JP2007254317A - Crop-increasing agent and method for using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a crop-increasing agent for various crops, which gives sufficient crop-increasing effects even by simple using methods comprising not only a spraying treatment but also a seed treatment or a target crop cultivation carrier treatment. <P>SOLUTION: This crop-increasing agent contains a compound represented by the general formula (I) äR<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP>, and R<SP>5</SP>are each H, a halogen, CN, an alkyl, an alkoxyalkyl, an aryl, an arylalkyl, an alkylcarbonyl, or the like; R<SP>6</SP>is -C(=W<SP>1</SP>)YR<SP>7</SP>[R<SP>7</SP>is H, an alkyl, an alkenyl, phenylcarbonyl, a heterocyclic carbonyl, an arylsulfonyl, or the like; Y is O, S, -N(R<SP>11</SP>)-, or -N(R<SP>11</SP>)O- (R<SP>11</SP>is H, an alkyl, a cycloalkyl, a substituted phenyl, or the like), or the like; W<SP>1</SP>is O, S]} as an active ingredient, and the method for using the same. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a crop yield-enhancing agent containing 4-cyclopropyl-1,2,3-thiadiazole derivative or a salt thereof as an active ingredient and a method for using the same.

  Conventionally, it is known that a compound having a plant growth regulating action or the like shows a crop yield-raising action (see, for example, Patent Documents 1 to 6). Moreover, it is known that a certain 1,2,3-thiadiazole derivative is useful as a plant disease control agent for agriculture and horticulture (for example, refer patent document 7 or 8). However, there is no description or suggestion about the yield-enhancing agent and method of use of crops containing the 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention as an active ingredient.

JP 54-81275 A JP-A-55-62066 JP 58-194804 A Japanese Patent Laid-Open No. 62-181206 JP-A-61-100504 Japanese Patent Publication No. 60-14001 JP-A-8-325110 Japanese Patent Laid-Open No. 2001-10909

  However, the above-mentioned conventional crop yield increaser and method for increasing crops have problems such that a sufficient yield increase effect cannot be expected and the treatment method is complicated, and a simple and reliable yield increaser and its method of use are required. It was.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention is a yield enhancer for various crops. As a result, the inventors have found that a sufficient yield increase effect can be obtained not only by spraying but also by a simple usage method of treating seeds or target crops so as to sow seeds or target crops, thereby completing the present invention.

｛式中、R¹、R²、R³、R⁴及びR⁵ は同一又は異なっても良く、水素原子；ハロゲン原子；シアノ基；（C₁-C₆）アルキル基；ハロ（C₁-C₆）アルキル基；（C₁-C₆）アルコキシ（C₁-C₆）アルキル基；（C₃-C₁₂）シクロアルキル基；ハロ（C₃-C₁₂）シクロアルキル基；（C₁-C₆）アルキルチオ（C₁-C₆）アルキル基；（C₂-C₆）アルケニル基；ハロ（C₂-C₆）アルケニル基；置換基Z（Z は後記。） により置換されても良いアリール基；置換基Z（Z は後記。）により環上に置換されても良いアリール（C₁-C₆）アルキル基；又は（C₁-C₆）アルキルカルボニル基を示す。 That is, the present invention relates to the general formula (I):

{Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ may be the same or different and are a hydrogen atom; a halogen atom; a cyano group; a (C ₁ -C ₆ ) alkyl group; a halo (C _1- (C ₆ ) alkyl group; (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group; (C ₃ -C ₁₂ ) cycloalkyl group; halo (C ₃ -C ₁₂ ) cycloalkyl group; (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group; (C ₂ -C ₆ ) alkenyl group; halo (C ₂ -C ₆ ) alkenyl group; substituent Z (Z is described later) A good aryl group; an aryl (C ₁ -C ₆ ) alkyl group which may be substituted on the ring by a substituent Z (Z 1 will be described later); or a (C ₁ -C ₆ ) alkylcarbonyl group.

R ⁶ is —C (═W ¹ ) YR ⁷ (wherein R ⁷ is a hydrogen atom; (C ₁ -C ₂₀ ) alkyl group; halo (C ₁ -C ₂₀ ) alkyl group; (C ₂ -C ₂₀ )) Alkenyl group; halo (C ₂ -C ₂₀ ) alkenyl group; (C ₂ -C ₂₀ ) alkynyl group; halo (C ₂ -C ₂₀ ) alkynyl group; (C ₃ -C ₁₂ ) cycloalkyl group; halo (C ₃ -C ₁₂ ) cycloalkyl group; (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group; (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group; substituent Z (Z is An aryl (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by the following formula; aryloxy (C ₁ -C ₆ ) optionally substituted on the ring by the substituent Z (Z will be explained later) An alkyl group; an arylthio (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by a substituent Z (Z is described later); an aryl group optionally substituted by a substituent Z (Z is described later); Carboxy (C ₁ -C ₆ ) alkyl group (C ₁ -C ₆ ) alkoxycarbonyl (C ₁ -C ₆ ) alkyl group; carbamoyl (C ₁ -C ₆ ) alkyl group; they may be the same or different, (C ₁ -C ₁₀ ) alkyl group, halo ( A C ₁ -C ₁₀ ) alkyl group, a (C ₂ -C ₁₀ ) alkenyl group, a (C ₃ -C ₁₀ ) cycloalkyl group, a phenyl group which may be substituted by a substituent Z (Z will be described later), or a substituent Carbamoyl (C ₁ -C) having 1 to 2 substituents on the nitrogen atom selected from a phenyl (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by a group Z (Z is described later) ₆ ) an alkyl group; a cyano (C ₁ -C ₆ ) alkyl group; a heterocyclic group optionally substituted by a substituent Z (Z is described later); and a substituent Z (Z is described later) substituted on the ring May be a heterocyclic (C ₁ -C ₆ ) alkyl group; (C ₁ -C ₂₀ ) alkylcarbonyl group; (C ₂ -C ₂₀ ) alkynylcarbonyl group;

(C ₂ -C ₆ ) alkenylcarbonyl group; (C ₃ -C ₆ ) cycloalkylcarbonyl group; substituent Z (Z
Is a postscript. ) A phenylcarbonyl group which may be substituted by a substituent; a heterocyclic carbonyl group which may be substituted by a substituent Z (Z will be described later); a (C ₁ -C ₂₀ ) alkylsulfonyl group; a halo (C ₁ -C ₂₀ ) An alkylsulfonyl group; an arylsulfonyl group which may be substituted by a substituent Z (Z will be described later); an aryl (C ₁ -C ₆ ) alkyl which may be substituted on the ring by a substituent Z (Z is described later) A sulfonyl group; —C (═W ² ) NR ⁸ R ⁹ (wherein R ⁸ and R ⁹ may be the same or different and are a hydrogen atom, a (C ₁ -C ₁₀ ) alkyl group, a halo (C ₁ -C); ₁₀ ) an alkyl group, a (C ₂ -C ₁₀ ) alkenyl group, a (C ₃ -C ₁₀ ) cycloalkyl group, a phenyl group which may be substituted with a substituent Z (Z is described later), a substituent Z (Z is below.) by which may be substituted on its ring a phenyl (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy group, the substituent Z (Z after . Good phenoxy group or a substituent Z (Z be substituted with) indicates infra.) By phenyl optionally substituted on the ring (C ₁ -C ₆₎ alkyl group. Furthermore, R ⁸ and R ⁹ Together are an oxygen atom, a sulfur atom or NR ¹⁰ (wherein R ¹⁰ is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group or a substituent Z (Z is described later)) .W ² represents an oxygen atom or a sulfur atom) which can show a better be interrupted (C ₂ -C ₆₎ alkylene group by a ^{_{group); -. SO 2 NR 8}} R 9 ( wherein,. R ⁸ and R ⁹ are the same as described above); or —N═C (R ⁸ ) R ⁹ (wherein R ⁸ and R ⁹ are the same as described above).

Y is an oxygen atom; a sulfur atom; —N (R ¹¹ ) — (wherein R ¹¹ is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a substituent Z ( Z is a phenyl group that may be substituted by the following.), A phenyl (C ₁ -C ₆ ) alkyl group that may be substituted on the ring by the substituent Z (Z is the following), (C ₁ -C ₁₀ ) Substituted by an alkylcarbonyl group, a (C ₂ -C ₁₀ ) alkynylcarbonyl group, a (C ₂ -C ₁₀ ) alkenylcarbonyl group, a (C ₃ -C ₆ ) cycloalkylcarbonyl group, and a substituent Z (Z is described later). A phenylcarbonyl group which may be substituted, or a heterocyclic carbonyl group which may be substituted by a substituent Z (Z is described later)); or -N (R ¹¹ ) O- (wherein R ¹¹ is as defined above. The same). ).
W ¹ represents an oxygen atom or a sulfur atom.

Z may be the same or different, halogen atom; hydroxyl group; cyano group; nitro group; (C ₁ -C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; (C ₃ -C ₁₂ ) cycloalkyl Group: halo (C ₃ -C ₁₂ ) cycloalkyl group, which may be the same or different, halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) Alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) Alkoxycarbonyl group, carbamoyl group, which may be the same or different, each having 1 to 5 substituents selected from substituted carbamoyl groups having substituent X (X will be described later) on the nitrogen atom May be the same or different, a halogen atom, a hydroxyl group, a cyano group, Toromoto, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆ ) an alkylthio group, a halo (C ₁ -C ₆ ) alkylthio group, a carboxyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, a carbamoyl group, or the same or different, and a substituent X (X is described later). A phenyl (C ₁ -C ₆ ) alkyl group optionally having 1 to 5 substituents selected from substituted carbamoyl groups on the nitrogen atom;

(C ₁ -C ₆ ) alkoxy group; halo (C ₁ -C ₆ ) alkoxy group; (C ₁ -C ₆ ) alkylthio group; halo (C ₁ -C ₆ ) alkylthio group; (C ₁ -C ₆ ) alkyl Halo (C ₁ -C ₆ ) alkylsulfinyl group; (C ₁ -C ₆ ) alkylsulfonyl group; halo (C ₁ -C ₆ ) alkylsulfonyl group; may be the same or different, and may be a halogen atom, hydroxyl group, Cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group, or the same or different, substituent X (X is described below) .) Having 1 to 5 substituents selected from substituted carbamoyl groups having on the nitrogen atom There phenoxy group; may be the same or different, a halogen atom, a hydroxyl group, a cyano group, a nitro group, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ Alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl A phenylthio group optionally having 1 to 5 substituents selected from a substituted carbamoyl group having a group or substituent X (X will be described later) on the nitrogen atom;

May be the same or different, and may be a halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group or substituent A phenylsulfinyl group which may have 1 to 5 substituents selected from substituted carbamoyl groups having X on the nitrogen atom (X may be the same or different; a halogen atom, a hydroxyl group, cyano; Group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆₎ alkylthio groups, halo (C ₁ -C ₆₎ alkylthio group, a carboxyl group, (C ₁ -C ₆₎ Alkoxycarbonyl group, a carbamoyl group or a substituent X (. X is below) 1-5 may have a substituent group phenylsulfonyl group selected from substituted carbamoyl group having on the nitrogen atom;

May be the same or different, and may be a halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group or substituent A phenyl (C ₁ -C ₆ ) alkyloxy group optionally having 1 to 5 substituents selected from a substituted carbamoyl group having X (X will be described later) on the nitrogen atom; a carboxyl group A (C ₁ -C ₆ ) alkoxycarbonyl group; a carbamoyl group optionally substituted by a substituent X (X is described later); (C ₁ -C ₆ ) an alkylcarbonyl group or the same or different, a halogen atom; , Hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, Halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) ₁ to 5 substituents selected from a substituted carbamoyl group having an alkylthio group, a carboxyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, a carbamoyl group or a substituent X (X is described later) on the nitrogen atom One or more substituents selected from phenylcarbonyl groups which may be present are shown.

X is a (C ₁ -C ₁₀ ) alkyl group; a halo (C ₁ -C ₁₀ ) alkyl group, which may be the same or different, and is a halogen atom, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group or halo (C ₁ -C ₆ ) alkylthio A phenyl group which may have 1 to 5 substituents selected from a group or the same or different, a halogen atom, a cyano group, a nitro group, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group or halo (C ₁ -C ₆ ) alkylthio group phenyl optionally from 1 to 5 substituents selected having on the ring indicates a (C ₁ -C ₆₎ alkyl group. );

（式中、Zは前記に同じくし、ｎは０〜４の整数を示す。W³及びW⁴は同一又は異なっても良く、酸素原子又は硫黄原子を示す。）又はシアノ基を示す。｝
で表される１，２，３−チアジアゾール誘導体又はその塩類を有効成分とする作物の増収剤及びその使用方法に関する。

(In the formula, Z is the same as described above, and n represents an integer of 0 to ^4. W ³ and W ⁴ may be the same or different and represent an oxygen atom or a sulfur atom.) Or a cyano group. }
And 1, a method for using the same.

  The present invention has an excellent yield increase effect as compared with the prior art, and it is possible to obtain a sufficient yield increase effect not only by spraying but also by a simple usage method in which seeds or target crops are treated with a cultivation carrier. The present invention provides a yield-increasing agent and a more effective method of using the yield-increasing agent.

In the definition of the general formula (I) of the 4-cyclopropyl-1,2,3-thiadiazole derivative of the present invention, “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
“(C ₁ -C ₆ ) alkyl group” means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, neopentyl group Represents a linear or branched alkyl group having 1 to 6 carbon atoms such as a normal hexyl group.
The “(C ₁ -C ₆ ) haloalkyl group” represents a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, for example, A trifluoromethyl group, a difluorotyl group, a perfluoroethyl group, a perfluoroisopropyl group, a chloromethyl group, a bromomethyl group, a 1-bromoethyl group, a 2,3-dibromopropyl group, and the like are shown.

“(C ₃ -C ₆ ) cycloalkyl group” means 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 2-methylcyclopropyl group, 2-methylcyclopentyl group, etc. An alicyclic alkyl group is shown.
“(C ₁ -C ₆ ) alkoxy group” means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy A linear or branched alkoxy group having 1 to 6 carbon atoms such as a group, a neopentyloxy group, and a normal hexyloxy group;

The “halo (C ₁ -C ₆ ) alkoxy group” represents a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, etc. are shown. The “(C ₁ -C ₆ ) alkoxycarbonyl group” means, for example, a linear or branched methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, tertiary butoxycarbonyl group, etc. A chain-like alkoxycarbonyl group having 1 to 6 carbon atoms is shown.
“(C ₁ -C ₆ ) alkylthio group” means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group , A linear or branched alkylthio group having 1 to 6 carbon atoms, such as an isopentylthio group and a normal hexylthio group.
“(C ₁ -C ₆ ) alkylsulfinyl group” means, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a pentylsulfinyl group, an isopentylsulfinyl group, and a normal hexylsulfinyl group.

“(C ₁ -C ₆ ) alkylsulfonyl group” means, for example, methylsulfonyl group, ethylsulfonyl group, normalpropylsulfonyl group, isopropylsulfonyl group, normalbutylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a pentylsulfonyl group, an isopentylsulfonyl group, and a normal hexylsulfonyl group is shown.
The “aryl group” refers to an aromatic group such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

The “heterocyclic group” refers to a 5- to 6-membered heterocyclic group having one or more hetero atoms, which may be the same or different, selected from an oxygen atom, a sulfur atom, or a nitrogen atom. Examples thereof include 5- to 6-membered heterocycles and condensed heterocycles such as thiazole, isothiazole, pyrazole, imidazole, oxazole, isoxazole, triazole, 1,2,3-thiadiazole, pyridine, pyrimidine, triazine, benzothiazole, quinoline and the like.
Examples of the salt of the 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, Examples include organic acid salts such as fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, salts with sodium ion, potassium ion, calcium ion, etc. it can.

  The 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention may contain one or a plurality of asymmetric centers in the structural formula, and two or more kinds thereof. The optical isomers and diastereomers may exist in the present invention, but the present invention includes all of the optical isomers and mixtures containing them in an arbitrary ratio. The 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) of the present invention is derived from a carbon-carbon double bond or a carbon-nitrogen double bond in the structural formula. Although two geometric isomers may exist, the present invention includes all the geometric isomers and a mixture in which they are contained in an arbitrary ratio.

In the compound represented by the general formula (I) of the present invention, R ¹ , R ² , R ³ , R ⁴ and R ⁵ may preferably be the same or different and are a hydrogen atom; a halogen atom; (C ₁ − C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; (C ₂ -C ₆ ) alkenyl group; halo (C ₂ -C ₆ ) alkenyl group; or substituent Z (Z is the same as above) A phenyl group which may be substituted by R ¹ is more preferably a hydrogen atom; a (C ₁ -C ₃ ) alkyl group; or a phenyl group which may be substituted with a halogen atom, and most preferably a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ may be the same or different, more preferably a hydrogen atom or a (C ₁ -C ₃ ) alkyl group, most preferably a hydrogen atom.

又はシアノ基であり、更に好ましくは-C(=W¹)YR⁷である。 R ⁶ is preferably -C (= W ¹ ) YR ⁷ ;

Or a cyano group, more preferably -C (= W ¹⁾ is YR ^7.

In the above formula, R ⁷ is preferably (C ₃ -C ₂₀ ) alkyl group; halo (C ₃ -C ₂₀ ) alkyl group; (C ₃ -C ₂₀ ) alkenyl group; halo (C ₃ -C ₂₀ ) alkenyl group (C ₃ -C ₂₀ ) alkynyl group; halo (C ₃ -C ₂₀ ) alkynyl group; (C ₄ -C ₁₂ ) cycloalkyl group; halo (C ₄ -C ₁₂ ) cycloalkyl group; (C ₁ -C ₆ ) an alkoxy (C ₁ -C ₆ ) alkyl group; a (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group; a substituent Z (Z is as defined above) may be substituted on the ring phenyl (C ₁ -C ₄₎ alkyl group; substituent Z (Z is the same.) which may be substituted on the ring by phenyloxy (C ₁ -C ₄₎ alkyl group; substituent Z (Z is . the same) by be substituted on the ring may phenylthio (C ₁ -C ₄₎ alkyl group; substituent Z (Z is may be substituted in the same) by the ring to the phenyl;. carbonitrile Shi (C ₁ -C ₆₎ alkyl group; (C ₁ -C ₆₎ alkoxycarbonyl (C ₁ -C ₆₎ alkyl group; a carbamoyl (C ₁ -C ₆₎ alkyl group;

May be the same or different, (C ₁ -C ₁₀ ) alkyl group, halo (C ₁ -C ₁₀ ) alkyl group, (C ₂ -C ₁₀ ) alkenyl group, (C ₃ -C ₁₀ ) cycloalkyl group, substituted From a phenyl group which may be substituted by a group Z (Z is the same as above), a phenyl (C ₁ -C ₆ ) alkyl group which may be substituted on the ring by a substituent Z (Z is the same as above) A carbamoyl (C ₁ -C ₆ ) alkyl group having 1 to 2 selected substituents on the nitrogen atom; a cyano (C ₁ -C ₆ ) alkyl group; and a substituent Z (Z is as defined above). An optionally substituted heterocyclic group; a (C ₁ -C ₂₀ ) alkylsulfonyl group; a halo (C ₁ -C ₂₀ ) alkylsulfonyl group; an aryl optionally substituted by a substituent Z (Z is as defined above) sulfonyl group or a ^{-N = C (R 8) R} 9 ( wherein, R ⁸ and R ⁹ may be the same or different, a hydrogen atom, (C ₁ -C ₆₎ alkyl group, C (C ₁ -C ₆₎ alkyl group, a (C ₃ -C ₆₎ cycloalkyl group or a substituent Z (Z is the same. Above) a phenyl group which may be substituted by preferably.), More preferably (C ₈ -C ₂₀ ) alkyl group; halo (C ₈ -C ₂₀ ) alkyl group; thiazolyl group;
Or it is a benzothiazolyl group.
Y is preferably an oxygen atom; a sulfur atom; —NH— or —NHO—, and W ¹ is preferably an oxygen atom or a sulfur atom.

Z may be the same or different, and may be the same or different, halogen atom; cyano group; nitro group; (C ₁ -C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; (C ₃ -C ₁₂ ) cycloalkyl Group: halo (C ₃ -C ₁₂ ) cycloalkyl group, which may be the same or different, halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) Alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) An alkoxycarbonyl group, a carbamoyl group, or the same or different, may have a substituent selected from a substituted carbamoyl group having a substituent X (X is the same as above) on a nitrogen atom Good phenyl group;

(C ₁ -C ₆ ) alkoxy group; halo (C ₁ -C ₆ ) alkoxy group; (C ₁ -C ₆ ) alkylthio group; halo (C ₁ -C ₆ ) alkylthio group; (C ₁ -C ₆ ) alkyl Halo (C ₁ -C ₆ ) alkylsulfinyl group; (C ₁ -C ₆ ) alkylsulfonyl group; halo (C ₁ -C ₆ ) alkylsulfonyl group; may be the same or different, and may be a halogen atom, hydroxyl group, Cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group, or the same or different, The same as the above) may have a substituent selected from a substituted carbamoyl group having a nitrogen atom Phenoxy group; it may be the same or different, a halogen atom, a hydroxyl group, a cyano group, a nitro group, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy Group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group Alternatively, they may be the same or different, and phenyl (C ₁ -C ₃ ) may have a substituent selected from a substituted carbamoyl group having a substituent X (X is the same as above) on a nitrogen atom. ) An alkyloxy group;

A carboxyl group; a (C ₁ -C ₆ ) alkoxycarbonyl group; a carbamoyl group or a (C ₁ -C ₆ ) alkylcarbonyl group which may be substituted by a substituent X (X is as defined above), and more preferably Is a halogen atom; a cyano group; a (C ₁ -C ₆ ) alkyl group; a halo (C ₁ -C ₆ ) alkyl group; which may be the same or different, a halogen atom, a cyano group, or a (C ₁ -C ₆ ) alkyl group , Halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆₎ A phenyl group optionally having a substituent selected from an alkylthio group or a (C ₁ -C ₆ ) alkoxycarbonyl group; a (C ₁ -C ₆ ) alkoxy group; a halo (C ₁ -C ₆ ) alkoxy group; (C ₁ -C ₆₎ alkylthio group; a halo (C ₁ -C ₆₎ alkylthio group; may be the same or different, halogen Child, cyano, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ A phenoxy group optionally having a substituent selected from a -C ₆ ) alkylthio group, a halo (C ₁ -C ₆ ) alkylthio group or a (C ₁ -C ₆ ) alkoxycarbonyl group; a carboxyl group; (C _1- C ₆ ) an alkoxycarbonyl group; a (C ₁ -C ₆ ) carbamoyl group or a (C ₁ -C ₆ ) alkylcarbonyl group optionally substituted by an alkyl group.
X is preferably a (C ₁ -C ₁₀ ) alkyl group.
n is preferably an integer of 0 to ^3, and W ³ and W ⁴ are preferably oxygen atoms.

  In the following, typical production methods of the compound of the present invention are shown schematically, but the present invention is not limited to these.

（式中、R¹、R²、R³、R⁴、R⁵、R⁷、R¹¹及びYは前記に同じくし、R'はC₁-C₆アルキル基を示し、R"はC₁-C₆アルキル基、C₁-C₆アルコキシ基又はアミノ基を示し、Halはハロゲン原子を示す。） Manufacturing method 1

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , R ¹¹ and Y are the same as above, R ′ represents a C ₁ -C ₆ alkyl group, and R ″ represents C _1. -C ₆ alkyl group, C ₁ -C ₆ alkoxy group or amino group, Hal represents a halogen atom.)

A hydrazone represented by general formula (IV) is obtained by reacting a ketoester represented by general formula (II) with a compound represented by general formula (III) in the presence or absence of an inert solvent. The hydrazones (IV) are isolated or not isolated and reacted with thionyl chloride in the presence or absence of an inert solvent, A 2,3-thiadiazolecarboxylic acid ester derivative is used, and the ester derivative (I-1) is isolated or not isolated, and a hydrolysis reaction is carried out in the presence or absence of an inert solvent to give a general formula (I -2, a compound represented by the general formula (V) with or without isolating the carboxylic acid derivative (I-2) as a 1,2,3-thiadiazole carboxylic acid derivative of the present invention In the presence or absence of a condensing agent It is possible to produce a 1,2,3-thiadiazole derivative of the present invention represented by formula (I-3) by the. The 1,2,3-thiadiazole derivative of the present invention represented by the general formula (I-3) is inactive to the 1,2,3-thiadiazole carboxylic acid derivative of the present invention represented by the general formula (I-2). The carboxylic acid halides represented by the general formula (VI) are obtained by halogenation in the presence or absence of a solvent, and the carboxylic acid halides (VI) are isolated or not isolated. It can also be produced by reacting with a compound represented by formula (V) in the presence or absence. In addition, when Y represents NR ¹¹ , the 1,2,3-thiadiazole derivative of the present invention represented by the general formula (I-3) is the 1,1 of the present invention represented by the general formula (I-1). It can also be produced by reacting a 2,3-thiadiazolecarboxylic acid ester derivative with a compound represented by the general formula (V) in the presence or absence of an inert solvent.

1-1) General formula (II) → General formula (IV)
Ketoesters represented by general formula (II), which are starting materials, can be produced by or according to methods described in known literature (J. Org. Chem., 43, 2078 (1978), etc.). it can. Examples of the compound represented by the general formula (III) include hydrazides, semicarbazides, carbazates and the like.
Although this reaction may or may not use a solvent, any solvent that does not significantly inhibit this reaction may be used. Examples include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. Chain, cyclic ethers such as diethyl ether, tetrahydrofuran (THF) and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3 -Dimethyl-2-imidazolinone, water, acetic acid, etc. Can be exemplified inert solvent, these inert solvents may be used singly or as mixtures of two or more.

An acid or a base can also be used in this reaction. Examples of acids used in this reaction include carboxylic acids such as formic acid, acetic acid and propionic acid, sulfonic acids such as methanesulfonic acid and paratoluenesulfonic acid, sulfuric acid, hydrochloric acid and the like. As the base, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5 4.0] tertiary amines such as undec-7-ene, nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, and the like. What is necessary is just to select the usage-amount of an acid or a base suitably in the range of 0.001-5 times mole with respect to the compound represented by general formula (II).
Since this reaction is an equimolar reaction, the compound represented by the general formula (III) may be used in an equimolar amount with respect to the ketoester represented by the general formula (II). Can also be used. The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

1-2) General formula (IV) → General formula (I-1)
Although this reaction may or may not use a solvent, any solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. For example, chain or cyclic such as diethyl ether, tetrahydrofuran, and dioxane. Ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and nitriles such as acetonitrile , Esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, and inert solvents such as 1,3-dimethyl-2-imidazolinone. These inert solvents can be used alone or in admixture of two or more.
What is necessary is just to select the usage-amount of thionyl chloride used for this reaction suitably in the range of equimolar-large excess with respect to the hydrazone represented by general formula (IV). The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

1-3) General formula (I-1) → General formula (I-2)
In this reaction, water is used as a solvent, but other solvents may be mixed and used as long as they do not significantly inhibit the reaction. For example, methanol, ethanol, propanol , Alcohols such as butanol and 2-propanol, chain or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogens such as methylene chloride, chloroform and carbon tetrachloride Hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, Dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc. Can be exemplified inert solvent, these inert solvents may be used singly or as mixtures of two or more.
Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide and lithium hydroxide. What is necessary is just to select the usage-amount of the base used for this reaction suitably in the range of 1-10 times mole with respect to the 1,2,3- thiadiazole carboxylic acid ester derivative represented by general formula (I-1). The reaction temperature is usually from −20 ° C. to 100 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used. The reaction time is not constant depending on the reaction scale, reaction temperature, etc. The selection may be made as appropriate.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

1-4) General formula (I-2) → General formula (I-3)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inert solvents such as dimethyl-2-imidazolinone and water It can be mentioned, these inert solvents may be used singly or as mixtures of two or more.

Examples of the condensing agent that can be used in this reaction include carbodiimides such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide hydrochloride, N, N'-carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide, diethyl phosphorocyanidate, phosphoric acid dichloride phenyl ester, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, trifluoroacetic anhydride, etc. be able to. What is necessary is just to select the usage-amount of a condensing agent suitably from the range of 1-5 times mole with respect to the 1,2,3-thiadiazolecarboxylic acid derivative represented by general formula (I-2).
A base can also be used in this reaction. Examples of the base used in this reaction include tertiary amines such as triethylamine, diisopropylethylamine, and 1,8-diazabicyclo [5.4.0] undec-7-ene. Nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine can be exemplified. What is necessary is just to select the usage-amount of a base suitably in the range of 0.1-5 times mole with respect to the 1,2,3-thiadiazolecarboxylic acid derivative represented by general formula (I-2).
Since this reaction is an equimolar reaction, the compound represented by the general formula (V) is used in an equimolar amount with respect to the 1,2,3-thiadiazolecarboxylic acid derivative represented by the general formula (I-2). While good, either reactant can be used in excess. The reaction temperature is usually from −20 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used. The reaction time is not constant depending on the reaction scale, reaction temperature, etc., but ranges from several minutes to 48 hours. The selection may be made as appropriate.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

1-5) General formula (I-2) → General formula (VI)
Although this reaction may or may not use a solvent, any solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. For example, chain or cyclic such as diethyl ether, tetrahydrofuran, and dioxane. Ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and nitriles such as acetonitrile , Esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, and inert solvents such as 1,3-dimethyl-2-imidazolinone. These inert solvents can be used alone or in admixture of two or more.
Examples of the halogenating agent that can be used in this reaction include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, phosphorus pentabromide and the like. What is necessary is just to select the usage-amount of a halogenating agent suitably from the range of 1-10 times mole with respect to the 1,2,3-thiadiazolecarboxylic acid derivative represented by general formula (I-2). The reaction temperature is usually from −20 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used. The reaction time is not constant depending on the reaction scale, reaction temperature, etc., but ranges from several minutes to 48 hours. The selection may be made as appropriate.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary. Moreover, it can also use for next reaction, without isolating a target object after completion | finish of this reaction.

1-6) General formula (VI) → General formula (I-3)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inert solvents such as dimethyl-2-imidazolinone and water It can be mentioned, these inert solvents may be used singly or as mixtures of two or more.
Examples of the base used in this reaction include sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and other inorganic bases, triethylamine, diisopropylethylamine, 1,8- Examples thereof include tertiary amines such as diazabicyclo [5.4.0] undec-7-ene, and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. What is necessary is just to select the usage-amount of a base suitably in the range of 1-5 times mole with respect to the compound represented by general formula (VI).
Since this reaction is an equimolar reaction, the compound represented by the general formula (V) is used in an equimolar amount with respect to the 1,2,3-thiadiazolecarboxylic acid derivative represented by the general formula (I-2). While good, either reactant can be used in excess. The reaction temperature is usually from −20 ° C. to 150 ° C., but can be carried out within the range of the reflux temperature of the inert solvent used, and the reaction time is the reaction scale,
Although it is not constant depending on the reaction temperature or the like, it may be appropriately selected within the range of several minutes to 48 hours.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

1-7) General formula (I-1) → General formula (I-3)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inert solvents such as dimethyl-2-imidazolinone and water It can be mentioned, these inert solvents may be used singly or as mixtures of two or more.
Since this reaction is an equimolar reaction, an equimolar amount of the compound represented by the general formula (V) is used with respect to the 1,2,3-thiadiazolecarboxylic acid ester derivative represented by the general formula (I-1). Any of the reactants can be used in excess. The reaction temperature is usually from −20 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used. The reaction time is not constant depending on the reaction scale, reaction temperature, etc., but ranges from several minutes to 48 hours. The selection may be made as appropriate.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、R¹、R²、R³、R⁴、R⁵、R⁸、R⁹及びR'は前記に同じ。）
一般式（I−４）で表される１，２，３−チアジアゾールカルボヒドラジド誘導体と一般式（VII）で表されるカルボニル化合物とを不活性溶媒の存在下又は不存在下に反応させることによって一般式（I−５）で表される１，２，３−チアジアゾール誘導体を製造することができる。一般式（I−４）で表される１，２，３−チアジアゾールカルボヒドラジド誘導体は製造方法１に準じて製造することができる。 Manufacturing method 2

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁸ , R ⁹ and R ′ are the same as above.)
By reacting a 1,2,3-thiadiazole carbohydrazide derivative represented by the general formula (I-4) with a carbonyl compound represented by the general formula (VII) in the presence or absence of an inert solvent. A 1,2,3-thiadiazole derivative represented by the general formula (I-5) can be produced. The 1,2,3-thiadiazole carbohydrazide derivative represented by the general formula (I-4) can be produced according to Production Method 1.

2-1) General formula (I-4) → General formula (I-5)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inactivation of dimethyl-2-imidazolinone, water, acetic acid, etc. The solvent can be exemplified, and these inert solvents may be used singly or as mixtures of two or more.
An acid can be used in this reaction. Examples of the acid used in this reaction include carboxylic acids such as formic acid, acetic acid and propionic acid, sulfonic acids such as methanesulfonic acid and paratoluenesulfonic acid, sulfuric acid, hydrochloric acid and the like. can do. What is necessary is just to select the usage-amount of an acid suitably in the range of 0.001-5 times mole with respect to the 1,2,3-thiadiazole carbohydrazide derivative represented by general formula (I-4).

Since this reaction is an equimolar reaction, equimolar amounts of the carbonyl compound represented by the general formula (VII) are used with respect to the 1,2,3-thiadiazole carbohydrazide derivative represented by the general formula (I-4). Any of the reactants can be used in excess. The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、R¹、R²、R³、R⁴、R⁵、R⁷ 及びYは前記に同じ。）
一般式（I−３）で表される１，２，３−チアジアゾール誘導体と硫化剤を反応させることにより一般式（I−６）で表される１，２，３−チアジアゾール誘導体を製造することができる。 Manufacturing method 3

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ and Y are the same as above)
Production of a 1,2,3-thiadiazole derivative represented by the general formula (I-6) by reacting a 1,2,3-thiadiazole derivative represented by the general formula (I-3) with a sulfurizing agent. Can do.

3-1) General formula (I-3) → General formula (I-6)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inactivation of dimethyl-2-imidazolinone, water, acetic acid, etc. The solvent can be exemplified, and these inert solvents may be used singly or as mixtures of two or more.
Examples of the sulfurizing agent that can be used in this reaction include Lawesson's reagent, phosphorus pentasulfide, and the like. What is necessary is just to select the usage-amount of a sulfurizing agent from the range of equimolar-large excess with respect to the 1,2,3- thiadiazole derivative represented by general formula (I-3). The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、R¹、R²、R³、R⁴、R⁵、Hal及びｎは前記に同じくし、Z¹はZと同じ意味を表す。） Manufacturing method 4

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Hal and n are the same as above, and Z ¹ represents the same meaning as Z.)

  The carboxylic acid halides represented by the general formula (VI) and the anthranilic acids represented by the general formula (VIII) are reacted in the presence or absence of an inert solvent and represented by the general formula (I-7). The 1,2,3-thiadiazole carboxanilide derivative is isolated, and the carboxanilide derivative (I-7) is isolated and then reacted with a dehydrating agent in the presence or absence of an inert solvent (I The oxazine derivative represented by -8) can be produced. Further, the carboxylic acid halides represented by the general formula (VI) and the anthranilic acids represented by the general formula (VIII) are reacted in the presence or absence of an inert solvent to directly produce the general formula (I-8 It is also possible to produce an oxazine derivative represented by

4-1) General formula (VI) → General formula (I-7)
This reaction can be carried out according to 1-6).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

4-2) General formula (I-7) → General formula (I-8)
This reaction may or may not use a solvent, but a solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. For example, methanol, ethanol, propanol, butanol, 2-propanol, etc. Alcohols, linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, 1,3- Inactivation of dimethyl-2-imidazolinone, water, acetic acid, etc. The solvent can be exemplified, and these inert solvents may be used singly or as mixtures of two or more.

Examples of dehydrating agents that can be used in this reaction include trifluoroacetic anhydride, acetic anhydride and other acid anhydrides, acetyl chloride, propionyl chloride, methyl chloroformate, isobutyl chloroformate and other acid chlorides, 1,3-dicyclohexylcarbodiimide, 1, Carbodiimides such as 3-diisopropylcarbodiimide, 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide hydrochloride, N, N′-carbonyldiimidazole, 2-chloro-1-methylpyridinium iodide, diethylphosphorus Examples thereof include nidate, phosphoric acid dichloride phenyl ester, cyanuric chloride, chlorosulfonyl isocyanate, thionyl chloride, phosphorus oxychloride and the like. What is necessary is just to select the usage-amount of a condensing agent suitably from the range of 1-5 times mole with respect to the 1,2,3- thiadiazole carboxanilide derivative represented by general formula (I-7).
The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

4-3) General formula (VI) → General formula (I-8)
In this reaction, the oxazine derivative represented by the general formula (I-8) can also be directly produced by extending the reaction time according to 4-1).

（式中、R¹、R²、R³、R⁴、R⁵、Z¹、ｎは前記に同じくす。）
一般式（I−８）で表されるオキサジン誘導体と硫化剤を反応させることにより一般式（I−９）で表されるチアジン誘導体を製造することができる。 Manufacturing method 5

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Z ¹ and n are the same as above.)
The thiazine derivative represented by the general formula (I-9) can be produced by reacting the oxazine derivative represented by the general formula (I-8) with a sulfurizing agent.

5-1) General formula (I-8) → General formula (I-9)
This reaction can be carried out according to 3-1).
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

（式中、R¹、R²、R³、R⁴、R⁵は前記に同じ。）
一般式（I−１０）で表される１，２，３−チアジアゾールカルボキサミド誘導体と脱水剤を不活性溶媒の存在下又は不存在下に反応させることにより一般式（I−１１）で表される５−シアノ−１，２，３−チアジアゾール誘導体を製造することができる。 Manufacturing method 6

(In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are the same as above.)
It is represented by the general formula (I-11) by reacting the 1,2,3-thiadiazole carboxamide derivative represented by the general formula (I-10) with a dehydrating agent in the presence or absence of an inert solvent. 5-Cyano-1,2,3-thiadiazole derivatives can be produced.

6-1) General formula (I-10) → General formula (I-11)
Although this reaction may or may not use a solvent, any solvent that can be used in this reaction may be any one that does not significantly inhibit this reaction. For example, chain or cyclic such as diethyl ether, tetrahydrofuran, and dioxane. Ethers, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and nitriles such as acetonitrile , Esters such as ethyl acetate, amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide, and inert solvents such as 1,3-dimethyl-2-imidazolinone. These inert solvents can be used alone or in admixture of two or more.
Examples of the dehydrating agent that can be used in this reaction include acetic anhydride, acid anhydrides such as trifluoroacetic anhydride, carbodiimides such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbimide, phosphorus oxychloride, Examples thereof include phosphorus pentachloride and thionyl chloride. What is necessary is just to select the usage-amount of a dehydrating agent suitably from the range of equimolar-large excess with respect to the 1,2,3- thiadiazole carboxamide derivative represented by general formula (I-10). The reaction temperature is usually 0 ° C. to 150 ° C., but it can be carried out in the range of the reflux temperature of the inert solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but in the range of several minutes to 48 hours. What is necessary is just to select suitably.
After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method and purifying by a recrystallization method, a distillation method, a column chromatography method or the like as necessary.

Representative examples of the 4-cyclopropyl-1,2,3-thiadiazole derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 3 below, but the present invention is not limited thereto. It is not something. The physical properties indicate melting point (° C.) or refractive index. For the compounds described as NMR in Table 1, ¹ H-NMR spectrum data are shown in Table 4.
In the following table, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, “Ph” represents a phenyl group, and “n-” represents Normal, “i-” is iso, “s-” is secondary, “t-” is tertiary, “c-” is an alicyclic hydrocarbon group, and “*” attached to the compound number. Indicates a salt of the compound of abbreviation B.
Abbreviations indicate the following compounds.

The yield-increasing agent of the present invention contains, as an active ingredient, a 4-cyclopropyl-1,2,3-thiadiazole derivative represented by the general formula (I) or a salt thereof. It can also be used by mixing with agents, fungicides, herbicides, plant growth regulators, fertilizers, etc., or can be used in combination.
In recent years, genetically modified crops (herbicide-tolerant crops, pest-resistant crops that incorporate genes produced by insecticidal proteins, disease-resistant crops that incorporate genes produced by resistance-inducing substances against diseases, crops that improve taste, and crops that improve preservation , Yield-enhancing crops, etc.), insect pheromones (communication agents for oysters and moths, etc.), IPM (total pest management) technology using natural enemy insects, etc. Can be used in combination with or systematized with these technologies.

  The yield-increasing agent of the present invention is generally used after being formulated into a convenient shape for use. That is, the active ingredient is mixed in an appropriate inert carrier, or if necessary, together with other auxiliary agents in an appropriate ratio and dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate agent. In the form of suspensions, emulsions, liquids, wettable powders, granules, powders, tablets, seed coatings, etc., they are formulated into suspensions or liquids suitable for spraying, coating, dipping, etc. And use it.

  The inert carrier that can be used in the preparation may be either solid or liquid. Examples of materials that can be used as the solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, tobacco stem flour, Walnut shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllite, etc.), silica {For example, diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersion silicic acid, also called hydrous finely divided silicon, hydrous silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder, pumice, calcined Diatomaceous earth, brick ground, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, phosphorous, ammonium nitrate, urea, and ammonium sulfate It can be mentioned compost or the like, which are used alone or in the form of a mixture of two or more.

  The material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (for example, acetone) , Methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (E.g. benzene, true , Xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropylpropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.) ), Amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), dimethyl sulfoxides, and the like.

  As other adjuvants, typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose, and singly, in some cases, two or more kinds of adjuvants are used together. In some cases it is possible to use no adjuvants at all. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting of the active ingredient compound, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene. Illustrative surfactants such as resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, higher alcohol sulfate be able to. In addition, for the purpose of stabilizing the dispersion of the active ingredient compound, adhesion and / or binding, the following auxiliary agents can be used, such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl Adjuvants such as alcohol, pine oil, coconut oil, bentonite, and lignin sulfonate can also be used.

  In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.

  The crops that can use the yield-enhancing agent of the present invention are not particularly limited, and examples thereof include cereals (for example, rice, barley, wheat, rye, oats, corn, potato, etc.), beans (soybeans, red beans, broad beans, peas). Fruit, peanuts, fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, almonds, bananas, strawberries, etc.), vegetables (cabbage, tomatoes, eggplant, spinach, broccoli, lettuce) ), Root vegetables (carrots, potatoes, sweet potatoes, radishes, lotus roots, turnips, etc.), crops for processing (cotton, hemp, kouzo, mitsumata, rapeseed, beet, hops, sugar cane, sugar beet, olives) , Rubber, coffee, tobacco, tea, etc.), moss (pumpkin, cucumber, watermelon, melon, etc.), pasture (orchard grass, sorghum, Mossy, clover, alfalfa, etc., turf (Korean turf, bentgrass, etc.), fragrance crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, orchid, etc.) Is mentioned. Among them, wheat and rice such as barley, wheat, rye and oat are suitable crops.

The method of using the yield-increasing agent of the present invention is to increase the yield of the crop as it is, or to dilute or appropriately suspend it with water or the like, and to effectively seed or sow the target crop or the target crop. What is necessary is just to use and apply a normal method to cultivation carriers etc., spraying, rice breeding seedling box application, seed dressing, seed treatment (seed dressing, seed soaking, etc.), seedling soaking treatment, planting hole treatment, stock It can be used in application methods such as original treatment, cropping treatment, and soil mixing. Moreover, you may process to the hydroponic liquid in hydroponics. It is particularly suitable for use as a so-called seed treatment, which is preferably used in a seed dressing or seed soaking method of the target crop.

As a seed treatment method, for example, a method of immersing seeds in a liquid state by diluting or not diluting a liquid or solid preparation and infiltrating the drug according to a usual method, a solid preparation or a liquid preparation is used as a seed. Method of adhering to the surface of the seed by mixing with a powder, dressing treatment, etc., mixing with a highly adhesive carrier such as resin, polymer, etc., coating the seed in a single layer or multiple layers, spraying around the seed simultaneously with planting And the like.
The “seed” for performing the seed treatment is broadly synonymous with the “reproduction plant body” in the present invention, and in addition to so-called seeds, bulbs, tubers, seeds, bulbs, stems for cutting plant cultivation, etc. Includes plants for vegetative propagation.
The “soil” or “cultivation carrier” in carrying out the method of use of the present invention indicates a support for cultivating a plant, and the material is not particularly limited, but may be a material on which a plant can grow. For example, it includes so-called various soils, seedling mats, water, etc., sand, vermiculite, cotton, paper, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, Pumice can also be included.

Examples of application methods to the soil include, for example, a method in which a liquid or solid preparation is diluted or not diluted with water and applied to the vicinity of a plant installation place or a nursery bed for raising seedlings, etc. The method of spraying in the vicinity or nursery, the method of spraying powder, wettable powder, wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, the planting hole before sowing or before planting the plant, Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
As a method for applying paddy rice to a seedling box, the dosage form may vary depending on the time of application such as application at seeding, greening period, application at transplanting, etc., but agents such as powder, granule wettable powder, granules, etc. Apply with a mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers. The time of application at the time of sowing may be before sowing, at the same time, after sowing, or after covering.

In field crops, such as wheat, it is preferable to treat the seeds or cultivating carrier close to the plant body from sowing to raising seedling. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on a cultivation carrier in the vicinity of the plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water.
As the seeding of the cultivated plant to be transplanted and the treatment at the seedling raising stage, in addition to the direct treatment on the seed, the irrigation treatment of the liquid drug or the granule spraying treatment to the nursery seedling bed is preferable. Moreover, it is also a preferable aspect that a granule is processed into a planting hole at the time of planting, or is mixed with a cultivation carrier in the vicinity of the transplantation site.

The yield-increasing agent of the present invention can be mixed or used in combination with other components as necessary. For example, when treating seeds, a repellent to avoid ingestion (including accidental ingestion) by animals such as birds. And other components can be included. Examples of repellents include odorous compounds such as naphthalene compounds, contact inhibitors such as castor oil, pine resin, polybutane, diphenylamine pentachlorophenol, quinone, zinc oxide, aromatic solvents, N- (trichloromethylthio) -4-cyclohexene- Bitter substances such as 1,2-carboximide, anthraquinone, copper oxalate, terpene oil, paradichlorobenzene, aryl isothiocyanate, amyl acetate, anethole, citrus oil, cresols, geranium oil or lavender oil, Menthol, methyl salicylate, nicotine, pentanethiol, pyridines, tributyltin chloride, thiram, ziram, carbamate insecticides (eg, methiocarb), guazatine, chlorinated cyclodiene insecticides (eg, endrin), organophosphorus insecticides ( Example If it is possible to illustrate the fenthion, etc.) and the like. As other components, as toxic substances or growth inhibitory substances (infertility agents), for example, 3-chloro-4-toluidine hydrochloride, strychnine, 20,25-diazacholesterol hydrochloride (code name: SC-12937), etc. Can be illustrated.

  The application amount of the yield-increasing agent of the present invention varies depending on the compounding ratio of the active ingredient compound, weather conditions, formulation form, application timing, application method, application location, target crop, etc. What is necessary is just to select suitably from the range of 0.1g-1000g per 1 are, and preferably the range of 1-100g is good. In seed treatment, the active ingredient compound per seed weight may be appropriately selected from the range of 0.0001 to 40% and applied, preferably 0.001 to 10%. Usually, the active ingredient compound per area is appropriately selected from the range of 0.1 to 1000 g, preferably 1 to 50 g. Moreover, about 0.0001 to 10% is good with respect to the cultivation carrier weight. When applying emulsions, wettable powders, suspensions, liquids, etc. diluted with water, the application concentration is 0.001 to 70% as an active ingredient. The liquid preparation or the like may be applied as it is without diluting the preparation.

Next, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples as long as the gist of the invention is not exceeded.
Production Example 1 Production of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylic acid (2-chlorobenzyl) (Compound No. 1-10) 4-cyclopropyl-1,2,3-thiadiazole carboxylic acid (1 g, 5.9 mmol) and 2-chloro-1-methylpyridinium iodide (1.8 g, 7.0 mmol), triethylamine (1.5 g, 15 mmol), 2-chlorobenzyl alcohol (0.92 grams, 6. 5 mmol) was dissolved and suspended in THF (15 ml) and stirred at room temperature for 10 hours. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to give 4-cyclopropyl-1,2,3-thiadiazole-5- 1.5 g of carboxylic acid (2-chlorobenzyl) was obtained.
Yield: 89%
Physical property: Melting point 54 ° C

Production Example 2 Production of 3′-chloro-4-cyclopropyl-4′-methyl-1,2,3-thiadiazole-5-carboxanilide (Compound No. 1-95) 4-cyclopropyl-1,2,3- Thiadiazolecarboxylic acid (4 g, 24 mmol), 2-chloro-1-methylpyridinium iodide (7.2 g, 28 mmol), triethylamine (5.9 g, 58 mmol), 2-chloro-4-methylaniline (3.7 g, 26 mmol) ) Was dissolved and suspended in THF (50 ml) and stirred at room temperature for 10 hours. Water was added to stop the reaction, and the mixture was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to give 3′-chloro-4-cyclopropyl-4′-methyl-1, 6.9 g of 2,3-thiadiazole-5-carboxanilide was obtained.
Yield: 99%
Physical properties: melting point 150-153 ° C.

Production Example 3 Production of 2- (4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonylamino) benzoic acid (Compound No. 1-98) 4-Cyclopropyl-1,2,3-thiadiazolecarboxylic To the acid (0.6 g, 3.5 mmol) was added thionyl chloride (4 ml), and the mixture was heated to reflux for 2 hours, then cooled and concentrated under reduced pressure.
-Cyclopropyl-1,2,3-thiadiazole-5-carboxylic acid chloride was obtained. This was then dissolved in THF (2 ml) and slowly added to a solution of sodium hydroxide (0.14 g, 3.5 mmol) and anthranilic acid (0.48 grams, 3.5 mmol) in water (7 ml). After stirring at room temperature for 4 hours, the mixture was acidified with concentrated hydrochloric acid and the resulting crystals were collected by filtration. The obtained crystals were washed with water and methanol to obtain 0.77 g of 2- (4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonylamino) benzoic acid.
Yield: 76%
Physical properties: ¹ H-NMR (TMS, δ value ppm, solvent: DMSO-d6)
1.2-1.35 (m, 4H), 2.7-2.9 (m, 1H), 7.30 (t, 3H), 7,70 (t, 1H), 8.05 (d, 1H),
8.46 (d, 1H), 11.95 (br, 1H)

Production Example 4 Production of 2′-cyano-4-cyclopropyl-1,2,3-thiadiazole-5-carboxanilide (Compound No. 1-100) 4-cyclopropyl-1,2,3-thiadiazole carboxylic acid (0 0.5 g, 2.9 mmol) and 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide hydrochloride (0.62 g, 3.2 mmol), 2-cyanoaniline (0.38 g, 3.2 mmol) in THF. Dissolved and suspended in (15 ml) and stirred at room temperature for 10 hours. Next, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 3N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order. After drying over anhydrous magnesium sulfate and concentrating under reduced pressure, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to give 2′-cyano-4-cyclopropyl-1,2,3-thiadiazole-5. -0.53 g of carboxanilide was obtained.
Yield: 68%
Physical property: Melting point 124 ° C

Production Example 5 Production of 4-cyclopropyl-1,2,3-thiadiazole-5-carbohydrazide (Compound No. 1-115) Hydrazine monohydrate (1.75 g, 35 mmol) was dissolved in ethanol (15 ml). 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate (1.29 g, 7 mmol) was added and stirred at room temperature for 10 hours. Ethanol was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with a mixed solvent of hexane-ethyl acetate to obtain 1.2 g of 4-cyclopropyl-1,2,3-thiadiazole-5-carbohydrazide.
Yield: 95%
Physical properties: ¹ H-NMR (TMS, δ value ppm, solvent: DMSO-d6)
1.12-1.30 (m, 4H), 3.30-3.45 (m, 1H), 4.73-5.25 (br, 2H), 9.42-10.04 (br, 1H)

Production Example 6 Production of N ′-(4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonyl) hydrazonobenzaldehyde (Compound No. 1-117) 4-cyclopropyl-1,2,3-thiadiazole -5-Carbohydrazide (1.22 g, 6.6 mmol) was dissolved in methanol (30 ml), benzaldehyde (0.72 g, 6.8 mmol) and 2 drops of concentrated sulfuric acid were added, and the mixture was stirred at room temperature for 10 hours. Methanol was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with a mixed solvent of hexane-ethyl acetate to obtain N ′-(4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonyl) hydrazonobenzaldehyde (1.71 g, 95%).
Yield: 95%
Physical properties: melting point 230-239 ° C.

Production Example 7 Production of N ′-(4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonyl) -N′-methylhydrazonobenzaldehyde (Compound No. 1-118) N′-Benzylidene-4- Cyclopropyl-1,2,3-thiadiazole-5-carbohydrazide (0.95 g, 3.5 mmol) was dissolved in dimethylformamide (30 ml), and potassium carbonate (0.55 g, 4 mmol), methyl iodide (0. 99 g, 7 mmol) was added and stirred at room temperature for 5 hours. After adding water, the mixture was extracted with ethyl acetate, and the organic layer was washed four times with water, successively with saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was washed with a mixed solvent of hexane-ethyl acetate and washed with N ′-(4-cyclopropyl-1,2,3-thiadiazol-5-ylcarbonyl) -N′-methylhydrazonobenzaldehyde. 95
g was obtained.
Yield: 95%
Physical property: Melting point 159.0-160.5 ° C

Production Example 8 Production of 3′-chloro-4-cyclopropyl-4′-methyl-1,2,3-thiadiazole-5-thiocarboxanilide (Compound No. 1-143) 3′-Chloro-4-cyclo Propyl-4′-methyl-1,2,3-thiadiazole-5-carboxanilide (0.5 g, 1.7 mmol) and Lawson's reagent (1 g, 2.5 mmol) are dissolved in toluene (10 ml) and heated to reflux for 3 hours. did. After cooling to room temperature, water was added and extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to give 3′-chloro-4-cyclopropyl-4′-methyl-1, 5.0 g of 2,3-thiadiazole-5-thiocarboxanilide was obtained.
Yield: 95%
Physical properties: Refractive index n _D 1.6698 (22 ° C.)

Production Example 9 Production of 4-cyclopropyl-1,2,3-thiadiazole-5-carbonitrile (Compound No. 3-1) 4-cyclopropyl-1,2,3-thiadiazole-5-carboxamide (4 g, 24 mmol) ) Was dissolved in toluene (15 ml), thionyl chloride (5 ml) was added, and the mixture was heated to reflux for 10 hours. After cooling to room temperature, the reaction was stopped by adding ice, neutralized by adding sodium hydrogen carbonate, and extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to give 4-cyclopropyl-1,2,3-thiadiazole-5-carbonitrile. 2.1 g was obtained.
Yield: 58%
Physical property: Refractive index n _D 1.5716 (26 ° C.)

Production Example 10 Production of 2- (4-cyclopropyl-1,2,3-thiadiazol-5-yl) -4H-3,1-benzoxazin-4-one (Compound No. 2-1) 2- (4 -Cyclopropyl-1,2,3-thiadiazol-5-ylcarbonylamino) benzoic acid (0.77 g, 2.7 mmol) and triethylamine (0.54 g, 5.3 mmol), 2-chloro-1-methylpyridinium iodide (0.82 g, 3.2 mmol) was dissolved and suspended in THF (15 ml) and stirred at room temperature for 10 hours. The insoluble material was then removed by filtration, and the filtrate was concentrated under reduced pressure. The produced crystal was washed with methanol to obtain 0.63 g of 2- (4-cyclopropyl-1,2,3-thiadiazol-5-yl) -4H-3,1-benzoxazin-4-one.
Yield: 87%
Physical property: Melting point 164-165 ° C

Reference Production Example 1 Production of methyl 3-cyclopropyl-3-oxopropionate Meldrum acid (50 g, 347 mmol) was dissolved in chloroform (550 ml), and pyridine (56 g, 700 mmol) was added. Next, a solution of cyclopropanecarboxylic acid chloride (40 g, 383 mmol) in chloroform (50 ml) was added dropwise at 10 ° C. or lower in an ice bath. After completion of the dropwise addition, the mixture was further stirred in an ice bath for 1 hour and at room temperature for 1 hour. Subsequently, after cooling again using an ice bath, 1N-HCl aqueous solution (500 ml) was added. This was extracted with chloroform, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Subsequently, methanol (500 ml) was added and dissolved, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the solvent was concentrated under reduced pressure, and the residue was distilled to obtain 40 g of methyl 3-cyclopropyl-3-oxopropionate.
Yield: 80%
Physical property: Boiling point 80 ° C (10mmHg)

Reference Production Example 2 Production of methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate Methyl 3-cyclopropyl-3-oxopropionate (10 g, 70 mmol) was dissolved in methanol (100 ml) to obtain carbazine. Methyl acid (6.3 g, 70 mmol) and p-toluenesulfonic acid (20 mg, 0.11 mol) were added. After stirring overnight at room temperature, methanol was distilled off under reduced pressure. Subsequently, toluene (10 ml) was added for dissolution, and thionyl chloride (20 ml) was slowly added dropwise in an ice bath. After completion of the dropwise addition, the mixture was stirred at room temperature for 4 hours, and then poured out into ice to stop the reaction, and neutralized with sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified using silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 9 g of compound 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate. It was.
Yield: 70%
Physical property: Melting point 47 ° C

Reference Production Example 3 Production of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylic acid Methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate (35 g, 190 mmol) in methanol (150 ml) In an ice bath, an aqueous solution (150 ml) of sodium hydroxide (15 g, 360 mmol) was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, and then methanol was distilled off under reduced pressure, followed by washing with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was washed with a hexane-ethyl acetate mixed solvent to obtain 28 g of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylic acid.
Yield: 86%
Physical properties: melting point 158-159 ° C.

Reference Production Example 4 Production of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxamide Methyl 4-cyclopropyl-1,2,3-thiadiazole-5-carboxylate (2 g, 11 mmol) in methanol (5 ml) Into the solution, aqueous ammonia (5 ml) was added and stirred at room temperature for 1 hour. Then, after concentration under reduced pressure, the residue was washed with hexane to obtain 1 g of 4-cyclopropyl-1,2,3-thiadiazole-5-carboxamide.
Yield: 55%
Physical property: Melting point 163 ° C

Although the typical formulation example and test example of this invention are shown below, this invention is not limited to these. In the preparation examples, “parts” means “parts by weight”.
Formulation Example 1
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts or more are uniformly mixed and dissolved to prepare an emulsion.
Formulation Example 2
Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts or more are mixed and ground uniformly to form a powder.

Formulation Example 3
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts 5 parts or more of calcium lignin sulfonate are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
Formulation Example 4
Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts or more are uniformly mixed and ground to obtain a wettable powder.

Test Example 1 Barley Increased Yield Effect Test by Seed Treatment Dissolve wettable powder prepared according to the example in a small amount of water and mix with barley (variety: Pastoral) seeds in a seed dressing machine to perform dressing treatment. Then, a drug dressed seed having a predetermined active ingredient dosage was obtained. Medicinal powdered seeds were sown in a 2 m × 10 m / ku field and cultivated according to the conventional method. 253 days after sowing, seeds were harvested from barley ears, the seed weight of each section was measured, and the yield was calculated in terms of seed weight per ha. In addition, the yield relative to the untreated section was calculated as an increased yield.

Claims (6)

Formula (I):

{In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁵ may be the same or different, hydrogen atom; halogen atom; cyano group; (C ₁ -C ₆ ) alkyl group; halo (C _1- (C ₆ ) alkyl group; (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group; (C ₃ -C ₁₂ ) cycloalkyl group; halo (C ₃ -C ₁₂ ) cycloalkyl group; (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group; (C ₂ -C ₆ ) alkenyl group; halo (C ₂ -C ₆ ) alkenyl group; substituted with substituent Z (Z will be described later) A good aryl group; an aryl (C ₁ -C ₆ ) alkyl group which may be substituted on the ring by a substituent Z (Z 1 will be described later); or a (C ₁ -C ₆ ) alkylcarbonyl group.
R ⁶ is —C (═W ¹ ) YR ⁷ (wherein R ⁷ is a hydrogen atom; (C ₁ -C ₂₀ ) alkyl group; halo (C ₁ -C ₂₀ ) alkyl group; (C ₂ -C ₂₀ )) Alkenyl group; halo (C ₂ -C ₂₀ ) alkenyl group; (C ₂ -C ₂₀ ) alkynyl group; halo (C ₂ -C ₂₀ ) alkynyl group; (C ₃ -C ₁₂ ) cycloalkyl group; halo (C ₃ -C ₁₂ ) cycloalkyl group; (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group; (C ₁ -C ₆ ) alkylthio (C ₁ -C ₆ ) alkyl group; substituent Z (Z is An aryl (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by the following formula; aryloxy (C ₁ -C ₆ ) optionally substituted on the ring by the substituent Z (Z will be explained later) An alkyl group; an arylthio (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by a substituent Z (Z is described later); an aryl group optionally substituted by a substituent Z (Z is described later); Carboxy (C ₁ -C ₆ ) alkyl group (C ₁ -C ₆ ) alkoxycarbonyl (C ₁ -C ₆ ) alkyl group; carbamoyl (C ₁ -C ₆ ) alkyl group; they may be the same or different, (C ₁ -C ₁₀ ) alkyl group, halo ( C ₁ -C ₁₀ ) alkyl group, (C ₂ -C ₁₀ ) alkenyl group, (C ₃ -C ₁₀ ) cycloalkyl group, phenyl group or substituent which may be substituted by substituent Z (Z is described later) Carbamoyl (C ₁ -C ₆₎ having 1 to 2 substituents on the nitrogen atom selected from a phenyl (C ₁ -C ₆ ) alkyl group optionally substituted on the ring by Z (Z is described later) ) Alkyl group; cyano (C ₁ -C ₆ ) alkyl group; heterocyclic group optionally substituted by substituent Z (Z is described later); substituted on ring by substituent Z (Z is described later) also heterocyclic (C ₁ -C ₆₎ alkyl; (C ₁ -C ₂₀₎ alkylcarbonyl group; (C ₂ -C ₂₀₎ alkynyl group; (C ₂ -C ₆₎ A Ke alkenyl carbonyl group; (C ₃ -C ₆₎ cycloalkyl group; substituent Z (. Z is later) phenyl carbonyl group optionally substituted by; be substituted by a substituent Z (Z is later.) Good heterocyclic carbonyl group; (C ₁ -C ₂₀ ) alkylsulfonyl group; halo (C ₁ -C ₂₀ ) alkylsulfonyl group; substituent Z (Z is described later) ) An arylsulfonyl group which may be substituted by a substituent; an aryl (C ₁ -C ₆ ) alkylsulfonyl group which may be substituted on the ring by a substituent Z (Z will be described later); —C (= W ² ) NR ⁸ R ⁹ (wherein R ⁸ and R ⁹ may be the same or different and are a hydrogen atom, a (C ₁ -C ₁₀ ) alkyl group, a halo (C ₁ -C ₁₀ ) alkyl group, (C ₂ -C ₁₀ )) An alkenyl group, a (C ₃ -C ₁₀ ) cycloalkyl group, a phenyl group which may be substituted by a substituent Z (Z will be described later), or a substituent Z (Z is described later) may be substituted on the ring By a phenyl (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group, a phenoxy group which may be substituted by a substituent Z (Z is described later), or a substituent Z (Z is described later). Represents a phenyl (C ₁ -C ₆ ) alkyloxy group which may be substituted on the ring, and R ⁸ and R ⁹ together represent an oxygen atom, a sulfur atom or NR ¹⁰ (wherein R ¹⁰ is a hydrogen atom, (C ₁ -C ₆₎ alkyl group or a substituent Z (Z is later.) Shows a phenyl group optionally substituted by.) May be interrupted by (C ₂ -C ₆₎ An alkylene group, W ² represents an oxygen atom or a sulfur atom); —SO ₂ NR ⁸ R ⁹ (wherein R ⁸ and R ⁹ are the same as above); or —N═C ( R ⁸ ) R ⁹ (wherein R ⁸ and R ⁹ are the same as above).
Y is an oxygen atom; a sulfur atom; —N (R ¹¹ ) — (wherein R ¹¹ is a hydrogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₃ -C ₆ ) cycloalkyl group, a substituent Z ( Z is a phenyl group that may be substituted by the following.), A phenyl (C ₁ -C ₆ ) alkyl group that may be substituted on the ring by the substituent Z (Z is the following), (C ₁ -C ₁₀ ) Substituted by an alkylcarbonyl group, a (C ₂ -C ₁₀ ) alkynylcarbonyl group, a (C ₂ -C ₁₀ ) alkenylcarbonyl group, a (C ₃ -C ₆ ) cycloalkylcarbonyl group, and a substituent Z (Z is described later). A phenylcarbonyl group which may be substituted, or a heterocyclic carbonyl group which may be substituted by a substituent Z (Z is described later)); or -N (R ¹¹ ) O- (wherein R ¹¹ is as defined above. The same). ).
W ¹ represents an oxygen atom or a sulfur atom.
Z may be the same or different, halogen atom; hydroxyl group; cyano group; nitro group; (C ₁ -C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; (C ₃ -C ₁₂ ) cycloalkyl Group: halo (C ₃ -C ₁₂ ) cycloalkyl group, which may be the same or different, halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) Alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) Alkoxycarbonyl group, carbamoyl group, which may be the same or different, each having 1 to 5 substituents selected from substituted carbamoyl groups having substituent X (X will be described later) on the nitrogen atom May be the same or different, a halogen atom, a hydroxyl group, a cyano group, Toromoto, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆ ) an alkylthio group, a halo (C ₁ -C ₆ ) alkylthio group, a carboxyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, a carbamoyl group, or the same or different, and a substituent X (X is described later). Phenyl (C ₁ -C ₆ ) alkyl group optionally having 1 to 5 substituents selected from substituted carbamoyl groups on the nitrogen atom; (C ₁ -C ₆ ) alkoxy group; halo (C ₁ -C ₆ ) alkoxy group; (C ₁ -C ₆ ) alkylthio group; halo (C ₁ -C ₆ ) alkylthio group; (C ₁ -C ₆ ) alkylsulfinyl group; halo (C ₁ -C ₆ ) Alkylsulfinyl group; (C ₁ -C ₆ ) alkylsulfonyl group; halo (C ₁ -C ₆ ) alkylsulfonyl group; Halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) an alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group or the same or different, Substituent X (X is described later. ), A phenoxy group which may have 1 to 5 substituents selected from substituted carbamoyl groups on the nitrogen atom; may be the same or different, and may be a halogen atom, a hydroxyl group, a cyano group, a nitro group, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆₎ alkylthio group, Selected from substituted carbamoyl groups having a halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group or substituent X (X is described later) on the nitrogen atom Phenylthio group which may have 1 to 5 substituents; may be the same or different, and may be a halogen atom, a hydroxyl group, a cyano group, a nitro group, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆₎ alkyl, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ Al Alkoxy group, (C ₁ -C ₆₎ alkylthio groups, halo (C ₁ -C ₆₎ alkylthio group, a carboxyl group, (C ₁ -C ₆₎ alkoxycarbonyl group, a carbamoyl group or a substituent X (X is below.) A phenylsulfinyl group which may have 1 to 5 substituents selected from substituted carbamoyl groups having on the nitrogen atom; they may be the same or different and are a halogen atom, a hydroxyl group, a cyano group, a nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, Selected from substituted carbamoyl groups having a halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group or substituent X (X is described later) on the nitrogen atom Phenylsulfo optionally having 1 to 5 substituents Le group; it may be the same or different, a halogen atom, a hydroxyl group, a cyano group, a nitro group, (C ₁ -C ₆₎ alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy Group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo (C ₁ -C ₆ ) alkylthio group, carboxyl group, (C ₁ -C ₆ ) alkoxycarbonyl group, carbamoyl group Or a phenyl (C ₁ -C ₆ ) alkyloxy group optionally having 1 to 5 substituents selected from substituted carbamoyl groups having a substituent X (X is described later) on the nitrogen atom A carboxyl group; a (C ₁ -C ₆ ) alkoxycarbonyl group; a substituent X (X is described later); ) A carbamoyl group which may be substituted by: a (C ₁ -C ₆ ) alkylcarbonyl group or the same or different, halogen atom, hydroxyl group, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆₎ alkyl group, (C ₁ -C ₆₎ alkoxy groups, halo (C ₁ -C ₆₎ alkoxy groups, (C ₁ -C ₆₎ alkylthio groups, halo (C ₁ -C ₆₎ alkylthio ₁ to 5 substituents selected from a substituted carbamoyl group having a group, a carboxyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, a carbamoyl group or a substituent X (X is described later) on the nitrogen atom. One or more substituents selected from phenylcarbonyl groups which may be used are shown.
X is a (C ₁ -C ₁₀ ) alkyl group; a halo (C ₁ -C ₁₀ ) alkyl group, which may be the same or different, and is a halogen atom, cyano group, nitro group, (C ₁ -C ₆ ) alkyl group, halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group or halo (C ₁ -C ₆ ) alkylthio A phenyl group which may have 1 to 5 substituents selected from a group or the same or different, a halogen atom, a cyano group, a nitro group, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group or halo (C ₁ -C ₆ ) alkylthio group phenyl optionally from 1 to 5 substituents selected having on the ring indicates a (C ₁ -C ₆₎ alkyl group. );

(In the formula, Z is the same as described above, and n represents an integer of 0 to ^4. W ³ and W ⁴ may be the same or different and represent an oxygen atom or a sulfur atom.) Or a cyano group. }, 1,2,3-thiadiazole derivative represented by the formula or a salt thereof. R ¹ , R ² , R ³ , R ⁴ and R ⁵ may be the same or different and are a hydrogen atom, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group or a phenyl group. Or a 1,2,3-thiadiazole derivative or a salt thereof according to claim 1, which represents a substituted phenyl group having 1 to 5 substituents Z (Z is the same as in claim 1), which may be the same or different. A crop yield enhancer that is an active ingredient. R ¹ , R ² , R ³ , R ⁴ and R ⁵ are hydrogen atoms, R ⁶ is —C (= W ¹ ) YR ⁷ (wherein W ¹ is an oxygen atom and Y is an oxygen atom or — NH- and R ⁷ may be the same or different and are a halogen atom, a (C ₁ -C ₆ ) alkyl group, a halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group and a halo A phenyl group which may be substituted by one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups, or the same or different, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a halo ( A phenyl group (C _1- ) optionally substituted by one or more substituents selected from a C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkoxy group and a halo (C ₁ -C ₆ ) alkoxy group C ₆ ) an alkyl group.) The crop yield-enhancing agent comprising the 1,2,3-thiadiazole derivative or a salt thereof according to claim 1 as an active ingredient.   The yield-enhancing agent according to any one of claims 1 to 3, wherein the crop is rice or wheat.   A method for using a yield increasing agent, comprising treating an effective amount of the yield increasing agent according to any one of claims 1 to 4 with a seed of a target crop or a cultivation carrier for seeding the target crop. A method for using a yield enhancer, comprising applying an effective amount of the yield enhancer according to any one of claims 1 to 4 to a target crop.