). The resulting product was purified by a YFLC-Wprep) to obtain 5.50 g of the desired product as a pale yellow resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.16 (s, 2H), 7.89 (d, J = 8.4 Hz, 2H), 7.42 (d, J = 8.4 Hz, 2H), 6.03 (s, 1H), 5.72 (d, J = 6.9Hz, 1H), 5.12 (qui, J = 6.9Hz, 1H), 3.86 (d, J = 17.4Hz, 1H), 3.76 (d, J = 17.4Hz, 1H) , 2.37 (sep, J = 6.9Hz, 1H), 1.49 (d, J = 6.9Hz, 3H), 1.16 and 1.14 (d, J = 6.9Hz, 6H).

Step 4; (S) -1- [4- [3- [3,5-bis (trifluoromethyl) phenyl] -4,4,4-trifluoro-2-butenoyl] phenyl] -N- (isobutyryl) Ethylamine production
(S) -1- [4- [3- [3,5-Bis (trifluoromethyl) phenyl] -4,4,4-trifluoro-3- (hydroxy) butyryl] phenyl] -N- (isobutyryl) To a solution of ethylamine (5.50 g) in toluene (10 ml) were added 4- (N, N-dimethylamino) pyridine (0.492 g) and acetic anhydride (3.10 g), and the mixture was stirred at 60 ° C. for 2 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, 40 ml of water was added and extracted with ethyl acetate (20 ml × 2). The organic layer was separated, washed with 20 ml of water, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual solid was washed with a mixed solvent of diisopropyl ether-hexane (1:10) to obtain 4.06 g of the desired product as pale yellow crystals.
Melting point: 161.0-162.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ7.85 and 7.72 (s, 2H), 7.89 (d, J = 8.1 Hz, 2H), 7.54 (s, 1H), 7.38 (d, J = 8.1 Hz, 2H), 5.64 (d, J = 6.9Hz, 1H), 5.11 (qui, J = 6.9Hz, 1H), 2.37 (sep, J = 6.9Hz, 1H), 1.46 (d, J = 6.9Hz, 3H), 1.17 and 1.14 (d, J = 6.9 Hz, 6H).

Step 5; (S) -1- [4- [5- [3,5-Bis (trifluoromethyl) phenyl] -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] phenyl]- Production of N- (isobutyryl) ethylamine
(S) -1- [4- [3- [3,5-Bis (trifluoromethyl) phenyl] -4,4,4-trifluoro-2-butenoyl] phenyl] -N- (isobutyryl) ethylamine To a solution of 534 g of N-methyl-2-pyrrolidinone and 2.7 ml of toluene, with stirring under ice cooling, 0.121 g of sodium hydroxide in 0.3 ml of water and 0.117 g of hydroxylamine sulfate in 0.5 ml of water Was added dropwise, and the mixture was stirred for 3.5 hours while allowing the temperature to rise naturally to room temperature. After completion of the reaction, 5 ml of water was added to the reaction mixture and extracted with ethyl acetate (5 ml × 2). The organic layer was separated, washed with 5 ml of water, dehydrated and dried in the order of saturated saline, then anhydrous magnesium sulfate, and reduced pressure. The solvent was distilled off under. The residue was purified by medium pressure preparative liquid chromatography (Yamazen Co., Ltd. medium pressure preparator; YFLC-Wprep) eluting with ethyl acetate-hexane (1: 5 to 1: 1 gradient). 0.27 g was obtained as white crystals.
Melting point: 103.0-104.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.07 (s, 2H), 7.95 (s, 1H), 7.64 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.4 Hz, 2H), 5.62 (d, J = 6.9Hz, 1H), 5.11 (qui, J = 6.9Hz, 1H), 4.18 (d, J = 17.4Hz, 1H), 3.72 (d, J = 17.4Hz, 1H) , 2.35 (sep, J = 6.9Hz, 1H), 1.48 (d, J = 6.9Hz, 3H), 1.17 and 1.14 (d, J = 6.9Hz, 6H).

  The substituted isoxazoline compound represented by the formula (1), which is the first active ingredient of the pesticidal composition of the present invention, can be produced according to the above production method and synthesis examples. Examples of substituted isoxazoline compounds produced in the same manner as in Synthesis Example 1 and Synthesis Example 2 are shown in Table 1, but the substituted isoxazoline compounds used as active ingredients in the pest control composition of the present invention are limited to these. It is not a thing.

In Table 1, the number representing the substitution position of the substituent (X) _m corresponds to the position of the number described in the following structural formula.

In the table, the substituent described as Et represents an ethyl group, and similarly n-Pr or Pr-n represents a normal propyl group, i-Pr or Pr-i represents an isopropyl group, c-Pr or Pr-c represents a cyclopropyl group, i-Bu or Bu-i represents an isobutyl group,
In the table, the notation of (S) of the substituent R ⁴ indicates that the absolute configuration of the substituent on the benzylic carbon atom is the S-configuration.

Furthermore, the notation “* 1” in the table means that the physical properties of the compound were “resinous”.
Table 1

―――――――――――――――――――――――――――――――――――――――
No. (X) m YR ⁴ R ² R ^1a mp (℃)
―――――――――――――――――――――――――――――――――――――――
01 3-Cl-5-CF3 H CH3 (S) CH2C≡CH Et * 1
02 3-Cl-5-CF3 Cl HH CH2Pr-c * 1
03 3-Cl-5-CF3 Br H Et CH2SO2CH3 * 1
04 3-Br-5-CF3 Cl HH n-Pr 148.0-149.5
05 3-Br-5-CF3 Cl H CH2C≡CH c-Pr * 1
06 3-Br-5-CF3 Cl H CH2C≡CH CH2SO2Et * 1
07 3-Br-5-CF3 Cl HH CH (SCH3) 2 134.0-135.0
08 3-Br-5-CF3 Br HH Et * 1
09 3-Br-5-CF3 Br H Et Et 69.0-71.0
10 3-Br-5-CF3 Br HH n-Pr 163.0-165.0
11 3-Br-5-CF3 Br H CH2CN c-Pr * 1
12 3-Br-5-CF3 Br HH i-Bu 164.0-166.0
13 3-Br-5-CF3 Br H CH2C≡CH CH2SO2CH3 * 1
14 3-Br-5-CF3 Br HH CH2SEt * 1
15 3-Br-5-CF3 Br HH CH2SO2Et 147.0-149.0
16 3-Br-5-CF3 Br H CH3 CH2SO2Et * 1
17 3-I-5-CF3 Cl HH Et 138.0-140.0
18 3-I-5-CF3 Cl HH n-Pr 154.0-156.0
19 3-I-5-CF3 Cl HH CH2SO2Et 145.0-148.0
20 3-I-5-CF3 Br HH n-Pr 178.0-180.0
21 3-I-5-CF3 Br HH CH2CF3 192.0-194.0
22 3,5- (CF3) 2 H CH3 (S) H i-Pr 103.0-104.0
23 3,5- (CF3) 2 Cl H Et Et * 1
24 3,5- (CF3) 2 Cl H CH2C≡CH c-Pr * 1
25 3,5- (CF3) 2 Cl H CH2CN CH2SO2CH3 * 1
26 3,5- (CF3) 2 Cl H CH2C≡CH CH2SCH3 148.0-149.0
27 3,5- (CF3) 2 Cl H CH2C≡CH CH2S (O) CH3 * 1
28 3,5- (CF3) 2 Cl H CH2C≡CH CH2SO2CH3 * 1
29 3,5- (CF3) 2 Cl H Et CH2SO2Et 75.0-78.0
30 3,5- (CF3) 2 Cl HH CH (SCH3) 2 130.0-132.0
31 3,5- (CF3) 2 Br HH CH2SO2Et 164.0-167.0
32 3,5-Br2-4-F Cl HH n-Pr 114.0-116.0
33 3,5-Br2-4-F Cl HH CH2SO2Et 114.0-116.0
34 3,5-Br2-4-F Cl H Et CH2SO2Et * 1
35 3-Cl-5-CF ₃ Cl HH CH ₂ SO ₂ Et 98.0-100.0
36 3-Br-5-CF ₃ Cl HH CH ₂ SO ₂ CH ₃ 125.0-128.0
37 3-Br-5-CF ₃ Cl HH CH ₂ SO ₂ Et 141.0-143.0
38 3,5- (CF ₃ ) ₂ Cl HH CH ₂ SO ₂ CH ₃ 160.5-162.5
―――――――――――――――――――――――――――――――――――――――
Of the compounds listed in Table 1, Table 1 shows ¹ H NMR data of compounds having no melting point.
Table 2 ―――――――――――――――――――――――――――――――――――――――
No. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
―――――――――――――――――――――――――――――――――――――――
01 δ7.82 (s, 1H), 7.75 (s, 1H), 7.68 (s, 1H), 7.63 (d, J = 7.8Hz, 2H),
7.36 (d, J = 7.8Hz, 2H), 6.0-6.15 and 5.15-5.25 (m, 1H),
4.14 and 4.13 (d, J = 17.4Hz, 1H), 3.5-3.9 (m, 3H), 2.3-2.7 (m, 2H),
2.20 and 2.12 (s, 1H), 1.61 (d, J = 6.9Hz, 3H), 1.22 (t, J = 7.5Hz, 3H).
02 δ7.80 (s, 1H), 7.74 (s, 1H), 7.70 (d, J = 1.5Hz, 1H), 7.68 (s, 1H),
7.52 (dd, J = 8.1, 1.5Hz, 1H), 7.47 (d, J = 8.1Hz, 1H), 6.42 (bs, 1H),
4.57 (d, J = 6.0Hz, 2H), 4.10 (d, J = 17.4Hz, 1H), 3.69 (d, J = 17.4Hz, 1H),
2.20 (d, J = 7.2Hz, 2H), 0.85-1.05 (m, 1H), 0.6-0.7 (m, 2H),
0.15-0.25 (m, 2H).
03 δ7.85-7.95 (m, 1H), 7.81 (s, 1H), 7.75 (s, 1H), 7.69 (s, 1H),
7.55-7.65 (m, 1H), 7.2-7.4 (m, 1H), 4.71 (s, 2H), 3.9-4.2 (m, 3H),
3.68 (d, J = 17.4Hz, 1H), 3.4-3.6 (m, 2H), 3.19 and 3.17 (s, 3H),
1.2-1.35 (s, 3H).
05 δ7.69 (s, 1H), 7.85 (s, 1H), 7.80 (s, 1H), 7.76 and 7.67 (bs, 1H),
7.57 and 7.54 (d, J = 7.8Hz, 1H), 7.36 and 7.35 (d, J = 7.8Hz, 1H),
4.94 and 4.81 (s, 2H), 4.32 and 4.23 (bs, 2H),
4.13 and 4.01 (d, J = 17.1Hz, 1H), 3.71 and 3.70 (d, J = 17.1Hz, 1H),
2.30 and 2.20 (bs, 1H), 1.85-1.95 and 1.45-1.55 (m, 1H), 1.0-1.1 (m, 2H),
0.85-0.95 (m, 1H), 0.7-0.8 (m, 1H).
06 δ7.95 (s, 1H), 7.84 (s, 1H), 7.79 (s, 1H), 7.75 and 7.72 (d, J = 1.5Hz, 1H),
7.60 and 7.55 (dd, J = 8.4, 1.5Hz, 1H), 7.36 and 7.34 (d, J = 8.4Hz, 1H),
4.91 and 4.83 (s, 2H), 4.26 (bs, 2H), 4.25 and 4.01 (s, 2H),
4.10 (d, J = 17.4Hz, 1H), 3.71 and 3.70 (d, J = 17.4Hz, 1H),
3.35 and 3.27 (q, J = 7.5Hz, 2H), 2.39 and 2.26 (t, J = 2.4Hz, 1H),
1.46 and 1.45 (t, J = 7.5Hz, 3H).
08 δ7.96 (s, 1H), 7.88 (s, 1H), 7.84 (s, 1H), 7.80 (s, 1H),
7.58 (d, J = 8.1Hz, 1H), 7.47 (d, J = 8.1Hz, 1H), 5.94 (bs, 1H),
4.52 (d, J = 6.3Hz, 2H), 4.10 (d, J = 17.4Hz, 1H), 3.68 (d, J = 17.4Hz, 1H),
2.26 (q, J = 7.5Hz, 2H), 1.17 (t, J = 7.5Hz, 3H).
11 δ7.96 (s, 1H), 7.96 and 7.85 (s, 1H), 7.85 (s, 1H), 7.80 (s, 1H),
7.67 (d, J = 8.1Hz, 1H), 7.30 (d, J = 8.1Hz, 1H), 4.90 (s, 2H), 4.36 (s, 2H),
4.12 (d, J = 17.4Hz, 1H), 3.70 (d, J = 17.4Hz, 1H), 1.5-1.65 (m, 1H),
1.05-1.15 (m, 2H), 0.8-0.9 (m, 2H).
13 δ7.96 (s, 1H), 7.94 and 7.91 (d, J = 1.8Hz, 1H), 7.84 (s, 1H), 7.79 (s, 1H),
7.68 and 7.61 (dd, J = 8.1, 1.8Hz, 1H), 7.34 and 7.31 (d, J = 8.1Hz, 1H),
4.85 and 4.82 (s, 2H), 4.29 and 4.01 (s, 2H),
4.27 and 4.23 (d, J = 2.4Hz, 2H), 4.12 and 4.10 (d, J = 17.4Hz, 1H),
3.70 and 3.68 (d, J = 17.4Hz, 1H), 3.20 and 3.15 (s, 3H),
2.40 and 2.27 (t, J = 2.4Hz, 1H).
14 δ7.95 (s, 1H), 7.88 (s, 1H), 7.84 (s, 1H), 7.79 (s, 1H),
7.58 (d, J = 8.1Hz, 1H), 7.4-7.5 (m, 1H), 7.46 (d, J = 8.1Hz, 1H),
4.56 (d, J = 6.3Hz, 2H), 4.10 (d, J = 17.4Hz, 1H), 3.68 (d, J = 17.4Hz, 1H),
3.27 (s, 2H), 2.53 (q, J = 7.5Hz, 2H), 1.23 (t, J = 7.5Hz, 3H).
16 δ7.96 (s, 1H), 7.94 and 7.90 (d, J = 1.5Hz, 1H), 7.85 (s, 1H), 7.79 (s, 1H),
7.67 and 7.61 (dd, J = 8.1, 1.5Hz, 1H), 7.35 and 7.21 (d, J = 8.1Hz, 1H),
4.76 and 4.74 (s, 2H), 4.10 (d, J = 17.4Hz, 1H), 4.16 and 3.98 (s, 2H),
3.68 (d, J = 17.4Hz, 1H), 3.25-3.4 (m, 2H), 3.21 and 3.03 (s, 3H),
1.46 and 1.45 (t, J = 7.5Hz, 3H).
23 δ8.08 (s, 2H), 7.97 (s, 1H), 7.77 and 7.67 (d, J = 1.8Hz, 1H),
7.5-7.6 (m, 1H), 7.2-7.35 (m, 1H), 4.71 and 4.59 (s, 2H),
4.19 and 4.17 (d, J = 17.4Hz, 1H), 3.75 and 3.73 (d, J = 17.4Hz, 1H),
3.45 and 3.34 (q, J = 7.2Hz, 2H), 2.47 and 2.23 (q, J = 7.2Hz, 2H),
1.05-1.25 (m, 6H).
24 δ8.08 (s, 2H), 7.97 (s, 1H), 7.77 and 7.67 (s, 1H), 7.5-7.6 (m, 1H),
7.3-7.45 (m, 1H), 4.94 and 4.81 (s, 2H), 4.31 and 4.22 (d, J = 2.4Hz, 2H),
4.19 and 4.17 (d, J = 17.4Hz, 1H), 3.75 and 3.73 (d, J = 17.4Hz, 1H),
2.31 and 2.20 (t, J = 2.4Hz, 1H), 1.85-1.95 and 1.45-1.55 (m, 1H),
1.0-1.2 (m, 2H), 0.9-1.0 and 0.7-0.85 (m, 2H).
25 δ8.07 (s, 2H), 7.97 (s, 1H), 7.80 and 7.76 (s, 1H), 7.55-7.7 (m, 1H),
7.38 (d, J = 7.1Hz, 1H), 4.88 (s, 2H), 4.44 and 4.26 (s, 2H),
4.28 and 4.19 (s, 2H), 4.19 and 4.17 (d, J = 17.4Hz, 1H),
3.75 and 3.74 (d, J = 17.4Hz, 1H), 3.19 and 3.13 (s, 3H).
27 δ8.07 (s, 2H), 7.97 (s, 1H), 7.77 and 7.72 (s, 1H), 7.5-7.65 (m, 1H),
7.47 and 7.33 (d, J = 7.4Hz, 1H), 4.65-5.05 (m, 2H), 4.33 (d, J = 19.2Hz, 1H),
4.17 (d, J = 17.4Hz, 1H), 4.0-4.25 (m, 2H), 3.7-3.85 (m, 1H),
3.74 and 3.73 (d, J = 17.4Hz, 1H), 2.78 (s, 3H),
2.37 and 2.26 (t, J = 2.4Hz, 1H).
28 δ8.07 (s, 2H), 7.97 (s, 1H), 7.77 and 7.73 (d, J = 1.8Hz, 1H),
7.55-7.65 (m, 1H), 7.3-7.4 (m, 1H), 4.89 and 4.84 (s, 2H),
4.26 and 4.23 (d, J = 2.4Hz, 2H), 4.18 and 4.17 (d, J = 17.4Hz, 1H),
4.29 and 4.03 (s, 2H), 3.74 and 3.72 (d, J = 17.4Hz, 1H),
3.19 and 3.15 (s, 3H), 2.40 and 2.26 (t, J = 2.4Hz, 1H).
34 δ7.75 (d, J = 6.0Hz, 2H), 7.70 (d, J = 1.5Hz, 1H), 7.5-7.65 (m, 1H),
7.2-7.45 (m, 1H), 4.76 and 4.72 (s, 2H), 4.06 and 4.05 (d, J = 17.4Hz, 1H),
4.13 and 3.94 (s, 2H), 3.68 and 3.66 (d, J = 17.4Hz, 1H),
3.55 and 3.46 (q, J = 7.2Hz, 2H), 3.34 and 3.31 (q, J = 7.5Hz, 2H),
1.45 and 1.44 (d, J = 7.2Hz, 3H), 1.26 and 1.17 (t, J = 7.5Hz, 3H).
―――――――――――――――――――――――――――――――――――――――
The substituted isoxazoline compound represented by the formula (1), which is the first active ingredient in the composition of the present invention and the method of the present invention, has an action mechanism of conventional organochlorine insecticides, organophosphorus insecticides, carbamates. It is different from drugs such as insecticides and pyrethroid insecticides and is effective against pests that have developed resistance to existing insecticides. In addition, the substituted isoxazoline compound represented by the formula (1) causes a certain amount of pests to die at an extremely low dose and has a residual effect, resulting in a remarkable control effect. is there. However, it goes without saying that it is difficult to completely control all pests in all fields by using only the substituted isoxazoline compound represented by the formula (1) alone.

On the other hand, the other active ingredient used together with the substituted isoxazoline compound represented by the formula (1) in the composition of the present invention and the method of the present invention is an insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal It is a well-known agent, and specific names are exemplified in Table 3 below. Some of these active ingredients have problems such as a narrow insecticidal / sterilizing spectrum and short residual effect, and at the same time, problems such as a significant decrease in the control effect due to the emergence of resistant pests or resistant bacteria have been pointed out. In order to obtain a satisfactory control effect, the amount of sprayed medicine and the number of sprays tend to increase, so from the viewpoint of environmental safety, such as an increased risk to humans and aquatic life. There are some that need improvement.
Table 3 ――――――――――――――――――― ―――――――――――――――――――
No. Active ingredient name (generic name) No. Active ingredient name (generic name)
―――――――――――――――――――――――――――――――――――――――
a Acibenzoral-S-methyl kh Vinclozoline
b Ashipetax ki Etaboxam
c Aldimorph kj Zinc naphthenate
d Isotianil kk Zinc sulfate
e Amisulbrom km Jiram
f Ambum kn Zoxamide
g Ampropylphos ko shiitake mycelium extract
h Anilazine kp shiitake fruiting body extract
i Azaconazole kq ZF-9646 (Test name)
k azoxystrobin kt beoxazine
n Benalaxyl-M ku Bithionol
o benodanil kv bronopol
p Benomyl kx Nitrapyrin
s Bench avalicarb-isopropyl ky octirinone
t Benchazole kz Oxolinic acid
y Vitertanol la oxytetracycline
z Bixafen lc Streptomycin
ab Bordeaux fluid lf Kazusahos
ac boscalido lh diclofenthion
ad bromuconazole lj etoprophos
ae bupirimate lk fenamifos
ah Lime sulfur mixture lm Phostiazate
aj Captan ln Fostietan
al carbendazim lo imisiahos
am carboxin lp isamidophos
an carpropamide lq isazofos
ao carvone lr methyl bromide
ap chestnut mixture ls methyl isothiocyanate
aq Quinomethionate lt Oxamyl
av chloronebu lu sodium azide
aw chloropicrin lw BYI-1921 (test name)
ax chlorothalonil lx MAI-08015 (test name)
az Clozolinate ly Acequinosyl
ba crimbazole lz acrinatrin
bc basic copper carbonate ma amidoflumet
bd cupric hydroxide mb amitraz
be copper naphthenate mc bifenazate
bf copper oleate mf clofentezin
bg Basic copper chloride mg Sienopyrafen
bh copper sulfate mh cyflumetofen
bi Basic copper sulfate mj Zicohol
bk cresol mk dienochlor
bl kufraneb ml etoxazole
bn cyazofamid mm phenazaquin
bq cyflufenamide mn phenbutatin-oxide
br Simoxanyl mo Fenothiocarb
bt cyproconazole mp fenpropatrin
bu cyprodinil mq fenpyroximate
bw dasomette mr full acripyrim
cc dichlorophen ms formate
ce Diclobutrazol mt Halfenprox
cf diclocimet mu hexithiazox
cg dichromedin mv milbemectin
ch Dichloran mw propargit
ci dietofencarb mx pyridaben
cj difenoconazole my pyrimidifene
ck diflumetrim mz spirodiclofen
cm Dimethomorph na Spiromesifene
cn dimoxystrobin nb tebufenpyrad
co diniconazole nd NNI-0711 (test name)
cp Diniconazole-M ne Abamectin
cr zino cup nf acephate
cs zinocup-4 ng acetamiprid
ct Zinocup-6 nh Aranicarb
cx diphenylamine ni aldicarb
db dithianon nj allethrin
dc DNP nk azinephos-ethyl
de dozin nl azinephos-methyl
df dorazoxolone nm bacillus thuringiensis
dg edifenhos nn bendiocarb
dh epoxyconazole no benfurthrin
di etaconazole np benfuracarb
dk Ethimol Mall nq Bensultap
dl ethoxyquin nr bifenthrin
dm etridiazole ns bistrifluron
dn famoxadone nt buprofezin
do phenamidon nv carbaryl
dr fenarimol nw carbofuran
ds fenbuconazole nx carbosulfan
dt fenfram ny cartap
du Fenhexamide nz Chloranthraniprolol
dv fenitropan oa chlorfenapyr
dw phenoxanyl ob chlorfenvinphos
dx fenpiclonil oc chlorfluazuron
dy Fenpropidin od Chlorpyrifos
dz Fenpropimorph oe Clopyrifos-methyl
ea Fentin of Chromafenozide
eb farbum og clothianidin
ec ferrimzone oh cyantraniprol
ed Fluazinam oi Cycloprotonline
ee fludioxonil oj cyfluthrin
eg fulmorph ok beta-cyfluthrin
eh fluopicolide ol cyhalothrin
ei fluopyram om gamma-cyhalothrin
ej Fluorimide on lambda-cyhalothrin
ek fluotrimazole oo cypermethrin
el Fluoxastrobin op alpha-cypermethrin
em Fluquinconazole oq beta-cypermethrin
en flusilazole or zeta-cypermethrin
eo fursulfamide os cifenotrin
ep flutolanil ot cyromazine
eq Flutianyl ou Deltamethrin
er Furtoria Hall ov Diafentiuron
es Folpet ow Diazinon
et fosetyl-aluminum ox dichlorvos
eu fuberidazole oy diflubenzuron
ev flaxil oz dimethoate
ew flametopir pb dinotefuran
ey fluconazole pd geophenolane
fa Fulmecyclox pe Disulfone
fe guazatine pf emamectin benzoate
fg Hexachlorobenzene pg Empentrin
fh hexaconazole ph endosulfan
fk hymexazole pi alpha-endosulfan
fl Imazaril pj EP
fm imibenconazole pk esfenvalerate
fn iminotadine-albesylate pm ethiprole
fo iminotadine acetate pn etofenprox
fp ipconazole po etrimfos
fq iprobenphos pq fenitrothion
fr iprodione pr fenocarb
fs iprovaricarb ps phenoxycarb
ft Isoprothiolane pt Fention
fu isopyrazam pu fenvalerate
fw kasugamycin pv fipronil
fx Cresoxime-methyl pw flonicamid
fy Mancapper py fulvendiamide
fz mancozeb pz full cycloxuron
ga mandipropamide qa flucitrinate
gb mannebu qb fullfenerim
ge mepanipyrim qc flufenoxuron
gf mepronil qe flumethrin
gg metalaxyl qf fullvalinate
gh metalaxyl-M qg tau-fulvalinate
gi metam qh honohos
gk metconazole qj furthiocarb
gm metofloxam qk halofenozide
gn methylam ql hexaflumuron
go metminostrobin qm hydramethylnon
gp metolaphenone qn imidacloprid
gq methosulfobac qo imiprotorin
gr mirneb qp indoxacarb
gs microbutanyl qq indoxacarb-MP
gu narbum qs isoprocarb
gv natamycin qt isoxathion
gw organic nickel qu lepimectin
gy nitrotal-isopropyl qv lufenuron
gz nuarimol qw malathion
ha off-race qx metaflumizone
hb orysastrobin qy metaaldehyde
hc oxadixyl qz methaclifos
hd oxyquinoline copper ra methamidophos
he oxpoconazole fumarate rb methidathion
hf oxycarboxin rc mesomil
hg pefazoate rd mesoprene
hh penconazole re methoxychlor
hi pencyclon rf methoxyphenozide
hj Pentachlorophenol rg Metofluthrin
hk pentiopyrad ri muscarua
hl orthophenylphenol rk nitenpyram
hn fusaride rl nobarulon
ho picoxystrobin rm nobiflumuron
hp pipelarin rn ometoate
hq Polycarbamate ro Oxydemeton-methyl
hr polyoxin rr parathion-methyl
hs polyoxin-D rs permethrin
ht potassium azide rt phenothrin
hu Potassium bicarbonate ru Fentate
hv probenazole rv folate
hw prochloraz rw ho salon
hx prosimidone rx phosmet
hy propamocarb hydrochloride rz phoxime
hz propiconazole sa pyrimicarb
ia propineb sc pirimiphos-methyl
ib proquinazide sd profenofos
id pyribencarb methyl sf prothiophos
ie Pyriphenox sh Pymetrozine
if pyrimethanil si pyracrofos
ig piroquiron sj pyrethrin
ii prothioconazole sk pyridalyl
ik pyraclostrobin sl pyrifluquinazone
io xenatorol sulfate sm pyriprol
ir quinoxyphene sn pyriproxyfen
is Kintozen so Resmetrine
iv sedaxan sp rotenone
iw silthiofam sq silafluophene
ix Cimeconazole sr spinetoram
iy sodium bicarbonate ss spinosad
iz Sodium hypochlorite st spirotetramate
en spiroxamine su sulfotep
jb sulfur sv sulfoxaflor
jc tebuconazole sx tebufenozide
je Tecolum sy Teflubenzuron
jf tetraconazole sz teflutrin
jg thiabendazole ta terbufos
jj tifluzamide tb tetrachlorobinphos
jm thiophanate-methyl tc tetramethrin
jn thiuram td dT-80-phthalthrin
jo thiazinyl te thiacloprid
jq Torquelophos-methyl tf thiamethoxam
jr trilfuranide tg thiocyclam
js triazimehon th thiodicarb
jt triazimenol ti thiophanox
jx triazoxide tk tolfenpyrad
jy tributyltin oxide tl tralomethrin
ka tricyclazole tm transfluthrin
kc trifloxystrobin tn triazamate
kd triflumizole to trichlorfon
ke triforin tp triflumuron
kf triticonazole tr ANM-138 (test name)
kg Validamycin ts ME-5343 (Test name)
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Under such circumstances, the present inventors have conducted intensive research with the goal of developing a method for controlling pests that exhibits excellent pest control activity and has less adverse effects on non-target organisms such as mammals, fish, natural enemies, and beneficial insects. As a result, the composition containing the substituted isoxazoline compound represented by the formula (1) or a salt thereof and an active ingredient having a known insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal activity It has been found that various pests can be controlled very effectively by using the product, and the present invention has been completed.

  The characteristics of the composition of the present invention and the method of the present invention are as follows. Firstly, the efficacy of insecticide, acaricide, nematicide, mollusc, bactericidal or bactericidal is clear as compared with the case where each drug is applied alone. In addition to being enhanced, it provides a fast-acting insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect. Second, the existing insecticidal, acaricidal, nematicidal, molluscicidal, broad insecticidal, acaricidal, nematicidal, molluscicidal, germicidal or bactericidal spectrum not seen in bactericides or bactericides It is that aftereffect is induced. Thirdly, compared to the case where each active ingredient is used alone, it is possible to reduce the amount of dropped drug.

  That is, the composition of the present invention and the method of the present invention exhibit synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effects. This synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect is predicted from the insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect of each single agent. The usefulness of the composition of the present invention and the method of the present invention can be said to be that it can exhibit a more reliable control effect than using each compound alone against various pests.

  Combination of a substituted isoxazoline compound represented by the formula (1) having such a synergistic pest control effect and an active ingredient having a known insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal activity Examples are given below. In the following notation, for example, “1 + a” represents a combination of the No. 1 compound in Table 1 and the acibenzolar-S-methyl of No. a in Table 3.

Examples of active ingredient combinations: 1 + a, 1 + b, 1 + c, 1 + d, 1 + e, 1 + f, 1 + g, 1 + h, 1 + i, 1 + k, 1 + n , 1 + o, 1 + p, 1 + s, 1 + t, 1 + y, 1 + z, 1 + ab, 1 + ac, 1 + ad, 1 + ae, 1 + ah, 1 + aj, 1 + al, 1 + am, 1 + an, 1 + ao, 1 + ap, 1 + aq, 1 + av, 1 + aw, 1 + ax, 1 + az, 1 + ba, 1 + bc, 1 + bd , 1 + be, 1 + bf, 1 + bg, 1 + bh, 1 + bi, 1 + bk, 1 + bl, 1 + bn, 1 + bq, 1 + br, 1 + bt, 1 + bu, 1 + bw, 1 + cc, 1 + ce, 1 + cf, 1 + cg, 1 + ch, 1 + ci, 1 + cj, 1 + ck, 1 + cm, 1 + cn, 1 + co, 1 + cp , 1 + cr, 1 + cs, 1 + ct, 1 + cx, 1 + db, 1 + dc, 1 + de, 1 + df, 1 + dg, 1 + dh, 1 + di, 1 + dk, 1 + dl, 1 + dm, 1 + dn, 1 + do, 1 + dr, 1 + ds, 1 + dt, 1 + du, 1 + dv, 1 + dw, 1 + dx, 1 + dy, 1 + dz , 1 + ea, 1 + eb, 1 + ec, 1 + ed, 1 + ee, 1 + eg, 1 + eh, 1 + ei, 1 + ej, 1 + ek, 1 + el, 1 + em, 1 + en, 1 + eo, 1 + ep, 1 + eq, 1 + er, 1 + es, 1 + et, 1 + eu, 1 + ev, 1 + ew, 1 + ey, 1 + fa, 1 + fe , 1 + fg, 1 + fh, 1 + fk, 1 + fl, 1 + fm, 1 + fn, 1 + fo, 1 + fp, 1 + fq, 1 + fr, 1 + fs, 1 + ft, 1 + fu, 1 + fw, 1 + fx, 1 + fy, 1 + fz, 1 + ga, 1 + gb, 1 + ge, 1 + gf, 1 + gg, 1 + gh, 1 + gi, 1 + gk , 1 + gm, 1 + gn, 1 + go, 1 + gp, 1 + gq, 1 + gr, 1 + gs, 1 + gu, 1 + gv, 1 + gw, 1 + gy, 1 + gz, 1 + ha, 1 + hb, 1 + hc, 1 + hd, 1 + he, 1 + hf, 1 + hg, 1 + hh, 1 + hi, 1 + hj, 1 + hk, 1 + hl, 1 + hn , 1 + ho, 1 + hp, 1 + hq, 1 + hr, 1 + hs, 1 + ht, 1 + hu, 1 + hv, 1 + hw, 1 + hx, 1 + hy, 1 + hz, 1 + ia, 1 + ib, 1 + id, 1 + ie, 1 + if, 1 + ig, 1 + ii, 1 + ik, 1 + io, 1 + ir, 1 + is, 1 + iv, 1 + iw , 1 + ix, 1 + iy, 1 + iz, 1 + ja, 1 + jb, 1 + jc, 1 + je, 1 + jf, 1 + jg, 1 + j j, 1 + jm, 1 + jn, 1 + jo, 1 + jq, 1 + jr, 1 + js, 1 + jt, 1 + jx, 1 + jy, 1 + ka, 1 + kc, 1 + kd, 1 + ke, 1 + kf, 1 + kg, 1 + kh, 1 + ki, 1 + kj, 1 + kk, 1 + km, 1 + kn, 1 + ko, 1 + kp, 1 + kq, 1 + kt, 1 + ku, 1 + kv, 1 + kx, 1 + ky, 1 + kz, 1 + la, 1 + lc, 1 + lf, 1 + lh, 1 + lj, 1 + lk, 1 + lm, 1 + ln, 1 + lo, 1 + lp, 1 + lq, 1 + lr, 1 + ls, 1 + lt, 1 + lu, 1 + lw, 1 + lx, 1 + ly, 1 + lz, 1 + ma, 1 + mb, 1 + mc, 1 + mf, 1 + mg, 1 + mh, 1 + mj, 1 + mk, 1 + ml, 1 + mm, 1 + mn, 1 + mo, 1 + mp, 1 + mq, 1 + mr, 1 + ms, 1 + mt, 1 + mu, 1 + mv, 1 + mw, 1 + mx, 1 + my, 1 + mz, 1 + na, 1 + nb, 1 + nd, 1 + ne, 1 + nf, 1 + ng, 1 + nh, 1 + ni, 1 + nj, 1 + nk, 1 + nl, 1 + nm, 1 + nn, 1 + no, 1 + np, 1 + nq, 1 + nr, 1 + ns, 1 + nt, 1 + nv, 1 + nw, 1 + nx, 1 + ny, 1 + nz, 1 + oa, 1 + ob, 1 + oc, 1 + od, 1 + oe, 1 + of, 1 + og, 1 + oh, 1 + oi, 1 + oj, 1 + ok, 1 + ol, 1 + om, 1 + on, 1 + oo, 1 + op, 1 + oq, 1 + or, 1 + os, 1 + ot, 1 + ou, 1 + ov, 1 + ow, 1 + ox, 1 + oy, 1 + oz, 1 + pb, 1 + pd, 1 + pe, 1 + pf, 1 + pg, 1 + ph, 1 + pi, 1 + pj, 1 + pk, 1 + pm, 1 + pn, 1 + po, 1 + pq, 1 + pr, 1 + ps, 1 + pt, 1 + pu, 1 + pv, 1 + pw, 1 + py, 1 + pz, 1 + qa, 1 + qb, 1 + qc, 1 + qe, 1 + qf, 1 + qg, 1 + qh, 1 + qj, 1 + qk, 1 + ql, 1 + qm, 1 + qn, 1 + qo, 1 + qp, 1 + qq, 1 + qs, 1 + qt, 1 + qu, 1 + qv, 1 + qw, 1 + qx, 1 + qy, 1 + qz, 1 + ra, 1 + rb, 1 + rc, 1 + rd, 1 + re, 1 + rf, 1 + rg, 1 + ri, 1 + rk, 1 + rl, 1 + rm, 1 + rn, 1 + ro, 1 + rr, 1 + rs, 1 + rt, 1 + ru, 1 + rv, 1 + rw, 1 + rx, 1 + rz, 1 + sa, 1 + sc, 1 + sd, 1 + sf, 1 + sh, 1 + si, 1 + sj, 1 + sk, 1 + sl, 1 + sm, 1 + sn, 1 + so, 1 + s p, 1 + sq, 1 + sr, 1 + ss, 1 + st, 1 + su, 1 + sv, 1 + sx, 1 + sy, 1 + sz, 1 + ta, 1 + tb, 1 + tc, 1 + td, 1 + te, 1 + tf, 1 + tg, 1 + th, 1 + ti, 1 + tk, 1 + tl, 1 + tm, 1 + tn, 1 + to, 1 + tp, 1 + tr, 1 + ts,
2 + a, 2 + b, 2 + c, 2 + d, 2 + e, 2 + f, 2 + g, 2 + h, 2 + i, 2 + k, 2 + n, 2 + o, 2 + p, 2 + s, 2 + t, 2 + y, 2 + z, 2 + ab, 2 + ac, 2 + ad, 2 + ae, 2 + ah, 2 + aj, 2 + al, 2 + am, 2 + an, 2 + ao, 2 + ap, 2 + aq, 2 + av, 2 + aw, 2 + ax, 2 + az, 2 + ba, 2 + bc, 2 + bd, 2 + be, 2+ bf, 2 + bg, 2 + bh, 2 + bi, 2 + bk, 2 + bl, 2 + bn, 2 + bq, 2 + br, 2 + bt, 2 + bu, 2 + bw, 2 + cc, 2 + ce, 2 + cf, 2 + cg, 2 + ch, 2 + ci, 2 + cj, 2 + ck, 2 + cm, 2 + cn, 2 + co, 2 + cp, 2 + cr, 2+ cs, 2 + ct, 2 + cx, 2 + db, 2 + dc, 2 + de, 2 + df, 2 + dg, 2 + dh, 2 + di, 2 + dk, 2 + dl, 2 + dm, 2 + dn, 2 + do, 2 + dr, 2 + ds, 2 + dt, 2 + du, 2 + dv, 2 + dw, 2 + dx, 2 + dy, 2 + dz, 2 + ea, 2 + eb, 2 + ec, 2 + ed, 2 + ee, 2 + eg, 2 + eh, 2 + ei, 2 + ej, 2 + ek, 2 + el, 2 + em, 2 + en, 2 + eo, 2 + ep, 2 + eq, 2 + er, 2 + es, 2 + et, 2 + eu, 2 + ev, 2 + ew, 2 + ey, 2 + fa, 2 + fe, 2 + fg, 2+ fh, 2 + fk, 2 + fl, 2 + fm, 2 + fn, 2 + fo, 2 + fp, 2 + fq, 2 + fr, 2 + fs, 2 + ft, 2 + fu, 2 + fw, 2 + fx, 2 + fy, 2 + fz, 2 + ga, 2 + gb, 2 + ge, 2 + gf, 2 + gg, 2 + gh, 2 + gi, 2 + gk, 2 + gm, 2+ gn, 2 + go, 2 + gp, 2 + gq, 2 + gr, 2 + gs, 2 + gu, 2 + gv, 2 + gw, 2 + gy, 2 + gz, 2 + ha, 2 + hb, 2 + hc, 2 + hd, 2 + he, 2 + hf, 2 + hg, 2 + hh, 2 + hi, 2 + hj, 2 + hk, 2 + hl, 2 + hn, 2 + ho, 2+ hp, 2 + hq, 2 + hr, 2 + hs, 2 + ht, 2 + hu, 2 + hv, 2 + hw, 2 + hx, 2 + hy, 2 + hz, 2 + ia, 2 + ib, 2 + id, 2 + ie, 2 + if, 2 + ig, 2 + ii, 2 + ik, 2 + io, 2 + ir, 2 + is, 2 + iv, 2 + iw, 2 + ix, 2+ iy, 2 + iz, 2 + ja, 2 + jb, 2 + jc, 2 + je, 2 + jf, 2 + jg, 2 + jj, 2 + jm, 2 + jn, 2 + jo, 2 + jq, 2 + jr, 2 + js, 2 + jt, 2 + jx, 2 + jy, 2 + ka, 2 + kc, 2 + kd, 2 + ke, 2 + kf, 2 + kg, 2 + kh, 2 + ki, 2 + kj, 2 + kk, 2 + km, 2 + kn, 2 + ko, 2 + kp, 2 + kq, 2 + kt, 2 + ku, 2 + kv, 2 + kx, 2 + ky, 2 + kz, 2 + la, 2 + lc, 2 + lf, 2 + lh, 2 + lj, 2 + lk, 2 + lm, 2 + ln, 2 + lo, 2 + lp, 2 + lq, 2 + lr, 2 + ls, 2 + lt, 2 + lu, 2 + lw, 2 + lx, 2 + ly, 2 + lz, 2 + ma, 2 + mb, 2 + mc, 2 + mf, 2 + mg, 2 + mh, 2 + mj, 2 + mk, 2+ ml, 2 + mm, 2 + mn, 2 + mo, 2 + mp, 2 + mq, 2 + mr, 2 + ms, 2 + mt, 2 + mu, 2 + mv, 2 + mw, 2 + mx, 2 + my, 2 + mz, 2 + na, 2 + nb, 2 + nd, 2 + ne, 2 + nf, 2 + ng, 2 + nh, 2 + ni, 2 + nj, 2 + nk, 2 + nl, 2 + nm, 2 + nn, 2 + no, 2 + np, 2 + nq, 2 + nr, 2 + ns, 2 + nt, 2 + nv, 2 + nw, 2 + nx, 2 + ny, 2 + nz, 2 + oa, 2 + ob, 2 + oc, 2 + od, 2 + oe, 2 + of, 2 + og, 2 + oh, 2 + oi, 2 + oj, 2 + ok, 2+ ol, 2 + om, 2 + on, 2 + oo, 2 + op, 2 + oq, 2 + or, 2 + os, 2 + ot, 2 + ou, 2 + ov, 2 + ow, 2 + ox, 2 + oy, 2 + oz, 2 + pb, 2 + pd, 2 + pe, 2 + pf, 2 + pg, 2 + ph, 2 + pi, 2 + pj, 2 + pk, 2 + pm, 2+ pn, 2 + po, 2 + pq, 2 + pr, 2 + ps, 2 + pt, 2 + pu, 2 + pv, 2 + pw, 2 + py, 2 + pz, 2 + qa, 2 + qb, 2 + qc, 2 + qe, 2 + qf, 2 + qg, 2 + qh, 2 + qj, 2 + qk, 2 + ql, 2 + qm, 2 + qn, 2 + qo, 2 + qp, 2+ qq, 2 + qs, 2 + qt, 2 + qu, 2 + qv, 2 + qw, 2 + qx, 2 + qy, 2 + qz, 2 + ra, 2 + rb, 2 + rc, 2 + rd, 2 + re, 2 + rf, 2 + rg, 2 + ri, 2 + rk, 2 + rl, 2 + rm, 2 + rn, 2 + ro, 2 + rr, 2 + rs, 2 + rt, 2+ ru, 2 + rv, 2 + rw, 2 + rx, 2 + rz, 2 + sa, 2 + sc, 2 + sd, 2 + sf, 2 + sh, 2 + si, 2 + sj, 2 + sk, 2 + sl, 2 + sm, 2 + sn, 2 + so, 2 + sp, 2 + sq, 2 + sr, 2 + ss, 2 + st, 2 + su, 2 + sv, 2 + sx, 2+ sy, 2 + sz, 2 + ta, 2 + tb, 2 + tc, 2 + td, 2 + te, 2 + tf, 2 + tg, 2 + th, 2 + ti, 2 + tk, 2 + tl, 2 + tm, 2 + tn, 2 + to, 2 + tp, 2 + tr, 2 + ts,
3 + a, 3 + b, 3 + c, 3 + d, 3 + e, 3 + f, 3 + g, 3 + h, 3 + i, 3 + k, 3 + n, 3 + o, 3 + p, 3 + s, 3 + t, 3 + y, 3 + z, 3 + ab, 3 + ac, 3 + ad, 3 + ae, 3 + ah, 3 + aj, 3 + al, 3 + am, 3 + an, 3 + ao, 3 + ap, 3 + aq, 3 + av, 3 + aw, 3 + ax, 3 + az, 3 + ba, 3 + bc, 3 + bd, 3 + be, 3 + bf, 3 + bg, 3 + bh, 3 + bi, 3 + bk, 3 + bl, 3 + bn, 3 + bq, 3 + br, 3 + bt, 3 + bu, 3 + bw, 3 + cc, 3 + ce, 3 + cf, 3 + cg, 3 + ch, 3 + ci, 3 + cj, 3 + ck, 3 + cm, 3 + cn, 3 + co, 3 + cp, 3 + cr, 3 + cs, 3 + ct, 3 + cx, 3 + db, 3 + dc, 3 + de, 3 + df, 3 + dg, 3 + dh, 3 + di, 3 + dk, 3 + dl, 3 + dm, 3 + dn, 3 + do, 3 + dr, 3 + ds, 3 + dt, 3 + du, 3 + dv, 3 + dw, 3 + dx, 3 + dy, 3 + dz, 3 + ea, 3 + eb, 3 + ec, 3 + ed, 3 + ee, 3 + eg, 3 + eh, 3 + ei, 3 + ej, 3 + ek, 3 + el, 3 + em, 3 + en, 3 + eo, 3 + ep, 3 + eq, 3 + er, 3 + es, 3 + et, 3 + eu, 3 + ev, 3 + ew, 3 + ey, 3 + fa, 3 + fe, 3 + fg, 3 + fh, 3 + fk, 3 + fl, 3 + fm, 3 + fn, 3 + fo, 3 + fp, 3 + fq, 3 + fr, 3 + fs, 3 + ft, 3 + fu, 3 + fw, 3 + fx, 3 + fy, 3 + fz, 3 + ga, 3 + gb, 3 + ge, 3 + gf, 3 + gg, 3 + gh, 3 + gi, 3 + gk, 3 + gm, 3 + gn, 3 + go, 3 + gp, 3 + gq, 3 + gr, 3 + gs, 3 + gu, 3 + gv, 3 + gw, 3 + gy, 3 + gz, 3 + ha, 3 + hb, 3 + hc, 3 + hd, 3 + he, 3 + hf, 3 + hg, 3 + hh, 3 + hi, 3 + hj, 3 + hk, 3 + hl, 3 + hn, 3 + ho, 3 + hp, 3 + hq, 3 + hr, 3 + hs, 3 + ht, 3 + hu, 3 + hv, 3 + hw, 3 + hx, 3 + hy, 3 + hz, 3 + ia, 3 + ib, 3 + id, 3 + ie, 3 + if, 3 + ig, 3 + ii, 3 + ik, 3 + io, 3 + ir, 3 + is, 3 + iv, 3 + iw, 3 + ix, 3 + iy, 3 + iz, 3 + ja, 3 + jb, 3 + jc, 3 + je, 3 + jf, 3 + jg, 3 + jj, 3 + jm, 3 + jn, 3 + jo, 3 + jq, 3 + jr, 3 + js, 3 + jt, 3 + jx, 3 + jy, 3 + ka, 3 + kc, 3 + kd, 3 + ke, 3 + kf, 3 + kg, 3 + kh, 3 + ki, 3 + kj, 3 + kk, 3 + km, 3 + kn, 3 + ko, 3 + kp, 3 + kq, 3 + kt, 3 + ku, 3 + kv, 3 + kx, 3 + ky, 3 + kz, 3 + la, 3 + lc, 3 + lf, 3 + lh, 3 + lj, 3 + lk, 3 + lm, 3 + ln, 3 + lo, 3 + lp, 3 + lq, 3 + lr, 3 + ls, 3 + lt, 3 + lu, 3 + lw, 3 + lx, 3 + ly, 3 + lz, 3 + ma, 3 + mb, 3 + mc, 3 + mf, 3 + mg, 3 + mh, 3 + mj, 3 + mk, 3 + ml, 3 + mm, 3 + mn, 3 + mo, 3 + mp, 3 + mq, 3 + mr, 3 + ms, 3 + mt, 3 + mu, 3 + mv, 3 + mw, 3 + mx, 3 + my, 3 + mz, 3 + na, 3 + nb, 3 + nd, 3 + ne, 3 + nf, 3 + ng, 3 + nh, 3 + ni, 3 + nj, 3 + nk, 3 + nl, 3 + nm, 3 + nn, 3 + no, 3 + np, 3 + nq, 3 + nr, 3 + ns, 3 + nt, 3 + nv, 3 + nw, 3 + nx, 3 + ny, 3 + nz, 3 + oa, 3 + ob, 3 + oc, 3 + od, 3 + oe, 3 + of, 3 + og, 3 + oh, 3 + oi, 3 + oj, 3 + ok, 3 + ol, 3 + om, 3 + on, 3 + oo, 3 + op, 3 + oq, 3 + or, 3 + os, 3 + ot, 3 + ou, 3 + ov, 3 + ow, 3 + ox, 3 + oy, 3 + oz, 3 + pb, 3 + pd, 3 + pe, 3 + pf, 3 + pg, 3 + ph, 3 + pi, 3 + pj, 3 + pk, 3 + pm, 3 + pn, 3 + po, 3 + pq, 3 + pr, 3 + ps, 3 + pt, 3 + pu, 3 + pv, 3 + pw, 3 + py, 3 + pz, 3 + qa, 3 + qb, 3 + qc, 3 + qe, 3 + qf, 3 + qg, 3 + qh, 3 + qj, 3 + qk, 3 + ql, 3 + qm, 3 + qn, 3 + qo, 3 + qp, 3 + qq, 3 + qs, 3 + qt, 3 + qu, 3 + qv, 3 + qw, 3 + qx, 3 + qy, 3 + qz, 3 + ra, 3 + rb, 3 + rc, 3 + rd, 3 + re, 3 + rf, 3 + rg, 3 + ri, 3 + rk, 3 + rl, 3 + rm, 3 + rn, 3 + ro, 3 + rr, 3 + rs, 3 + rt, 3 + ru, 3 + rv, 3 + rw, 3 + rx, 3 + rz, 3 + sa, 3 + sc, 3 + sd, 3 + sf, 3 + sh, 3 + si, 3 + sj, 3 + sk, 3 + sl, 3 + sm, 3 + sn, 3 + so, 3 + sp, 3 + sq, 3 + sr, 3 + ss, 3 + st, 3 + su, 3 + sv, 3 + sx, 3 + sy, 3 + sz, 3 + ta, 3 + tb, 3 + tc, 3 + td, 3 + te, 3 + tf, 3 + tg, 3 + th, 3 + ti, 3 + tk, 3 + tl, 3 + tm, 3 + tn, 3 + to, 3 + tp, 3 + tr, 3 + ts,
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37 + a, 37 + b, 37 + c, 37 + d, 37 + e, 37 + f, 37 + g, 37 + h, 37 + i, 37 + k, 37 + n, 37 + o, 37+ p, 37 + s, 37 + t, 37 + y, 37 + z, 37 + ab, 37 + ac, 37 + ad, 37 + ae, 37 + ah, 37 + aj, 37 + al, 37 + am, 37 + an, 37 + ao, 37 + ap, 37 + aq, 37 + av, 37 + aw, 37 + ax, 37 + az, 37 + ba, 37 + bc, 37 + bd, 37 + be, 37 + bf, 37 + bg, 37 + bh, 37 + bi, 37 + bk, 37 + bl, 37 + bn, 37 + bq, 37 + br, 37 + bt, 37 + bu, 37 + bw, 37 + cc, 37 + ce, 37 + cf, 37 + cg, 37 + ch, 37 + ci, 37 + cj, 37 + ck, 37 + cm, 37 + cn, 37 + co, 37 + cp, 37 + cr, 37 + cs, 37 + ct, 37 + cx, 37 + db, 37 + dc, 37 + de, 37 + df, 37 + dg, 37 + dh, 37 + di, 37 + dk, 37 + dl, 37 + dm, 37 + dn, 37 + do, 37 + dr, 37 + ds, 37 + dt, 37 + du, 37 + dv, 37 + dw, 37 + dx, 37 + dy, 37 + dz, 37 + ea, 37 + eb, 37 + ec, 37 + ed, 37 + ee, 37 + eg, 37 + eh, 37 + ei, 37 + ej, 37 + ek, 37 + el, 37 + em, 37 + en, 37 + eo, 37 + ep, 37 + eq, 37 + er, 37 + es, 37 + et, 37 + eu, 37 + ev, 37 + ew, 37 + ey, 37 + fa, 37 + fe, 37 + fg, 37+ fh, 37 + fk, 37 + fl, 37 + fm, 37 + fn, 37 + fo, 37 + fp, 37 + fq, 37 + fr, 37 + fs, 37 + ft, 37 + fu, 37 + fw, 37 + fx, 37 + fy, 37 + fz, 37 + ga, 37 + gb, 37 + ge, 37 + gf, 37 + gg, 37 + gh, 37 + gi, 37 + gk, 37 + gm, 37 + gn, 37 + go, 37 + gp, 37 + gq, 37 + gr, 37 + gs, 37 + gu, 37 + gv, 37 + gw, 37 + gy, 37 + gz, 37 + ha, 37 + hb, 37 + hc, 37 + hd, 37 + he, 37 + hf, 37 + hg, 37 + hh, 37 + hi, 37 + hj, 37 + hk, 37 + hl, 37 + hn, 37 + ho, 37 + hp, 37 + hq, 37 + hr, 37 + hs, 37 + ht, 37 + hu, 37 + hv, 37 + hw, 37 + hx, 37 + hy, 37 + hz, 37 + ia, 37 + ib, 37 + id, 37 + ie, 37 + if, 37 + ig, 37 + ii, 37 + ik, 37 + io, 37 + ir, 37 + is, 37 + iv, 37 + iw, 37 + ix, 37 + iy, 37 + iz, 37 + ja, 37 + jb, 37 + jc, 37 + je, 37 + jf, 37 + jg, 37 + jj, 37 + jm, 37 + jn, 37 + jo, 37 + jq, 37 + jr, 37 + js, 37 + jt, 37 + jx, 37 + jy, 37 + ka, 37 + kc, 37 + kd, 37 + ke, 37 + kf, 37 + kg, 37 + kh, 37 + ki, 37 + kj, 37 + kk, 37 + km, 37 + kn, 37 + ko, 37 + kp, 37 + kq, 37 + kt, 37 + ku, 37 + kv, 37 + kx, 37 + ky, 37 + kz, 37 + la, 37 + lc, 37 + lf, 37 + lh, 37 + lj, 37 + lk, 37 + lm, 37 + ln, 37 + lo, 37 + lp, 37 + lq, 37 + lr, 37 + ls, 37 + lt, 37 + lu, 37 + lw, 37 + lx, 37 + ly, 37+ lz, 37 + ma, 37 + mb, 37 + mc, 37 + mf, 37 + mg, 37 + mh, 37 + mj, 37 + mk, 37 + ml, 37 + mm, 37 + mn, 37 + mo, 37 + mp, 37 + mq, 37 + mr, 37 + ms, 37 + mt, 37 + mu, 37 + mv, 37 + mw, 37 + mx, 37 + my, 37 + mz, 37 + na, 37 + nb, 37 + nd, 37 + ne, 37 + nf, 37 + ng, 37 + nh, 37 + ni, 37 + nj, 37 + nk, 37 + nl, 37 + nm, 37 + nn, 37 + no, 37 + np, 37 + nq, 37 + nr, 37 + ns, 37 + nt, 37 + nv, 37 + nw, 37 + nx, 37 + ny, 37 + nz, 37 + oa, 37 + ob, 37 + oc, 37 + od, 37 + oe, 37 + of, 37 + og, 37 + oh, 37 + oi, 37 + oj, 37 + ok, 37 + ol, 37 + om, 37 + on, 37 + oo, 37 + op, 37 + oq, 37 + or, 37 + os, 37 + ot, 37 + ou, 37 + ov, 37 + ow, 37 + ox, 37 + oy, 37 + oz, 37 + pb, 37 + pd, 37 + pe, 37 + pf, 37 + pg, 37 + ph, 37 + pi, 37 + pj, 37 + pk, 37 + pm, 37 + pn, 37 + po, 37 + pq, 37 + pr, 37 + ps, 37 + pt, 37 + pu, 37 + pv, 3 7 + pw, 37 + py, 37 + pz, 37 + qa, 37 + qb, 37 + qc, 37 + qe, 37 + qf, 37 + qg, 37 + qh, 37 + qj, 37 + qk, 37 + ql, 37 + qm, 37 + qn, 37 + qo, 37 + qp, 37 + qq, 37 + qs, 37 + qt, 37 + qu, 37 + qv, 37 + qw, 37 + qx, 37 + qy, 37 + qz, 37 + ra, 37 + rb, 37 + rc, 37 + rd, 37 + re, 37 + rf, 37 + rg, 37 + ri, 37 + rk, 37 + rl, 37 + rm, 37 + rn, 37 + ro, 37 + rr, 37 + rs, 37 + rt, 37 + ru, 37 + rv, 37 + rw, 37 + rx, 37 + rz, 37 + sa, 37 + sc, 37 + sd, 37 + sf, 37 + sh, 37 + si, 37 + sj, 37 + sk, 37 + sl, 37 + sm, 37 + sn, 37 + so, 37 + sp, 37 + sq, 37 + sr, 37 + ss, 37 + st, 37 + su, 37 + sv, 37 + sx, 37 + sy, 37 + sz, 37 + ta, 37 + tb, 37 + tc, 37 + td, 37 + te, 37 + tf, 37 + tg, 37 + th, 37 + ti, 37 + tk, 37 + tl, 37 + tm, 37 + tn, 37 + to, 37 + tp, 37 + tr, 37 + ts,
38 + a, 38 + b, 38 + c, 38 + d, 38 + e, 38 + f, 38 + g, 38 + h, 38 + i, 38 + k, 38 + n, 38 + o, 38 + p, 38 + s, 38 + t, 38 + y, 38 + z, 38 + ab, 38 + ac, 38 + ad, 38 + ae, 38 + ah, 38 + aj, 38 + al, 38 + am, 38 + an, 38 + ao, 38 + ap, 38 + aq, 38 + av, 38 + aw, 38 + ax, 38 + az, 38 + ba, 38 + bc, 38 + bd, 38 + be, 38 + bf, 38 + bg, 38 + bh, 38 + bi, 38 + bk, 38 + bl, 38 + bn, 38 + bq, 38 + br, 38 + bt, 38 + bu, 38 + bw, 38 + cc, 38 + ce, 38 + cf, 38 + cg, 38 + ch, 38 + ci, 38 + cj, 38 + ck, 38 + cm, 38 + cn, 38 + co, 38 + cp, 38 + cr, 38 + cs, 38 + ct, 38 + cx, 38 + db, 38 + dc, 38 + de, 38 + df, 38 + dg, 38 + dh, 38 + di, 38 + dk, 38 + dl, 38 + dm, 38 + dn, 38 + do, 38 + dr, 38 + ds, 38 + dt, 38 + du, 38 + dv, 38 + dw, 38 + dx, 38 + dy, 38 + dz, 38 + ea, 38 + eb, 38 + ec, 38 + ed, 38 + ee, 38 + eg, 38 + eh, 38 + ei, 38 + ej, 38 + ek, 38 + el, 38 + em, 38 + en, 38 + eo, 38 + ep, 38 + eq, 38 + er, 38 + es, 38 + et, 38 + eu, 38 + ev, 38 + ew, 38 + ey, 38 + fa, 38 + fe, 38 + fg, 38 + fh, 38 + fk, 38 + fl, 38 + fm, 38 + fn, 38 + fo, 38 + fp, 38 + fq, 38 + fr, 38 + fs, 38 + ft, 38 + fu, 38 + fw, 38 + fx, 38 + fy, 38 + fz, 38 + ga, 38 + gb, 38 + ge, 38 + gf, 38 + gg, 38 + gh, 38 + gi, 38 + gk, 38 + gm, 38 + gn, 38 + go, 38 + gp, 38 + gq, 38 + gr, 38 + gs, 38 + gu, 38 + gv, 38 + gw, 38 + gy, 38 + gz, 38 + ha, 38 + hb, 38 + hc, 38 + hd, 38 + he, 38 + hf, 38 + hg, 38 + hh, 38 + hi, 38 + hj, 38 + hk, 38 + hl, 38 + hn, 38 + ho, 38 + hp, 38 + hq, 38 + hr, 38 + hs, 38 + ht, 38 + hu, 38 + hv, 38 + hw, 38 + hx, 38 + hy, 38 + hz, 38 + ia, 38 + ib, 38 + id, 38 + ie, 38 + if, 38 + ig, 38 + ii, 38 + ik, 38 + io, 38 + ir, 38 + is, 38 + iv, 38 + iw, 38 + ix, 38 + iy, 38 + iz, 38 + ja, 38 + jb, 38 + jc, 38 + je, 38 + jf, 38 + jg, 38 + jj, 38 + jm, 38 + jn, 38 + jo, 38 + jq, 38 + jr, 38 + js, 38 + jt, 38 + jx, 38 + jy, 38 + ka, 38 + kc, 38 + kd, 38 + ke, 38 + kf, 38 + kg, 38 + kh, 38 + ki, 38 + kj, 38 + kk, 38 + km, 38 + kn, 38 + ko, 38 + kp, 38 + kq, 38 + kt, 38 + ku, 38 + kv, 38 + kx, 38 + ky, 38 + kz, 38 + la, 38 + lc, 38 + lf, 38 + lh, 38 + lj, 38 + lk, 38 + lm, 38 + ln, 38 + lo, 38 + lp, 38 + lq, 38 + lr, 38 + ls, 38 + lt, 38 + lu, 38 + lw, 38 + lx, 38 + ly, 38 + lz, 38 + ma, 38 + mb, 38 + mc, 38 + mf, 38 + mg, 38 + mh, 38 + mj, 38 + mk, 38 + ml, 38 + mm, 38 + mn, 38 + mo, 38 + mp, 38 + mq, 38 + mr, 38 + ms, 38 + mt, 38 + mu, 38 + mv, 38 + mw, 38 + mx, 38 + my, 38 + mz, 38 + na, 38 + nb, 38 + nd, 38 + ne, 38 + nf, 38 + ng, 38 + nh, 38 + ni, 38 + nj, 38 + nk, 38 + nl, 38 + nm, 38 + nn, 38 + no, 38 + np, 38 + nq, 38 + nr, 38 + ns, 38 + nt, 38 + nv, 38 + nw, 38 + nx, 38 + ny, 38 + nz, 38 + oa, 38 + ob, 38 + oc, 38 + od, 38 + oe, 38 + of, 38 + og, 38 + oh, 38 + oi, 38 + oj, 38 + ok, 38 + ol, 38 + om, 38 + on, 38 + oo, 38 + op, 38 + oq, 38 + or, 38 + os, 38 + ot, 38 + ou, 38 + ov, 38 + ow, 38 + ox, 38 + oy, 38 + oz, 38 + pb, 38 + pd, 38 + pe, 38 + pf, 38 + pg, 38 + ph, 38 + pi, 38 + pj, 38 + pk, 38 + pm, 38 + pn, 38 + po, 38 + pq, 38 + pr, 38 + ps, 38 + pt, 38 + pu, 38 + pv, 3 8 + pw, 38 + py, 38 + pz, 38 + qa, 38 + qb, 38 + qc, 38 + qe, 38 + qf, 38 + qg, 38 + qh, 38 + qj, 38 + qk, 38 + ql, 38 + qm, 38 + qn, 38 + qo, 38 + qp, 38 + qq, 38 + qs, 38 + qt, 38 + qu, 38 + qv, 38 + qw, 38 + qx, 38 + qy, 38 + qz, 38 + ra, 38 + rb, 38 + rc, 38 + rd, 38 + re, 38 + rf, 38 + rg, 38 + ri, 38 + rk, 38 + rl, 38 + rm, 38 + rn, 38 + ro, 38 + rr, 38 + rs, 38 + rt, 38 + ru, 38 + rv, 38 + rw, 38 + rx, 38 + rz, 38 + sa, 38 + sc, 38 + sd, 38 + sf, 38 + sh, 38 + si, 38 + sj, 38 + sk, 38 + sl, 38 + sm, 38 + sn, 38 + so, 38 + sp, 38 + sq, 38 + sr, 38 + ss, 38 + st, 38 + su, 38 + sv, 38 + sx, 38 + sy, 38 + sz, 38 + ta, 38 + tb, 38 + tc, 38 + td, 38 + te, 38 + tf, 38 + tg, 38 + th, 38 + ti, 38 + tk, 38 + tl, 38 + tm, 38 + tn, 38 + to, 38 + tp, 38 + tr, 38 + ts.

In such a combination of active ingredients, in combination with the substituted isoxazoline compound represented by the formula (1), specific examples of known active ingredients whose synergistically improving control effect on mites, in particular, are as follows: It is shown in Table 4 below.
Table 4 ――――――――――――――――――― ―――――――――――――――――――
No. Active ingredient name (generic name) No. Active ingredient name (generic name)
―――――――――――――――――――――――――――――――――――――――
ly acekinosyl mm phenazaquin
oa chlorfenapyr mn phenbutatin-oxide
mg Sienopyrafen mv Milbemectin
mh cyflumetofen mw propargite
mk dienochlor mz spirodiclofen
ml etoxazole na spiromesifen ――――――――――――――――――― ―――――――――――――――――――
Further, in such combinations of active ingredients, known active ingredients that, in combination with the substituted isoxazoline compound represented by the formula (1), synergistically improve the control effect on aphids and whiteflies in particular. Specific examples of these are shown in Table 5 below.
Table 5 ――――――――――――――――――― ―――――――――――――――――――
No. Active ingredient name (generic name) No. Active ingredient name (generic name)
―――――――――――――――――――――――――――――――――――――――
nf acephate sh pymetrozine
ng acetamiprid mx pyridaben
og clothianidin sl Pyrifluquinazone
pb dinotefuran st spirotetramate
pm ethiprole sv sulfoxaflor
pw flonicamid te thiacloprid
qn imidacloprid tf thiamethoxam
rk Nitenpyram tk Torfenpyrad------------------------
Furthermore, in such combinations of active ingredients, specific examples of known active ingredients whose synergistic improvement in the control effect against the tobacco tobacco is obtained by combining with the substituted isoxazoline compound represented by the formula (1) These are shown in Table 6 below.
Table 6 ―――――――――――――――――――― ―――――――――――――――――――
No. Active ingredient name (generic name) No. Active ingredient name (generic name)
―――――――――――――――――――――――――――――――――――――――
ne Abamectin pf Emamectin benzoate
nf acephate py fulvendiamide
nm bacillus thuringiensis qc flufenoxuron
nz Chloranthraniprolol qq Indoxacarb-MP
oa chlorfenapyr qu lepimectin
of Chromafenozide rc Mesomil
oh Cyantraniprolol rs Permethrin
on lambda-cyhalothrin sk pyridalyl
oo cypermethrin sr spinetoram
ou Deltamethrin ss Spinosad ――――――――――――――――――――――――――――――――――――――――
A suitable mixing ratio of the substituted isoxazoline compound represented by the formula (1) and the compound selected from the active ingredient group A in the composition of the present invention and the method of the present invention is 1 weight of the compound represented by the formula (1). The amount selected from the active ingredient group A is usually 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, and more preferably 0.1 to 10 parts by weight.

  The preferred treatment amount of the active ingredient in the composition of the present invention and the method of the present invention depends on the type of target pest to be controlled, etc., but usually the substituted isoxazoline compound represented by the formula (1) is 0.1 to 1000 ga. i./ha, the active ingredient group A is selected from 0.1 to 1000 ga.i./ha, preferably the compound represented by the formula (1) is 1 to 300 ga.i./ha. One selected from the active ingredient group A is 1 to 300 ga.i./ha.

  The composition of the present invention and the method of the present invention have various adverse effects in human living environments such as so-called agricultural pests and agricultural diseases that damage agricultural and horticultural crops and trees, so-called livestock pests parasitic on livestock and poultry, and houses. Effectively applied to pest control of so-called sanitary pests, so-called stored-grain pests that harm grains stored in warehouses, and mites, crustaceans, molluscs, nematodes that occur and harm in similar situations it can. Specific examples of insects, ticks, crustaceans, mollusks, nematodes and diseases that can be controlled using the composition or the method of the present invention include those shown below. The target pests of the inventive composition and the method of the present invention are not limited to these.

Pests include Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholitamagnan ima, Mona ), Leguminous moth (Leguminivora glycinivorella), bean sprout (Matsumuraeses phaseoli), Pandemis heparana, prickly moth (Bucculatrix pyrivorella), peach leaf moth (Lyonetia clerkella), olimon malt moth , Golden moth (Phyllonorycter ringoniella), citrus green moth (Phyllocnistis citrella), green moth (Acrolepiopsis sapporensis), wild moth (Acrolepiopsis suzukiella), black moth (Plutella xylostella), oyster leaf moth (Stathmop) oda masinissa, Bombyx moth (Helcystogramma triannulella), Cotton beetle (Pectinophora gossypiella), Peachinophorus (Carposina niponensis), Cydlinga pomonella, Paratha lepida, Chinal suppressor cis (Chilo suppressalis) Common moth (Conogethes punctiferalis), Cotton moth (Diaphania indica), White-faced tiger moth (Elasmopalpus lignosellus), White-faced tiger moth (Etiella zinckenella), Glyphodes pyloalis, Nymalia dal furnacalis), Apricot scapulalis, European corn borer (Ostrinia nubilalis), Shibata toga (Parapediasia teterrella), Parnara guttata, Pieris brassica e), white butterfly (Pieris rapae crucivora), mugwort duck (Ascotis selenaria), soy bean looper (Pseudoplusia includens), Chadokuga (Euproctis pseudoconspersa), gypsy moth (Lymantria dispar), yellow croaker (Orgyia thyella) , Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigno, Autographa nigrisigno, Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea), Tobacco bud worm (Heliothis virescens), Mamestra brassicae, Naranga aenescens, Ayayoto (Pseudaletia sep) arata, Southern army worm (Spodoptera eridania), Shirooptera exigua, Fall army worm (Spodoptera frugiperda), Cotton leaf worm (Spodoptera littoralis), Spodoptera litura, Spodoptera litura, Spodoptera pitura, Spodoptera era ni), grapeberry moss (Endopiza viteana), tomato horn worm (Manduca quinquemaculata), tobacco horn worm (Manduca sexta) and other Lepidoptera insects,
Thrips thrips (Frankliniella intonsa), Thrips thrips (Frankliniella occidentalis), Black thrips (Trips thrips) The Thysanoptera insect,
Douganebububu (Anomala cuprea), Japanese common squirrel (Anomala rufocuprea), Coreo hanamuri (Gametis jucunda), Nagapakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineata) Shimetsutsuki (Melanotus tamsuyensis), Tobacco beetle (Lasioderma serricorne), Himetaketakekisui (Epuraea domina), Common beetle (Epilachna varivestis), Onijuya vigintioctomaculna, Vitus Tenebrio molitor, Tribolium castaneum, Anoplophora glabripennis, Anoplophora malasiaca, Monochamumukiri (Monochamukiri) s alternatus, yellowtail beetle (Psacothea hilaris), grape beetle (Xylotrechus pyrrhoderus), cucumber beetle (Aulacophora femoralis), aphid beetle (Chaetocnema concinna), southern corn rootworm (Diabrotica undecimpunctata), western corn rotworm ), Northern corn rootworm (Diabrotica barberi), rice beetle (Oulema oryzae), killer whale beetle (Phyllotreta striolata), nasal beetle (Psylliodes angusticollis), cotton weevil (Anthonomus grandis), chinchu weevil (oso bruchu) (Craphognatus leucoloma), weevil (Cylas formicarius), weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), rice weevil Lissohoptrus oryzophilus, horned weevil (Otiorhynchus sulcatus), peach beetle weevil (Rhynchites heros), granary weevil (Sitophilus granarius), beetle weevil (Sitophilus zeamais), moth veterinary moth (Sphenophilus zeamais) Coleoptera insects such as Paederus fuscipes)
Spotted beetle (Dolycoris baccarum), sea turtle (Eurydema rugosa), bark beetle (Eysarcoris aeneus), beetle beetle (Eysarcoris lewisi), white beetle (Eysarcoris ventralis), subtilus , Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, tiger p Stink bugs (Leptocorisa chinensis), Rasptortus clavatus, Red beetle bugs (Rhopalus msculatus), Blissus leucopterus, Cavelerius saccharivorus, Cavelerius saccharivorus Memushi (Togo hemipterus), red beetle bug (Dysdercus cingulatus), azalea (Stephanitis pyrioides), black beetle turtle (Halticus insularis), sandy beetle turtle (Lygus lineolaris), natus moth beetle (Stenodema tusno tusric) , Rice gossip turtle (Trigonotylus caelestialium), white-spotted leafhopper (Arboridia apicalis), green-winged leafhopper (Balclutha saltuella), butterfly leafhopper (Epiacanthus stramineus), potato leaf hopper (Empoasca fabae), leaf-hopper ), Chanomidori Himebai (Empoasca onukii), Mamenomidori Himekobai (Empoasca sakaii), Himejiten Tennokami (Macrosteles striifrons), Sun Leafhopper (Nephotettix cinctinceps), Cotton Free Hopper (Psuedatomoscelis seriatu s), brown planthopper (Laodelphax striatella), brown planthopper (Nilaparvata lugens), white planthopper (Sogatella furcifera), citrus leaf killer (Diaphorina citri), pear lice (Psylla pyrisuga), citrus white moth (Al) Whiteflies (Bemisia tabaci), Citrus whiteflies (Dialeurodes citri), Onsite whiteflies (Trialeurodes vaporariorum), Grape aphids (iteus vitifolii), Cotton aphids (Aphis gossypii), Snowflies (Aphis spiraecos), Moa Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Planococcus citri), Fujicona scale insect (Planococcus kuraunhiae), stag beetle scale (Pseudococcus comstocki), horn beetle (Ceroplastes ceriferus), ruby rot beetle (Ceroplastes rubens), red beetle scale (Aonidiella aurantii) peridium scale theae), Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Exis yanim Hemiptera insect,
Soybean flies (Asphondylia yushimai), mud fly (Sitodiplosis mosellana), Mexican fruit fly (Anastrepha ludens), fruit fly (Bactrocera cucurbitae), citrus fruit fly (Bactrocera dorsalis), green leaf fly (Ceritis flies) Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Scarlet fly (Liriomyza bryoniae), Scarlet fly (Liriomyza chinensis), Tomato leaflet (Liriomyza flies) (Liriomyza flies) platura), sugar beet fly (Pegomya cunicularia), apple magot (Rhagoletis pomonella), hessian fly (Mayetiola destructor), house fly (Musca domestica), sand flies (Stomoxys calcitrans) , Sheep flies (Melophagus ovinus), cattle flies (Hypoderma bovis), mosquito flies (Hypoderma lineatum), sheep flies (Oestrus ovis), tsetse flies (Glossina palpalis, Glossina morsitans), prosimulium tributa (Prosimulium matozous) albipunctatus), Toepanaganukaka (Leptoconops nipponensis), Culex pipiens pallens, Aedes aegypti, Aedes albopicutus, Aphididae (Anopheles hyracanus sinesis)
Bumblebee (Apethymus kuri), Arrange pagana, Sedge bee (Athalia infumata), Bee (Athalia rosae), Bee (Neodiprion sertifer), Dryocosmus kuriphilelli, E Hymenoptera insects such as Camponotus japonicus, Vespa mandarina, Argentine ant (Linepithema humile), Pharaoh ant (Monomorium pharaonis), Bulldock ant (Myrmecia spp.), Fire ant (Solenopsis spp.),
Orthogonal insects such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, Sistocerca gregaria, etc.,
Blattaria insects such as black cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica), German cockroach (Blattella germanica),
Isoptera insects such as the termite (Coptotermes formosanus), the white termite (Cryptotermes domesticus), the American white termite (Incisitermes minor), the white termite (Reticulitermes speratus), the white termite (Odontotermes formosanus),
Collembola insects such as Onychiurus folsomi, Onychiurus sibiricus, Bourletiella hortensis,
Siphonaptera insects such as the catfish (Ctenocephalides canis), the cat flea (Ctenocephalides felis), the chicken flea (Echidnophaga gallinacea), the human flea (Pulex irritans), and the Xenopsylla cheopis
Cuclotogaster heterographa, cow lice (Damalinia bovis), wolffish lice (Goniodes dissmilis), blue wings (Goniodes gallinae), bald wings (Goniodes gigas), chicken wings , Insects such as Menacanthus pallidulus, Menacanthus stramineus, Mennopon gallinae, Trichodectes canis etc.,
Bovine lice (Haematopinus eurysternus, Haematopinus quadripertusus), pig lice (Haematopinus suis), buffalo lice (Haematopinus tuberculatus), dog lice (Linognathus setosus), bovine white lice (Linognathus vituri), capsicum ura
Dust mites such as cyclamen dust mite (Phytonemus pallidus), chano dust mite (Polyphagotarsonemus latus), sword butterfly mite (Tarsonemus bilobatus),
Spider mites (Penthaleus erythrocephalus), wheat mites (Penthaleus major), etc.
Spider mites such as rice spider mite (Oligonychus shinkajii), citrus spider mite (Panonychus citri), blue spider mite (Panonychus mori), apple spider mite (Panonychus ulmi), kanzawa spider mite (Tetranychus kanzawai), spider mite (Tetranychus urticae), etc.
Chinese cabbage mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), Tomato rust mite (Aculops lycopersici), Citrus radix (Aculops pelekassi), Apple rust mite (Aculus schlechtendali), Green rust mite (Eriophyes chitrastrostrum) )
Acarid mites such as Robin tick (Rhizoglyphus robini), Stag beetle (Tyrophagus putrescentiae), Spinach Scarlet mite (Tyrophagus similis),
Bee mites such as honeybee mite (Varroa jacobsoni),
Lone star tick (Amblyomma americanum), Gulf of Mexico tick (Amblyomma maculatum), Boophilus microplus, Rocky Mountain tick (Dermacentor andersoni), West Coast tick (Dermacentor occidentalis), American dog tick (Dermacentor variabilis) tick (Haemaphysalis campanulata), yellow tick (Haemaphysalis flava), white tick (Haemaphysalis longicornis), white tick (Haemaphysalis megaspinosa), red tick (Ixodes nipponensis), tick tick (Ixodes ovatus) (Ixodes ricinus), black tick (Ixodes scapularis), red tick (Ornithodoros moubata pacifcus), tick such as Rhipicephalus sanguineus,
Crawfish ticks (Cheyletiella blakei), rabbit ticks (Cheyletiella parasitovorax), crayfish ticks (Cheyletiella yasguri), etc.
Acne mites, such as Inodecarid mites (Demodex canis), Caterpillar mites (Demodex cati),
Cucumber mites such as bovine cucumber mite (Psoroptes cummunis), rabbit cucumber mite (Psoroptes cuniculi), sheep cucumber mite (Psoroptes ovis),
Hymenid mites, such as Choriotes boris, Caterpillar mite (Notoedres cati), Otodectes cynotis, Sarcoptes scabiei, etc.,
Tsutsugamushi, such as Miyagata pine tsutsugamushi (Helenicula miyagawai), red tsutsugamushi (Leptotrombidium akamushi), hornet tsutsugamushi (Leptotrombidium pallida), scallop (Leptotrombidium scutellare),
Mite mite such as house mite (Ornithonyssus bacoti), avian mite (Ornithonyssus sylviarum),
Acarid mites such as the chicken mite (Megninia cubitalis) and the mite mite (Pterolichus obtusus),
Crustaceans such as Armadillidium vulgare,
Gastropods such as Pomacea canaliculata, African mussel (Achatina fulica), Slug (Meghimatium bilineatum), Chaukoura slug (Limax marginatus), Uskawamai (Acusta despecta sieboldiana), Mishamai mai (Euhadra peliomphala)
Southern nematode nematode (Prathylenchus coffeae), Red beetle nematode (Prathylenchus penetrans), Luminous nematode (Prathylenchus vulnus), Potato cyst nematode (Globodera rostochiensis), Soy cyst nematode (Heterodera eus) Nematodes such as root-knot nematodes (Meloidogyne incognita), rice-spotted nematodes (Aphelenchoides besseyi), and pine wood nematodes (Bursaphelenchus xylophilus).

  On the other hand, diseases include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), wheat powdery mildew (Erysiphe graminis f.sp.hordei, f.sp. .tritici), leafy leaf disease (Pyrenophoragraminea), net leaf disease (Pyrenophora teres), leaf blight (Gibberella zeae), rust disease (Puccinia striiformis, P.graminis, P.recondita, P.hordei), snow rot ( Tipula sp., Micronectriella nivais), Bare Scab (Ustilago tritici, U.nuda), Eye spot (Pseudocercosporella herpotrichoides), Cloud disease (Rhynchosporium secalis), Leaf blight (Septoria tritici), Blight (Leptosphaeria nodorum), Citrus sunspot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitalum, P.italicum), apple monilia (Selerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera) lcucotricha), spotted leaf disease (Alternaria mali) , Black streak (Venturia inaequalis), pear black streak (Venturia nashicola), black spot (Alternaria kikuchiana), red streak (Gymnosporangium haracanum), peach streak (Sclerolinia cinerea), black streak (Cleadosporium carpophilum), fomo Rot (Phomopsis sp.), Grape downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), oyster Anthracnose (Gloeosporium kakj), deciduous leaf disease (Cercospora kakj, Mycosphaerella nawae), downy mildew (Pseudoperenospora cubensis), anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight Mycosphaerella melonis), plague of tomatoes (Phytophthora infestans), ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), brown rot of eggplant (Phomopsis vexans), powdery mildew (Erysiphe cichora) coarum), cruciferous vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae), leek rust (Puccinia allii), soybean purple spot (Cercospora kikuchii), black scab (Elsinoe glycines), sunspot (Diaporthe phaseololum), bean anthracnose (Colletotrichum lindemuthianum), black peanut (Mycosphaerella personatum), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), potato summer plague (Alternaria solani) ), Strawberry powdery mildew (Sphaerotheca humuli), tea net blast (Exobasidium reticulatum), white star disease (Elsinoe leucospila), tobacco red star disease (Alternaria lingipes), powdery mildew (Erysiphe cichoracearum), anthracnose ( Colletotrichum tabacum), sugar beet brown spot (Cercospora beticola), rose black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum brown spot (Septoria ch rysanthemiindici), white rust (Puccinia horiana), various crops of gray mold (Botrytis cinerea) and various crops of mycosis (Sclerotinia sclerotiorum).

  That is, the composition of the present invention and the method of the present invention are extremely effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, or pyrethroid compounds, Eyes (Lepidoptera), common moths (Thysanoptera), Coleoptera (Coleoptera), Hemiptera (Hymenoptera and Hemiptera), Diptera (Flyes), Hymenoptera (Hymenoptera), Straight Insects, ticks, such as eyes (Grasshoppers), reticulates (Roaches), isoptera (Termites), slime (Coleoptera), relics (Fleas), lice and lice It is possible to effectively control pests belonging to crustaceans, gastropods, nematodes and the like at low concentrations. On the other hand, the composition of the present invention and the method of the present invention are extremely useful for mammals, fish, crustaceans, and beneficial insects (natural insects such as honeybees, bumblebees, and other natural enemies such as honeybees, wasps, mistletoe flies, mosquitoes, and tick mites). It has useful features with few adverse effects.

  When the substituted isoxazoline compound represented by the formula (1) and the active ingredient shown in Table 3 above are combined, the composition of the present invention and the method of the present invention are particularly effective against mites and hemipods. Although it has an excellent synergistic effect, it exhibits a better synergistic effect on mites, such as citrus mite, urticae, and kanzawa spider mites, and aphids and whiteflies among the Hemiptera pests.

  The composition of the present invention and the method of the present invention can be effectively applied to the control of endoparasites such as livestock, poultry and pets. Specific examples of endoparasites that can be controlled using the composition of the present invention or the method of the present invention include, but are not limited to, those shown below.

Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Esphagostomum Genus (Oesophagostomum), Chabertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis ), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxacaris, Parascaris, and other nematodes ,
Filariidae nematodes such as Wuchereria, Blueia, Onchoceca, Dirofilaria, Loa
Dracunculidae nematodes such as the genus Deacunculus,
Dogworms (Dipylidium caninum), caterpillars (Taenia taeniaeformis), rodents (Taenia solium), striped tapeworms (Taenia saginata), contracted tapeworms (Hymenolepis diminuta), Beneden tapeworms (Moniezia benedeni), Tapeworms such as Diphyllobothrium latum, Manson cleftworm (Diphyllobothrium erinacei), Echinococcus granulosus, Echinococcus multilocularis,
Fasciola hepatica (F. gigantica), Westermann lung fluke (Paragonimus westermanii), hypertrophic fluke (Fasciolopsic bruski), pancreatic fluke (Eurytrema pancreaticum, E. coelomaticum), liver fluke (Clonorchis sinensis), Schistosoma Schistosoma japonicum), Schistosoma haematobium, Schistosoma mansoni, etc.,
Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria bovis Eimeria spp., Such as Eimeria ovinoidalis,
Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia (Giardia spp.), Toxoplasma spp., Entamoeba histolytica, Theileria spp. And the like.

  In using the composition of the present invention as an agrochemical, one or more selected from the substituted isoxazoline compound represented by the formula (1) and a salt thereof, and one or more selected from the active ingredient group A are used. Can be used as a mixture as is, but usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreeze agent, binder, caking agent Add inhibitors, disintegrants, antifoaming agents, antiseptics and anti-decomposition agents, etc., solubilize soluble emulsion, emulsifiable concentrate, wettable powder, water soluble powder, Granule wettable powder (water dispersible granule), water soluble granule (suspension concentrate), emulsion (concentrated emulsion), suspoemulsion (suspoemulsion), microemulsion (microemulsion) In addition, it can be put to practical use in preparations of any dosage form such as dustable powder, granule, tablet, and emulsifiable gel. Further, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.

  Examples of the solid carrier include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, siegrite, and allophane. Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example, calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay and calcined diatomaceous earth Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such as tobacco stalks, fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.) and fertilizers.

Examples of the liquid carrier, such as xylene, alkyl (C ₉ or C _10, etc.) benzene, phenylxylylethane and alkyl (C ₁ or C _3, etc.) aromatic hydrocarbons such as naphthalene, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, Ethers such as pyrene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and γ-butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialkyl esters of glutamic acid, Esters such as adipic acid dialkyl ester and phthalic acid dialkyl ester, acid amides such as N-alkyl (C ₁ , C ₈ or C ₁₂ ) pyrrolidone, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil Oils and fats, dimethyl sulfoxide and water.

  These solid and liquid carriers may be used alone or in combination of two or more.

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, Killsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfonate, salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxy Ethylene (mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg polyacrylate, polymaleate and Copolymers of maleic acid and olefins, etc.) and anionic surfactants such as polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, amino acid types and beties Amphoteric surfactants such as mold, and silicone-based surfactants and fluorinated surfactants.

  The content of these surfactants is not particularly limited, but a range of 0.05 to 20 parts by weight is usually desirable with respect to 100 parts by weight of the preparation of the composition of the present invention. These surfactants may be used alone or in combination of two or more.

  The dosage of the composition of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally 0.005 to 50 kg per hectare (ha) is appropriate as the amount of active ingredient.

  Next, formulation examples of preparations when using the composition of the present invention are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight, and “active ingredient” is a generic name for the substituted isoxazoline compound represented by the formula (1) and salts thereof and those selected from the active ingredient group A.

[Wettable powder]
Active ingredient 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts Others include, for example, anti-caking agents and decomposition inhibitors.

[Milk]
Active ingredient 0.1-30 parts Organic solvent 45-95 parts Surfactant 4.9-30 parts Water 0-50 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors, and the like.

[Suspension]
Active ingredient 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, antifreezing agents, thickeners and the like.

[Granule wettable powder]
Active ingredient 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.

(Liquid)
Active ingredient 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.

[Granule]
Active ingredient 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts Others include, for example, binders, decomposition inhibitors and the like.

[Dust]
Active ingredient 0.01-30 parts Solid support 65-99.99 parts Others 0-5 parts Others include, for example, drift inhibitors and decomposition inhibitors.

  Next, although the formulation example which uses this invention composition as an active ingredient is shown more concretely, this invention is not limited to these.

  In the following formulation examples, “parts” means parts by weight.

[Formulation Example 1] Wetting Agent Compound No. 23 10 parts active ingredient no. sd 10 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound No. 06 3 parts active ingredient no. ms 2 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 15 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.

[Composition Example 3] Emulsion Compound No. 04 2 parts active ingredient no. sr 2 parts DBE 36 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name of INVISTA)
Isobutyl adipate 30 parts N-methylpyrrolidone 10 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
6 parts of rhodacal 70BC (anionic surfactant: Rhodia brand name)
The above is uniformly mixed to obtain an emulsion.

[Composition Example 4] Emulsion Compound No. 16 2 parts active ingredient no. ps 2 parts DBE 11 parts (mixture of dimethyl adipate, dimethyl glutarate, dimethyl succinate: trade name of INVISTA)
Isobutyl adipate 30 parts N-methylpyrrolidone 5 parts Soprophor BSU 14 parts (Nonionic surfactant: Rhodia trade name)
6 parts of rhodacal 70BC (anionic surfactant: Rhodia brand name)
Propylene glycol 10 parts Water 20 parts or more are mixed uniformly to make an emulsion.

[Formulation Example 5] Suspension Compound No. 03 15 parts active ingredient no. md 10 parts Agrisol S-710 10 parts (nonionic surfactant: trade name of Kao Corporation)
Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name)
Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.

[Composition Example 6] Granule wettable powder Compound No. 32 40 parts active ingredient no. nd 35 parts Haitenol NE-15 5 parts (anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 7] Granule compound No. 15 3 parts active ingredient no. nc 2 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to form granules.

[Composition Example 8] Powder Compound No. 29 2 parts active ingredient no. mx 1 part Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts or more uniformly mixed and pulverized to obtain a powder.

  In use, each of the above preparations is diluted 1 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha).

  On the other hand, when the composition of the present invention is used as a controlling agent for ectoparasites or endoparasites of mammals and birds as domestic animals and pets, 1 selected from substituted isoxazoline compounds represented by the formula (1) and salts thereof Parenteral administration such as oral administration, injection (intramuscular, subcutaneous, intravenous, intraperitoneal), or the like, together with a pharmaceutical additive, the species or two or more species and one or more species selected from the active ingredient group A; Transdermal administration such as immersion, spraying, bathing, washing, pouring-on and spotting-on and dusting; can be administered by nasal administration. The composition of the present invention can also be administered as a molded product using strips, plates, bands, collars, ear marks, limbs / bands, labeling devices, and the like. In administration, any dosage form suitable for the administration route of the composition of the present invention can be used.

  Arbitrary forms to be prepared include solid preparations such as powders, granules, wettable powders, pellets, tablets, large pills, capsules, molded products containing active compounds; injection solutions, oral solutions, skin Liquid preparations used above or in body cavities; solution preparations such as pour-on, spot-on, flowable, and emulsion; semi-solid preparations such as ointments and gels.

  The solid preparation can be used mainly for oral administration or diluted with water for transdermal administration or environmental treatment. The solid preparation contains one or more selected from the substituted isoxazoline compound represented by the formula (1) and a salt thereof, and one or more selected from the active ingredient group A, if necessary. Can be prepared by mixing with suitable excipients and changing to the desired shape. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, cellulose, crushed grains, and starches.

  The injectable solution can be administered intravenously, intramuscularly and subcutaneously. The injectable solution is one or more selected from the substituted isoxazoline compound represented by the formula (1) and a salt thereof, and active ingredient group A. One or more selected from the above can be dissolved in a suitable solvent and, if necessary, prepared by adding additives such as solubilizers, acids, bases, buffer salts, antioxidants and protective agents. . Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like. Examples of solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester. Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester and n-butanol.

  Oral solutions can be administered directly or diluted. It can be prepared in the same manner as an injectable solution.

  Flowables, emulsions, etc. can be administered directly or diluted transdermally or by environmental treatment.

  Solutions for use on the skin can be administered by dripping, spreading, rubbing, spraying, spraying or applying by dipping (dipping, bathing or washing). These solutions can be prepared in the same manner as injection solutions.

  Pour-on and spot-on agents are selected from substituted isoxazoline compounds represented by the formula (1) and salts thereof by dropping or spraying on a limited area of the skin. 1 type or 2 types or more selected from active ingredient group A can be immersed in the skin and allowed to act systemically. Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers and adhesives may be added.

  Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, acetone, Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxymethylene-1,3 -Dioxolane. Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides and fatty alcohols. Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.

  The emulsion can be administered orally, transdermally or as an injection. The emulsion comprises one or more selected from the substituted isoxazoline compound represented by the formula (1) and a salt thereof and one or more selected from the active ingredient group A in a hydrophobic phase or hydrophilicity. Dissolve in the phase and homogenize it with other phase solvents with appropriate emulsifiers, if necessary, with further aids such as colorants, absorption enhancers, protectants, antioxidants, sunscreens and thickeners Can be prepared.

As hydrophobic phase (oil), paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain esters of saturated fatty acids shaped for short chain length fatty acids and chain length _C 16 _{-C 18,} isopropyl myristate, caprylic / capric acid esters of saturated fatty alcohols of isopropyl palmitate, chain length _C 12 _{-C 18,} isopropyl stearate Oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol, oleyl alcohol It is below.

  Examples of the hydrophilic phase include water, propylene glycol, glycerin, and sorbitol.

  Emulsifiers include nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc. Activating agents; amphoteric surfactants such as disodium N-lauryl β-iminodipropionate and lecithin; anionic properties such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate Surfactant; Cationic surfactants such as cetyltrimethylammonium chloride are listed.

  Various adjuvants can be further contained in the composition of the present invention. Examples of auxiliary agents that can be used include thickeners, organic solvents, antifreezing agents, antifoaming agents, antibacterial and antifungal agents, coloring agents, and the like.

  The thickening agent is not particularly limited, and organic, inorganic natural products, synthetic products and semi-synthetic products can be used. For example, heteropolysaccharides such as xanthan gum (xanthan gum), welan gum and rhamzan gum, polyvinyl alcohol, polyvinyl Water-soluble polymer compounds such as pyrrolidone, polyacrylic acid, sodium polyacrylate and polyacrylamide, cellulose derivatives such as methylcellulose, carboxymethylcellulose, carboxyethylcellulose, hydroxyethylcellulose and hydroxypropylcellulose, montmorillonite, saponite, hectorite, bentonite and laponite And smectite clay minerals such as synthetic smectites. These thickeners may be used alone or in combination of two or more, and the ratio in the case of mixing can be freely selected. These thickeners may be added as they are, or those previously dispersed in water may be added. Moreover, content in this invention composition can also be selected freely.

  As the antifreezing agent, for example, ethylene glycol, diethylene glycol, propylene glycol, glycerin and the like can be used. Preferred are propylene glycol and glycerin. Moreover, content in this invention composition can also be selected freely.

  Other adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, a copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.

  Semi-solid preparations can be administered by application on the skin or spreading or introduction into body cavities. Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.

  Further, an antifoaming agent such as a silicone emulsion, an antibacterial and antifungal agent, a coloring agent, and the like may be blended.

[Test example]
Next, in order to clarify the usefulness of the present invention, it will be specifically described in the following efficacy test examples, but the present invention is not limited thereto.

[Test Example 1] Efficacy test against the spider mite The compound described in Table 1 above and the active ingredient described in Table 4 above are each 10% emulsion (25% wettable powder depending on the compound). A pharmaceutical solution having a predetermined concentration was prepared by diluting the formulation with water containing a spreading agent. Next, the cut kidney beans (about 5 mm × 5 mm) were placed on a moist filter paper, and then 10 adult spider mites were inoculated per leaf piece. The prepared test leaf pieces were each sprayed with 5 ml of a chemical solution of a predetermined concentration, air-dried and covered with a hole, and stored in a thermostatic chamber at 25 ° C. so that the leaf pieces did not dry. The number of dead insects after 4 days was investigated, and the dead insect rate was calculated from the following formula. The test was conducted in a two-ward system.

Mortality (%) = dead insects / test insects x 100
The synergy was calculated from the mortality rate for each chemical concentration using the Colby method (Colby SR 1976, Weeds 15, 20-22). The calculation method is as follows.

E = X + Y-XY / 100
X: observed value of agent A at x concentration (death rate)
Y: Observed value of B agent at y concentration (death rate)
E: Expected death rate during mixing of agent A and agent B
The obtained result is analyzed as a synergistic action if the observed value is larger than the expected value, an antagonistic action if the expected value is larger than the observed value, and an additive action if the observed value is the same as the expected value. Table 7 shows combinations showing synergistic effects.
Table 7 ――――――――――――――――――――――――――――――――――
Active ingredient Concentration (ppm) Death rate (%)
――――――――――――――――――――――――――――――――――
Compound No. 3 50 45
Compound No. 4 10 45
Compound No. 5 10 55
Compound No. 6 50 35
Compound No. 8 10 55
Compound No. 9 50 45
Compound No. 10 10 60
Compound No. 15 10 45
Compound No. 16 50 35
Compound No. 23 50 30
Compound No. 29 50 25
Compound No. 32 10 55
Compound No. 33 10 50
Compound No. 36 10 40
Compound No. 37 10 35
Compound No. 38 10 50
Active ingredient ly 1 65
Active ingredient oa 1 60
Active ingredient pf 1 60
Active ingredient mg 2 55
Active ingredient mh 2 50
Active ingredient mx 3 65
Active ingredient ml 50 0
Active ingredient mm 1 40
Active ingredient mn 20 30
Active ingredient mv 1 55
Active ingredient mw 15 45
Active ingredient mz 50 60
Active ingredient na 50 45
Compound No.3 + active ingredient ly 50 + 1 90
Compound No.3 + active ingredient oa 50 + 1 85
Compound No.3 + active ingredient pf 50 + 1 85
Compound No.3 + active ingredient mg 50 + 2 90
Compound No.3 + active ingredient mh 50 + 2 90
Compound No. 3 + active ingredient mx 50 + 3 100
Compound No.3 + active ingredient ml 50 + 50 55
Compound No.3 + active ingredient mm 50 + 1 75
Compound No.3 + active ingredient mn 50 + 20 70
Compound No.3 + active ingredient mv 50 + 1 85
Compound No.3 + active ingredient mw 50 + 15 75
Compound No. 3 + active ingredient mz 50 + 50 90
Compound No.3 + active ingredient na 50 + 50 80
Compound No. 4 + active ingredient ly 10 + 1 100
Compound No.4 + active ingredient oa 10 + 1 100
Compound No.4 + active ingredient pf 10 + 1 80
Compound No.4 + active ingredient mg 10 + 2 95
Compound No.4 + active ingredient mh 10 + 2 100
Compound No. 4 + active ingredient mx 10 + 3 100
Compound No.4 + active ingredient ml 10 + 50 60
Compound No.4 + active ingredient mm 10 + 1 100
Compound No. 4 + active ingredient mn 10 + 20 100
Compound No. 4 + active ingredient mv 10 + 1 90
Compound No.4 + active ingredient mw 10 + 15 95
Compound No. 4 + active ingredient mz 10 + 50 100
Compound No.4 + active ingredient na 10 + 50 100
Compound No. 5 + active ingredient ly 10 + 1 100
Compound No.5 + active ingredient oa 10 + 1 95
Compound No.5 + active ingredient pf 10 + 1 100
Compound No.5 + active ingredient mg 10 + 2 85
Compound No.5 + active ingredient mh 10 + 2 95
Compound No. 5 + active ingredient mx 10 + 3 90
Compound No.5 + active ingredient ml 10 + 50 65
Compound No.5 + active ingredient mm 10 + 1 95
Compound No. 5 + active ingredient mn 10 + 20 80
Compound No.5 + active ingredient mv 10 + 1 100
Compound No.5 + active ingredient mw 10 + 15 100
Compound No. 5 + active ingredient mz 10 + 50 95
Compound No. 5 + active ingredient na 10 + 50 100
Compound No. 6 + active ingredient ly 50 + 1 85
Compound No. 6 + active ingredient oa 50 + 1 80
Compound No. 6 + active ingredient pf 50 + 1 85
Compound No.6 + active ingredient mg 50 + 2 80
Compound No. 6 + active ingredient mh 50 + 2 80
Compound No. 6 + active ingredient mx 50 + 3 90
Compound No. 6 + active ingredient ml 50 + 50 55
Compound No. 6 + active ingredient mm 50 + 1 75
Compound No. 6 + active ingredient mn 50 + 20 60
Compound No. 6 + active ingredient mv 50 + 1 80
Compound No. 6 + active ingredient mw 50 + 15 70
Compound No. 6 + active ingredient mz 50 + 50 80
Compound No. 6 + active ingredient na 50 + 50 75
Compound No. 8 + active ingredient ly 10 + 1 95
Compound No.8 + active ingredient oa 10 + 1 100
Compound No. 8 + active ingredient pf 10 + 1 100
Compound No.8 + active ingredient mg 10 + 2 90
Compound No. 8 + active ingredient mh 10 + 2 100
Compound No. 8 + active ingredient mx 10 + 3 90
Compound No.8 + active ingredient ml 10 + 50 65
Compound No. 8 + active ingredient mm 10 + 1 100
Compound No. 8 + active ingredient mn 10 + 20 80
Compound No. 8 + active ingredient mv 10 + 1 95
Compound No. 8 + active ingredient mw 10 + 15 90
Compound No. 8 + active ingredient mz 10 + 50 100
Compound No. 8 + active ingredient na 10 + 50 95
Compound No. 9 + active ingredient ly 50 + 1 85
Compound No. 9 + active ingredient oa 50 + 1 100
Compound No. 9 + active ingredient pf 50 + 1 95
Compound No. 9 + active ingredient mg 50 + 2 80
Compound No. 9 + active ingredient mh 50 + 2 95
Compound No. 9 + active ingredient mx 50 + 3 85
Compound No. 9 + active ingredient ml 50 + 50 60
Compound No. 9 + active ingredient mm 50 + 1 80
Compound No. 9 + active ingredient mn 50 + 20 85
Compound No. 9 + active ingredient mv 50 + 1 80
Compound No. 9 + active ingredient mw 50 + 15 90
Compound No. 9 + active ingredient mz 50 + 50 95
Compound No. 9 + active ingredient na 50 + 50 80
Compound No. 10 + active ingredient ly 10 + 1 95
Compound No. 10 + active ingredient oa 10 + 1 100
Compound No. 10 + active ingredient pf 10 + 1 100
Compound No.10 + active ingredient mg 10 + 2 100
Compound No. 10 + active ingredient mh 10 + 2 100
Compound No. 10 + active ingredient mx 10 + 3 100
Compound No.10 + active ingredient ml 10 + 50 90
Compound No.10 + active ingredient mm 10 + 1 95
Compound No. 10 + active ingredient mn 10 + 20 100
Compound No.10 + active ingredient mv 10 + 1 100
Compound No. 10 + active ingredient mw 10 + 15 90
Compound No. 10 + active ingredient mz 10 + 50 95
Compound No. 10 + active ingredient na 10 + 50 95
Compound No. 15 + active ingredient ly 10 + 1 100
Compound No.15 + active ingredient oa 10 + 1 95
Compound No.15 + active ingredient pf 10 + 1 100
Compound No.15 + active ingredient mg 10 + 2 100
Compound No.15 + active ingredient mh 10 + 2 80
Compound No. 15 + active ingredient mx 10 + 3 95
Compound No.15 + active ingredient ml 10 + 50 60
Compound No.15 + active ingredient mm 10 + 1 100
Compound No. 15 + active ingredient mn 10 + 20 100
Compound No.15 + active ingredient mv 10 + 1 80
Compound No.15 + active ingredient mw 10 + 15 100
Compound No. 15 + active ingredient mz 10 + 50 100
Compound No.15 + active ingredient na 10 + 50 100
Compound No. 16 + active ingredient ly 50 + 1 90
Compound No.16 + active ingredient oa 50 + 1 80
Compound No.16 + active ingredient pf 50 + 1 80
Compound No.16 + active ingredient mg 50 + 2 80
Compound No.16 + active ingredient mh 50 + 2 85
Compound No. 16 + active ingredient mx 50 + 3 90
Compound No.16 + active ingredient ml 50 + 50 50
Compound No.16 + active ingredient mm 50 + 1 70
Compound No. 16 + active ingredient mn 50 + 20 65
Compound No.16 + active ingredient mv 50 + 1 80
Compound No.16 + active ingredient mw 50 + 15 85
Compound No. 16 + active ingredient mz 50 + 50 80
Compound No. 16 + active ingredient na 50 + 50 75
Compound No.23 + active ingredient ly 50 + 1 85
Compound No.23 + active ingredient oa 50 + 1 80
Compound No. 23 + active ingredient pf 50 + 1 95
Compound No.23 + active ingredient mg 50 + 2 95
Compound No.23 + active ingredient mh 50 + 2 90
Compound No. 23 + active ingredient mx 50 + 3 80
Compound No.23 + active ingredient ml 50 + 50 45
Compound No.23 + active ingredient mm 50 + 1 70
Compound No. 23 + active ingredient mn 50 + 20 75
Compound No.23 + active ingredient mv 50 + 1 75
Compound No. 23 + active ingredient mw 50 + 15 90
Compound No. 23 + active ingredient mz 50 + 50 85
Compound No. 23 + active ingredient na 50 + 50 75
Compound No. 29 + active ingredient ly 50 + 1 100
Compound No. 29 + active ingredient oa 50 + 1 80
Compound No. 29 + active ingredient pf 50 + 1 100
Compound No.29 + active ingredient mg 50 + 2 95
Compound No. 29 + active ingredient mh 50 + 2 95
Compound No. 29 + active ingredient mx 50 + 3 100
Compound No. 29 + active ingredient ml 50 + 50 50
Compound No. 29 + active ingredient mm 50 + 1 85
Compound No. 29 + active ingredient mn 50 + 20 60
Compound No. 29 + active ingredient mv 50 + 1 80
Compound No. 29 + active ingredient mw 50 + 15 100
Compound No. 29 + active ingredient mz 50 + 50 75
Compound No. 29 + active ingredient na 50 + 50 90
Compound No. 32 + active ingredient ly 10 + 1 90
Compound No.32 + active ingredient oa 10 + 1 100
Compound No.32 + active ingredient pf 10 + 1 95
Compound No.32 + active ingredient mg 10 + 2 85
Compound No.32 + active ingredient mh 10 + 2 85
Compound No. 32 + active ingredient mx 10 + 3 90
Compound No.32 + active ingredient ml 10 + 50 95
Compound No.32 + active ingredient mm 10 + 1 100
Compound No. 32 + active ingredient mn 10 + 20 100
Compound No.32 + active ingredient mv 10 + 1 100
Compound No.32 + active ingredient mw 10 + 15 100
Compound No. 32 + active ingredient mz 10 + 50 100
Compound No. 32 + active ingredient na 10 + 50 100
Compound No. 33 + active ingredient ly 10 + 1 100
Compound No.33 + active ingredient oa 10 + 1 100
Compound No.33 + active ingredient pf 10 + 1 95
Compound No.33 + active ingredient mg 10 + 2 90
Compound No. 33 + active ingredient mh 10 + 2 85
Compound No. 33 + active ingredient mx 10 + 3 95
Compound No.33 + active ingredient ml 10 + 50 60
Compound No.33 + active ingredient mm 10 + 1 100
Compound No. 33 + active ingredient mn 10 + 20 95
Compound No.33 + active ingredient mv 10 + 1 100
Compound No. 33 + active ingredient mw 10 + 15 90
Compound No. 33 + active ingredient mz 10 + 50 95
Compound No.33 + active ingredient na 10 + 50 100
Compound No. 36 + active ingredient ly 10 + 1 100
Compound No. 36 + active ingredient oa 10 + 1 100
Compound No. 36 + active ingredient pf 10 + 1 90
Compound No. 36 + active ingredient mg 10 + 2 80
Compound No. 36 + active ingredient mh 10 + 2 80
Compound No. 36 + active ingredient mx 10 + 3 90
Compound No.36 + active ingredient ml 10 + 50 70
Compound No. 36 + active ingredient mm 10 + 1 100
Compound No. 36 + active ingredient mn 10 + 20 100
Compound No. 36 + active ingredient mv 10 + 1 100
Compound No. 36 + active ingredient mw 10 + 15 100
Compound No. 36 + active ingredient mz 10 + 50 100
Compound No. 36 + active ingredient na 10 + 50 100
Compound No. 37 + active ingredient ly 10 + 1 95
Compound No.37 + active ingredient oa 10 + 1 95
Compound No.37 + active ingredient pf 10 + 1 100
Compound No.37 + active ingredient mg 10 + 2 100
Compound No.37 + active ingredient mh 10 + 2 100
Compound No. 37 + active ingredient mx 10 + 3 100
Compound No.37 + active ingredient ml 10 + 50 100
Compound No.37 + active ingredient mm 10 + 1 100
Compound No. 37 + active ingredient mn 10 + 20 100
Compound No.37 + active ingredient mv 10 + 1 100
Compound No. 37 + active ingredient mw 10 + 15 100
Compound No. 37 + active ingredient mz 10 + 50 100
Compound No. 38 + active ingredient na 10 + 50 95
Compound No. 38 + active ingredient ly 10 + 1 95
Compound No. 38 + active ingredient oa 10 + 1 95
Compound No. 38 + active ingredient pf 10 + 1 90
Compound No.38 + active ingredient mg 10 + 2 100
Compound No.38 + active ingredient mh 10 + 2 100
Compound No. 38 + active ingredient mx 10 + 3 100
Compound No.38 + active ingredient ml 10 + 50 80
Compound No. 38 + active ingredient mm 10 + 1 100
Compound No. 38 + active ingredient mn 10 + 20 100
Compound No.38 + active ingredient mv 10 + 1 100
Compound No. 38 + active ingredient mw 10 + 15 100
Compound No. 38 + active ingredient mz 10 + 50 100
Compound No. 38 + active ingredient na 10 + 50 100
――――――――――――――――――――――――――――――――――
[Test Example 2] Efficacy test against peach aphid Each of the compounds listed in Table 1 and the compounds listed in Table 5 were each 10% emulsion (25% wettable powder depending on the compound). The formulation was diluted with water containing a spreading agent to prepare a chemical solution having a predetermined concentration. Next, after putting the cut kanban leaves (about 5 mm × 5 mm) into a petri dish, 7 adult peach aphids per leaf piece were inoculated. The prepared test leaf pieces were each sprayed with 4 ml of a chemical solution of a predetermined concentration, covered, and stored in a thermostatic chamber at 25 ° C. After 4 days, the number of dead insects (including larvae) was investigated, and the death rate was calculated from the following formula. The test was conducted in a two-ward system.

Mortality (%) = dead insects / test insects x 100
The synergy was calculated from the mortality rate for each chemical concentration using the Colby method (Colby SR 1976, Weeds 15, 20-22). The calculation method is as follows.

E = X + Y-XY / 100
X: observed value of agent A at x concentration (death rate)
Y: Observed value of B agent at y concentration (death rate)
E: Expected death rate during mixing of agent A and agent B
The obtained result is analyzed as a synergistic action if the observed value is larger than the expected value, an antagonistic action if the expected value is larger than the observed value, and an additive action if the observed value is the same as the expected value. Table 8 shows combinations that showed synergistic action.
Table 8 ――――――――――――――――――――――――――――――――――
Active ingredient Concentration (ppm) Death rate (%)
――――――――――――――――――――――――――――――――――
Compound No. 3 50 36
Compound No. 4 100 47
Compound No. 5 50 56
Compound No. 6 50 52
Compound No. 8 100 32
Compound No. 9 100 45
Compound No. 10 100 24
Compound No. 15 100 42
Compound No. 16 50 48
Compound No. 23 100 33
Compound No. 24 100 53
Compound No. 29 100 32
Compound No. 32 100 47
Compound No. 36 100 52
Compound No. 37 100 32
Compound No. 38 100 31
Active ingredient nf 100 54
Active ingredient ng 0.5 53
Active ingredient og 0.5 46
Active ingredient pb 0.5 43
Active ingredient pw 1 59
Active ingredient qn 0.5 62
Active ingredient rk 0.5 44
Active ingredient sh 1 62
Active ingredient mx 50 32
Active ingredient sl 1 32
Active ingredient st 50 56
Active ingredient sv 0.5 63
Active ingredient te 0.5 23
Active ingredient tf 0.5 48
Active ingredient tk 3 42
Compound No. 3 + active ingredient nf 50 + 100 83
Compound No. 3 + active ingredient ng 50 + 0.5 77
Compound No. 3 + active ingredient og 50 + 0.5 100
Compound No. 3 + active ingredient pb 50 + 0.5 92
Compound No.3 + active ingredient pw 50 + 1 83
Compound No.3 + active ingredient qn 50 + 0.5 81
Compound No. 3 + active ingredient rk 50 + 0.5 74
Compound No.3 + active ingredient sh 50 + 1 79
Compound No. 3 + active ingredient mx 50 + 50 68
Compound No.3 + active ingredient sl 50 + 1 67
Compound No.3 + active ingredient st 50 + 50 91
Compound No.3 + active ingredient sv 50 + 0.5 100
Compound No. 3 + active ingredient te 50 + 0.5 76
Compound No. 3 + active ingredient tf 50 + 0.5 89
Compound No. 3 + active ingredient tk 50 + 3 95
Compound No. 4 + active ingredient nf 100 + 100 100
Compound No. 4 + active ingredient ng 100 + 0.5 83
Compound No. 4 + active ingredient og 100 + 0.5 79
Compound No. 4 + active ingredient pb 100 + 0.5 86
Compound No.4 + active ingredient pw 100 + 1 81
Compound No. 4 + active ingredient qn 100 + 0.5 96
Compound No. 4 + active ingredient rk 100 + 0.5 79
Compound No. 4 + active ingredient sh 100 + 1 86
Compound No. 4 + active ingredient mx 100 + 50 75
Compound No.4 + active ingredient sl 100 + 1 73
Compound No. 4 + active ingredient st 100 + 50 87
Compound No. 4 + active ingredient sv 100 + 0.5 93
Compound No. 4 + active ingredient te 100 + 0.5 100
Compound No. 4 + active ingredient tf 100 + 0.5 83
Compound No. 4 + active ingredient tk 100 + 3 76
Compound No. 5 + active ingredient nf 50 + 100 94
Compound No. 5 + active ingredient ng 50 + 0.5 91
Compound No. 5 + active ingredient og 50 + 0.5 83
Compound No. 5 + active ingredient pb 50 + 0.5 100
Compound No.5 + active ingredient pw 50 + 1 99
Compound No. 5 + active ingredient qn 50 + 0.5 100
Compound No. 5 + active ingredient rk 50 + 0.5 87
Compound No.5 + active ingredient sh 50 + 1 88
Compound No. 5 + active ingredient mx 50 + 50 76
Compound No.5 + active ingredient sl 50 + 1 91
Compound No. 5 + active ingredient st 50 + 50 89
Compound No. 5 + active ingredient sv 50 + 0.5 95
Compound No. 5 + active ingredient te 50 + 0.5 74
Compound No. 5 + active ingredient tf 50 + 0.5 98
Compound No. 5 + active ingredient tk 50 + 3 82
Compound No. 6 + active ingredient nf 50 + 100 100
Compound No. 6 + active ingredient ng 50 + 0.5 83
Compound No. 6 + active ingredient og 50 + 0.5 85
Compound No. 6 + active ingredient pb 50 + 0.5 88
Compound No. 6 + active ingredient pw 50 + 1 96
Compound No. 6 + active ingredient qn 50 + 0.5 93
Compound No. 6 + active ingredient rk 50 + 0.5 92
Compound No. 6 + active ingredient sh 50 + 1 91
Compound No. 6 + active ingredient mx 50 + 50 89
Compound No. 6 + active ingredient sl 50 + 1 87
Compound No. 6 + active ingredient st 50 + 50 91
Compound No. 6 + active ingredient sv 50 + 0.5 96
Compound No. 6 + active ingredient te 50 + 0.5 100
Compound No. 6 + active ingredient tf 50 + 0.5 79
Compound No. 6 + active ingredient tk 50 + 3 85
Compound No. 8 + active ingredient nf 100 + 100 74
Compound No. 8 + active ingredient ng 100 + 0.5 87
Compound No. 8 + active ingredient og 100 + 0.5 78
Compound No. 8 + active ingredient pb 100 + 0.5 96
Compound No.8 + active ingredient pw 100 + 1 85
Compound No. 8 + active ingredient qn 100 + 0.5 86
Compound No. 8 + active ingredient rk 100 + 0.5 73
Compound No. 8 + active ingredient sh 100 + 1 69
Compound No. 8 + active ingredient mx 100 + 50 64
Compound No.8 + active ingredient sl 100 + 1 76
Compound No. 8 + active ingredient st 100 + 50 92
Compound No. 8 + active ingredient sv 100 + 0.5 84
Compound No. 8 + active ingredient te 100 + 0.5 84
Compound No. 8 + active ingredient tf 100 + 0.5 78
Compound No. 8 + active ingredient tk 100 + 3 89
Compound No. 9 + active ingredient nf 100 + 100 82
Compound No. 9 + active ingredient ng 100 + 0.5 96
Compound No. 9 + active ingredient og 100 + 0.5 78
Compound No. 9 + active ingredient pb 100 + 0.5 87
Compound No. 9 + active ingredient pw 100 + 1 83
Compound No. 9 + active ingredient qn 100 + 0.5 91
Compound No. 9 + active ingredient rk 100 + 0.5 90
Compound No. 9 + active ingredient sh 100 + 1 93
Compound No. 9 + active ingredient mx 100 + 50 76
Compound No. 9 + active ingredient sl 100 + 1 74
Compound No. 9 + active ingredient st 100 + 50 85
Compound No. 9 + active ingredient sv 100 + 0.5 88
Compound No. 9 + active ingredient te 100 + 0.5 72
Compound No. 9 + active ingredient tf 100 + 0.5 99
Compound No. 9 + active ingredient tk 100 + 3 81
Compound No. 10 + active ingredient nf 100 + 100 76
Compound No. 10 + active ingredient ng 100 + 0.5 78
Compound No. 10 + active ingredient og 100 + 0.5 79
Compound No. 10 + active ingredient pb 100 + 0.5 77
Compound No.10 + active ingredient pw 100 + 1 81
Compound No. 10 + active ingredient qn 100 + 0.5 83
Compound No. 10 + active ingredient rk 100 + 0.5 76
Compound No. 10 + active ingredient sh 100 + 1 65
Compound No. 10 + active ingredient mx 100 + 50 69
Compound No. 10 + active ingredient sl 100 + 1 94
Compound No. 10 + active ingredient st 100 + 50 86
Compound No. 10 + active ingredient sv 100 + 0.5 78
Compound No. 10 + active ingredient te 100 + 0.5 64
Compound No. 10 + active ingredient tf 100 + 0.5 77
Compound No. 10 + active ingredient tk 100 + 3 66
Compound No. 15 + active ingredient nf 100 + 100 84
Compound No. 15 + active ingredient ng 100 + 0.5 89
Compound No. 15 + active ingredient og 100 + 0.5 93
Compound No. 15 + active ingredient pb 100 + 0.5 78
Compound No.15 + active ingredient pw 100 + 1 96
Compound No. 15 + active ingredient qn 100 + 0.5 100
Compound No. 15 + active ingredient rk 100 + 0.5 88
Compound No. 15 + active ingredient sh 100 + 1 76
Compound No. 15 + active ingredient mx 100 + 50 94
Compound No. 15 + active ingredient sl 100 + 1 100
Compound No. 15 + active ingredient st 100 + 50 82
Compound No. 15 + active ingredient sv 100 + 0.5 100
Compound No. 15 + active ingredient te 100 + 0.5 63
Compound No. 15 + active ingredient tf 100 + 0.5 75
Compound No. 15 + active ingredient tk 100 + 3 96
Compound No. 16 + active ingredient nf 50 + 100 81
Compound No. 16 + active ingredient ng 50 + 0.5 79
Compound No. 16 + active ingredient og 50 + 0.5 78
Compound No. 16 + active ingredient pb 50 + 0.5 79
Compound No. 16 + active ingredient pw 50 + 1 91
Compound No. 16 + active ingredient qn 50 + 0.5 87
Compound No. 16 + active ingredient rk 50 + 0.5 96
Compound No.16 + active ingredient sh 50 + 1 100
Compound No. 16 + active ingredient mx 50 + 50 86
Compound No. 16 + active ingredient sl 50 + 1 87
Compound No. 16 + active ingredient st 50 + 50 100
Compound No. 16 + active ingredient sv 50 + 0.5 99
Compound No. 16 + active ingredient te 50 + 0.5 68
Compound No. 16 + active ingredient tf 50 + 0.5 84
Compound No. 16 + active ingredient tk 50 + 3 76
Compound No. 23 + active ingredient nf 100 + 100 76
Compound No. 23 + active ingredient ng 100 + 0.5 93
Compound No. 23 + active ingredient og 100 + 0.5 95
Compound No. 23 + active ingredient pb 100 + 0.5 99
Compound No.23 + active ingredient pw 100 + 1 97
Compound No. 23 + active ingredient qn 100 + 0.5 91
Compound No. 23 + active ingredient rk 100 + 0.5 90
Compound No. 23 + active ingredient sh 100 + 1 90
Compound No. 23 + active ingredient mx 100 + 50 100
Compound No. 23 + active ingredient sl 100 + 1 83
Compound No. 23 + active ingredient st 100 + 50 89
Compound No. 23 + active ingredient sv 100 + 0.5 97
Compound No. 23 + active ingredient te 100 + 0.5 67
Compound No. 23 + active ingredient tf 100 + 0.5 73
Compound No. 23 + active ingredient tk 100 + 3 84
Compound No. 24 + active ingredient nf 100 + 100 86
Compound No. 24 + active ingredient ng 100 + 0.5 84
Compound No. 24 + active ingredient og 100 + 0.5 89
Compound No.24 + active ingredient pb 100 + 0.5 100
Compound No.24 + active ingredient pw 100 + 1 100
Compound No.24 + active ingredient qn 100 + 0.5 100
Compound No. 24 + active ingredient rk 100 + 0.5 100
Compound No. 24 + active ingredient sh 100 + 1 89
Compound No. 24 + active ingredient mx 100 + 50 94
Compound No.24 + active ingredient sl 100 + 1 90
Compound No. 24 + active ingredient st 100 + 50 85
Compound No. 24 + active ingredient sv 100 + 0.5 96
Compound No. 24 + active ingredient te 100 + 0.5 76
Compound No. 24 + active ingredient tf 100 + 0.5 100
Compound No. 24 + active ingredient tk 100 + 3 88
Compound No. 29 + active ingredient ng 100 + 100 76
Compound No. 29 + active ingredient ng 100 + 0.5 74
Compound No. 29 + active ingredient og 100 + 0.5 69
Compound No. 29 + active ingredient pb 100 + 0.5 69
Compound No. 29 + active ingredient pw 100 + 1 83
Compound No. 29 + active ingredient qn 100 + 0.5 84
Compound No. 29 + active ingredient rk 100 + 0.5 95
Compound No. 29 + active ingredient sh 100 + 1 97
Compound No. 29 + active ingredient mx 100 + 50 68
Compound No. 29 + active ingredient sl 100 + 1 66
Compound No. 29 + active ingredient st 100 + 50 78
Compound No. 29 + active ingredient sv 100 + 0.5 77
Compound No. 29 + active ingredient te 100 + 0.5 56
Compound No. 29 + active ingredient tf 100 + 0.5 73
Compound No. 29 + active ingredient tk 100 + 3 63
Compound No. 32 + active ingredient ng 100 + 100 84
Compound No. 32 + active ingredient ng 100 + 0.5 87
Compound No. 32 + active ingredient og 100 + 0.5 83
Compound No. 32 + active ingredient pb 100 + 0.5 76
Compound No.32 + active ingredient pw 100 + 1 89
Compound No. 32 + active ingredient qn 100 + 0.5 86
Compound No. 32 + active ingredient rk 100 + 0.5 81
Compound No. 32 + active ingredient sh 100 + 1 83
Compound No. 32 + active ingredient mx 100 + 50 77
Compound No.32 + active ingredient sl 100 + 1 90
Compound No. 32 + active ingredient st 100 + 50 86
Compound No. 32 + active ingredient sv 100 + 0.5 89
Compound No. 32 + active ingredient te 100 + 0.5 63
Compound No. 32 + active ingredient tf 100 + 0.5 86
Compound No. 32 + active ingredient tk 100 + 3 79
Compound No. 36 + active ingredient mx 100 + 50 77
Compound No. 36 + active ingredient sl 100 + 1 79
Compound No. 36 + active ingredient st 100 + 50 84
Compound No. 36 + active ingredient sv 100 + 0.5 100
Compound No. 36 + active ingredient te 100 + 0.5 76
Compound No. 36 + active ingredient tf 100 + 0.5 99
Compound No. 36 + active ingredient tk 100 + 3 83
Compound No. 37 + active ingredient ng 100 + 100 92
Compound No. 37 + active ingredient ng 100 + 0.5 93
Compound No. 37 + active ingredient og 100 + 0.5 86
Compound No. 37 + active ingredient pb 100 + 0.5 87
Compound No. 37 + active ingredient pw 100 + 1 92
Compound No. 37 + active ingredient qn 100 + 0.5 90
Compound No. 37 + active ingredient rk 100 + 0.5 88
Compound No. 37 + active ingredient sh 100 + 1 79
Compound No. 37 + active ingredient mx 100 + 50 68
Compound No. 37 + active ingredient sl 100 + 1 67
Compound No. 37 + active ingredient st 100 + 50 84
Compound No. 37 + active ingredient sv 100 + 0.5 89
Compound No. 37 + active ingredient te 100 + 0.5 94
Compound No. 37 + active ingredient tf 100 + 0.5 92
Compound No. 37 + active ingredient tk 100 + 3 97
Compound No. 38 + active ingredient ng 100 + 100 74
Compound No. 38 + active ingredient ng 100 + 0.5 73
Compound No. 38 + active ingredient og 100 + 0.5 70
Compound No. 38 + active ingredient pb 100 + 0.5 100
Compound No. 38 + active ingredient pw 100 + 1 100
Compound No. 38 + active ingredient qn 100 + 0.5 95
Compound No. 38 + active ingredient rk 100 + 0.5 84
Compound No. 38 + active ingredient sh 100 + 1 89
Compound No. 38 + active ingredient mx 100 + 50 100
Compound No. 38 + active ingredient sl 100 + 1 68
Compound No. 38 + active ingredient st 100 + 50 79
Compound No. 38 + active ingredient sv 100 + 0.5 69
Compound No. 38 + active ingredient te 100 + 0.5 50
Compound No. 38 + active ingredient tf 100 + 0.5 82
Compound No. 38 + active ingredient tk 100 + 3 67
――――――――――――――――――――――――――――――――――
Test Example 3 Efficacy Test for Tobacco Whitefly (B Biotype) Each of the compounds listed in Table 1 and the compounds listed in Table 5 were each 10% emulsion (25% depending on the compound). The preparation was diluted with water containing a spreading agent to prepare a drug solution having a predetermined concentration. Next, the cut kidney beans (about 3 cm in diameter) were placed on moist filter paper, and 10 tobacco whitefly adults were inoculated per leaf piece. The prepared test leaf pieces were each sprayed with 5 ml of a chemical solution of a predetermined concentration, covered with a net, and stored in a thermostatic chamber at 25 ° C. so that the leaf pieces did not dry. The number of dead insects after 4 days was investigated, and the dead insect rate was calculated from the following formula. The test was conducted in a two-ward system.

Mortality (%) = dead insects / test insects x 100
The synergy was calculated from the mortality rate for each chemical concentration using the Colby method (Colby SR 1976, Weeds 15, 20-22). The calculation method is as follows.

E = X + Y-XY / 100
X: observed value of agent A at x concentration (death rate)
Y: Observed value of B agent at y concentration (death rate)
E: Expected death rate during mixing of agent A and agent B
The obtained result is analyzed as a synergistic action if the observed value is larger than the expected value, an antagonistic action if the expected value is larger than the observed value, and an additive action if the observed value is the same as the expected value. Table 9 shows the combinations that showed synergistic action.
Table 9 ――――――――――――――――――――――――――――――――――
Active ingredient Concentration (ppm) Death rate (%)
――――――――――――――――――――――――――――――――――
Compound No. 3 100 23
Compound No. 4 100 60
Compound No. 5 100 41
Compound No. 6 100 32
Compound No. 8 100 65
Compound No. 9 100 55
Compound No. 10 100 45
Compound No. 15 100 30
Compound No. 16 100 35
Compound No. 17 50 55
Compound No. 23 100 30
Compound No. 29 100 20
Compound No. 32 50 30
Compound No. 36 100 32
Compound No. 37 100 20
Compound No. 38 100 24
Active ingredient nf 100 31
Active ingredient ng 10 44
Active ingredient og 10 62
Active ingredient pb 10 55
Active ingredient pw 10 36
Active ingredient qn 10 33
Active ingredient rk 10 53
Active ingredient sh 3 42
Active ingredient mx 1 45
Active ingredient sl 1 57
Active ingredient st 100 34
Active ingredient sv 50 50
Active ingredient te 10 32
Active ingredient tf 5 43
Active ingredient tk 5 34
Compound No. 3 + active ingredient nf 100 + 100 60
Compound No. 3 + active ingredient ng 100 + 10 65
Compound No. 3 + active ingredient og 100 + 10 75
Compound No. 3 + active ingredient pb 100 + 10 65
Compound No.3 + active ingredient pw 100 + 10 55
Compound No.3 + active ingredient qn 100 + 10 55
Compound No. 3 + active ingredient rk 100 + 10 70
Compound No. 3 + active ingredient sh 100 + 3 80
Compound No. 3 + active ingredient mx 100 + 1 65
Compound No.3 + active ingredient sl 100 + 1 70
Compound No. 3 + active ingredient st 100 + 100 55
Compound No. 3 + active ingredient sv 100 + 50 70
Compound No. 3 + active ingredient te 100 + 10 55
Compound No. 3 + active ingredient tf 100 + 5 75
Compound No. 3 + active ingredient tk 100 + 5 65
Compound No. 4 + active ingredient nf 100 + 100 95
Compound No. 4 + active ingredient ng 100 + 10 100
Compound No. 4 + active ingredient og 100 + 10 100
Compound No. 4 + active ingredient pb 100 + 10 95
Compound No.4 + active ingredient pw 100 + 10 90
Compound No. 4 + active ingredient qn 100 + 10 95
Compound No. 4 + active ingredient rk 100 + 10 90
Compound No. 4 + active ingredient sh 100 + 3 100
Compound No. 4 + active ingredient mx 100 + 1 100
Compound No.4 + active ingredient sl 100 + 1 95
Compound No. 4 + active ingredient st 100 + 100 90
Compound No. 4 + active ingredient sv 100 + 50 85
Compound No. 4 + active ingredient te 100 + 10 100
Compound No. 4 + active ingredient tf 100 + 5 100
Compound No. 4 + active ingredient tk 100 + 5 95
Compound No. 5 + active ingredient nf 100 + 100 70
Compound No. 5 + active ingredient ng 100 + 10 85
Compound No. 5 + active ingredient og 100 + 10 90
Compound No. 5 + active ingredient pb 100 + 10 85
Compound No.5 + active ingredient pw 100 + 10 75
Compound No.5 + active ingredient qn 100 + 10 70
Compound No. 5 + active ingredient rk 100 + 10 80
Compound No. 5 + active ingredient sh 100 + 3 90
Compound No.5 + active ingredient mx 100 + 1 80
Compound No.5 + active ingredient sl 100 + 1 85
Compound No. 5 + active ingredient st 100 + 100 75
Compound No. 5 + active ingredient sv 100 + 50 80
Compound No. 5 + active ingredient te 100 + 10 65
Compound No. 5 + active ingredient tf 100 + 5 85
Compound No. 5 + active ingredient tk 100 + 5 70
Compound No. 6 + active ingredient nf 100 + 100 65
Compound No. 6 + active ingredient ng 100 + 10 65
Compound No. 6 + active ingredient og 100 + 10 80
Compound No. 6 + active ingredient pb 100 + 10 75
Compound No. 6 + active ingredient pw 100 + 10 85
Compound No. 6 + active ingredient qn 100 + 10 65
Compound No. 6 + active ingredient rk 100 + 10 70
Compound No. 6 + active ingredient sh 100 + 3 65
Compound No. 6 + active ingredient mx 100 + 1 80
Compound No. 6 + active ingredient sl 100 + 1 85
Compound No. 6 + active ingredient st 100 + 100 90
Compound No. 6 + active ingredient sv 100 + 50 80
Compound No. 6 + active ingredient te 100 + 10 65
Compound No. 6 + active ingredient tf 100 + 5 65
Compound No. 6 + active ingredient tk 100 + 5 80
Compound No. 8 + active ingredient nf 100 + 100 95
Compound No. 8 + active ingredient ng 100 + 10 100
Compound No. 8 + active ingredient og 100 + 10 100
Compound No. 8 + active ingredient pb 100 + 10 100
Compound No. 8 + active ingredient pw 100 + 10 100
Compound No. 8 + active ingredient qn 100 + 10 95
Compound No. 8 + active ingredient rk 100 + 10 90
Compound No. 8 + active ingredient sh 100 + 3 90
Compound No.8 + active ingredient mx 100 + 1 95
Compound No. 8 + active ingredient sl 100 + 1 100
Compound No. 8 + active ingredient st 100 + 100 100
Compound No. 8 + active ingredient sv 100 + 50 95
Compound No. 8 + active ingredient te 100 + 10 85
Compound No. 8 + active ingredient tf 100 + 5 85
Compound No. 8 + active ingredient tk 100 + 5 95
Compound No. 9 + active ingredient nf 100 + 100 75
Compound No. 9 + active ingredient ng 100 + 10 80
Compound No. 9 + active ingredient og 100 + 10 90
Compound No. 9 + active ingredient pb 100 + 10 90
Compound No. 9 + active ingredient pw 100 + 10 95
Compound No. 9 + active ingredient qn 100 + 10 75
Compound No. 9 + active ingredient rk 100 + 10 90
Compound No. 9 + active ingredient sh 100 + 3 95
Compound No. 9 + active ingredient mx 100 + 1 85
Compound No. 9 + active ingredient sl 100 + 1 100
Compound No. 9 + active ingredient st 100 + 100 85
Compound No. 9 + active ingredient sv 100 + 50 85
Compound No. 9 + active ingredient te 100 + 10 75
Compound No. 9 + active ingredient tf 100 + 5 90
Compound No. 9 + active ingredient tk 100 + 5 90
Compound No. 10 + active ingredient nf 100 + 100 75
Compound No. 10 + active ingredient ng 100 + 10 80
Compound No. 10 + active ingredient og 100 + 10 90
Compound No. 10 + active ingredient pb 100 + 10 95
Compound No. 10 + active ingredient pw 100 + 10 80
Compound No. 10 + active ingredient qn 100 + 10 85
Compound No. 10 + active ingredient rk 100 + 10 80
Compound No. 10 + active ingredient sh 100 + 3 75
Compound No. 10 + active ingredient mx 100 + 1 75
Compound No. 10 + active ingredient sl 100 + 1 100
Compound No. 10 + active ingredient st 100 + 100 80
Compound No. 10 + active ingredient sv 100 + 50 95
Compound No. 10 + active ingredient te 100 + 10 90
Compound No. 10 + active ingredient tf 100 + 5 100
Compound No. 10 + active ingredient tk 100 + 5 100
Compound No. 16 + active ingredient nf 100 + 100 75
Compound No. 16 + active ingredient ng 100 + 10 75
Compound No. 16 + active ingredient og 100 + 10 90
Compound No. 16 + active ingredient pb 100 + 10 95
Compound No. 16 + active ingredient pw 100 + 10 100
Compound No. 16 + active ingredient qn 100 + 10 80
Compound No. 16 + active ingredient rk 100 + 10 75
Compound No. 16 + active ingredient sh 100 + 3 80
Compound No.16 + active ingredient mx 100 + 1 85
Compound No.16 + active ingredient sl 100 + 1 85
Compound No. 16 + active ingredient st 100 + 100 95
Compound No. 16 + active ingredient sv 100 + 50 95
Compound No. 16 + active ingredient te 100 + 10 95
Compound No. 16 + active ingredient tf 100 + 5 80
Compound No. 16 + active ingredient tk 100 + 5 100
Compound No.17 + active ingredient nf 50 + 100 100
Compound No. 17 + active ingredient ng 50 + 10 100
Compound No. 17 + active ingredient og 50 + 10 100
Compound No. 17 + active ingredient pb 50 + 10 100
Compound No. 17 + active ingredient pw 50 + 10 95
Compound No.17 + active ingredient qn 50 + 10 100
Compound No. 17 + active ingredient rk 50 + 10 95
Compound No. 17 + active ingredient sh 50 + 3 100
Compound No.17 + active ingredient mx 50 + 1 90
Compound No.17 + active ingredient sl 50 + 1 100
Compound No. 17 + active ingredient st 50 + 100 100
Compound No. 17 + active ingredient sv 50 + 50 100
Compound No. 17 + active ingredient te 50 + 10 100
Compound No.17 + active ingredient tf 50 + 5 100
Compound No. 17 + active ingredient tk 50 + 5 100
Compound No. 23 + active ingredient nf 100 + 100 65
Compound No. 23 + active ingredient ng 100 + 10 75
Compound No. 23 + active ingredient og 100 + 10 85
Compound No. 23 + active ingredient pb 100 + 10 75
Compound No.23 + active ingredient pw 100 + 10 70
Compound No. 23 + active ingredient qn 100 + 10 80
Compound No. 23 + active ingredient rk 100 + 10 85
Compound No. 23 + active ingredient sh 100 + 3 75
Compound No. 23 + active ingredient mx 100 + 1 100
Compound No. 23 + active ingredient sl 100 + 1 75
Compound No. 23 + active ingredient st 100 + 100 65
Compound No. 23 + active ingredient sv 100 + 50 80
Compound No. 23 + active ingredient te 100 + 10 70
Compound No. 23 + active ingredient tf 100 + 5 70
Compound No. 23 + active ingredient tk 100 + 5 70
Compound No. 29 + active ingredient nf 100 + 100 55
Compound No. 29 + active ingredient ng 100 + 10 80
Compound No. 29 + active ingredient og 100 + 10 75
Compound No. 29 + active ingredient pb 100 + 10 75
Compound No. 29 + active ingredient pw 100 + 10 55
Compound No. 29 + active ingredient qn 100 + 10 55
Compound No. 29 + active ingredient rk 100 + 10 95
Compound No. 29 + active ingredient sh 100 + 3 65
Compound No. 29 + active ingredient mx 100 + 1 60
Compound No. 29 + active ingredient sl 100 + 1 70
Compound No. 29 + active ingredient st 100 + 100 55
Compound No. 29 + active ingredient sv 100 + 50 85
Compound No. 29 + active ingredient te 100 + 10 55
Compound No. 29 + active ingredient tf 100 + 5 70
Compound No. 29 + active ingredient tk 100 + 5 90
Compound No. 32 + active ingredient nf 50 + 100 95
Compound No. 32 + active ingredient ng 50 + 10 95
Compound No. 32 + active ingredient og 50 + 10 100
Compound No. 32 + active ingredient pb 50 + 10 100
Compound No. 32 + active ingredient pw 50 + 10 100
Compound No. 32 + active ingredient qn 50 + 10 90
Compound No. 32 + active ingredient rk 50 + 10 85
Compound No. 32 + active ingredient sh 50 + 3 90
Compound No.32 + active ingredient mx 50 + 1 100
Compound No.32 + active ingredient sl 50 + 1 85
Compound No. 32 + active ingredient st 50 + 100 70
Compound No. 32 + active ingredient sv 50 + 50 100
Compound No. 32 + active ingredient te 50 + 10 65
Compound No. 32 + active ingredient tf 50 + 5 100
Compound No. 32 + active ingredient tk 50 + 5 95
Compound No. 36 + active ingredient nf 100 + 100 75
Compound No. 36 + active ingredient ng 100 + 10 80
Compound No. 36 + active ingredient og 100 + 10 80
Compound No. 36 + active ingredient pb 100 + 10 90
Compound No. 36 + active ingredient pw 100 + 10 100
Compound No. 36 + active ingredient qn 100 + 10 100
Compound No. 36 + active ingredient rk 100 + 10 100
Compound No. 36 + active ingredient sh 100 + 3 80
Compound No. 36 + active ingredient mx 100 + 1 80
Compound No. 36 + active ingredient sl 100 + 1 85
Compound No. 36 + active ingredient st 100 + 100 90
Compound No. 36 + active ingredient sv 100 + 50 95
Compound No. 36 + active ingredient te 100 + 10 100
Compound No. 36 + active ingredient tf 100 + 5 80
Compound No. 36 + active ingredient tk 100 + 5 80
Compound No. 37 + active ingredient nf 100 + 100 65
Compound No. 37 + active ingredient ng 100 + 10 60
Compound No. 37 + active ingredient og 100 + 10 85
Compound No. 37 + active ingredient pb 100 + 10 70
Compound No. 37 + active ingredient pw 100 + 10 90
Compound No. 37 + active ingredient qn 100 + 10 55
Compound No. 37 + active ingredient rk 100 + 10 70
Compound No. 37 + active ingredient sh 100 + 3 100
Compound No. 37 + active ingredient mx 100 + 1 90
Compound No. 37 + active ingredient sl 100 + 1 70
Compound No. 37 + active ingredient st 100 + 100 55
Compound No. 37 + active ingredient sv 100 + 50 95
Compound No. 37 + active ingredient te 100 + 10 100
Compound No. 37 + active ingredient tf 100 + 5 60
Compound No. 37 + active ingredient tk 100 + 5 65
Compound No. 38 + active ingredient nf 100 + 100 95
Compound No. 38 + active ingredient ng 100 + 10 65
Compound No. 38 + active ingredient og 100 + 10 80
Compound No. 38 + active ingredient pb 100 + 10 70
Compound No. 38 + active ingredient pw 100 + 10 65
Compound No. 38 + active ingredient qn 100 + 10 70
Compound No. 38 + active ingredient rk 100 + 10 100
Compound No. 38 + active ingredient sh 100 + 3 85
Compound No. 38 + active ingredient mx 100 + 1 70
Compound No. 38 + active ingredient sl 100 + 1 80
Compound No. 38 + active ingredient st 100 + 100 65
Compound No. 38 + active ingredient sv 100 + 50 55
Compound No. 38 + active ingredient te 100 + 10 95
Compound No. 38 + active ingredient tf 100 + 5 80
Compound No. 38 + active ingredient tk 100 + 5 55
――――――――――――――――――――――――――――――――――

  The composition of the present invention and the method of the present invention can be used for controlling various pests.

Claims (12)

Formula (1):

[Wherein, A ¹ , A ² , A ³ and A ⁴ each independently represents CY or a nitrogen atom,
G represents a benzene ring, a nitrogen-containing 6-membered aromatic heterocycle, a furan ring, a thiophene ring or a 5-membered aromatic heterocycle containing two or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom;
L is -C (R ⁴ ) (R ^4a )-, -C (R ⁴ ) (R ^4a ) CH _2- , -CH ₂ C (R ⁴ ) (R ^4a )-, -N (R ^4b )- Or -C (R ⁴ ) (R ^4a ) N (R ^4b )-
X is a halogen atom, cyano, nitro, azide, —SCN, —SF ₅ , C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ⁵ , C ₃ -C ₈ cycloalkyl , optionally substituted by R ⁵ _(C 3 ~C ₈₎ cycloalkyl, optionally substituted by _{E-1~E-21, C 2} ~C 6 _{^{alkenyl, R 5 (C 2 ~C 6}} ) alkenyl , C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halocycloalkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted by R ⁵ , —OH, —OR ⁶ , — ^{_{OS (O) 2 R 6,}} -SH, -S (O) r R 6, -N (R 8) R 7, -N = C (R 8a) R 7a, -C (O) R 9, -C (R ⁹ ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , M-3, M-13, M-30, -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , M-23 to M-26, M-28, M _{-29, -S (O) 2 OR} 10, -S (O) ^{N (R 12) R 11,} -Si (R 13a) (R 13b) R 13, phenyl, _{(Z) n1} represents phenyl or D-1 to D-38 substituted by, m is an integer of 2 or more When represented, each X may be the same as or different from each other;
Further, when two Xs are adjacent to each other, the two adjacent Xs are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -CH ₂ CH ₂ N (R ¹⁴ )-, -CH ₂ N (R ¹⁴ ) CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -OCH ₂ CH ₂ S-, -CH ₂ CH = CH-,- OCH = CH-, -SCH = CH-, -N (R ¹⁴ ) CH = CH-, -OCH = N-, -SCH = N-, -N (R ¹⁴ ) CH = N-, -N (R ¹⁴ By forming N = CH-, -CH = CHCH = CH-, -OCH ₂ CH = CH-, -N = CHCH = CH-, -N = CHCH = N- or -N = CHN = CH- In addition, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each X is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted by Z Well, moreover, when two or more Z are substituted at the same time, each Z may be the same as or different from each other. At best,
Y is a hydrogen atom, a halogen atom, cyano, nitro, _{azido, -SCN, -SF 5, C 1} ~C 6 alkyl, optionally substituted by R ⁵ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, (C ₃ -C ₈ ) cycloalkyl optionally substituted by R ⁵ , E-1 to E-21, C ₂ -C ₆ alkenyl, optionally substituted by R ⁵ (C ₂ -C ₆₎ alkenyl, C ₂ -C ₆ alkynyl, optionally substituted by R ⁵ _(C 2 _{~C 6)} ^{alkynyl, -OH, -OR 6, -OS (} O) 2 R 6, -SH, -S ( ^{_{O) r R 6, -N (}} R 8) R 7, -N (R 8) C (O) R 9a, -N = C (R 8a) R 7a, -C (O) N (R 12) R ¹¹ , —C (S) N (R ¹² ) R ¹¹ , —Si (R ^13a ) (R ^13b ) R ¹³ , phenyl, phenyl substituted by (Z) _n1 or D-1 to D-38; When two or more Y are present simultaneously, each Y may be the same as or different from each other. Well,
Further, when two Ys are adjacent to each other, the two adjacent Ys are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -SCH ₂ S-, -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH ₂ -,- CH ₂ OCH ₂ O-, -OCH ₂ CH ₂ O-, -OCH ₂ CH ₂ S-, -SCH ₂ CH ₂ S-, -OCH = N-, -SCH = N-, -CH = CHCH = CH- , -CH = CHCH = N-, -CH = CHN = CH-, -CH = NCH = CH- or -N = CHCH = CH- to form a 5-membered ring with the carbon atom to which each Y binds Alternatively, a 6-membered ring may be formed, and at this time, a hydrogen atom bonded to each carbon atom forming the ring may be optionally substituted with Z, and further substituted with two or more Z at the same time. Each Z may be the same as or different from each other,
R ¹ is a hydrogen atom, —C (O) R ^1a , —C (O) OR ^1b , —C (O) SR ^1b , —C (O) N (R ^1d ) R ^1c , —C (S) R ^{1a, -C (S) oR 1b} , -C (S) SR 1b, -C (S) N (R 1d) R 1c, -S (O) 2 R 1b , or ^{_{-S (O) 2 N (R}} 1d ) ^Represents R ^1c
R ^1a is hydrogen atom, C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted by R ¹⁵ _{(C 3} -C ₁₂₎ cycloalkyl, E-1~E-21, C 2 ~C 12 alkenyl, optionally substituted by R ¹⁵ _(C 2 ~C ₁₂₎ alkenyl, C ₅ -C ₁₂ cycloalkenyl, C ₅ ~ C ₁₂ halocycloalkenyl, C ₂ -C ₁₂ alkynyl, (C ₂ -C ₁₂ ) alkynyl optionally substituted by R ¹⁵ , —C (O) R ⁹ , —C (O) R ^9a , —C (R ⁹ ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , -C (R ⁹ ) = NN (R ¹⁷ ) R ¹⁶ , -C (O) OR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , M-4, phenyl, (Z) _n1 substituted phenyl or D-1 to D-38,
R ^1b is optionally substituted by C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, R ¹⁵ _(C 3 _{~C 12} ) cycloalkyl, E-2~E-5, E -7, E-13, E-14, E-16, C 2 ~C 12 alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, phenyl, (Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D-8~D-10, D-12~D- 19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ^1c is a hydrogen atom, C ₁ -C ₁₂ alkyl, optionally substituted by R ¹⁵ _(C 1 _{~C 12)} alkyl, C ₃ -C ₁₂ cycloalkyl, optionally substituted by R ¹⁵ _{(C 3} -C ₁₂₎ cycloalkyl, E-2~E-7, E -13~E-21, C 2 ~C 12 alkenyl, C ₂ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ Haloalkynyl, -C (O) R ⁹ , -C (O) R ^9a , -C (R ⁹ ) = NOR ¹⁰ , -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) ^{N (R 12) R 11,} M-7, M-17, -C (S) R 9, -C (S) OR 10, -C (S) SR 10, -C (S) N (R 12) R ¹¹ , M-9, M-19, —OR ¹⁰ , —S (O) ₂ R ¹⁰ , —S (O) ₂ N (R ¹² ) R ¹¹ , —N (R ¹⁷ ) R ¹⁶ , phenyl, ( Z) represents phenyl substituted by _n1 , D-1 to D-25 or D-27 to D-38;
R ^1d is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkylthio _(C 1 _{~C 4)} alkyl, cyano _(C 1 _{~C 6)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, C ₃ -C ₆ alkenyl or _C 3 -C ₆ alkynyl Or R ^1d together with R ^1c forms a C ₂ -C ₆ alkylene chain to form a 3-7 membered ring with the nitrogen atom to which R ^1c and R ^1d are bonded. represents good, this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and C ₁ -C ₆ alkyl group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylaminocarbonyl groups, C -C ₆ haloalkylcarbonyl aminocarbonyl group, di (C ₁ -C ₆ alkyl) aminocarbonyl group, may be optionally substituted by oxo or thioxo group,
R ² is a hydrogen atom, cyano, C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ^15a , C ₃ -C ₁₂ cycloalkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ haloalkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ ^{haloalkynyl, -C (O) R 9,} -C (O) R 9a, -C (O) OR 10, -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (O) C (O) OR ¹⁰ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , C ₁ -C ₁₂ alkoxy, C ₁ -C ₁₂ haloalkoxy, —SR ¹⁰ , —S (O) ₂ R ¹⁰ , —SN (R ^17a ) R ^16a , phenyl, (Z) _n1 Represents phenyl or D-32 substituted by R ⁵ , or R ² together with R ¹ forms a C _{4 to} C ₆ alkylene chain, so that 5 together with the nitrogen atom to which R ¹ and R ² are bonded. Represents that a 7-membered ring may be formed. Alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and _C 1 -C ₆ alkyl group, C ₁ -C ₆ alkylidene group, -CHO group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ haloalkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ haloalkoxycarbonyl groups, C ₁ -C ₆ alkylaminocarbonyl group, C ₁ -C ₆ halo alkylaminocarbonyl group, di _{(C 1} -C ₆ alkyl) aminocarbonyl group, a phenyl group, D-32 group, D-34 group may be optionally substituted by oxo or thioxo group,
R ³ represents a halogen atom, cyano, optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ⁵ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ⁵ ( C ₃ -C ₈₎ cycloalkyl, E-1~E-21, C 3 ~C 6 alkenyl, optionally substituted by R ⁵ _(C 2 _{~C 6)} alkenyl, C ₃ -C ₆ alkynyl, R ⁵ (C ₂ -C ₆ ) alkynyl, —OR ⁶ , —S (O) _r R ⁶ , —N (R ¹² ) R ¹¹ , —C (O) R ⁹ , —C (R ⁹ ) optionally substituted by ) = NOH, -C (R ⁹ ) = NOR ¹⁰ , M-3, M-13, M-30, -C (O) OR ¹⁰ , -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , -Si (R ^13a ) (R ^13b ) R ¹³ , -P ( O) (OR ¹⁸ ) ₂ , phenyl, phenyl substituted by (Z) _n1 or D-1 to D-38,
R ⁴ is a hydrogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C _{6 alkoxycarbonyl, -C (O) NH 2,} -C (S) NH 2, phenyl, (Z) phenyl substituted by _{n1, D-1, D-} 2, D-9, D-10 or D-32 Or when A ¹ or A ⁴ represents CY, R ⁴ together with Y represents —CH ₂ CH ₂ —, —CH ₂ O—, —CH ₂ S (O) _r — , —CH ₂ N (R ⁷ ) —, —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ CH ₂ S (O) _r —, —CH ₂ CH ₂ N (R ⁷ ) -, -CH ₂ OCH _2- , -CH ₂ S (O) _r CH ₂ -or -CH ₂ N (R ⁷ ) CH ₂ -to form a 5-membered ring with atoms to which R ⁴ and Y are bonded Alternatively, a condensed ring may be formed by forming a 6-membered ring, in which case a hydrogen atom bonded to each carbon atom forming the 5-membered or 6-membered ring. May be optionally substituted halogen atom, by C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl group,
R ^4a represents a hydrogen atom or C ₁ -C ₆ alkyl, or R ^4a together with R ⁴ forms a C ₂ -C ₅ alkylene chain, thereby binding R ⁴ and R ^4a . Represents that a 3- to 6-membered ring may be formed together with a carbon atom, and this alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a C ₁ -C ₄ alkyl group, —CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, C ₁ -C ₄ alkylaminocarbonyl group, C ₁ -C ₄ halo alkylaminocarbonyl group, di _(C 1 -C ₄ alkyl) amino Optionally substituted by a carbonyl group or a phenyl group,
R ^4b is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₃ -C ₆ cycloalkylcarbonyl, C ₃ -C ₆ halocycloalkyl carbonyl, represents C ₁ -C ₆ alkoxycarbonyl or _C 1 -C ₆ haloalkoxycarbonyl,
D-1 to D-38 each represent an aromatic heterocycle represented by the following structural formula;

Z is a halogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy (C ₁ -C C ₄ ) alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkylthio (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfinyl (C ₁ -C ₄ ) Alkyl, C ₁ -C ₄ haloalkylsulfinyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylsulfonyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkylsulfonyl (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, -OH, C ₁ ~C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkylsulfonyloxy, C ₁ -C ₆ haloalkyl sulfonyloxy, C ₁ -C ₆ alkylthio, C ₁ C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ haloalkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, -NH _2, C ₁ ~C ₆ alkyl amino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, —C (O) NH ₂ , C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ haloalkyl aminocarbonyl, di _(C 1 -C ₆ alkyl) _{aminocarbonyl, -C (S) NH 2,} -S (O) 2 NH 2, C 1 ~C 6 alkylaminosulfonyl, di _(C 1 -C ₆ alkyl) Represents aminosulfonyl or phenyl, and when n1, n2, n3 or n4 represents an integer of 2 or more, each Z may be the same as or different from each other;
Further, when two Zs are adjacent, the two adjacent Zs are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, —CH. ₂ CH ₂ S-, -CH ₂ SCH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ O-, -CH ₂ CH ₂ OCH _2- , -CH ₂ OCH ₂ O- , —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S—, —OCH ₂ CH ₂ S— or —CH═CH—CH═CH— to form a carbon atom to which each Z is bonded. may form a 5- or 6-membered ring, this time with each a hydrogen atom a halogen atom bonded to the carbon atoms forming the ring, a cyano group, a nitro groups, C ₁ -C ₄ alkyl groups, C ₁ -C ₄ haloalkyl group, may be optionally substituted by C ₁ -C ₄ alkoxy or _C 1 -C ₄ alkylthio group,
E-1 to E-21 each represent a saturated heterocyclic ring represented by the following structural formula,

R ⁵ is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, C _{3 to} C ₈ halocycloalkyl, E-1 to E-21, —OH, —OR ⁶ , —SH, —S (O) _r R ⁶ , -N (R ⁸ ) R ⁷ , -N (R ⁸ ) C (O) R ^9a , -C (O) OR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -Si (R ^13a ) (R ^13b ) R ¹³ , phenyl, (Z) phenyl substituted by _n1 or D-1 to D-38;
R ⁶ is optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ²² _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ²² _(C 3 _{~C 8} ) cycloalkyl, E-2~E-5, E -7, E-13, E-14, E-16, E-17, E-20, C 2 ~C 6 alkenyl, optionally substituted by R ²² and _(C 2 _{~C 6)} alkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, optionally substituted by R ²² _(C 3 _{~C 6)} alkynyl , C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D-8~D -10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ ^{haloalkynyl, -C (O) R 9,} -C (O) OR 10, -C (O) SR ¹⁰ , -C (O) N (R ¹² ) R ¹¹ , -C (S) OR ¹⁰ , -C (S) SR ¹⁰ , -C (S) N (R ¹² ) R ¹¹ , -C (O) C (O) R ¹⁰ , —C (O) C (O) OR ¹⁰ , —OH, —S (O) ₂ R ¹⁰ , —S (O) ₂ N (R ¹² ) R ¹¹ , —P (O) ( OR ¹⁸ ) ₂ or -P (S) (OR ¹⁸ ) ₂
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, -CHO, C ₁ -C ₆ alkylcarbonyl, or represents C ₁ -C ₆ haloalkylcarbonyl or _C 1 -C ₆ alkoxycarbonyl, or , R ⁸ together with R ⁷ represents a C _{2 to} C ₆ alkylene chain, thereby forming a 3- to 7-membered ring with the nitrogen atom to which R ⁷ and R ⁸ are bonded; in this case the alkylene chain is an oxygen atom, may contain one sulfur atom or a nitrogen atom, and optionally substituted halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, the oxo group or thioxo group May have been
R ^7a represents C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₃ -C ₆ alkenyloxy, phenoxy or phenoxy substituted by (Z) _n1 ;
R ^8a represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ alkenyl, phenyl or phenyl substituted by (Z) _{n 1} , or R ^8a is R ^7a Together with C ₄ -C ₆ alkylene chain to form a 5- to 7-membered ring together with the carbon atoms to which R ^7a and R ^8a are attached. May contain one oxygen or sulfur atom,
R ⁹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- 4~E-7, E13~E-16, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₂ -C ₆ alkynyl or represents _C 2 -C ₆ haloalkynyl,
R ^9a represents phenyl, phenyl substituted by (Z) _n1 , naphthyl or D-1 to D-38;
R ¹⁰ is C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E-2 -E -5, E-7, E- 13, E-14, E-16~E-21, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4~D-6, D- 8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ¹¹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²² , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- _{2 to} E-7, E-13 to E-21, C _{2 to} C ₆ alkenyl, C _{2 to} C ₆ haloalkenyl, C _{3 to} C ₆ alkynyl, C _{3 to} C ₆ haloalkynyl, phenyl, (Z) _n1 Represents phenyl, D-1 to D-25 or D-27 to D-38, substituted by
R ¹² is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkylthio _(C 1 _{~C 4)} alkyl, cyano _(C 1 _{~C 4)} alkyl, or represents C ₃ -C ₆ alkenyl or _C 3 -C ₆ alkynyl, or, R ¹² is R ^{11 represents} a C _{2 to} C ₆ alkylene chain to form a 3 to 7 membered ring together with the nitrogen atom to which R ¹¹ and R ¹² are bonded, and this alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group or a C It is optionally substituted by ₁ -C ₄ alkoxycarbonyl group The
R ¹³ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, phenyl or phenyl substituted by (Z) _{n 1} ,
R ^13a and R ^13b each independently represent C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy;
R ¹⁴ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₄ alkoxycarbonyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxycarbonyl (C ₁ -C ₄₎ alkyl, phenyl _(C 1 -C ₄₎ alkyl, _(Z) phenyl substituted by _{n1 (C} 1 -C ₄₎ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₃ ~ C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, phenyl or phenyl substituted by (Z) _n1
Further, when Z is present at the adjacent position to R ¹⁴ is, -CH ₂ and adjacent R ¹⁴ and _{Z CH 2 CH 2 CH 2 -} , -CH = CH-CH = CH-, -N = CH- An atom to which each of R ¹⁴ and Z is bonded by forming CH = CH-, -CH = N-CH = CH-, -CH = CH-N = CH- or -CH = CH-CH = N- may form a 6-membered ring with a substituted this time, a hydrogen atom is a halogen atom attached to each carbon atom forming the ring, optionally by C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl group May have been
R ¹⁵ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, hydroxy (C ₃ -C ₈ ) cycloalkyl, C ₁ -C ₄ alkoxy (C ₃ -C ₈₎ cycloalkyl, E-1~E-21, C 5 ~C 10 cycloalkyl, C ₅ -C ₁₀ halo ^{cycloalkenyl, -OR 23, -N (R 24} ) R 23, -SH, -S (O ) _r R ²⁵ , -S (O) _q (R ²⁵ ) = NR ²⁰ , -C (O) R ²⁶ , -C (R ²⁶ ) = NOH, -C (R ²⁶ ) = NOR ²⁷ , -C (O ) OH, -C (O) OR ²⁷ , -C (O) SR ²⁷ , -C (O) N (R ²⁹ ) R ²⁸ , -C (O) N (R ²⁹ ) OR ²⁷ , -C (O) N (R ²⁹ ) N (R ^28a ) R ²⁸ , -C (O) C (O) OR ²⁷ , -C (S) OR ²⁷ , -C (S) SR ²⁷ , -C (S) N (R ²⁹ ) R ²⁸ , -C (= NR ²⁸ ) OR ²⁷ , -C (= NR ²⁸ ) SR ²⁷ , -C (= NR ²⁹ ) N (R ^28a ) R ²⁸ , -C (= NOR ²⁷ ) N (R ^{29 _{) R 28, -S (O)}} 2 OH, -S (O) 2 OR 27, -S (O) 2 N (R 29) R 28, -Si (R 13 ^{) (R 13b) R 13,} -P (O) (OR 18) 2, -P (S) (OR 18) 2, -P ( _{phenyl) 2,} -P _{(O) (phenyl) 2,} M-1 ~ M-30, phenyl, (Z) phenyl substituted by _n1 , naphthyl or D-1 to D-38;
R ^15a is a halogen atom, cyano, nitro, C _{3 to} C ₈ cycloalkyl, E-4 to E-6, E-13 to E-15, C _{5 to} C ₁₀ cycloalkenyl, —OR ²³ , —N ( ^{R 24) R 23, -S (} O) r R 25, -C (O) R 26, -C (R 26) = NOH, -C (R 26) = NOR 27, M-3, -C (O ) OR ²⁷ , -C (O) SR ²⁷ , -C (O) N (R ²⁹ ) R ²⁸ , M-7, M-17, -C (S) OR ²⁷ , -C (S) SR ²⁷ ,- C (S) N (R ²⁹ ) R ²⁸ , M-9, M-19, -C (O) C (O) OR ²⁷ , -S (O) ₂ N (R ²⁹ ) R ²⁸ , -Si (R ^{13a) (R 13b) R 13} , -P (O) (OR 18) 2, -P (S) (OR 18) 2, phenyl, phenyl substituted by _{(Z) n1, D-1~D} -3 , D-7, D-10, D-11, D-22 or D-32 to D-35,
M-1 to M-30 each represents a partially saturated heterocyclic ring represented by the following structural formula,

R ¹⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E- 2~E-7, E-13~E- 21, C 2 ~C 6 alkenyl, C ₂ -C ₆ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo cycloalkenyl, C ₃ -C ₆ alkynyl, C ₃ -C ₆ ^{haloalkynyl, -C (O) R 26,} -C (O) OR 27, -C (O) SR 27, -C (O) N (R 29) R 28, -C (S) R ²⁶ , -C (S) OR ²⁷ , -C (S) SR ²⁷ , -C (S) N (R ²⁹ ) R ²⁸ , -S (O) ₂ R ²⁷ , -S (O) ₂ N (R ²⁹ ) R ²⁸ , -P (O) (OR ¹⁸ ) ₂ , -P (S) (OR ¹⁸ ) ₂ , phenyl, phenyl substituted by (Z) _{n 1} , D-1 to D-25 or D-27 to D-38
R ¹⁷ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ haloalkoxy _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₄ alkylsulfonyl _(C 1 -C ₄₎ alkyl, C ₁ -C ₄ haloalkylsulfonyl _(C 1 -C ₄₎ alkyl, cyano _(C 1 -C ₄₎ alkyl, C ₁ -C ₄ alkoxycarbonyl (C ₁ -C ₄₎ alkyl, phenyl _(C 1 _{~C 4)} alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, or represents C ₃ -C ₆ alkynyl or _C 3 -C ₆ haloalkynyl, Alternatively, R ¹⁷ is to form a _C 2 -C ₆ alkylene chain together with ^{R 16} Ri represents that may form a 3- to 7-membered ring together with the nitrogen atom to which R ¹⁶ and R ¹⁷ are attached, the time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₂ alkoxy _(C 1 -C ₂₎ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group or _{C 1} -C ₄ alkoxy may be optionally substituted by a carbonyl group,
R ^16a is C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy (C ₁ -C ₁₂ ) alkyl, cyano (C ₁ -C ₁₂ ) alkyl, C ₁ -C ₁₂ alkoxycarbonyl _(C 1 _{~C 12)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{n1 (C} 1 _{~C 4)} alkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ halo alkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, C ₁ -C ₁₂ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, -C (O) ON = C (CH 3) SCH 3, -C (O) ON = C (SCH ₃ ) C (O) N (CH ₃ ) ₂ represents phenyl or phenyl substituted by (Z) _n1 ;
R ^17a is C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy (C ₁ -C ₁₂ ) alkyl, cyano (C ₁ -C ₁₂ ) alkyl, C ₁ -C ₁₂ alkoxycarbonyl _(C 1 _{~C 12)} alkyl, phenyl _(C 1 _{~C 4)} alkyl, _(Z) phenyl substituted by _{n1 (C} 1 _{~C 4)} alkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ halo alkenyl, C ₃ -C ₁₂ alkynyl, C ₃ -C ₁₂ haloalkynyl, phenyl or _(Z) or represents phenyl which is substituted by _n1, or, R ^17a together with ^{R 16a} _C 4 _{~C 7} alkylene By forming a chain, it represents that a 5- to 8-membered ring may be formed together with the nitrogen atom to which R ^16a and R ^17a are bonded. At this time, the alkylene chain may contain one oxygen atom or sulfur atom. , and _C 1 _~C May be optionally substituted by alkyl or C ₁ -C ₄ alkoxy group,
R ¹⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁹ is a halogen atom, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, hydroxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxycarbonyl _(C 1 -C ₄₎ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylamino, di _(C 1 -C ₆ alkyl) amino, C ₁ ~ C ₆ alkoxycarbonyl, phenyl or phenyl substituted by (Z) _{n 1} , and when p1 to p8 represent an integer of 2 or more, each R ¹⁹ may be the same as or different from each other. Well, furthermore, when two R ¹⁹ are substituted on the same carbon atom, the two R ¹⁹ together are oxo, thioxo, imino, C ₁ -C ₄ alkylimino, C ₁ -C ₄ alkoxy imino or _C 1 -C ₄ alkylidene It indicates that may form,
R ²⁰ is a hydrogen atom, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₁ -C ₆ alkylsulfonyl or C ₁ -C ₆ haloalkylsulfonyl,
R ²¹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, -OH, ^{benzyloxy, -C (O) R 31,} -C (O) OR 32, -C (O) SR 32, -C (O) N (R 34 ) R ³³ , -C (S) N (R ³⁴ ) R ³³ , -S (O) ₂ R ³² , -P (O) (OR ¹⁸ ) ₂ , -P (S) (OR ¹⁸ ) ₂ , phenyl, (Z) represents phenyl or D-3 substituted by _n1 ,
R ²² is a halogen atom, cyano, C _{3 to} C ₈ cycloalkyl, C _{3 to} C ₈ halocycloalkyl, E-1 to E-21, C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ haloalkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ haloalkylsulfonyl, C ₁ -C ₆ alkylamino, di _(C 1 -C ₆ alkyl) amino, - CHO, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₁ -C ₆ alkylaminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, phenyl, (Z) phenyl substituted by _n1 or D-1 to D-38,
R ²³ is a hydrogen atom, C ₁ -C ₈ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 8)} alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted by R ³⁰ _{(C 3} ˜C ₈ ) cycloalkyl, E-2 to E-7, E-13 to E-21, C _{3 to} C ₈ alkenyl, (C _{3 to} C ₈ ) alkenyl optionally substituted by R ³⁰ , C ₃ to C ₈ alkynyl, (C ₃ -C ₈ ) alkynyl optionally substituted by R ³⁰ , —C (O) R ³¹ , —C (O) OR ³² , —C (O) SR ³² , —C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) R ³² , -C (O) C (O) OR ³² , -C (S) R ³¹ , -C (S) OR ³² , -C (S) SR ³² , -C (S) N (R ³⁴ ) R ³³ , -S (O) ₂ R ³² , -S (O) ₂ N (R ³⁴ ) R ³³ , -Si (R ^13a ) (R ^{13b) R 13, -P (O} ) (OR 18) 2, -P (S) (OR 18) 2, phenyl, _(Z) phenyl substituted by _{n1, D-1, D-} 2, D-4 ~ D-6, D-8 ~ D-10, D-12 ~ D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ²⁴ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₄ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₄ ). Alkyl, C ₁ -C ₄ alkylthio (C ₁ -C ₄ ) alkyl, cyano (C ₁ -C ₄ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C _{1 to} C ₆ alkoxy, phenyl or phenyl substituted by (Z) _{n 1} , or R ²⁴ together with R ²³ forms a C _{2 to} C ₅ alkylene chain to form R ²³ and R ²⁴ represents that a 3- to 6-membered ring may be formed together with the nitrogen atom to which ²⁴ is bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom, C _1- C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ Alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, a phenyl group, optionally substituted by a phenyl group, an oxo group or a thioxo group substituted by (Z) _n1 Often,
R ²⁵ is, C ₁ -C ₈ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 8)} alkyl, optionally substituted by C ₃ -C ₈ cycloalkyl, R ³⁰ _(C 3 _{~C 8} ) cycloalkyl, optionally substituted by E-2~E-5, E- 7, E-13, E-14, E-16, C 3 ~C 8 _{^{alkenyl, R 30 (C 3 ~C 8}} ) alkenyl, C ₃ -C ₈ alkynyl, optionally substituted by R ³⁰ _(C 3 _{~C 8)} ^{alkynyl, -C (O) R 31,} -C (O) OR 32, -C (O) SR 32, -C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) R ³² , -C (O) C (O) OR ³² , -C (S) R ³¹ , -C (S) OR ³² , —C (S) SR ³² , —C (S) N (R ³⁴ ) R ³³ , —SH, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, phenylthio, (Z) _n1 substituted been ^{phenylthio, -P (O) (OR 18} ) 2, -P (S) (OR 18) 2, phenyl, (Z) phenyl substituted by _{n1, D-9, D-} 10 It represents D-12, D-14~D-17, D-30 or D-32~D-35,
R ²⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl (C ₁ -C ₄ ) alkyl, C ₁ -C ₆ alkoxy (C ₁ -C ₄ ). alkyl, C ₁ -C ₆ haloalkoxy _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ alkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ haloalkylthio _(C 1 _{~C 4)} alkyl, C ₁ -C ₆ alkylsulfonyl _(C 1 ~C ₄₎ alkyl, C ₁ -C ₆ haloalkylsulfonyl _(C 1 ~C ₄₎ alkyl, phenyl _(C 1 ~C ₄₎ alkyl, phenyl substituted by _{(Z) n1 (C} 1 _{~C 4)} represents alkyl, C ₃ -C ₆ cycloalkyl, phenyl substituted by phenyl or _{(Z) n1,}
R ²⁷ is optionally substituted by C ₁ -C ₆ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, R ³⁰ _(C 3 _{~C 8} ) cycloalkyl, optionally substituted by E-2~E-5, E- 7, E-13, E-14, E-16, C 2 ~C 6 _{^{alkenyl, R 30 (C 2 ~C 6}} ) Alkenyl, C ₃ -C ₆ alkynyl, (C ₃ -C ₆ ) alkynyl, phenyl optionally substituted by R ³⁰ , phenyl, (Z) _{n 1} substituted phenyl, D-1, D-2, D-4 D-6, D-8 to D-10, D-12 to D-19, D-21, D-23, D-25, D-27 or D-30 to D-38,
R ²⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, optionally substituted by R ³⁰ _(C 1 _{~C 6)} alkyl, C ₃ -C ₈ cycloalkyl, optionally substituted by R ³⁰ _{(C 3} ˜C ₈ ) cycloalkyl, E-1 to E-7, E-13 to E-21, C _{2 to} C ₆ alkenyl, (C _{2 to} C ₆ ) alkenyl optionally substituted by R ³⁰ , C ₃ to C ₈ alkynyl, (C ₃ -C ₆ ) alkynyl optionally substituted by R ³⁰ , phenyl, (Z) phenyl substituted by _{n 1} , D-1 to D-25 or D-27 to D-38 ,
R ^28a represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ²⁹ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ³⁰ , C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C Represents ₆ alkynyl, C ₃ -C ₆ haloalkynyl, phenyl or phenyl substituted by (Z) _{n 1} , or R ²⁹ together with R ²⁸ forms a C ₂ -C ₅ alkylene chain. , R ²⁸ and R ²⁹ may form a 3- to 6-membered ring together with the nitrogen atom to which R ²⁸ and R ²⁹ are bonded, and this alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ alkoxycarbonyl group, a phenyl group, substituted by _{(Z) n1} Depending on the phenyl group or oxo group Optionally substituted,
R ³⁰ is a halogen atom, cyano, nitro, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halocycloalkyl, E-4, E-5, E-8, E-9, E-11, E- 13, E-14, E- 17, E-18, E-20, -OH, -OR 32, -OC (O) R 31, -OC (O) OR 32, -OC (O) N (R 34 ) R ³³ , -OC (S) N (R ³⁴ ) R ³³ , -SH, -S (O) _r R ³² , -SC (O) R ³¹ , -SC (O) OR ³² , -SC (O) N (R ³⁴ ) R ³³ , -SC (S) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) R ³³ , -N (R ³⁴ ) CHO, -N (R ³⁴ ) C (O) R ³¹ , -N (R ³⁴ ) C (O) OR ³² , -N (R ³⁴ ) C (O) SR ³² , -N (R ³⁴ ) C (O) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) C (S) N (R ³⁴ ) R ³³ , -N (R ³⁴ ) S (O) ₂ R ³² , -C (O) R ³¹ , -C (O) OH, -C (O) OR ³² , -C (O) SR ³² , -C (O) N (R ³⁴ ) R ³³ , -C (O) C (O) OR ³² , -Si (R ^13a ) (R ^13b ) R ¹³ , -P (O ) (substituted by _{^{OR 18) 2, -P (S}} ) (OR 18) 2, -P ( _{phenyl) 2,} -P (O) _{(phenyl) 2,} phenyl, _{(Z) n1} The phenyl or D-1~D-38,
R ³¹ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-4, E-5 , E-13, E-14, C 2 ~C 8 alkenyl, C ₂ -C ₈ haloalkenyl, C ₅ -C ₁₀ cycloalkenyl, C ₅ -C ₁₀ halo represents cycloalkenyl, C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl, phenyl, phenyl or D-1 to D-38 substituted by _{(Z) n1,}
R ³² is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, E-4, E-5 , C ₂ -C ₈ represents alkenyl, C ₂ -C ₈ haloalkenyl, a C ₃ -C ₈ alkynyl or phenyl,
R ³³ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ³⁵ , C ₃ -C ₆ cycloalkyl, E-4, E-5 _{, E-13, C 2 ~C} 8 alkenyl, C ₂ -C ₈ haloalkenyl, C ₃ -C ₈ alkynyl, phenyl, phenyl substituted by _{(Z) n1, D-1~D} -25 or D-27 ~ Represents D-38,
R ³⁴ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ alkynyl, or R ³⁴ Represents that, together with R ³³ , a C _{2 to} C ₅ alkylene chain may be formed to form a 3 to 6 membered ring together with the nitrogen atom to which R ³³ and R ³⁴ are bonded. alkylene chain oxygen atom may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy group, -CHO group, C ₁ -C ₄ alkylcarbonyl group , C ₁ -C ₄ alkoxycarbonyl group, may be optionally substituted by a phenyl group substituted by a phenyl group or (Z) _n1,
R ³⁵ is cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-4, E-5, E-13, E-14, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, phenoxy, _{(Z) n1} phenoxy substituted by, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, phenylthio, _(Z) phenylthio substituted by _n1, C ₁ -C ₄ alkylsulfonyl , C ₁ -C ₄ haloalkylsulfonyl, phenylsulfonyl, _(Z) phenylsulfonyl substituted by _{^{n1, -N (R 37) R}} 36, C 1 ~C 6 alkyl carbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ ~ C ₆ alkoxycarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, tri (C ₁ -C ₄ alkyl) silyl, phenyl, phenyl substituted by (Z) _{n 1} , naphthyl or D-1 -D-38 Represents
R ³⁶ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ haloalkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenylcarbonyl or phenyl substituted by (Z) _n1 Represents carbonyl,
R ³⁷ represents a hydrogen atom or C ₁ -C ₆ alkyl,
m represents an integer of 0 to 5;
n1 represents an integer of 1 to 5,
n2 represents an integer of 0 to 4,
n3 represents an integer of 0 to 3,
n4 represents an integer of 0 to 2,
n5 represents an integer of 0 or 1,
p1 represents an integer of 0 to 2,
p2 represents an integer of 0 to 3,
p3 represents an integer of 0 to 4,
p4 represents an integer of 0 to 5;
p5 represents an integer of 0 to 6,
p6 represents an integer of 0 to 7,
p7 represents an integer of 0 to 8,
p8 represents an integer of 0 to 9,
q represents an integer of 0 or 1,
r represents an integer of 0 to 2. ]
Insecticides, acaricides, nematicides, and molluscs containing one or more selected from the substituted isoxazoline compounds represented by the formula and salts thereof and one or more selected from the following active ingredient group A Animal, bactericidal or bactericidal composition.
Active ingredient group A: acibenzoral-S-methyl, acipetax, aldimorph, allyl alcohol, amisulbrom, ambam, ampropylphos, anilazine, azaconazole, adithylam, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanyl, benomyl, Benquinox, Ventallon, Bench Avaricarb-Isopropyl, Benchazole, Benzacryl, Benzamorph, Binapacryl, Biphenyl, Vitertanol, Bixaphene, Blasticidin-S, Bordeaux Solution, Boscalid, Bromuconazole, Bupirimate, Butiobate, Butylamine, Lime Sulfur Agent, captafol, captan, carbamorph, carbendazim, carboxin, carpropamide, carvone, chess Tonmixture, quinomethionate, clobenazone, chloraniformane, chloranil, chlorphenazole, chloronebu, chlorpicrin, chlorothalonil, chlorquinox, clozolinate, crimbasol, copper acetate, basic copper carbonate, cupric hydroxide, copper Naphthenate, Copper Oleate, Basic Copper Chloride, Copper Sulfate, Basic Copper Sulfate, Copper Zinc Chromate, Cresol, Cufuraneb, Cuprobam, Cyazofamide, Cyclafamide, Cycloheximide, Cyflufenamide, Simoxanyl, Cipendazole, Cyproconazole, Cyprodinil, Ciproflam , Dazomet, debacarb, decafentin, dehydroacetate, dicloflurane, dicron, dichlorophen, diclozoline, diclobutra , Diclocimet, diclomedin, dichlorane, diethofencarb, diphenoconazole, diflumetrim, dimethymol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobutone, dinocup, dinocup-4, dinocup-6, dinoctone, dinosulphonedinoterone , Dipyrithione, disulfiram, ditalimphos, dithianon, denouc, dodemorph, dozin, drazoxolone, edifenphos, epoxiconazole, ethaboxam, ethaconazole, etem, etilimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminophen Buconazole, Fenfram, Fenhexamide, Fenitropan, phenoxanyl, fenpicuronyl, fenpropidin, fenpropimorph, fentin, farbam, ferimzone, fluazinam, fludioxonil, flumethoverl, flumorph, fluopicolide, fluopyram, fluorimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, Flusulfamide, flutolanil, fluthianyl, flutriahol, phorpet, fosetyl-aluminum, fuberidazole, flaraxil, furametopyl, flucarbanil, fluconazole, fluconazole-cis, flumeciclos, furophanate, gliodin, griseofulvin, guazatine, haracrinate, hexachlorobenzene, hexacobenzene Nazole, hexyl thiophos, sulfuric acid Xyquinoline, himexazole, imazalyl, imibenconazole, iminoctadine-arbesylate, iminotazine acetate, ipconazole, iprobenphos, iprodione, iprovalicarb, isothianyl, isoprothiolane, isopyrazam, isovaradione, kasugamycin, cresoxime-methyl, mancapmandimanp , Mevenil, mecarbine zid, mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole, metasulfocarb, metofloxam, methylam, methinostrobin, metolaphenone, metsulfofax, milneb, microbutanyl, microzotan, myna , Organic nickel, nitrostyrene, nitrota -Isopropyl, Nualimol, Off-race, Orisatrobin, Oxazixyl, Copper oxyquinoline, Oxpoconazole fumarate, Oxycarboxyl, Pephrazoate, Penconazole, Pencyclon, Pentachlorophenol, Penthiopyrad, Orthophenylphenol, Phosfeifene, Fusalide, Picoxy Strobin, Piperalin, Polycarbamate, Polyoxin, Polyoxin-D, Potassium azide, Potassium bicarbonate, Probenazole, Prochloraz, Procimidone, Propamocarb hydrochloride, Propiconazole, Propineb, Proquinazide, Pyrazophos, Pyribencarb methyl, Pyrifenox, Pyrimethanyl, pyrokilone, prothiocarb, prothioconazole, pyracarbollide, pyraclostrobin, pyri Dinitrile, Pyrocyclol, Piroxiflu, Quinacetol-Sulfate, Quinazomide, Quinconazole, Quinoxyphene, Quintozen, Rabenzazole, Salicylanilide, Sedaxan, Silthiofam, Cimeconazole, Sodium bicarbonate, Sodium hypochlorite, Spiroxamine, Sulfur, Tebuconazole, Technazene, Column Tetraconazole, thiabendazole, thiadifluor, thiosiophene, tifluzamide, thiochlorfenhim, thiophanate, thiophanate-methyl, thiuram, thiazinyl, thioximide, tolcrophos-methyl, tolylfuranide, triadimethone, triadimenol, triamifos, trialimol , Triazbutyl, triazoxide, tributyltin oxide, trichlamide, tricycle Zole, Tridemorph, Trifloxystrobin, Triflumizole, Trifolin, Triticonazole, Validamycin, Vinclozoline, Zaliramide, Zincnaphthenate, Zinc sulfate, Dineb, Diram, Zoxamide, Shiitake mycelium extract, Shiitake fruiting body extract, ZF-9646, aureofandine, benzalkonium chloride, betoxazine, bithionol, bronopol, formaldehyde, nitrapirine, octyrinone, oxolinic acid, oxytetracycline, ribavirin, streptomycin, teclophthalam, aldoxycarb, kazusafos, davyphene, diclofenthion, DSP , Etioprophos, phenamiphos, phensulfothione, phostiazete, fostiethane, imiciaphos, isamidephos Isazophos, methyl bromide, methyl isothiocyanate, oxamyl, sodium azide, thionadine, BYI-1921, MAI-08015, acequinosyl, acrinathrin, amidoflumet, amitraz, bifenazate, bromopropyrate, chlorobenzilate, clofentezine, cienopyrafen , Cyflumetofene, cyhexatin, dicohol, dienochlor, etoxazole, phenazaquin, fenbutatin-oxide, phenothiocarb, fenpropatoline, fenpyroximate, fluacrylpyrim, formethanate, halfenprox, hexithiazox, milbemectin, propargite, pyridaben, spirimidifen , Tebufenpyrad, thioquinox, N 1-0711, abamectin, acephate, acetamiprid, alanic carb, aldicarb, allesulin, azinephos-ethyl, azinephos-methyl, bacillus thuringiensis, bendiocarb, benfurthrin, benfuracarb, bensultap, bifenthrin, bistrifluron, buprofezin , Carbaryl, carbofuran, carbosulfan, cartap, chloranthraniliprole, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyantraniliprole, cycloprotorin, cifluthrin, Beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermeth Phosphorus, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, ciphenothrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos, dinotefuran, geophenolane, disulfone, emamectin benzoate, Empentrin, endosulfan, alpha-endosulfan, EPN, esfenvalerate, etiofencarb, ethiprole, etofenprox, etrimphos, fenfluthrin, fenitrothion, fenocarb, phenoxycarb, fenthion, fenvalerate, fipronil, flonicamid, fluazulon, flubenzilamide, full Cycloxuron, flucitrinate, furfu Nelim, flufenoxuron, flufenprox, flumethrin, fulvalinate, tau-fluvalinate, phonofos, formothione, furthiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, imiprotoline, indoxacarb, indoxacarb-MP, Isofenphos, isoprocarb, isoxathion, repimectin, rufenuron, malathion, metaflumizone, metaldehyde, methacryfos, methamidophos, metidathion, mesomil, mesoprene, methoxychlor, methoxyphenozide, metoflutrin, monocrotophos, muscarua, nicotine sulfate, nitenpyramtone, fludemetholone -Methyl, oxydeprophos, parathion, parathi N-methyl, permethrin, phenothrin, phentoate, folate, hosalon, phosmet, phosphamidone, phoxime, pirimicurve, pirimiphos-ethyl, pyrimiphos-methyl, profenofos, propaphos, prothiophos, protrifenbut, pymetrozine, pyracrophos, pyrethrin, pyridalyl, pyrifluquinazone , Pyriprole, pyriproxyfen, resmethrin, rotenone, silafluophene, spinetoram, spinosad, spirotetramate, sulfotepeptol, sulfoxafurol, sulprophos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorobinphos, tetramethrin, d-T-80 -Phthalthrin, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiopha Knox, thiometone, tolfenpyrad, tralomethrin, transfluthrin, triazamate, trichlorfone, triflumuron, bamidthione, ANM-138 and ME-5343. In equation (1),
A ¹ represents CY or a nitrogen atom,
A ² and A ³ represent CH,
A ⁴ represents CH or a nitrogen atom,
G represents a benzene ring,
L represents —CH (R ⁴ ) —
X represents a halogen atom, cyano, —SF ₅ , C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkoxy or C ₁ -C ₂ haloalkylthio, and when m represents 2 or 3, each X is They may be the same or different from each other,
Y is a hydrogen atom, a halogen atom, cyano, nitro, methyl, ethyl, C ₁ -C ₂ haloalkyl, C ₂ -C ₃ alkynyl, C ₁ -C ₂ haloalkoxy, C ₁ -C ₂ haloalkylthio or -C ( S) NH ₂
R ¹ represents —C (O) R ^1a , —C (O) SR ^1b , —C (O) N (R ^1d ) R ^1c or —C (S) R ^1a ,
R ^1a is C ₁ -C ₄ alkyl, (C ₁ -C ₄ ) alkyl optionally substituted by R ¹⁵ , C ₃ -C ₄ cycloalkyl, E-4, E-5, C ₂ -C ₄ alkenyl. , C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl, (Z) _n1 substituted phenyl or D-32,
R ^1b represents C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl,
R ^1c represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ^1d represents a hydrogen atom or C ₁ -C ₄ alkyl;
R ² represents a hydrogen atom, C ₁ -C ₄ alkyl, (C ₁ -C ₂ ) alkyl substituted by R ^15a , C ₃ -C ₄ alkenyl or C ₃ -C ₄ alkynyl,
R ³ represents C ₁ -C ₂ haloalkyl,
R ⁴ represents a hydrogen atom, cyano, methyl, ethynyl or —C (S) NH ₂ , or when A ¹ represents CY, R ⁴ together with Y represents —CH ₂ CH ₂ By forming-or -CH ₂ CH ₂ CH _{2-, a} condensed ring may be formed by forming a 5-membered ring or 6-membered ring with the atoms to which R ⁴ and Y are bonded,
Z represents a halogen atom, cyano, nitro or C ₁ -C ₄ alkylthio, when n1 and n2 represents an integer of 2 or more, each Z may be the even or different from each other the same as each other,
R ¹⁵ is a halogen atom, C ₃ -C ₄ cycloalkyl, methoxy, ethoxy, C ₁ -C ₂ haloalkoxy, —N (R ²⁴ ) R ²³ , —S (O) _r R ²⁵ , —S (O) _q (R ²⁵ ) = NR ²⁰ or —C (O) N (R ²⁹ ) R ²⁸
R ^15a is cyano, C ₃ -C ₄ cycloalkyl, methoxy, ethoxy, C ₁ -C ₂ haloalkoxy, —N (R ²⁴ ) R ²³ , methoxycarbonyl, ethoxycarbonyl, —C (O) N (R ²⁹ ) Represents R ²⁸ or —C (S) NH ₂ ;
R ²⁰ represents a hydrogen atom or C ₁ -C ₂ haloalkylcarbonyl,
R ²³ represents cyano (C ₁ -C ₂ ) alkyl, —C (O) R ³¹ , methoxycarbonyl or ethoxycarbonyl,
R ²⁴ represents a hydrogen atom, methoxycarbonyl or ethoxycarbonyl,
R ²⁵ represents methyl, ethyl, C ₁ -C ₂ haloalkyl or cyanomethyl;
R ²⁸ represents a hydrogen atom, methyl or ethyl,
R ²⁹ represents a hydrogen atom or methyl;
R ³¹ represents methyl, ethyl, C ₁ -C ₂ haloalkyl or cyclopropyl;
m represents an integer of 1 to 3,
n1 represents an integer of 1 to 3,
n2 represents an integer of 0 to 2,
The composition of claim 1, wherein p6 represents 0. In equation (1),
A ¹ represents CY,
A ⁴ represents CH,
X represents a halogen atom or trifluoromethyl, and when m represents 2 or 3, each X may be the same as or different from each other;
Y represents a hydrogen atom, a halogen atom, nitro or methyl,
R ¹ represents —C (O) R ^1a or —C (O) NHR ^1c ;
R ^1a represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₂ ) alkyl, optionally substituted by R ¹⁵ , cyclopropyl, E-4 or E-5,
R ^1c represents C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, cyclopropyl, allyl or propargyl;
R ² represents a hydrogen atom, methyl, ethyl, cyclopropylmethyl, methoxymethyl, ethoxymethyl, cyanomethyl, allyl or propargyl,
R ³ represents trifluoromethyl or chlorodifluoromethyl,
R ⁴ represents a hydrogen atom, cyano or methyl,
R ¹⁵ represents cyclopropyl or —S (O) _r R ²⁵ ;
A composition according to claim _2, wherein R ²⁵ represents methyl, ethyl or C ₁ -C ₂ haloalkyl. In equation (1),
R ¹ represents -C (O) R ^1a ;
R ^1a represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, cyclopropylmethyl or cyclopropyl,
R ² represents a hydrogen atom, methyl, ethyl, cyanomethyl or propargyl,
R ³ represents trifluoromethyl,
The composition according to claim 3, wherein R ⁴ represents a hydrogen atom or methyl. In equation (1),
R ¹ represents -C (O) R ^1a ;
R ^1a represents methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, ethylthiomethyl, ethylsulfinylmethyl, ethylsulfonylmethyl or bis (methylthio) methyl;
R ² represents a hydrogen atom, methyl, ethyl, cyanomethyl or propargyl,
R ³ represents trifluoromethyl,
The composition according to claim 3, wherein R ⁴ represents a hydrogen atom or methyl. One or more selected from the substituted isoxazoline compounds represented by the formula (1) according to claim 1 and a salt thereof and one or more selected from the following active ingredient group B: An insecticidal or acaricidal composition containing.
Active ingredient group B: acequinosyl, chlorfenapyr, sienopyrafen, cyflumetofene, dienochlor, etoxazole, phenazaquin, fenbutatin-oxide, milbemectin, propargite, spirodiclofen and spiromesifen. One or more selected from the substituted isoxazoline compound represented by the formula (1) according to claim 1 and a salt thereof, and one or more selected from the following active ingredient group C: An insecticide composition containing the composition.
Active ingredient group C: acephate, acetamiprid, clothianidin, dinotefuran, etiprol, flonicamid, imidacloprid, nitenpyram, pymetrozine, pyridaben, pyrifluquinazone, spirotetramate, sulfoxafurol, thiacloprid, thiamethoxam and tolfenpyrad. One or more selected from the substituted isoxazoline compounds represented by the formula (1) according to claim 1 and a salt thereof and one or more selected from the following active ingredient group D: An insecticide composition containing the composition.
Active ingredient group D: Abamectin, acephate, Bacillus thuringiensis, chloranthraniprol, chlorfenapyr, chromafenozide, cyantraniliprole, lambda-cyhalothrin, cypermethrin, deltamethrin, emamectin benzoate, fulvendiamide, flufenoxuron, indoxa Carb-MP, lepimectin, mesomil, permethrin, pyridalyl, spinetoram and spinosad.   1 type or 2 types or more selected from the substituted isoxazoline compound and its salt represented by Formula (1) of Claims 1-5, and 1 type or 2 selected from the active ingredient group A of Claim 1 A method for controlling pests or diseases by treating more than one species simultaneously or in close proximity.   One or more selected from the substituted isoxazoline compounds represented by the formula (1) according to claim 1 and a salt thereof and one or two selected from the active ingredient group B according to claim 6 A method for controlling pests or ticks that treats more than one species simultaneously or in close proximity.   One or more selected from the substituted isoxazoline compounds represented by the formula (1) according to claim 1 to 5 and salts thereof, and one or two selected from the active ingredient group C according to claim 7. A method for controlling pests by treating more than one species simultaneously or in close proximity.   One or more selected from the substituted isoxazoline compounds represented by the formula (1) according to claim 1 to 5 and salts thereof, and one or two selected from the active ingredient group D according to claim 8. A method for controlling pests by treating more than one species simultaneously or in close proximity.