JP2015172030A - Haloalkylsulfonamide derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a safe herbicide that has an effect on a variety of weeds at a low dosage, and alleviates problems such as soil contamination and an influence on succeeding crops.SOLUTION: A herbicide comprises, for example, a haloalkylsulfonamide derivative represented by the following general formula and/or salt thereof as an active ingredient, where Rrepresents a H atom, an alkoxycarbonyl group or the like, and Rrepresents a H atom, an alkoxycarbonyl group, an optionally substituted C1-C6 alkyl group, a tetrahydropyranyl group or the like.

Description

  The present invention relates to a novel haloalkylsulfonamide derivative and a salt thereof, and an agrochemical, particularly a herbicide, containing the haloalkylsulfonamide derivative and a salt thereof as an active ingredient. The agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.

  For example, Patent Documents 1 to 10 disclose certain haloalkylsulfonamide derivatives, but do not disclose any haloalkylsulfonamide derivatives according to the present invention.

International Publication No. 2004/011429 International Publication No. 2006/090792 International Publication No. 2008/059948 International Publication No. 2008/102908 International Publication No. 2010/026989 International Publication No. 2010/119906 International Publication No. 2013/061973 JP 2008-074840 A JP 2008-074841 A JP 2010-280638 A

  The object of the present invention is a highly safe and effective herbicide active ingredient that reliably shows effects on various weeds at a lower dose, and has reduced problems such as soil contamination and effects on subsequent crops. It is to provide useful chemical substances.

  As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that the novel haloalkylsulfonamide derivatives represented by the following formula (1) according to the present invention have excellent herbicidal activity and targets. The present invention has been completed by discovering that it is a highly useful compound that has a high safety against certain crops and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

  That is, the present invention relates to the following [1] to [6].

[1]
Formula (1):

[Wherein A represents -CH = CH- or a sulfur atom,
W represents an oxygen atom or a sulfur atom,
X is a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 3 -C _{6 cycloalkyl,} C 3 -C _{6 halocycloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ halo _alkenyl, C 2 -C _{6 alkynyl,} C 2 -C ₆ haloalkynyl, cyano, -C ^{(O) R 46,} _hydroxy, C 1 -C _{6 alkoxy,} C 1 -C ₆ haloalkoxy, amino, nitro or -S (O) When _q7 R ⁴⁹ is represented and m represents an integer of 2 or more, each X may be the same as or different from each other, and when two Xs are adjacent to each other, two adjacent X is _{-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 _{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— may form a 5-membered or 6-membered ring with the carbon atom to which each of the two Xs is bonded, when the hydrogen atoms bonded to each carbon atom forming the ring may be optionally substituted by halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
m represents an integer of 0, 1 or 2;
n represents an integer of 1, 2, 3 or 4;
p represents an integer of 0 or 1,
R ¹ represents C ₁ -C ₆ haloalkyl,
R ² is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 10} _(C 1 ~C _{6) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally substituted by ^{R 10} _{(C 3} -C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 10} _(C 2 ~C _{6) alkenyl,} optionally substituted by C 2 -C ₆ ^{alkynyl, R 10} _(C 2 ~ C ₆ ) represents alkynyl, —C (O) R ¹¹ or —S (O) ₂ R ¹² ,
R ³ and R ⁴ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy or _C 1 -C ₆ represent a haloalkoxy, or ^{by R 3} to form a _C 2 -C ₆ alkylene chain together with ^{R 4,} the carbon ^{to which R 3} and ^{R 4} are bonded Represents that a 3- to 7-membered ring may be formed together with the atoms;
R ⁵ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 27} _(C 1 ~C _{6) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally substituted by ^{R 27} _{(C 3} -C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 27} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 27} _(C 2 ~ C ₆₎ represents an ^alkynyl, -C (O) R ^28, and -S _(O) ^{2 R 30} or D-1~D-9,
R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , C ₃ -C ₆ cycloalkyl, R optionally substituted by ³⁹ _(C 3 ~C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 39} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^{alkynyl, R 39} optionally substituted by _(C 2 _{~C 6)} alkynyl, ^{phenyl, (R} ₄₀₎ phenyl substituted by ^{_{q5, -C (O) R 41}} , cyano, ^{-OR 42} or -S _(O) q6 ^{R 43} Or R ⁶ and R ⁷ on the same carbon may form a C ₂ -C ₆ alkylene chain together to form a 3- to 7-membered ring with the carbon atoms to which they are attached. The table At this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, or R ⁶ and R ⁷ on the same carbon with one another bond, it may form a = CH ₂ or carbonyl And when n = 2-4, R ⁶ and R ⁷ together with R ⁶ or R ⁷ on different carbons form a C ₂ -C ₆ alkylene chain, thereby binding carbon atoms. The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and R ⁶ and R ⁷ may be on different carbons. R ⁶ or R ⁷ may be the same or different, and R ⁶ and R ⁷ together with R ⁶ or R ⁷ on adjacent carbons may represent a bond,
R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , C ₃ -C ₆ cycloalkyl, R optionally substituted by ³⁹ _(C 3 ~C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 39} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^{alkynyl, R 39} optionally substituted by _(C 2 _{~C 6)} alkynyl, ^{phenyl, (R} ₄₀₎ phenyl substituted by ^{_{q5, -C (O) R 41}} , cyano, ^{-OR 42} or -S _(O) q6 ^{R 43} Or R ⁸ and R ⁹ on the same carbon may form a C ₂ -C ₆ alkylene chain together to form a 3- to 7-membered ring with the carbon atoms to which they are attached. The table At this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, or R ⁸ and R ⁹ on the same carbon with one another bond, it may form a = CH ₂ or carbonyl Represents
D-1 to D-9 each represent a ring represented by the following structural formula;

R ¹⁰ represents a halogen atom, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , —C (O) R ¹⁴ , —OR ¹⁵ or —S (O) _{q 2} R ¹⁹ ,
R ¹¹ _is, C 1 _{-C 12} ^alkyl, substituted optionally substituted by ^{R 20} _(C 1 ~C _{12) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally by ^{R 20} _(C 3 ~C ₆ ) _cycloalkyl, optionally substituted by C 2 -C _{6 ^{alkenyl, R 20 (C 2 ~C 6}} ) _alkenyl, optionally substituted by C 2 -C _{6 ^{alkynyl, R 20 (C 2 ~C 6}} ) It represents alkynyl, ^{phenyl, (R} ₁₃₎ phenyl substituted by _{^{q1, -OR 21, -N (R}} 22) R 23 or ^{-SR 24,}
R ¹² represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} or —N (R ²⁵ ) R ²⁶ ,
R ¹³ represents a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{6 alkoxy,} C 1 -C ₆ haloalkoxy, amino or nitro, q1 is an integer of 2 or more Each R ¹³ may be the same as or different from each other, and when two R ¹³ are adjacent to each other, the two adjacent R ¹³ 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 = By forming the H-, 2 two together with the carbon atoms bonded thereto to R ¹³ may form a 5- or 6-membered ring, this time, the hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁴ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ¹⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} or —C (O) R ¹⁶ ,
R ¹⁶ represents C ₁ -C ₆ alkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , C ₁ -C ₆ alkoxy or —N (R ¹⁷ ) R ¹⁸ ,
R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ¹⁷ together with R ¹⁸ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ¹⁹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ²⁰ represents a halogen atom, C ₃ -C ₆ cycloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or phenoxy,
R ²¹ _is, C 1 _{-C 12} ^alkyl, substituted optionally substituted by ^{R 20} _(C 1 ~C _{12) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally by ^{R 20} _(C 3 ~C ₆ ) _cycloalkyl, optionally substituted by C 2 -C _{6 ^{alkenyl, R 20 (C 2 ~C 6}} ) _alkenyl, optionally substituted by C 2 -C _{6 ^{alkynyl, R 20 (C 2 ~C 6}} ) Represents alkynyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ;
R ²² and R ²³ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ²² together with R ²³ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ²⁴ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁵ and R ²⁶ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ²⁵ together with R ²⁶ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ²⁷ is a halogen atom, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ halocycloalkyl, —C (O) R ³¹ , —OR ³² , —N (R ³³ ) R ³⁴ , —S (O). _q4 R ^35, tri _(C 1 -C ₆ alkyl) a silyl or D-1~D-9,
R ²⁸ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, It represents -N ^{(R 36)} R ³⁷ or ^{-SR 38,}
R ²⁹ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, amino or nitro, and q 3 represents an integer of 2 or more. Each R ²⁹ may be the same as or different from each other, and when two R ²⁹ are adjacent to each other, the two adjacent R ²⁹ 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 = By forming the H-, 2 two together with the carbon atoms to which each R ²⁹ is bonded may form a 5- or 6-membered ring, this time, the hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁰ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³¹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy,
R ³² represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³³ and R ³⁴ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ³³ together with R ³⁴ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ³⁵ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³⁶ and R ³⁷ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ³⁶ together with R ³⁷ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ³⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁹ represents a halogen atom, C ₃ -C ₆ cycloalkyl, phenyl, hydroxy, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy,
R ⁴⁰ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, amino or nitro, and q 5 represents an integer of 2 or more. Each R ⁴⁰ may be the same as or different from each other, and when two R ⁴⁰ are adjacent to each other, the two adjacent R ⁴⁰ 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 = By forming the H-, 2 one respective R ⁴⁰ may form a 5- or 6-membered ring together with the carbon atoms to which they are attached this case, hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁴¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, C ₁ -C ₆ halo. alkoxy or ^{-N (R 44)} R ^45,
R ⁴² represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, phenyl substituted by phenyl or ^(R _{40) q5,}
R ⁴³ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ⁴⁰ ) _q5 ,
R ⁴⁴ and R ⁴⁵ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ⁴⁴ together with R ⁴⁵ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ⁴⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or —N (R ⁴⁷ ) R ⁴⁸ ,
R ⁴⁷ and R ⁴⁸ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ⁴⁷ together with R ⁴⁸ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ⁴⁹ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
q1 represents an integer of 1, 2, 3, 4 or 5,
q2 represents an integer of 0, 1 or 2,
q3 represents an integer of 1, 2, 3, 4 or 5;
q4 represents an integer of 0, 1 or 2,
q5 represents an integer of 1, 2, 3, 4 or 5,
q6 and q7 each independently represent an integer of 0, 1 or 2;
t1 represents an integer of 0, 1, 2, 3, 4 or 5;
t2 represents an integer of 0, 1, 2, 3 or 4;
t3 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
t4 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. ] The haloalkyl sulfonamide derivative represented by these, or its salt.

[2]
A represents -CH = CH-,
W represents an oxygen atom,
R ² is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁰ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -C (O) Represents R ¹¹ or —S (O) ₂ R ¹² ,
R ³ and R ⁴ represent a hydrogen atom,
R ⁵ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C Represents ₆ alkynyl, -C (O) R ²⁸ or D-7,
R ⁶ and R ⁷ are each independently a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , phenyl, —C (O) R ^41. , Cyano, —OR ⁴² or —S (O) _q6 R ⁴³ , or R ⁶ and R ⁷ on the same carbon together to form a C ₂ alkylene chain, thereby binding together carbon atoms It represents that a 3-membered ring may be formed, or R ⁶ and R ⁷ on the same carbon may be bonded to each other to form ═CH ₂ or carbonyl, and n = 2 to 4 Where R ⁶ and R ⁷ together with R ⁶ or R ⁷ on different carbons form a C ₂ -C ₆ alkylene chain to form a 4-6 membered ring with the carbon atoms to which it is attached. R ⁶ and R ⁷ are different from each other. R ⁶ or R ⁷ on the same carbon may be the same or different, and R ⁶ and R ⁷ together with R ⁶ or R ⁷ on the adjacent carbon can represent a bond,
R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , phenyl, —C (O) R ^41. , Cyano, —OR ⁴² or —S (O) _q6 R ⁴³ , or R ⁸ and R ⁹ on the same carbon together to form a C ₂ alkylene chain, thereby binding together carbon atoms Represents that a 3-membered ring may be formed, or that R ⁸ and R ⁹ on the same carbon may be bonded to each other to form ═CH ₂ or carbonyl,
R ¹⁰ represents phenyl, —C (O) R ¹⁴ , —OR ¹⁵ or —S (O) _q2 R ¹⁹ ,
R ¹¹ is C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ²⁰ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, phenyl, —OR ²¹ or — SR ²⁴
R ¹² represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ¹³ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy;
R ¹⁴ represents C ₁ -C ₆ alkoxy or phenyl;
R ¹⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or —C (O) R ¹⁶ ,
R ¹⁶ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy;
R ¹⁹ represents C ₁ -C ₆ alkyl,
R ²⁰ represents a halogen atom or phenoxy,
R ²¹ represents C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ²⁰ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or phenyl,
R ²⁴ represents C ₁ -C ₆ alkyl,
R ²⁷ is a halogen ^{atom, -C (O) R 31,} -OR 32, tri _(C 1 -C ₆ alkyl) a silyl or D-1,
R ²⁸ and R ³¹ each independently represent C ₁ -C ₆ alkoxy;
R ³² represents C ₁ -C ₆ alkyl,
R ³⁹ represents a halogen atom, phenyl, hydroxy or C ₁ -C ₆ alkoxy;
R ⁴¹ represents hydroxy or C ₁ -C ₆ alkoxy;
R ⁴² is a hydrogen _atom, C 1 -C ₆ alkyl or phenyl,
R ⁴³ represents the haloalkylsulfonamide derivative or a salt thereof according to the above-mentioned [1], wherein R ⁴³ represents C ₁ -C ₆ alkyl or phenyl.

[3]
R ⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁷ , —C (O) R ²⁸ or D-7,
R ⁶ , R ⁷ , R ⁸ and R ⁹ are the haloalkylsulfonamide derivatives or salts thereof according to the above [2], wherein each represents a hydrogen atom.

[4]
R ² represents a hydrogen atom or —C (O) R ¹¹ ,
R ¹¹ represents -OR ²¹ ;
R ²¹ _is haloalkyl sulfonamide derivative or a salt thereof described in [3] representing the C 1 -C ₆ alkyl.

[5]
An agrochemical containing one or more selected from the haloalkylsulfonamide derivatives and salts thereof described in [1] to [4] as active ingredients.

[6]
A herbicide containing, as an active ingredient, one or more selected from the haloalkylsulfonamide derivatives and salts thereof described in [1] to [4] above.

  The compound of the present invention has excellent herbicidal activity against various weeds and high safety against target crops, and has little adverse effect on non-target organisms such as mammals, fish and beneficial insects. Persistence and light environmental impact.

  Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields, and orchards.

  The compounds included in the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, and the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio. In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.

  Among the compounds included in the present invention, those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like. Salt of inorganic acid such as salt, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salt of sulfonic acid such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as 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, etc. A salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds included in the present invention, those that can be converted into metal salts according to conventional methods include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or a salt of aluminum.

  Next, specific examples of each substituent shown in the present specification are shown below. Here, n- represents normal, i- represents iso, s- represents secondary, and tert- represents tertiary, and Ph represents phenyl.

  Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.

The notation of C _a -C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a carbon number of _a to _b , for example, methyl group, ethyl group, n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon number of _a to _b , and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include, for example, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. Selected in a range of numbers.

In the present specification, C _a -C _b alkenyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-dimethyl-2-propenyl group and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkynyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1,1-dimethyl-2-propynyl group, etc. Each of which is selected for each specified number of carbon atoms.

In the present specification, C _a -C _b haloalkyl is represented by a linear or branched chain having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the number of carbon atoms designated.

In the present specification, C _a -C _b haloalkenyl is a linear or branched chain in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is ab. And an unsaturated hydrocarbon group having one or more double bonds in the molecule, and when substituted by two or more halogen atoms, the halogen atoms may be the same as each other Or they may be different from each other. For example, 1-chloroethenyl group, 2-chloroethenyl group, 2-fluoroethenyl group, 2,2-dichloroethenyl group, 3-chloro-2-propenyl group, 3-fluoro-2-propenyl group, 2-chloro-2- Specific examples include a propenyl group, a 4-chloro-3-butenyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b haloalkynyl represents a linear or branched chain in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is a to b. And an unsaturated hydrocarbon group having one or more triple bonds in the molecule, such as chloroethynyl group, fluoroethynyl group, bromoethynyl group, 3-chloro-2-propynyl group, 4-chloro A 2-butynyl group or the like is given as a specific example, and is selected within the range of each designated number of carbon atoms.

The notation of C _a -C _b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxy group, ethoxy group, propyloxy group, i- Propyloxy group, butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group, pentyloxy group, 1-methylbutyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 1,1 -Dimethylpropyloxy group, 1,2-dimethylpropyloxy group, 2,2-dimethylpropyloxy group, 1-ethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group, 3 -Methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2-dimethyl Tyloxy group, 1,3-dimethylbutyloxy group, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group, 3,3-dimethylbutyloxy group, 1-ethylbutyloxy group, 2-ethylbutyl Specific examples include oxy group, 1,1,2-trimethylpropyloxy group, 1,2,2-trimethylpropyloxy group, 1-ethyl-1-methylpropyloxy group, 1-ethyl-2-methylpropyloxy group, etc. Each selected within a range of each specified number of carbon atoms.

The notation of C _a -C _b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy. Group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoromethoxy group, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, bromomethoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group 2-bromoethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2- Trichloroethoxy group, 2,2,2-trifluoroethoxy group, 1-fluoro Lopyloxy group, 2-fluoropropyloxy group, 3-fluoropropyloxy group, 3-chloropropyloxy group, 3-bromopropyloxy group, 1-fluorobutyloxy group, 2-fluorobutyloxy group, 3-fluorobutyloxy Specific examples include a group, a 4-fluorobutyloxy group, a 4-chlorobutyloxy group, and the like, and each group is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylcarbonyl in the present specification represents an alkyl-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, CH ₃ C (O) -group. , CH ₃ CH ₂ C (O) — group, CH ₃ CH ₂ CH ₂ C (O) — group, (CH ₃ ) ₂ CHC (O) — group, CH ₃ (CH ₂ ) ₃ C (O) — group , (CH ₃ ) ₂ CHCH ₂ C (O) — group, CH ₃ CH ₂ CH (CH ₃ ) C (O) — group, (CH ₃ ) ₃ CC (O) — group, CH ₃ (CH ₂ ) ₄ Specific examples include a C (O) — group, a CH ₃ (CH ₂ ) ₅ C (O) — group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkoxycarbonyl in the present specification represents an alkyl-O—C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, CH ₃ OC (O) — Group, CH ₃ CH ₂ OC (O) — group, CH ₃ CH ₂ CH ₂ OC (O) — group, (CH ₃ ) ₂ CHOC (O) — group, CH ₃ (CH ₂ ) ₃ OC (O) — Specific examples include a group, (CH ₃ ) ₂ CHCH ₂ OC (O) — group, (CH ₃ ) ₃ COC (O) — group, etc., and each is selected within the range of the designated number of carbon atoms.

The notation of tri (C _a -C _b alkyl) silyl in the present specification includes a trimethylsilyl group, a triethylsilyl group, and the like as specific examples, and is selected within the range of each designated number of carbon atoms.

Specific examples of the notation “R ³ and R ⁴ can be bonded to each other to form a ^3- to 7-membered ring” in the present specification include, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane and the like. , Selected for each specified number of atoms.

In the present specification, “R ⁶ represents that, together with R ⁷ , a C _{2 to} C ₆ alkylene chain may be formed to form a 3 to 7 membered ring with the carbon atoms to be bonded. The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom. Specific examples of the notation include, for example, aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine- 2-one, thiazolidine, thiazolidine-2-one, imidazolidine, imidazolidin-2-one, piperidine, piperidin-2-one, morpholine, tetrahydro-1,3-oxazin-2-one, thiomorpholine, tetrahydro-1 , 3-thiazin-2-one, piperazine, tetrahydropyrimidin-2-one, homopiperidine Homo-2-one and the like, may be selected from the range number of each of the specified atoms.

Notation such as _(C a ~C _b) alkyl optionally substituted by R ¹⁰ herein, by any R ^10, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted a~ It represents an alkyl group as defined above consisting of b, and is selected in the range of the respective designated number of carbon atoms. At this time, when there are two or more substituents R ¹⁰ on each (C _a -C _b ) alkyl group, each R ¹⁰ may be the same as or different from each other.

Notation such as (C a _{-C b)} cycloalkyl optionally substituted by R ¹⁰ herein, by any R ^10, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted a It represents a cycloalkyl group having the above meaning consisting of ˜b, and is selected in the range of the respective designated number of carbon atoms. At this time, when there are two or more substituents R ¹⁰ on each (C _a -C _b ) cycloalkyl group, each R ¹⁰ may be the same as or different from each other.

Notation such as _(C a ~C _b) alkenyl optionally substituted by R ¹⁰ herein, by any R ^10, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted a~ It represents an alkenyl group having the above-mentioned meaning consisting of b, and is selected within the range of each designated number of carbon atoms. At this time, when two or more substituents R ¹⁰ on each (C _a -C _b ) alkenyl group are present, each R ¹⁰ may be the same as or different from each other.

Notation such as _(C a ~C _b) alkynyl optionally substituted by R ¹⁰ herein, by any R ^10, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted a~ It represents an alkynyl group as defined above consisting of b, and is selected within the range of each designated number of carbon atoms. At this time, when two or more substituents R ¹⁰ on each (C _a -C _b ) alkynyl group are present, each R ¹⁰ may be the same as or different from each other.

  Next, the manufacturing method of this invention compound is demonstrated below.

Manufacturing method A
The haloalkylsulfonamide derivative represented by the formula (1) can be produced, for example, by reacting the compound represented by the formula (2) with the compound represented by the formula (3).

Formula (2) [wherein W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n, and p represent the same meaning as described above. Or a salt thereof and formula (3) [wherein R ⁵ represents the same meaning as described above. The compound represented by the formula (1) by reacting the compound represented by the formula or a salt thereof in a solvent or without a solvent, using a base if necessary, and adding an additive if necessary. Inventive compounds can be prepared.

  In this reaction, the compound represented by the formula (3) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (2).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone and water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and diphenyl ether, alcohols such as methanol and ethanol, and aromatic carbonization such as benzene, toluene and xylene Examples include hydrogen, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When using a base, the base used can be an organic base such as triethylamine, pyridine, 4- (dimethylamino) pyridine, or an inorganic base such as potassium carbonate, sodium carbonate, potassium acetate, sodium acetate, and the formula It can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by (2).

  When an additive is used, the additive used is an ether such as 1,4,7,10,13,16-hexaoxacyclooctadecane or a quaternary ammonium salt such as tetra n-butylammonium bromide. And can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by Formula (2).

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available.

Manufacturing method B
The haloalkylsulfonamide derivative represented by the formula (1) can be produced, for example, by reacting the compound represented by the formula (4) with the compound represented by the formula (5).

Formula (4) which can be produced according to the method described in Production Method A [wherein W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n and p represent the same meaning as described above. Or a salt thereof and formula (5) [wherein R ⁵ represents the same meaning as described above, and L represents a leaving group such as a halogen atom. The compound represented by the formula (1) by reacting the compound represented by the formula or a salt thereof in a solvent or without a solvent, using a base if necessary, and adding an additive if necessary. Inventive compounds can be prepared.

  In this reaction, the compound represented by the formula (5) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (4).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  In the case of using a base, examples of the base used include organic bases such as triethylamine, pyridine, and 4- (dimethylamino) pyridine, and inorganic bases such as potassium carbonate, sodium carbonate, and sodium bicarbonate. ) Can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented.

  When an additive is used, the additive used is an ether such as 1,4,7,10,13,16-hexaoxacyclooctadecane or a quaternary ammonium salt such as tetra n-butylammonium bromide. It can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by formula (4).

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  Some of the compounds represented by formula (5) are known compounds, and some of them are commercially available.

In the production method A to the production method B, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated in ice water, poured into ice water, concentrated after extraction with an organic solvent, and then subjected to normal post-treatment. Inventive compounds 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) can be synthesized according to the reaction formula 1 shown below.

  Reaction formula 1

(Manufacturing process 1)
Formula (6) [wherein W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n, and p represent the same meaning as described above. Or a salt thereof and a brominating agent in a solvent or in the absence of a solvent, using a base if necessary, and adding an additive if necessary to react with the compound (7) [Wherein, W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n and p represent the same meaning as described above. The compound represented by this can be manufactured.

  In this reaction, the brominating agent can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by Formula (6).

  Examples of the brominating agent used include quaternary ammonium salts such as phenyltrimethylammonium bromide and phenyltrimethylammonium tribromide.

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, tetrachloride Examples thereof include halogenated hydrocarbons such as carbon and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When a base is used, examples of the base used include organic bases such as triethylamine, pyridine, 4- (dimethylamino) pyridine, diisopropylethylamine, and inorganic bases such as potassium carbonate and sodium carbonate. Formula (6) Can be used in the range of 0.1 to 50 equivalents relative to 1 equivalent of the compound represented by formula (1).

  When an additive is used, as the additive used, a silylating agent such as trimethylsilyl trifluoromethanesulfonate can be used, and 0.1 to 50 equivalents relative to 1 equivalent of the compound represented by formula (6) It can be used in the range.

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  The reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent, and the compound represented by formula (7) is obtained. 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.

  Further, the compound represented by the formula (7) produced by this method can be used as it is in the next step without isolation and purification.

Some of the compounds represented by formula (6) are known compounds and can be produced according to known methods. For example, it can manufacture according to the method described in international publication 2010/026989, international publication 2013/061973, etc.
(Manufacturing process 2)
A compound represented by formula (7) or a salt thereof, and formula (8) [wherein M represents a metal atom such as sodium or potassium, and V represents C _{1 to} C ₆ alkyl. ] Or a salt thereof in a solvent or in the absence of a solvent, and if necessary, an additive is added to react to react with the compound represented by formula (9) [wherein W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n, and p represent the same meaning as described above. The compound represented by this can be manufactured.

  In this reaction, the compound represented by formula (8) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by formula (7).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone and water, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and 1,2-dichloroethane, n-pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.

  When an additive is used, the additive used is an ether such as 1,4,7,10,13,16-hexaoxacyclooctadecane or a quaternary ammonium salt such as tetra n-butylammonium bromide. It can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by formula (7).

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  The reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent, and the compound represented by formula (9) is obtained. 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.

  Further, the compound represented by the formula (9) produced by this method can be used as it is in the next step without isolation and purification.

Some of the compounds represented by formula (8) are known compounds, and some of them are commercially available.
(Manufacturing process 3)
By reacting the compound represented by the formula (9) or a salt thereof with a base in a solvent or without a solvent, the compound represented by the formula (10) [wherein W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , m, n, and p have the same meaning as described above. The compound represented by this can be manufactured.

  In this reaction, the base can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by Formula (9).

  Examples of the base to be used include organic bases such as triethylamine, pyridine and 4- (dimethylamino) pyridine, and inorganic bases such as potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide.

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone and water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and diphenyl ether, alcohols such as methanol and ethanol, and aromatic carbonization such as benzene, toluene and xylene Examples thereof include aliphatic hydrocarbons such as hydrogen, n-pentane, and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  The reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent, and the compound represented by the formula (10) is obtained. 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.

Further, the compound represented by the formula (10) produced by this method can be used as it is in the next step without isolation and purification.
(Manufacturing process 4)
A compound represented by the formula (2) is produced by reacting the compound represented by the formula (10) or a salt thereof with an oxidizing agent in a solvent or without a solvent, and if necessary, an additive is added. can do.

  In this reaction, the oxidizing agent can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by Formula (10).

  Examples of the oxidizing agent used include chromate such as pyridium chlorochromate and pyridium dichromate, manganese compounds such as potassium permanganate and manganese dioxide, 1,1,1-triacetoxy-1,1-dihydro-1 , 2-benzoiodoxol-3- (1H) -one (Dess-Martin Periodinane) and the like, a radical compound such as a 2,2,6,6-tetramethylpiperidine-1-oxy radical, Etc.

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, water, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When an additive is used, the additive used is an ether such as 1,4,7,10,13,16-hexaoxacyclooctadecane or a quaternary ammonium salt such as tetra n-butylammonium bromide. And can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by Formula (10).

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  After completion of the reaction, the reaction mixture is directly concentrated or dissolved in an organic solvent, washed and then concentrated in water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent, resulting in a production intermediate that becomes a raw material compound of production method A You can get a body. 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.

  Further, the production intermediate produced by this method can be used as it is in the next step without isolation and purification.

  Next, examples of compounds included in the present invention are shown in Table 1. However, the compounds of the present invention are not limited thereto. In the table, “Me” represents a methyl group. Similarly, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, Ph represents a phenyl group, n- represents normal, and i- represents Each means iso.

In the formula, U represents U-1 [wherein R ² represents the same meaning as described above. ] Or U-2 [wherein R ² represents the same meaning as described above. ] Represents a structure represented by

  Moreover, the substituent represented by D-7a in the table represents the following structure.

[Table 1]
―――――――――――――――――― ――――――――――――――――――
UR ² R ⁵ UR ² R ⁵
―――――――――――――――――― ――――――――――――――――――
U-1 HH U-2 HH
U-1 H Me U-2 H Me
U-1 H Et U-2 H Et
U-1 H n-Pr U-2 H n-Pr
U-1 H i-Pr U-2 H i-Pr
U-1 H n-Bu U-2 H n-Bu
U-1 H i-Bu U-2 H i-Bu
U-1 H CH ₂ Ph U-2 H CH ₂ Ph
U-1 H CH ₂ C (O) OEt U-2 H CH ₂ C (O) OEt
U-1 H CH ₂ CH ₂ OMe U-2 H CH ₂ CH ₂ OMe
U-1 H CH ₂ CH ₂ Cl U-2 H CH ₂ CH ₂ Cl
U-1 H D-7a U-2 H D-7a
U-1 H CH ₂ CH ₂ Si (Me) ₃ U-2 H CH ₂ CH ₂ Si (Me) ₃
U-1 H CF ₂ H U-2 H CF ₂ H
U-1 HC (O) OEt U-2 HC (O) OEt
U-1 C (O) OEt H U-2 C (O) OEt H
U-1 C (O) OEt Me U-2 C (O) OEt Me
U-1 C (O) OEt Et U-2 C (O) OEt Et
U-1 C (O) OEt n-Pr U-2 C (O) OEt n-Pr
U-1 C (O) OEt i-Pr U-2 C (O) OEt i-Pr
U-1 C (O) OEt n-Bu U-2 C (O) OEt n-Bu
U-1 C (O) OEt i-Bu U-2 C (O) OEt i-Bu
U-1 C (O) OEt CH ₂ Ph U-2 C (O) OEt CH ₂ Ph
U-1 C (O) OEt CH ₂ C (O) OEt U-2 C (O) OEt CH ₂ C (O) OEt
U-1 C (O) OEt CH ₂ CH ₂ OMe U-2 C (O) OEt CH ₂ CH ₂ OMe
U-1 C (O) OEt CH ₂ CH ₂ Cl U-2 C (O) OEt CH ₂ CH ₂ Cl
U-1 C (O) OEt D-7a U-2 C (O) OEt D-7a
U-1 C (O) OEt CH ₂ CH ₂ Si (Me) ₃ U-2 C (O) OEt CH ₂ CH ₂ Si (Me) ₃
U-1 C (O) OEt CF ₂ H U-2 C (O) OEt CF ₂ H
U-1 C (O) OEt C (O) OEt U-2 C (O) OEt C (O) OEt
―――――――――――――――――― ――――――――――――――――――
The compound of the present invention can be used as a herbicide for paddy fields in any treatment method of soil treatment and foliage treatment under flooded water. As paddy field weeds, for example, weeping family (Potamogetonaceatiaceae) represented by Potamogeton distinctus, etc. ) Weed, Azegaya (Leptochloa chinensis), Echinochloa crus-galli, Echinochloa oryzicola, Ashiaki (Homalocenchrus japonocus) Gramineae weed, Kurowai (Eleocharis kuroguwai), Firefly (Sirpus juncoides), Shizuus sarius (Cirpus sarius) Cyperaceae weeds, Spirodella polyrhiza, Lemna paucicostata, and other species such as Lemnaceae weeds, and Dendrobinous weeds (Murdannia coesae). Nochoria korsakowii) and scallops (Pontederiaceae) and other species such as the mosquito family (Elatine triamdra) Lythaceae weeds represented by, Lythigia epilobioides weeds, Oenotheraceae weeds, Dopatrium junceum, Graonilop olia, Azena (Lindernia pyxidaria), American Azena (Lindernia dubia), and the like, Agrocynoceae (Rosaceae), rosaneceae (Aesyomenine indica), etc. Examples thereof include Compositae weeds represented by Bidens tripartita.

  In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any treatment method of soil treatment, soil admixture treatment, and foliage treatment. Examples of upland field weeds include Solanumae weeds represented by Solanum nigrum and Datura stramonium, Sauranaceae weeds represented by Grunum carolinianum, Aiaceae cereals (Gaeumaceae) (Abutilon theophrasti) and malvaaceae weeds represented by Sida spinosa, etc., Ipomoea purpurea, etc. and Ipomoea spps. Convolvulaceae weed, Amaran (Amaran) hus lividus) and slender amaranth (Amaranthus retroflexus) Amaranthaceae represented by such (Amaranthaceae) weeds, cocklebur (xanthium pensylvanicum), ragweed (Ambrosia artemisiaefolia), sunflower (Helianthus annuus), galinsoga quadriradiata (Galinsoga ciliata), western thorns thistle (Cirsium arvense, Sorgio vulgaris, Erigeron annus, and other species of Compositae weeds, Roppa indica, Shirapis arvensis Ca a bursaceae weed, represented by a Bursapastoris, etc. Weeds represented by, for example, Polygonaceae weeds represented by, for example, Polygonum bulvoluis, Polygonum convolvulus, olulaceae, etc. (Portulacaceae) weeds, white-spotted (Chenopodium album), red-breasted (Chenopodium falifolium), weeds (Chenopodiacee) weeds represented by weeds (Cenopodiaceae) The Weeds such as Sphaphulariaceae represented by Veronica persica, Ceminaurae weeds represented by Commelina communis, etc., and Lamium urumiles. Euphorbiaceae (Euphorbiaceae) and other species such as Euphorbiaceae (Galium spurium), representatives of Euphorbiaceula (Euporbiaacea) Rubyaceae Weeds such as Violaceae weeds represented by weeds and violets (Viola mandhurica) and leguminous weeds represented by Sesbania exaltata and Cassia obtusifolia, etc. Broad-leaved weeds such as the representative Oxsaldasee. Wild sorghum (Sorgham dichotomiflorum), Johnson grass (Sorghum halo chilli), Echinochloa cru-galli var. Crus-galli , Barnyard grass (Digitaria ciliaris), oats (Avena fatua), blackgrass (Alopecurus myosuroides), barnyard grass (Eleusine indica), Enocologia (Sateria viridis), Akinosae faberi) and water foxtail (Alopecurus aegualis) gramineous weeds (Graminaceous weeds typified etc.) and Cyperus (Cyperus rotundus, Cyperus esculentus) Cyperaceae weeds (Cyperaceous weeds typified like).

  Further, the compound of the present invention can be used for soil treatment, soil admixture treatment, and foliage treatment in non-agricultural lands such as turf, playground, open space, roadsides, and track ends in addition to the fields of agriculture and horticulture such as paddy fields, upland fields and orchards. It can also be used in the processing method. The weeds include those mentioned in upland and orchard weeds, Poa annua, Taraxacum officinale, Conyzaol samsensis, Cardamine minx, (Hydrocotyl sibthorpioides), Plantago asiatica, Cyperus brevifolia, Kyllinga brevifolia, Equisetum arvense and the like.

  The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.

  In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.

Preferred herbicides to be used in combination with the compound of the present invention include, for example, acetochlor (acetochlor / generic name), acifluorfen (acifluorfen / generic name), aclonifen (aclonifen / generic name), alachlor (alachlor / (Generic name), alloxidim (alloxydim / generic name), sodium alloxidim-sodium / generic name, ametrine (generic name), amicarbazone (generic name), amidosulfuron (common name), Aminocyclopyrachlor (generic name), salts and esters of aminocyclopyracryl (aminocyclopirachlo) r-salts and esters, aminopyralides (generic names), salts and esters of aminopyralides (aminopyridid-salts and esters), amiprophos-methyl (common names), amitrol (common names) (Anifofos / generic name), ashram (asulam / generic name), atrazine (atrazine / generic name), azaphenidin (azafenidin / generic name), azimusulfuron (generic name), beflubutamid (generic name), beazoline Benazolin-ethyl / generic name), bencarbazone / generic name , Benfluralin (benfulin / generic name), benfrate (benfurateate / generic name), bensulfuron methyl (bensulfuron-methyl / generic name), bensulide (bensulide / generic name), bentazone (sodium name), bentazone (sodium) bentazone-sodium / generic name), bentazone salt (bentazone-salts), benziocarb (general name), benzfendizone (generic name), benzobicyclon (generic name), benzophenap (generic name) benzofenap / generic name), bialaphos (generic name), bialaphos sodium ( bialaphos-sodium / generic name), bicyclopyrone (bicyclopyrone / generic name), bifenox (bifenox / generic name), bispyribac (bispyribac / generic name), bispilibac sodium (bispyribac-sodium / generic name), bromacil (birocil) (Generic name), bromobutide (generic name), bromophenoxime (generic name), bromoxynil (generic name), salts and esters of bromoxynil (general name) and butachlor (general name) , Butafenacil (generic name), butamifos (butamifos) (Generic name), butenachlor (butenachlor / generic name), butralin (butralin / generic name), butroxydim (butoxydim / generic name), butyrate (butylate / generic name), fenfentrol (calfenstrole / generic name), carbetamid (carbetamide / common name) ), Carfentrazone-ethyl, chloromethoxyphene (generic name), chloromethoxynyl (generic name), chloramben (general name), chloramben salts and esters (chloramben-salts and esters) ), Chloransrammethyl l / generic name), chlorflurenol-methyl / generic name, chloridazon / generic name, chlorimuron-ethyl / generic name, chlorobromuron / generic name, Chlorotoluron (generic name), chloroxuron (generic name), chlorphthalim (general name), chloroprofam (general name), chloro IPC (chloroprophlon / generic name), chlorosulfuron (chlorsulfuron) Name), chlorthal dimethyl (general name), chlorthiamid ( hlorthiamid / generic name), sinidone ethyl (cinidon-ethyl / generic name), cinmesulin (generic name), sinosulfuron (cynosulfuron / generic name), cletodim (generic name), clodina hop (generic name) Hoppropargyl (clodinafop-propargyl / generic name), clomazone (clomazone / generic name), clomeprop (cloproprop), clopyralid (general name), clopyralid salts and esters (clopyralid-salts) , Cumylron / generic name, cyanazin / general ), Cycloate (common name), Cyclosulfamuron (common name), Cycloxydim (common name), Cyhalohop-butyl (common name), Dalapon (common name), Dazomet (generic name), desmedifam (desmedifam / generic name), desmethrin (desmetrin / generic name), dicamba (dicamba / generic name), dicamba salts and esters (dicamba-salts and esters), diclobenil / Generic name), diclohop (dicofop / generic name), diclohop-methyl (dicofop-methyl / generic name), dichroic Diproprop (generic name), Dichlorprop-salts and esters, Dichloroprop-P (generic name), P Dichloroprop salts and esters (dichlorprop-P-salts) and esters, diclosram (generic name), difenzo coat (difenzoquat / generic name), diflufenican (generic name), diflufenzopyr (generic name), diflufenzopyr sodium Name), dimipeperate (generic name), dimetamethrin (dimet) hammetrin / generic name), dimethachlor (dimethachlor / generic name), dimethenamide (dimethenamide / generic name), P-dimethenamide (dimethenamide-p / generic name), dimesipine (dimethipine / generic name), dinitroamine (dinitramine / name) Dinoceb (dinoseb / generic name), dinoterb (dinotarb / generic name), DNOC / generic name, diphenamide (generic name), diquat (generic name), dithiopyr (dithiopyl / generic name), diuron (generic name) Name), DSMA / generic name, dymron (generic name), endothal (endothal / generic name), EPTC / generic name, esprocarb (es rocarb / generic name, ethalfluralin (ethalfluralin / generic name), ethamethsulfuron-methyl (ethamesulfuron-methyl / generic name), etofumesate (generic name), etebenzanid / etulonyl (sulfur) / Generic name), flazasulfuron (generic name), fenoxaprop (generic name), phenoxaprop-ethyl (generic name), phenoxasulfone (generic name), fentolazamide (generic name) fentrazamide (generic name), flamprop (generic name), fraza Ruflon (flazasulfuron / generic name), florasulam (general name), fluazifop (fluazifop / generic name), fluazifopbutyl (common name), fluazolate (fluazolate / generic name), sodium flukazone ( flucarbazone-sodium / generic name), flucetsulfuron (generic name), fluchloralin (generic name), flufenacet (generic name), flufenpyrethyl (flufenpyl-ethyl) (Flumetsulam / generic name), full microrack pentyl (one) Name), flumioxazin (generic name), fluometuron (fluometuron / generic name), fluoroglycophene-ethyl (generic name), flupirsulfuron (generic name), flupoxam (general name) , Flurenol (fluronol / generic name), fluridone (fluridone / generic name), flurochloridone (flurochloridone / generic name), fluroxypyr (generic name), fluroxypyr ester (fluroxypyr-esters), fluprimir f Generic name), Flutamon (flutatone / generic name), Fruthiaset methyl fluciacet-methyl / generic name), fomesafen (formesafen / generic name), foramsulfuron (formamsulfuron / generic name), fosamine (general name), glufosinate / generic name, glufosinate-mmonium Name), glyphosate (glyphosate / generic name), glyphosate ammonium (glyphosate-ammonium / generic name), glyphosate isopropylamine (glyphosate-iso-propylammonium / generic name), glyphosate potassium (glyphosate-potassium / common name, sodium) glyphosate-s odium / generic name), glyphosate-trimesium / generic name, haloxifene / general name, salts and esters of haloxifen-salts and esters), halosafen / generic name ), Halosulfuron (generic name), halosulfuron methyl (halosulfuron-methyl / generic name), haloxyhop (generic name), haloxyhop-methyl (generic name), hexazinone (generic name) ), Imazametabenzmethyl (imazamethabenz-methyl / generic name), imazamox (i azamox / generic name), Imazapiku (imazapic / generic name), imazapyr (imazapyr / generic name), imazethapyr (imazethapyr / generic name), imazaquin (imazaquin / generic name), imazosulfuron (i
mazosulfuron / generic name), indanophan (generic name), indazifram (generic name), iodosulfuron-methyl-sodium / generic name, ioxynil octoate / general name And esters (ioxynil-salts and esters), ipfencarbazone (ipfencarbazone / generic name), isoproturon (isoproturon / generic name), isouron (isouron / generic name), isoxaben (isoxaben / generic name), isoxaflu Thor (isoxafulle / generic name), carbutylate / general ), KUH-110 (test name), lactofen (lactofen / generic name), renacil (lenacyl / generic name), linuron (linuron / generic name), maleic hydrazide (generic name), MCPA (generic name) , Salts and esters of MCPA (MCPA-salts and esters), MCPB (generic name), salts and esters of MCPB (MCPB-salts and esters), mecoprop (MCPP / generic name), salts and esters of mecoprop (mecoprop) Salts and esters), P mecoprop (P, MCPP-P / generic name), P mecoprop salts and esters (mecoprop-P-salts and es) ers), mefenacet (mefenacet / generic name), mefluidide (mefluideide / generic name), mesosulfuron-methyl (generic name), mesotrione (mesotrione / generic name), metam (metam / generic name), metamihop (meta) / Generic name), metamitron (generic name), metazachlor (metazachlor / generic name), metabenzthiazuron (generic name), metazosulfuron (generic name), methazozoline (generic name) Methyl azide (methyl azide / common name), methyl bromide (common name), Tildimrone (methyl dyron / generic name), methyl iodide (methyl iodide / generic name), metbenzuron (metobenzuron / generic name), metolachlor (metolachlor / generic name), S-metolachlor (metolachlor-S / generic name), Methoslam (metosulam / generic name), metryvudine (metribuzin / generic name), metsulfuron-methyl (metsulfuron-methyl / generic name), methoxuron (metoxuron / generic name), molinate (generic / generic name), monolinuron (mononylon / name) ), Monosulfuron (generic name), monosulfuron-methyl (monosulfuron-methyl) / Generic name), MSMA / generic name, naproanilide / generic name, napropamide / generic name, naptalam / generic name, naptalam-sodium / generic name, nebulon / (Generic name), nicosulfuron (generic name), norflurazon (norflurazon / generic name), OK-701 (test name), oleic acid (oleic acid / generic name), olvencarb (generic name), orthosulfam Ron (orthosulfamuron / generic name), oryzalin (oryzalin / generic name), oxadialgyl (generic name), oxadiazone (oxadia) zon / generic name), oxasulfuron (generic name), oxadichromemephone (general name), oxyfluorfen (generic name), paraquat (common name), pelargonic acid (common name), Pendimethalin (generic name), penoxsulam (generic name), pentanochlor (pentanochlor / generic name), pentoxazone (generic name), petoxamide (genetic name), phenmedidimeth ph -Ethyl / generic name), picloram (picloram / generic name), picroram salt and Esters (picloram-salts and esters), picolinafen (picolinafene / generic name), pinoxaden (pinoxaden / generic name), piperophos (piperophos / generic name), pretilaclor (pretilachlor / generic name), primisulfur methyl (Generic name), prodiamine (prodiamin / generic name), profluazole (proflazole / generic name), proxidim (profoxydim / generic name), prometon (promethon / generic name), promethrin (prometrin / generic name), propachlor proploror (generic name), propanil (propanil / generic name), propaxahop (Propaquizafop / generic name), propazine (propazin / generic name), propham (propham / generic name), propisochlor (propisochlor / generic name), propoxycarbazone sodium (propoxycarbazone-sodium / generic name) propylisulfuron (generic name), propyzamide (generic name), pullsulfocarb (general name), prosulfuron (general name), pyraclonil (general name), pyraflufen-ethyl (Generic name), pyrasulfotol (general name), pyrazolinate (pyr) zolynate / generic name), pyrazosulfuron / generic name, pyrazosulfuron-ethyl / generic name, pyrazoxifen / generic name / pyribenzoxim / pyb , Pyridafor (pyridafol / generic name), pyridate (pyridate / generic name), pyriftalide (pyriftalid / generic name), pyriminobac-methyl / generic name, pyrimisulfan (pyrimisulfan / generic name), pyrithio Buck sodium (pyrithiobac-sodium / generic name), pyroxasulfone pyroxasulfone / generic name), piroxislam (pyroxsuram / generic name), quinclorac (quinocracac / generic name), quinamelac (generic name / generic name), quinoclamamine (common name), quizalofop (common name) Hop ethyl (quizalofop-ethyl / generic name), quizalofop-tefuryl (quizalofop-tefuryl / generic name), P quizalofop (quizalofop-P / generic name), P quizalofop-ethyl (common name) ), Pquizalofop-P-tefuryl / generic name, rimsulfuron / generic name, saflufe Nasil (saflufenacil / generic name), cetoxidim (sethoxydim / generic name), ciduron (generic name), simazine (simazine / generic name), simethrin (simmetrin / generic name), sulcotrione (sulcotrione / generic name) Fentrazone (sulfentrazone / generic name), sulfometuron-methyl (sulfomethuron-methyl / generic name), sulfosulfuron (sulfosulfuron / generic name), cyclopyrimorate (cyclopyrimorate / generic name, SW-065 / test name) , TCBA (2,3,6-TBA / generic name), salts and esters of TCBA (2,3,6-TBA-salts and esters), TCTP (chl rthal-dimethyl, tetrochlorothiophene / generic name, tebutam (tebutamone / generic name), tebuthiuron / generic name, tefuryltrione / generic name, tembotrione / raxy texilotem (Generic name), terbacil (terbacyl / generic name), terbumeton (general name), terbuthylazine (general name), terbutrin (generic name), tetrapion (tetrapion / general name), tenyl chlor Generic name), thiazafluron luron / generic name), thiazopyr (generic name), thidazimine (generic name), thidiazulone (generic name), thiencarbazone-methyl (generic name), thifensulfuron methyl methyl / generic name), topramezon (generic name), tolalkoxidim (generic name), triafamon (general name), triarate (general name), triasulfuron (general name), triasulfuron / generic name triaziflam / generic name), tribenuron-methyl / Generic name), triclopyr (triclopyr / generic name), salts and esters of triclopyr (triclopyr-salts and esters), tridiphane (generic name), trietazine (generic name), trifloxysulfuron / Generic name), trifluralin (trifluralin / generic name), triflusulfuron methyl (triflusulfuron-methyl / generic name), tritosulfuron (tritosulfuron / generic name), 2,4-PA (generic name), 2,4- Salts and esters of PA (2,4-PA-salts and esters), 2,4-DB (generic name), salts and esters of 2,4-DB (2,4-DB-sa lts and esters). These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.

  As the safener, for example, AD-67, Benoxacol (benoxacor / generic name), cloquintocet-mexyl (generic name), ciomethrinil (cyomerinil / generic name), dichlormid (dichlormid / generic name), Dicyclonone (common name), cyprosulfamide (generic name), dietrate (generic name), DKA-24, dimron (common name), fenchlorazole-ethyl (general name) ), Fencrolim (general name), hexime (general name), flurazole (generic name), fluxofeni (Fluxofenim / generic name), flirazole (furilazole / generic name), isoxadifen (isoxadifen / generic name), isoxadifen-ethyl (isoxadifen-ethyl / generic name), MCPA, mecoprop (generic name), mefenpyr (mefenpy) / Generic name), mefenpyr-ethyl (mefenpyr-ethyl / generic name), mefenpyr-diethyl (mefenpyr-diethyl / generic name), mephenate (mephenate / generic name), MG-191, NA (Naphtalic anhydride), OM (Octamethylene-diamin), oxabetrinyl (oxabetrilin / generic name), PPG-1292, R-29148, etc. Can be mentioned. These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.

  In applying the compound of the present invention as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, a solid carrier. Add anti-caking agent, disintegrant, anti-decomposition agent, etc., and put to practical use in any dosage form such as wettable powder, emulsion, flowable, dry flowable, liquid, powder, granule or gel. be able to. In addition, from the viewpoint of labor saving and safety improvement, the preparation of any dosage form can be enclosed in a water-soluble package.

  Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.

  Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. And acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, 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 aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned.

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

  The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.

  In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.

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

Next, formulation examples of the preparation when the compound of the present invention is used 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.
Wettable compound of the present invention 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.
Emulsified compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.
Flowable agent compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners. It is done.
Dry flowable agent compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts Others include, for example, binders, decomposition inhibitors, etc. .
Liquid compound of the present invention 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.
Granules of the present invention compound 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.
Powder Compound of the Present Invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-10 parts Others include, for example, drift inhibitors and decomposition inhibitors.

  In use, the preparation is sprayed as it is or diluted 1 to 10,000 times with water.

Formulation Examples Next, specific examples of agrochemical formulations containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto. In the following formulation examples, “parts” means parts by weight.
[Formulation Example 1] Wetting Agent Compound No. 1-01 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (Anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Carplex # 80 2 parts (Synthetic hydrous silicate: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.
[Composition Example 2] Milk Compound No. of the present invention. 1-01 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.
[Composition Example 3] Flowable Agent Compound No. 1-01 25 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 0.02 parts Water 64.48 parts After uniformly mixing the above, wet milling to obtain a flowable agent.
[Composition Example 4] Dry flowable agent Compound No. 1-01 75 parts Hightenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80 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 and stirred and kneaded, granulated with an extrusion granulator, and dried to obtain a dry flowable agent.
[Formulation Example 5] Granule The present compound No. 1-01 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and kneaded, granulated with an extrusion granulator, and dried to form granules.

  In the following, the present invention will be described in more detail by specifically describing, as examples, synthesis examples and test examples of haloalkylsulfonamide derivatives represented by the formula (1) used as the active ingredient in the herbicide of the present invention. However, the present invention is not limited by these.

Moreover, the proton nuclear magnetic resonance chemical shift value of the Example was measured at 300 MHz using Me ₄ Si (tetramethylsilane) as a reference material. Moreover, the solvent used for the measurement is described in the following synthesis examples. Moreover, the symbol in the proton nuclear magnetic resonance chemical shift value of an Example represents the following meaning.
s: singlet, brs: broad singlet, d: doublet, t: triplet, q: quintet, m: multiplet Synthesis Example [Synthesis Example 1]
Synthesis of 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl] -3- (hydroxyimino) piperidin-2-one (present compound No. 1-02) 1- [2- (N-trifluoromethanesulfonyl) ) Aminobenzyl] piperidine-2,3-dione (0.13 g, 0.31 mmol) and 3 ml of ethanol were added hydroxylamine hydrochloride (26 mg, 0.37 mmol) at room temperature. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure. The obtained residue was purified by silica gel chromatography [n-hexane: ethyl acetate = 9: 1 to 1: 9 (volume ratio, the same shall apply hereinafter)] to obtain 67 mg of the desired product as a pale yellow solid.

Melting point: 72-75 ° C
[Synthesis Example 2]
Synthesis of 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] -3- (methoxyimino) piperidin-2-one (present compound No. 1-04) 1- [2- ( N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] piperidine-2,3-dione (101 mg, 0.24 mmol) and ethanol 3 ml in a mixed solution at room temperature with methoxyamine hydrochloride (24 mg, 0.29 mmol). And sodium acetate (49 mg, 0.60 mmol) was added. After the addition was complete, the reaction mixture was stirred overnight at room temperature. After completion of the stirring, 30 ml of saturated aqueous potassium hydrogen sulfate solution was added to stop the reaction, and the reaction solution was extracted with ethyl acetate (30 ml × 2 times). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 1: 9) to obtain 80 mg of the desired product as a white solid.

Melting point: 72-75 ° C
[Synthesis Example 3]
Synthesis of 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] -3-[(ethoxycarbonyloxy) imino] piperidin-2-one (the present compound No. 1-27) 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl] -3- (hydroxyimino) piperidin-2-one (0.04 g, 0.11 mmol), sodium bicarbonate (0.05 g, 0.60 mmol) and 5 ml of acetonitrile To the mixed solution was added ethyl chloroformate (0.06 g, 0.55 mmol) at room temperature. After completion of the addition, the reaction mixture was stirred for 6 hours under heating to reflux. After completion of stirring, 10 ml of water was added to stop the reaction, and the reaction solution was extracted with toluene (10 ml × 2 times). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1-3: 7) to obtain 7 mg of the desired product as a resin.
¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz); δ 7.49-7.35 (m, 3H), 7.23-7.18 (m, 1H), 4.99 (d, J = 15 .5 Hz, 2H), 4.63 (d, J = 15.5 Hz, 2H), 4.44-4.31 (m, 4H), 3.38-3.29 (m, 2H), 2.97. -2.85 (m, 2H), 2.01-1.89 (m, 2H), 1.45-1.29 (m, 6H).
[Reference Example 1]
1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] piperidine-2,3-dione Step 1; 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] Synthesis of -3-bromopiperidin-2-one 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] piperidin-2-one (14.5 g, 35.5 mmol), triethylamine (5. 37 g, 53.2 mmol) and 50 ml of dichloromethane were added trimethylsilyl trifluoromethanesulfonate (9.47 g, 42.6 mmol) under ice cooling. After completion of the addition, the reaction mixture was stirred for 1 hour under ice cooling. After completion of stirring, phenyltrimethylammonium tribromide (20.0 g, 53.2 mmol) was added to the reaction mixture under ice cooling. After the addition was complete, the reaction mixture was stirred overnight at room temperature. After the stirring, 100 ml of 1N hydrochloric acid aqueous solution was added to stop the reaction, and the reaction solution was extracted with ethyl acetate (100 ml × 2 times). The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated solid was washed with diisopropyl ether and collected by filtration to obtain 15.9 g of the desired product as a pale yellow solid.

Melting point: 97-99 ° C
Step 2: Synthesis of 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl] -3-acetoxypiperidin-2-one 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl]- To a mixed solution of 3-bromopiperidin-2-one (10.0 g, 20.5 mmol) and acetonitrile 50 ml, 1,4,7,10,13,16-hexaoxacyclooctadecane (164 mg, 0.62 mmol) at room temperature. ) And potassium acetate (8.05 g, 82.0 mmol). After completion of the addition, the reaction mixture was stirred for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 1: 9) to obtain 8.76 g of the desired product as a white solid.

Melting point: 106-108 ° C
Step 3; Synthesis of 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl] -3-hydroxypiperidin-2-one 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl] -3-acetoxypiperidine- To a mixed solution of 2-one (8.55 g, 21.7 mmol) and 20 ml of methanol, potassium carbonate (1.50 g, 10.9 mmol) was added at room temperature. After completion of the addition, the reaction mixture was stirred at room temperature for 4 hours. After completion of the stirring, 30 ml of saturated aqueous potassium hydrogen sulfate solution was added to stop the reaction, and the reaction solution was extracted with ethyl acetate (100 ml × 2 times). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 1: 9) to obtain 7.04 g of the objective product as a colorless liquid.
¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz); δ 11.25 (brs, 1H), 7.62 (d, 1H, J = 8.0 Hz), 7.41 (t, 1H, J = 8) .0 Hz), 7.35-7.15 (m, 2H), 4.61 (d, 1H, J = 14.6 Hz), 4.38 (d, 1H, J = 14.6 Hz), 4.20. -4.05 (m, 1H), 3.55-3.40 (m, 2H), 2.30-2.20 (m, 1H), 2.05-1.80 (m, 2H), 1 .80-1.60 (m, 2H).
Step 4: Synthesis of 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] -3-hydroxypiperidin-2-one 1- [2- (N-trifluoromethanesulfonyl) aminobenzyl]- To a mixed solution of 3-hydroxypiperidin-2-one (7.68 g, 21.8 mmol), sodium hydrogen carbonate (2.75 g, 32.7 mmol) and 20 ml of acetonitrile at room temperature, ethyl chloroformate (3.55 g, 32 0.7 mmol) was added. After completion of the addition, the reaction mixture was stirred for 3 hours under heating to reflux. After completion of stirring, 100 ml of water was added to stop the reaction, and the reaction solution was extracted with ethyl acetate (100 ml × 2 times). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 1: 9) to obtain 5.54 g of the objective product as a colorless liquid.
¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz); δ 7.55-7.15 (m, 4H), 5.00-4.80 (m, 1H), 4.55-4.25 (m , 3H), 4.20-4.05 (m, 1H), 3.76 (d, 1H, J = 8.8 Hz), 3.25-3.10 (m, 2H), 2.40-2 .20 (m, 1H), 1.95-1.65 (m, 3H), 1.33 (t, 3H, J = 7.1 Hz).
Step 5; Synthesis of 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) aminobenzyl] piperidine-2,3-dione 1- [2- (N-ethoxycarbonyl-N-trifluoromethanesulfonyl) amino Benzyl] -3-hydroxypiperidin-2-one (0.26 g, 0.61 mmol) and dichloromethane (10 ml) were mixed with 1,1,1-triacetoxy-1,1-dihydro-1,2- under ice cooling. Benziodoxol-3- (1H) -one (0.31 g, 0.73 mmol) was added. After completion of the addition, the reaction mixture was stirred at room temperature for 3 hours. After completion of the stirring, 50 ml of a saturated aqueous sodium hydrogen carbonate solution was added to stop the reaction, and the reaction solution was extracted with chloroform (50 ml × 2 times). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane: ethyl acetate = 9: 1 to 1: 9) to obtain 0.27 g of the desired product as a white solid.

Melting point: 95-97 ° C
The compound of the present invention can be synthesized according to the above synthesis examples. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 3 are shown in Tables 2 to 5, but the present invention is not limited to these. In the table, “Me” represents a methyl group. Similarly, Et is an ethyl group, Pr is a propyl group, Bu is a butyl group, Ph is a phenyl group, n- is normal, and i- is iso. Represents each.

  In the table, “m.p.” represents “melting point”, and “* 1” represents “resinous”.

  Moreover, the substituent represented by D-7a in the table represents the following structure.

[Table 2]

――――――――――――――――――――――――――――――――――
No. R ² R ⁵ mp (℃)
――――――――――――――――――――――――――――――――――
1-01 HH 124-128
1-02 C (O) OEt H 72-75
1-03 H Me 137-138
1-04 C (O) OEt Me 72-75
1-05 H Et 131-133
1-06 C (O) OEt Et * 1
1-07 H n-Pr 122-130
1-08 C (O) OEt n-Pr * 1
1-09 H i-Pr 124-134
1-10 C (O) OEt i-Pr * 1
1-11 H n-Bu 116-124
1-12 C (O) OEt n-Bu * 1
1-13 H i-Bu 116-120
1-14 C (O) OEt i-Bu * 1
1-15 C (O) OEt CH ₂ C (O) OEt * 1
1-16 H CH ₂ Ph 129-133
1-17 C (O) OEt CH ₂ Ph * 1
1-18 H CH ₂ CH ₂ OMe * 1
1-19 C (O) OEt CH ₂ CH ₂ OMe * 1
1-20 H CH ₂ CH ₂ Cl 149-150
1-21 C (O) OEt CH ₂ CH ₂ Cl * 1
1-22 H D-7a 141-142
1-23 C (O) OEt D-7a 124-126
1-24 H CH ₂ CH ₂ Si (Me) ₃ * 1
1-25 C (O) OEt CH ₂ CH ₂ Si (Me) ₃ * 1
1-26 H CF ₂ H * 1
1-27 C (O) OEt C (O) OEt * 1
――――――――――――――――――――――――――――――――――
[Table 3]

――――――――――――――――――――――――――――――――――
No. R ² R ⁵ mp (℃)
――――――――――――――――――――――――――――――――――
2-01 C (O) OEt Me * 1
――――――――――――――――――――――――――――――――――
[Table 4]

――――――――――――――――――――――――――――――――――
No. R ² R ⁵ mp (℃)
――――――――――――――――――――――――――――――――――
3-01 H Me * 1
――――――――――――――――――――――――――――――――――
[Table 5]

――――――――――――――――――――――――――――――――――
No. R ² R ⁵ mp (℃)
――――――――――――――――――――――――――――――――――
4-01 C (O) OEt Me * 1
――――――――――――――――――――――――――――――――――
Table ¹ shows the ¹ H-NMR data of the compounds of the present invention which have no melting point.

The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent using Me ₄ Si (tetramethylsilane) as a reference substance. The symbols in Table 6 have the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, q: quintet, m: multiplet.
[Table 6]
――――――――――――――――――――――――――――――――――――――
No. ¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
――――――――――――――――――――――――――――――――――――――
1-06 δ7.45-7.30 (m, 3H), 7.20 (d, J = 8.1Hz, 1H), 4.98 (d, J = 15.9Hz, 1H), 4.60
(d, J = 15.9Hz, 1H), 4.45-4.25 (m, 2H), 3.29 (t, J = 6.3Hz, 2H), 2.85-2.65
(m, 2H), 1.95-1.80 (m, 2H), 1.33 (t, J = 7.2Hz, 3H), 1.31 (t, J = 7.2Hz,
3H).
1-08 δ7.50-7.30 (m, 3H), 7.21 (d, J = 7.8Hz, 1H), 4.98 (d, J = 15.6Hz, 1H), 4.60
(d, J = 15.6Hz, 1H), 4.45-4.25 (m, 4H), 3.29 (t, J = 5.1Hz, 2H), 2.85-2.65
(m, 2H), 1.95-1.80 (m, 2H), 1.75 (q, J = 7.2Hz, 2H), 1.31 (t, J = 7.2Hz,
3H), 0.96 (t, J = 7.2Hz, 3H).
1-10 δ7.50-7.30 (m, 3H), 7.21 (d, J = 7.5Hz, 1H), 4.99 (d, J = 15.6Hz, 1H), 4.70-
4.60 (m, 1H), 4.59 (d, J = 15.6Hz, 1H), 4.45-4.25 (m, 2H), 3.28 (t, J =
5.1Hz, 2H), 2.85-2.65 (m, 2H), 1.90-1.80 (m, 2H), 1.31 (d, J = 6.6Hz,
6H), 1.31 (t, J = 7.2Hz, 3H).
1-12 δ7.50-7.30 (m, 3H), 7.21 (d, J = 7.8Hz, 1H), 4.99 (d, J = 15.6Hz, 1H), 4.58
(d, J = 15.6Hz, 1H), 4.45-4.25 (m, 4H), 3.29 (t, J = 5.1Hz, 2H), 2.85-2.65
(m, 2H), 1.90-1.80 (m, 2H), 1.75-1.65 (m, 2H), 1.50-1.35 (m, 2H), 1.32
(d, J = 7.2Hz, 3H), 0.94 (t, J = 7.2Hz, 3H).
1-14 δ7.50-7.30 (m, 3H), 7.21 (d, J = 7.5Hz, 1H), 4.98 (d, J = 15.6Hz, 1H), 4.59
(d, J = 15.6Hz, 1H), 4.45-4.25 (m, 2H), 4.10 (d, J = 6.9Hz, 2H), 3.29 (t,
J = 5.4Hz, 2H), 2.85-2.65 (m, 2H), 2.20-2.00 (m, 1H), 1.95-1.80 (m, 2H),
1.31 (t, J = 7.2Hz, 3H), 0.94 (d, J = 6.9Hz, 6H).
1-15 δ7.50-7.35 (m, 3H), 7.22 (d, J = 7.8Hz, 1H), 4.95 (d, J = 15.6Hz, 1H), 4.88
(s, 2H), 4.63 (d, J = 15.6Hz, 1H), 4.45-4.25 (m, 2H), 3.76 (s, 3H), 3.31
(t, J = 5.1Hz, 2H), 2.95-2.75 (m, 2H), 1.95-1.80 (m, 2H), 1.31 (t, J =
7.2Hz, 3H).
1-17 δ7.48-7.18 (m, 9H), 5.36 (s, 2H), 4.98 (d, J = 15.5Hz, 2H), 4.60 (d, J =
15.5Hz, 2H), 4.41-4.27 (m, 2H), 3.33-3.22 (m, 2H), 2.85-2.70 (m, 2H),
1.96-1.83 (m, 2H), 1.34-1.27 (m, 3H).
1-18 δ11.1 (brs, 1H), 7.62 (d, J = 7.5Hz, 1H), 7.38-7.30 (m, 1H), 7.24-7.11
(m, 2H), 4.59 (s, 2H), 4.49-4.41 (m, 2H), 3.74-3.66 (m, 2H), 3.54-3.47
(m, 2H), 3.35 (s, 3H), 2.78-2.69 (m, 2H), 1.95-1.87 (m, 2H).
1-19 δ7.49-7.33 (m, 3H), 7.23-7.18 (m, 1H), 4.97 (d, J = 15.4Hz, 1H), 4.61 (d,
J = 15.4Hz, 1H), 4.50-4.29 (m, 4H), 3.73-3.68 (m, 2H), 3.40 (s, 3H), 3.30-
3.26 (m, 2H), 2.87-2.77 (m, 2H), 1.93-1.82 (m, 2H), 1.35-1.29 (m, 3H).
1-21 δ7.49-7.33 (m, 3H), 7.24-7.18 (m, 1H), 4.95 (d, J = 15.4Hz, 1H), 4.63 (d,
J = 15.4Hz, 1H), 4.57-4.51 (m, 2H), 4.44-4.29 (m, 2H), 3.82-3.76 (m, 2H),
3.33-3.26 (m, 2H), 2.86-2.77 (m, 2H), 1.94-1.82 (m, 2H), 1.39-1.27 (m,
3H).
1-24 δ11.0 (brs, 1H), 7.56 (d, J = 8.0Hz, 1H), 7.40-7.35 (m, 1H), 7.30-7.10
(m, 2H), 4.55 (s, 2H), 4.42-4.32 (m, 2H), 3.75-3.54 (m, 2H), 2.70-2.64
(m, 2H), 1.96-1.85 (m, 2H), 1.08-0.99 (m, 2H), -0.03 (s, 9H).
1-25 δ7.42-7.14 (m, 4H), 4.58-4.23 (m, 4H), 4.60-4.53 (m, 2H), 3.28-3.20 (m,
2H), 2.77-2.65 (m, 2H), 1.96-1.79 (m, 2H), 1.33-1.26 (m, 3H), 1.09-
0.99 (m, 2H), -0.04 (s, 9H).
1-26 δ10.9 (brs, 1H), 7.59 (d, J = 7.7Hz, 1H), 7.45-7.39 (m, 1H), 7.37-7.27
(m, 2H), 6.85 (t, J = 72.1Hz, 1H), 4.61 (s, 2H), 3.72-3.66 (m, 2H), 2.89
-2.82 (m, 2H), 2.08-1.95 (m, 2H).
1-27 δ7.49-7.35 (m, 3H), 7.23-7.18 (m, 1H), 4.99 (d, J = 15.5Hz, 2H), 4.63 (d,
J = 15.5Hz, 2H), 4.44-4.31 (m, 4H), 3.38-3.29 (m, 2H), 2.97-2.85 (m, 2H),
2.01-1.89 (m, 2H), 1.45-1.29 (m, 6H).
2-01 δ7.50-7.35 (m, 3H), 7.22 (d, J = 7.5Hz, 1H), 4.83 (d, J = 15.3Hz, 1H), 4.57
(d, J = 15.3Hz, 1H), 4.45-4.30 (m, 2H), 4.08 (s, 3H), 3.40-3.25 (m, 2H),
2.80 (t, J = 6.3Hz, 2H), 1.40-1.30 (m, 3H).
3-01 δ10.8 (brs, 1H), 7.68-7.55 (m, 1H), 7.42-7.33 (m, 1H), 7.31-7.18 (m,
2H), 4.52 (s, 2H), 3.98 (s, 3H), 3.54-3.44 (m, 2H), 2.52-2.46 (m, 2H),
1.78-1.60 (m, 4H).
4-01 δ7.50-7.17 (m, 4H), 4.82-4.66 (m, 2H), 4.45-4.29 (m, 2H), 3.85 (s, 3H),
3.52-3.24 (m, 4H), 2.71-2.51 (m, 2H), 1.39-1.22 (m, 3H).
――――――――――――――――――――――――――――――――――――――
Test Example Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples, but the present invention is not limited thereto.

[Test Example 1] Herbicidal effect test by pretreatment of weed generation under flooding conditions After alluvial soil was put into a 1 / 30,000 are styrene cup, water was added and mixed to create a flooding condition with a depth of 4 cm. After seeding nobies, firefly and koigi in the cup, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose and treated on the water surface. The cup was placed in a greenhouse at 25 to 30 ° C. to grow the plant, and 3 weeks after the chemical treatment, the herbicidal effect on various plants was examined according to the following criteria. The results are shown in Table 7.

Criterion 5 ... More than 90% of herbicide rate (almost completely dead)
4 ... Herbicidal Rate 70% or more and less than 90% 3 ... Herbicidal Rate 40% or more and less than 70% 2 ... Herbicidal Rate 20% or more and less than 40% 1 ... Herbicidal Rate 5% or more but less than 20% 0 ... Herbicidal Rate Less than 5% (almost effective) None)
[Test Example 2] Herbicidal effect test by treatment with weed growing season under flooded conditions After alluvial soil was put into a 1 / 30,000 are styrene cup, water was added and mixed to create a flooded condition with a depth of 4 cm. Nobies, firefly, and oak seeds were mixed in the cup and placed in a greenhouse at 25-30 ° C. to grow plants. When Nobies, Firefly and Konagi reached the 1st to 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the herbicidal effect on various plants was examined according to the criteria of Test Example 1. The results are shown in Table 8.

[Test Example 3] Herbicidal effect test by soil treatment Put sterilized flooded soil into a plastic box 21 cm long, 13 cm wide, 7 cm deep, and then use Nobier, Japanese hive, Enokorogusa, Oatus, Suzumenoteppo, Italian ryegrass, Blackgrass, Ichibi , Ragweed, green-headed dragonfly, white-tailed rice, Inuta, Jacobula, Jaegula, corn, soybean, rice, wheat and beet seeds were sown in a spot shape and covered with about 1.5 cm of soil. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the soil surface. Three weeks after the drug treatment, the herbicidal effect on various plants was examined according to the criteria of Test Example 1. The results are shown in Table 9.

[Test Example 4] Herbicidal effect test by foliar treatment Put sterilized piled soil in a plastic box 21cm long, 13cm wide, 7cm deep, nobies, barbarella, green grass, oats, hornbill, Italian ryegrass, blackgrass, ichibi , Ragweed, green-headed dragonfly, white-leafed beetle, common beetle, chickweed, yamgra, blue-billed corn, corn, soybean, rice, wheat and beet seeds were sown in a spot shape, covered with about 1.5 cm, and then placed in a greenhouse at 25 to 30 ° C. Growing plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the herbicidal effect on various plants was examined according to the criteria of Test Example 1. The results are shown in Table 10.

The symbols in Tables 7 to 10 represent the following meanings.
A: Nobies, B: Firefly, C: Konagi, D: Beetle, E: Enokirogusa, F: Oats, G: Prunus, H: Italian ryegrass, I: Ichibibi, J: Aogaeto, K: Shiroza, L: Hakobe, M : Yaemugura, N: Blackgrass, O: Giant corn, a: Transplanted rice, b: Corn, c: Soybean, d: Direct sowing rice, e: Wheat, f: Beet The treatment dose (g / a) is 1 When converted per round (1a), it means that the concentration is adjusted so as to be processed by the number of g described.
[Table 7]
―――――――――――――――――――――――――
No. Treatment dose ABC a
(g / a)
―――――――――――――――――――――――――
1-01 2.52 4 5 5 1
1-02 2.52 5 5 5 0
1-03 2.52 5 5 5 0
1-04 2.52 5 5 5 0
1-05 2.52 5 5 5 2
1-06 2.52 5 5 5 0
1-07 2.52 5 5 5 0
1-08 2.52 5 5 5 0
1-09 2.52 5 5 5 0
1-10 2.52 5 5 5 0
1-11 2.52 5 5 5 0
1-12 2.52 5 5 5 0
1-13 2.52 5 5 5 1
1-14 2.52 5 5 5 0
1-15 2.52 5 4 4 0
1-16 2.52 5 5 5 1
1-17 2.52 5 5 5 0
1-18 2.52 4 5 5 1
1-19 2.52 5 5 5 0
1-20 2.52 5 5 5 0
1-21 2.52 5 5 5 0
1-22 2.52 5 5 5 0
1-23 2.52 5 5 5 1
1-24 2.52 5 5 5 0
1-25 2.52 5 5 5 0
1-26 2.52 5 5 5 0
1-27 1.62 5 5 5 2
2-01 2.52 5 5 5 0
3-01 2.52 5 5 5 0
4-01 2.00 5 5 5 3
―――――――――――――――――――――――――
[Table 8]
―――――――――――――――――――――――――
No. Treatment dose ABC
(g / a)
―――――――――――――――――――――――――
1-01 2.52 4 5 4
1-02 2.52 4 5 5
1-03 2.52 5 5 5
1-04 2.52 5 5 5
1-05 2.52 5 5 5
1-06 2.52 5 5 5
1-07 2.52 5 5 5
1-08 2.52 5 5 5
1-09 2.52 5 5 5
1-10 2.52 5 5 5
1-11 2.52 4 5 5
1-12 2.52 4 5 5
1-13 2.52 3 5 5
1-14 2.52 3 5 5
1-15 2.52 1 4 3
1-16 2.52 4 5 5
1-17 2.52 4 5 5
1-18 2.52 4 5 5
1-19 2.52 5 5 5
1-20 2.52 5 5 5
1-21 2.52 5 5 5
1-22 2.52 5 5 5
1-23 2.52 5 5 5
1-24 2.52 4 5 5
1-25 2.52 5 5 5
1-26 2.52 5 5 5
1-27 1.62 4 5 5
2-01 2.52 3 5 5
3-01 2.52 5 5 5
4-01 2.00 5 5 5
―――――――――――――――――――――――――
[Table 9]
―――――――――――――――――――――――――――――――――――――
No. Treatment dose ADEFGHIJKLMNO bcdef
(g / a)
―――――――――――――――――――――――――――――――――――――
1-01 3.2 5 5 5 0 5 0 0 3 0 2 3 4 3 0 0 0 0
1-02 3.2 4 4 4 0 5 2 0 4 0 3 4 4 2 1 0 0 0
1-03 3.2 5 5 5 3 5 5 5 5 5 5 4 5 4 5 4 5 1 4
1-04 3.2 5 5 5 3 5 5 5 5 5 5 5 5 3 4 5 2 4
1-05 3.2 5 5 5 3 5 5 5 5 5 5 5 5 5 4 4 5 4 5
1-06 3.2 5 5 5 2 5 5 5 5 4 5 4 5 4 4 0 4 5 5
1-07 3.2 5 5 5 3 5 5 5 5 5 5 5 4 0 4 4 1 5
1-08 3.2 5 5 5 2 5 5 4 5 5 5 5 3 3 0 4 2 3
1-09 3.2 5 5 5 0 5 5 2 5 4 4 4 5 4 4 0 4 0 4
1-10 3.2 5 5 5 0 5 4 1 5 3 5 5 3 3 0 4 0 4
1-11 3.2 5 5 5 3 5 5 3 5 4 4 5 3 2 0 4 0 1
1-12 3.2 4 5 4 1 5 3 1 5 4 3 0 2 3 1 0 3 1 0
1-13 3.2 5 5 5 4 5 5 5 5 5 4 5 5 0 0 5 4
1-14 3.2 4 5 5 2 5 5 0 5 3 4 4 4 0 0 2 3 2
1-15 3.2 5 5 4 0 3 3 0 2 0 3 0 1 0 0 0
1-16 3.2 5 4 4 1 5 5 3 5 3 4 5 3 3 0 3 0 2
1-17 3.2 4 3 3 2 5 5 0 4 3 4 4 4 0 0 1 2 1
1-18 3.2 5 5 5 4 5 5 5 5 5 4 5 4 4 1 5 5 5
1-19 3.2 3 5 5 4 3 5 5 5 5 5 5 4 4 3 5 4 5
1-20 3.2 5 5 5 4 5 5 5 5 5 5 5 4 4 0 5 4 4
1-21 3.2 3 5 5 3 3 5 5 5 5 4 5 4 3 0 5 3 4
1-22 3.2 5 5 5 3 5 4 4 5 5 5 5 4 3 4 5 0 5
1-23 3.2 0 5 5 3 0 4 5 5 5 4 5 3 2 2 5 1 5
1-24 3.2 0 2 0 0 0 3 1 4 3 4 1 0 0 0 0 2
1-25 3.2 0 2 0 0 0 1 1 4 3 4 0 3 0 0 0 0 0 1
1-26 3.2 5 5 5 0 5 3 5 5 5 5 3 5 0 3 3 0 3
1-27 2.0 3 4 3 0 4 2 2 0 3 3 3 2 0 0 0 0 2
2-01 3.2 5 5 5 5 5 5 5 5 4 3 5 4 3 0 5 4
3-01 3.2 5 5 5 2 5 5 4 5 4 4 5 3 4 0 4 3 0
4-01 2.5 5 5 4 0 5 3 3 4 3 3 5 2 0 0 4 0 4
―――――――――――――――――――――――――――――――――――――
[Table 10]
―――――――――――――――――――――――――――――――――――――
No. Treatment dose ADEFGHIJKLMNO bcdef
(g / a)
―――――――――――――――――――――――――――――――――――――
1-01 3.2 4 5 4 0 5 1 4 4 3 4 3 4 1 4 5 3 3 4
1-02 3.2 5 4 3 0 3 0 4 3 4 4 4 4 3 2 4 3 0 4
1-03 3.2 5 5 5 1 5 4 5 5 4 5 4 4 3 4 5 4 2 2
1-04 3.2 5 5 5 2 5 4 4 5 4 4 4 5 4 1 4 4 3 4
1-05 3.2 4 5 5 3 4 4 5 5 4 4 5 4 4 4 4 4 0 4
1-06 3.2 5 5 5 1 5 4 5 5 4 4 4 4 3 4 4 4 1 0
1-07 3.2 4 4 4 0 4 2 4 5 5 4 5 4 3 4 5 3 0 4
1-08 3.2 4 4 4 0 5 3 4 5 4 4 5 3 4 4 3 3 0 4
1-09 3.2 4 4 4 0 3 3 3 4 4 4 5 4 3 4 4 4 0 3
1-10 3.2 4 4 4 0 4 3 4 4 4 5 5 3 3 3 4 3 0 2
1-11 3.2 4 4 4 0 5 1 4 4 4 4 4 4 3 4 4 3 1 2
1-12 3.2 4 3 4 0 4 1 3 4 3 4 5 2 1 4 3 3 2 0
1-13 3.2 4 4 4 2 4 3 3 4 4 4 4 3 3 4 3 4 3 0
1-14 3.2 3 4 4 3 4 0 4 5 4 4 5 3 2 3 3 3 4 0
1-15 3.2 4 3 3 0 5 0 1 3 0 4 3 2 2 2 3 0 0 0
1-16 3.2 4 4 3 0 3 2 3 4 4 4 4 5 3 4 0 3 0 3
1-17 3.2 4 3 3 0 4 4 4 4 4 4 4 4 3 3 3 3 0 1
1-18 3.2 4 5 4 3 5 2 3 0 3 3 4 5 2 3 3 3 3 3
1-19 3.2 0 2 3 3 3 4 5 4 4 4 4 4 3 3 3 3 3 3
1-20 3.2 0 3 3 2 3 3 3 5 4 4 4 4 2 4 3 4 0 3
1-21 3.2 0 4 3 1 3 3 3 4 3 4 4 4 3 3 3 3 1 3
1-22 3.2 3 4 4 3 5 3 4 5 5 4 4 4 3 3 4 4 2 3
1-23 3.2 0 4 5 4 0 2 4 5 4 3 4 5 3 5 5 3 3 3
1-24 3.2 0 4 4 0 0 2 0 5 4 4 5 3 2 0 3 3 3 3
1-25 3.2 0 3 3 3 0 3 3 5 4 4 4 3 2 1 3 2 2 3
1-26 3.2 5 5 4 0 5 3 4 4 5 5 5 3 3 1 4 4 0 3
1-27 2.0 3 3 4 0 3 1 3 3 3 4 4 3 3 0 4 1 0 3
2-01 3.2 4 4 4 4 5 4 3 3 3 3 4 4 3 0 3 4 2 2
3-01 3.2 3 4 3 0 5 3 4 4 3 3 4 5 3 4 4 3 1 0
4-01 2.5 3 4 3 0 5 3 3 3 2 3 4 5 3 2 0 3 0 0
―――――――――――――――――――――――――――――――――――――

  The haloalkylsulfonamide derivative of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Claims (6)

Formula (1):

[Wherein A represents -CH = CH- or a sulfur atom,
W represents an oxygen atom or a sulfur atom,
X is a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 3 -C _{6 cycloalkyl,} C 3 -C _{6 halocycloalkyl,} C 2 -C _{6 alkenyl,} C 2 -C ₆ halo _alkenyl, C 2 -C _{6 alkynyl,} C 2 -C ₆ haloalkynyl, cyano, -C ^{(O) R 46,} _hydroxy, C 1 -C _{6 alkoxy,} C 1 -C ₆ haloalkoxy, amino, nitro or -S (O) When _q7 R ⁴⁹ is represented and m represents an integer of 2 or more, each X may be the same as or different from each other, and when two Xs are adjacent to each other, two adjacent X is _{-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 _{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— may form a 5-membered or 6-membered ring with the carbon atom to which each of the two Xs is bonded, when the hydrogen atoms bonded to each carbon atom forming the ring may be optionally substituted by halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
m represents an integer of 0, 1 or 2;
n represents an integer of 1, 2, 3 or 4;
p represents an integer of 0 or 1,
R ¹ represents C ₁ -C ₆ haloalkyl,
R ² is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 10} _(C 1 ~C _{6) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally substituted by ^{R 10} _{(C 3} -C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 10} _(C 2 ~C _{6) alkenyl,} optionally substituted by C 2 -C ₆ ^{alkynyl, R 10} _(C 2 ~ C ₆ ) represents alkynyl, —C (O) R ¹¹ or —S (O) ₂ R ¹² ,
R ³ and R ⁴ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy or _C 1 -C ₆ represent a haloalkoxy, or ^{by R 3} to form a _C 2 -C ₆ alkylene chain together with ^{R 4,} the carbon ^{to which R 3} and ^{R 4} are bonded Represents that a 3- to 7-membered ring may be formed together with the atoms;
R ⁵ is a hydrogen _atom, C 1 -C ₆ ^alkyl, optionally substituted by ^{R 27} _(C 1 ~C _{6) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally substituted by ^{R 27} _{(C 3} -C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 27} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^alkynyl, optionally substituted by ^{R 27} _(C 2 ~ C ₆₎ represents an ^alkynyl, -C (O) R ^28, and -S _(O) ^{2 R 30} or D-1~D-9,
R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , C ₃ -C ₆ cycloalkyl, R optionally substituted by ³⁹ _(C 3 ~C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 39} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^{alkynyl, R 39} optionally substituted by _(C 2 _{~C 6)} alkynyl, ^{phenyl, (R} ₄₀₎ phenyl substituted by ^{_{q5, -C (O) R 41}} , cyano, ^{-OR 42} or -S _(O) q6 ^{R 43} Or R ⁶ and R ⁷ on the same carbon may form a C ₂ -C ₆ alkylene chain together to form a 3- to 7-membered ring with the carbon atoms to which they are attached. The table At this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, or R ⁶ and R ⁷ on the same carbon with one another bond, it may form a = CH ₂ or carbonyl And when n = 2-4, R ⁶ and R ⁷ together with R ⁶ or R ⁷ on different carbons form a C ₂ -C ₆ alkylene chain, thereby binding carbon atoms. The alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and R ⁶ and R ⁷ may be on different carbons. R ⁶ or R ⁷ may be the same or different, and R ⁶ and R ⁷ together with R ⁶ or R ⁷ on adjacent carbons may represent a bond,
R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , C ₃ -C ₆ cycloalkyl, R optionally substituted by ³⁹ _(C 3 ~C _{6) cycloalkyl,} C 2 -C ₆ ^alkenyl, optionally substituted by ^{R 39} _(C 2 ~C _{6) alkenyl,} C 2 -C ₆ ^{alkynyl, R 39} optionally substituted by _(C 2 _{~C 6)} alkynyl, ^{phenyl, (R} ₄₀₎ phenyl substituted by ^{_{q5, -C (O) R 41}} , cyano, ^{-OR 42} or -S _(O) q6 ^{R 43} Or R ⁸ and R ⁹ on the same carbon may form a C ₂ -C ₆ alkylene chain together to form a 3- to 7-membered ring with the carbon atoms to which they are attached. The table At this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, or R ⁸ and R ⁹ on the same carbon with one another bond, it may form a = CH ₂ or carbonyl Represents
D-1 to D-9 each represent a ring represented by the following structural formula;

R ¹⁰ represents a halogen atom, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , —C (O) R ¹⁴ , —OR ¹⁵ or —S (O) _{q 2} R ¹⁹ ,
R ¹¹ _is, C 1 _{-C 12} ^alkyl, substituted optionally substituted by ^{R 20} _(C 1 ~C _{12) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally by ^{R 20} _(C 3 ~C ₆ ) _cycloalkyl, optionally substituted by C 2 -C _{6 ^{alkenyl, R 20 (C 2 ~C 6}} ) _alkenyl, optionally substituted by C 2 -C _{6 ^{alkynyl, R 20 (C 2 ~C 6}} ) It represents alkynyl, ^{phenyl, (R} ₁₃₎ phenyl substituted by _{^{q1, -OR 21, -N (R}} 22) R 23 or ^{-SR 24,}
R ¹² represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} or —N (R ²⁵ ) R ²⁶ ,
R ¹³ represents a halogen _atom, C 1 -C _{6 alkyl,} C 1 -C _{6 haloalkyl,} C 1 -C _{6 alkoxy,} C 1 -C ₆ haloalkoxy, amino or nitro, q1 is an integer of 2 or more Each R ¹³ may be the same as or different from each other, and when two R ¹³ are adjacent to each other, the two adjacent R ¹³ 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 = By forming the H-, 2 two together with the carbon atoms bonded thereto to R ¹³ may form a 5- or 6-membered ring, this time, the hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁴ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ¹⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} or —C (O) R ¹⁶ ,
R ¹⁶ represents C ₁ -C ₆ alkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , C ₁ -C ₆ alkoxy or —N (R ¹⁷ ) R ¹⁸ ,
R ¹⁷ and R ¹⁸ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ¹⁷ together with R ¹⁸ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ¹⁹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ²⁰ represents a halogen atom, C ₃ -C ₆ cycloalkyl, phenyl, phenyl substituted by (R ¹³ ) _{q 1} , C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy or phenoxy,
R ²¹ _is, C 1 _{-C 12} ^alkyl, substituted optionally substituted by ^{R 20} _(C 1 ~C _{12) alkyl,} C 3 -C ₆ ^cycloalkyl, optionally by ^{R 20} _(C 3 ~C ₆ ) _cycloalkyl, optionally substituted by C 2 -C _{6 ^{alkenyl, R 20 (C 2 ~C 6}} ) _alkenyl, optionally substituted by C 2 -C _{6 ^{alkynyl, R 20 (C 2 ~C 6}} ) Represents alkynyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ;
R ²² and R ²³ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ²² together with R ²³ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ²⁴ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁵ and R ²⁶ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ²⁵ together with R ²⁶ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ²⁷ is a halogen atom, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ halocycloalkyl, —C (O) R ³¹ , —OR ³² , —N (R ³³ ) R ³⁴ , —S (O). _q4 R ^35, tri _(C 1 -C ₆ alkyl) a silyl or D-1~D-9,
R ²⁸ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, It represents -N ^{(R 36)} R ³⁷ or ^{-SR 38,}
R ²⁹ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, amino or nitro, and q 3 represents an integer of 2 or more. Each R ²⁹ may be the same as or different from each other, and when two R ²⁹ are adjacent to each other, the two adjacent R ²⁹ 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 = By forming the H-, 2 two together with the carbon atoms to which each R ²⁹ is bonded may form a 5- or 6-membered ring, this time, the hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁰ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³¹ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy,
R ³² represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³³ and R ³⁴ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ³³ together with R ³⁴ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ³⁵ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ²⁹ ) _{q 3} ;
R ³⁶ and R ³⁷ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ³⁶ together with R ³⁷ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ³⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁹ represents a halogen atom, C ₃ -C ₆ cycloalkyl, phenyl, hydroxy, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy,
R ⁴⁰ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, amino or nitro, and q 5 represents an integer of 2 or more. Each R ⁴⁰ may be the same as or different from each other, and when two R ⁴⁰ are adjacent to each other, the two adjacent R ⁴⁰ 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 = By forming the H-, 2 one respective R ⁴⁰ may form a 5- or 6-membered ring together with the carbon atoms to which they are attached this case, hydrogen atoms bonded to each carbon atom forming the ring Is optionally substituted by a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ⁴¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, hydroxy, C ₁ -C ₆ alkoxy, C ₁ -C ₆ halo. alkoxy or ^{-N (R 44)} R ^45,
R ⁴² represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl, phenyl substituted by phenyl or ^(R _{40) q5,}
R ⁴³ represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ⁴⁰ ) _q5 ,
R ⁴⁴ and R ⁴⁵ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ⁴⁴ together with R ⁴⁵ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to be bonded, in which case the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and a halogen atom , C ₁ -C ₆ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, formyl group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group or oxo group May be replaced with
R ⁴⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or —N (R ⁴⁷ ) R ⁴⁸ ,
R ⁴⁷ and R ⁴⁸ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl, or R ⁴⁷ together with R ⁴⁸ forms a C ₂ -C ₆ alkylene chain. It indicates that the 3- to 7-membered ring together with the nitrogen atom may be formed to be, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen atom, C ₁ -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl group _may be optionally substituted by C 1 -C ₆ alkoxycarbonyl group or an oxo group ,
R ⁴⁹ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
q1 represents an integer of 1, 2, 3, 4 or 5,
q2 represents an integer of 0, 1 or 2,
q3 represents an integer of 1, 2, 3, 4 or 5;
q4 represents an integer of 0, 1 or 2,
q5 represents an integer of 1, 2, 3, 4 or 5,
q6 and q7 each independently represent an integer of 0, 1 or 2;
t1 represents an integer of 0, 1, 2, 3, 4 or 5;
t2 represents an integer of 0, 1, 2, 3 or 4;
t3 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
t4 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. ] The haloalkyl sulfonamide derivative represented by these, or its salt. A represents -CH = CH-,
W represents an oxygen atom,
R ² is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁰ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -C (O) Represents R ¹¹ or —S (O) ₂ R ¹² ,
R ³ and R ⁴ represent a hydrogen atom,
R ⁵ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ²⁷ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C Represents ₆ alkynyl, -C (O) R ²⁸ or D-7,
R ⁶ and R ⁷ are each independently a hydrogen atom, halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , phenyl, —C (O) R ^41. , Cyano, —OR ⁴² or —S (O) _q6 R ⁴³ , or R ⁶ and R ⁷ on the same carbon together to form a C ₂ alkylene chain, thereby binding together carbon atoms It represents that a 3-membered ring may be formed, or R ⁶ and R ⁷ on the same carbon may be bonded to each other to form ═CH ₂ or carbonyl, and n = 2 to 4 Where R ⁶ and R ⁷ together with R ⁶ or R ⁷ on different carbons form a C ₂ -C ₆ alkylene chain to form a 4-6 membered ring with the carbon atoms to which it is attached. R ⁶ and R ⁷ are different from each other. R ⁶ or R ⁷ on the same carbon may be the same or different, and R ⁶ and R ⁷ together with R ⁶ or R ⁷ on the adjacent carbon can represent a bond,
R ⁸ and R ⁹ are each independently a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ³⁹ , phenyl, —C (O) R ^41. , Cyano, —OR ⁴² or —S (O) _q6 R ⁴³ , or R ⁸ and R ⁹ on the same carbon together to form a C ₂ alkylene chain, thereby binding together carbon atoms Represents that a 3-membered ring may be formed, or that R ⁸ and R ⁹ on the same carbon may be bonded to each other to form ═CH ₂ or carbonyl,
R ¹⁰ represents phenyl, —C (O) R ¹⁴ , —OR ¹⁵ or —S (O) _q2 R ¹⁹ ,
R ¹¹ is C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ²⁰ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, phenyl, —OR ²¹ or — SR ²⁴
R ¹² represents C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, phenyl or phenyl substituted by (R ¹³ ) _q1 ,
R ¹³ represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ alkoxy;
R ¹⁴ represents C ₁ -C ₆ alkoxy or phenyl;
R ¹⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or —C (O) R ¹⁶ ,
R ¹⁶ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy;
R ¹⁹ represents C ₁ -C ₆ alkyl,
R ²⁰ represents a halogen atom or phenoxy,
R ²¹ represents C ₁ -C ₁₂ alkyl, (C ₁ -C ₁₂ ) alkyl optionally substituted by R ²⁰ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or phenyl,
R ²⁴ represents C ₁ -C ₆ alkyl,
R ²⁷ is a halogen ^{atom, -C (O) R 31,} -OR 32, tri _(C 1 -C ₆ alkyl) a silyl or D-1,
R ²⁸ and R ³¹ each independently represent C ₁ -C ₆ alkoxy;
R ³² represents C ₁ -C ₆ alkyl,
R ³⁹ represents a halogen atom, phenyl, hydroxy or C ₁ -C ₆ alkoxy;
R ⁴¹ represents hydroxy or C ₁ -C ₆ alkoxy;
R ⁴² is a hydrogen _atom, C 1 -C ₆ alkyl or phenyl,
The haloalkylsulfonamide derivative or a salt thereof according to claim 1, wherein R ⁴³ represents C ₁ -C ₆ alkyl or phenyl. R ⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted with R ²⁷ , —C (O) R ²⁸ or D-7,
The haloalkylsulfonamide derivative or a salt thereof according to claim 2, wherein R ⁶ , R ⁷ , R ⁸ and R ⁹ represent a hydrogen atom. R ² represents a hydrogen atom or —C (O) R ¹¹ ,
R ¹¹ represents -OR ²¹ ;
The haloalkylsulfonamide derivative or a salt thereof according to claim 3, wherein R ²¹ represents C _{1 to} C ₁₂ alkyl.   An agrochemical containing one or more selected from the haloalkylsulfonamide derivatives and salts thereof according to claim 1 as active ingredients.   A herbicide containing, as an active ingredient, one or more selected from the haloalkylsulfonamide derivatives and salts thereof according to claim 1.