JP2014024830A - Delphacidae control method - Google Patents

Delphacidae control method Download PDF

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JP2014024830A
JP2014024830A JP2013065654A JP2013065654A JP2014024830A JP 2014024830 A JP2014024830 A JP 2014024830A JP 2013065654 A JP2013065654 A JP 2013065654A JP 2013065654 A JP2013065654 A JP 2013065654A JP 2014024830 A JP2014024830 A JP 2014024830A
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group
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rice
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Emiko Sakamoto
えみ子 坂本
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Sumitomo Chemical Co Ltd
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Priority to JP2013065654A priority Critical patent/JP2014024830A/en
Priority to PCT/JP2013/066531 priority patent/WO2013191115A1/en
Priority to CN201380032265.3A priority patent/CN104427871A/en
Priority to KR1020147035570A priority patent/KR20150023412A/en
Priority to TW102121379A priority patent/TW201412735A/en
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/10Insect repellent

Abstract

PROBLEM TO BE SOLVED: To provide a Delphacidae control method.SOLUTION: The Delphacidae control method includes a step, in transplanting culture of rice, for applying to the ground for raising rice seedlings an effective amount of a compound represented in formula (I) (each symbol in the formula is as defined in the description), or an effective amount of a Delphacidae control composition containing a compound represented in formula (I) and one or more compounds selected from group (A): isotianil, probenazole, tiadinil, tricyclazole, orysastrobin and pyroquilon. This Delphacidae control method has an excellent control effect for Delphacidae.

Description

本発明は、ウンカ類の防除方法に関する。   The present invention relates to a method for controlling planthoppers.

ウンカ類は、米の収量に多大な影響を及ぼすため、その防除がイネの栽培において必要とされており、ウンカ類の防除に使用できる種々の薬剤が知られている(例えば、特許文献1及び特許文献2参照。)。しかしながら、これらの薬剤を用いた防除方法の効果は必ずしも十分ではなく、より高い効果を有する防除方法が求められていた。   Since planthoppers have a great influence on the yield of rice, their control is required in rice cultivation, and various drugs that can be used for controlling planthoppers are known (for example, Patent Document 1 and (See Patent Document 2). However, the effect of the control method using these chemicals is not always sufficient, and a control method having a higher effect has been demanded.

特開昭61−267575号公報JP-A 61-267575 特開昭63−316771号公報JP-A-63-316771

本発明は、ウンカ類の防除方法を提供することを課題とする。   An object of the present invention is to provide a method for controlling planthoppers.

本発明者等は、ウンカ類の防除に有効な方法を鋭意検討した結果、イネの移植栽培において、下記式(I)で示される化合物の有効量、又は、下記式(I)で示される化合物と下記群(A)より選ばれる1種以上の化合物とを含有するウンカ類防除組成物の有効量を、イネの育苗地に施用することにより、ウンカ類を防除することができることを見出した。
すなわち、本発明とは以下の[1]〜[8]の通りである。
[1] イネの移植栽培において、式(I)

Figure 2014024830
[式中、
1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、1個以上のハロゲン原子を有していてもよいC1−C3アルキルスルファニル基、シアノ基、ハロゲン原子又はR4を表し、
nは、0〜3のいずれかの整数を表し、
4は、以下の式で示されるR4a及びR4bのいずれかの基
Figure 2014024830
{式中、
5a及びR5bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基又はハロゲン原子を表し、
a及びZbは同一又は相異なり、0、1又は2を表し、
5a及びR5bがそれぞれ2個ある場合、それぞれのR5a及びR5bは同一又は相異なっていてもよい。}を表し、
2は、以下の式で示されるR2a、R2b及びR2cのいずれかの基
Figure 2014024830
{式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。}を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物の有効量を、イネの育苗地に施用する工程を有するウンカ類の防除方法。
[2] 前記式(I)で示される化合物が、当該式(I)において、
2が、以下の式で示されるR2a及びR2bのいずれかの基
Figure 2014024830
[式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。]である化合物である[1]に記載のウンカ類の防除方法。
[3] 式(I)で示される化合物の有効量を、イネの移植5日前〜2日前に施用する[1]又は[2]に記載のウンカ類の防除方法。
[4] イネの移植栽培において、式(I)
Figure 2014024830
[式中、
1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、1個以上のハロゲン原子を有していてもよいC1−C3アルキルスルファニル基、シアノ基、ハロゲン原子又はR4を表し、
nは、0〜3のいずれかの整数を表し、
4は、以下の式で示されるR4a及びR4bのいずれかの基
Figure 2014024830
{式中、
5a及びR5bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基又はハロゲン原子を表し、
a及びZbは同一又は相異なり、0、1又は2を表し、
5a及びR5bがそれぞれ2個ある場合、それぞれのR5a及びR5bは同一又は互いに相異なっていてもよい。}を表し、
2は、以下の式で示されるR2a、R2b及びR2cのいずれかの基
Figure 2014024830
{式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。}を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物と、群(A)より選ばれる1種以上の化合物とを含有するウンカ類防除組成物の有効量を、イネの育苗地に施用する工程を有するウンカ類の防除方法。
群(A):イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンからなる群。
[5] 前記式(I)で示される化合物が、当該式(I)において、
2が、以下の式で示されるR2a及びR2bのいずれかの基
Figure 2014024830
[式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。]である化合物である[4]に記載のウンカ類の防除方法。
[6] 式(I)で示される化合物と、群(A)より選ばれる1種以上の化合物との含有量の比が、重量比で10:1〜1:100であるウンカ類防除組成物を用いる[4]又は[5]に記載のウンカ類の防除方法。
[7] ウンカ類防除組成物の有効量を、イネの移植5日前〜2日前に施用する[4]〜[6]のいずれかに記載のウンカ類の防除方法。
[8] ウンカ類が、トビイロウンカ、セジロウンカまたはヒメトビウンカである[1]〜[7]のいずれかに記載のウンカ類の防除方法。 As a result of intensive studies on methods effective for controlling planthoppers, the present inventors have found that in transplanting cultivation of rice, an effective amount of a compound represented by the following formula (I) or a compound represented by the following formula (I) It has been found that planthoppers can be controlled by applying an effective amount of a planthopper control composition containing at least one compound selected from the following group (A) to rice seedlings.
That is, the present invention is as follows [1] to [8].
[1] In transplantation cultivation of rice, the formula (I)
Figure 2014024830
[Where:
R 1 has a C1-C4 alkyl group which may have one or more halogen atoms, a C2-C4 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C4 alkoxy group, an optionally substituted C1-C3 alkylsulfanyl group, a cyano group, a halogen atom or R 4 ;
n represents any integer of 0 to 3,
R 4 represents any group of R 4a and R 4b represented by the following formula:
Figure 2014024830
{Where,
R 5a and R 5b are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms, cyano Represents a group or a halogen atom,
Z a and Z b are the same or different and represent 0, 1 or 2,
When there are two R 5a and R 5b , each R 5a and R 5b may be the same or different. },
R 2 represents any group of R 2a , R 2b and R 2c represented by the following formula:
Figure 2014024830
{Where,
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. }.
Incidentally, when n is 2 or 3, a plurality of R 1 may be different from each other. ] The control method of the planthopper which has the process of applying the effective amount of the compound shown by this to the rice seedling nursery.
[2] The compound represented by the formula (I) is represented by the formula (I):
R 2 is any group of R 2a and R 2b represented by the following formula:
Figure 2014024830
[Where:
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. ] The method for controlling planthoppers according to [1], which is a compound.
[3] The method for controlling planthoppers according to [1] or [2], wherein an effective amount of the compound represented by the formula (I) is applied 5 to 2 days before transplanting rice.
[4] In transplantation cultivation of rice, the formula (I)
Figure 2014024830
[Where:
R 1 has a C1-C4 alkyl group which may have one or more halogen atoms, a C2-C4 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C4 alkoxy group, an optionally substituted C1-C3 alkylsulfanyl group, a cyano group, a halogen atom or R 4 ;
n represents any integer of 0 to 3,
R 4 represents any group of R 4a and R 4b represented by the following formula:
Figure 2014024830
{Where,
R 5a and R 5b are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms, cyano Represents a group or a halogen atom,
Z a and Z b are the same or different and represent 0, 1 or 2,
When there are two R 5a and R 5b , each R 5a and R 5b may be the same or different from each other. },
R 2 represents any group of R 2a , R 2b and R 2c represented by the following formula:
Figure 2014024830
{Where,
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. }.
Incidentally, when n is 2 or 3, a plurality of R 1 may be different from each other. ] The control method of the planthopper which has the process of applying the effective amount of the planthopper control composition containing the compound shown by 1 and 1 or more types of compounds chosen from a group (A) to a rice seedling raising place.
Group (A): A group consisting of isothianyl, probenazole, thiazinyl, tricyclazole, orisatrobin and pyroxylone.
[5] The compound represented by the formula (I) is represented by the formula (I):
R 2 is any group of R 2a and R 2b represented by the following formula:
Figure 2014024830
[Where:
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. ] The method for controlling planthoppers according to [4], which is a compound.
[6] The planthopper control composition in which the ratio of the content of the compound represented by the formula (I) and one or more compounds selected from the group (A) is 10: 1 to 1: 100 by weight. [4] or [5] method for controlling planthoppers according to [5].
[7] The method for controlling planthoppers according to any one of [4] to [6], wherein an effective amount of the planthopper control composition is applied 5 to 2 days before transplanting rice.
[8] The planthopper control method according to any one of [1] to [7], wherein the planthopper is a brown planthopper, white-spotted planthopper, or a brown planthopper.

本発明によれば、ウンカ類を防除することができる。   According to the present invention, planthoppers can be controlled.

本発明のウンカ類の防除方法は、イネの移植栽培において、前記式(I)で示される化合物(以下、本メソイオン化合物と記す。)の有効量、又は、前記式(I)で示される化合物と前記群(A)より選ばれる1種以上の化合物(以下、本化合物Aと記す。)とを含有するウンカ類防除組成物(以下、本防除組成物と記す。)の有効量を、イネの育苗地に施用する工程を有することを特徴とする。   The planthopper control method of the present invention comprises an effective amount of a compound represented by the above formula (I) (hereinafter referred to as the present mesoionic compound) or a compound represented by the above formula (I) in transplanting cultivation of rice. And an effective amount of a planthopper control composition (hereinafter referred to as the present control composition) containing at least one compound selected from the group (A) (hereinafter referred to as the present compound A). It has the process applied to the nursery of this.

式(I)における、R1、R2a、R2b、R2c、R3a、R3b、R4a、R4b、R5a及びR5bで示される各置換基としては、それぞれ次のものが挙げられる。 In the formula (I), examples of the substituents represented by R 1 , R 2a , R 2b , R 2c , R 3a , R 3b , R 4a , R 4b , R 5a and R 5b are as follows. It is done.

本発明において、C1−C4アルキル基とは、炭素原子数が1〜4個よりなる直鎖状又は分岐鎖状のアルキル基を意味し、例えば、メチル基、エチル基、プロピル基、1−メチルエチル基、ブチル基、1−メチルプロピル基、2−メチルプロピル基、1,1−ジメチルエチル基が挙げられる。   In the present invention, the C1-C4 alkyl group means a linear or branched alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and a 1-methyl group. Examples include an ethyl group, a butyl group, a 1-methylpropyl group, a 2-methylpropyl group, and a 1,1-dimethylethyl group.

本発明において、C2−C4アルケニル基とは、炭素原子数が2〜4個よりなる直鎖状又は分岐鎖状で、且つ分子内に1個又は2個以上の二重結合を有する不飽和炭化水素基を意味し、例えば、ビニル基、1−プロペニル基、2−プロペニル基、1−メチルビニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、2−メチル−2−プロペニル基が挙げられる。   In the present invention, the C2-C4 alkenyl group is a linear or branched chain having 2 to 4 carbon atoms and an unsaturated carbonization having one or more double bonds in the molecule. Means a hydrogen group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2-propenyl group Is mentioned.

本発明において、C1−C4アルコキシ基とは、炭素原子数が1〜4個よりなる直鎖状又は分岐鎖状のアルキル−O−で示される基を意味し、例えば、メトキシ基、エトキシ基、プロポキシ基、1−メチルエトキシ基、ブトキシ基、1−メチルプロポキシ基、2−メチルプロポキシ基及び1,1−ジメチルエトキシ基が挙げられる。   In the present invention, the C1-C4 alkoxy group means a group represented by a linear or branched alkyl-O— having 1 to 4 carbon atoms, such as a methoxy group, an ethoxy group, Examples include propoxy group, 1-methylethoxy group, butoxy group, 1-methylpropoxy group, 2-methylpropoxy group and 1,1-dimethylethoxy group.

本発明において、C1−C3アルキルスルファニル基とは、炭素原子数が1〜3個よりなるアルキル−S−で示される基を意味し、例えば、メチルスルファニル基、エチルスルファニル基、プロピルスルファニル基及びイソプロピルスルファニル基が挙げられる。   In the present invention, the C1-C3 alkylsulfanyl group means a group represented by alkyl-S- having 1 to 3 carbon atoms, such as a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and isopropyl. A sulfanyl group is mentioned.

本発明において、「1個以上のハロゲン原子を有していてもよい」とは、2個以上のハロゲン原子を有している場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。また、「1個以上の」とは、特に断りのない限り、1個以上であり、且つ原子もしくは基が結合し得る最大の個数以下を意味する。   In the present invention, “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same or different from each other. Also good. In addition, “one or more” means one or more and the maximum number of atoms or groups to which atoms or groups can be bonded, unless otherwise specified.

1、R3a、R3b、R5a及びR5bで示される、ハロゲン原子としては、例えばフッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。 Examples of the halogen atom represented by R 1 , R 3a , R 3b , R 5a and R 5b include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

1、R3a、R3b、R5a及びR5bで示される、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基としては、例えば、メチル基、フルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、クロロメチル基、ジクロロメチル基、トリクロロメチル基、エチル基、ペンタフルオロエチル基、2,2,2−トリフルオロエチル基、2,2,2−トリクロロエチル基、プロピル基、1−メチルエチル基、1−トリフルオロメチルテトラフルオロエチル基、ブチル基、2−メチルプロピル基、1−メチルプロピル基及び1,1−ジメチルエチル基が挙げられる。 Examples of the C1-C4 alkyl group optionally having one or more halogen atoms represented by R 1 , R 3a , R 3b , R 5a and R 5b include a methyl group, a fluoromethyl group, and a difluoromethyl group. Group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, ethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, propyl group 1-methylethyl group, 1-trifluoromethyltetrafluoroethyl group, butyl group, 2-methylpropyl group, 1-methylpropyl group and 1,1-dimethylethyl group.

1で示される、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基としては、例えば、2−プロペニル基、3−クロロ−2−プロペニル基、2−クロロ−2−プロペニル基、3,3−ジクロロ−2−プロペニル基、2−ブテニル基、3−ブテニル基及び2−メチル−2−プロペニル基が挙げられる。 Examples of the C2-C4 alkenyl group represented by R 1 which may have one or more halogen atoms include 2-propenyl group, 3-chloro-2-propenyl group, 2-chloro-2-propenyl group. Groups, 3,3-dichloro-2-propenyl group, 2-butenyl group, 3-butenyl group and 2-methyl-2-propenyl group.

1、R5a及びR5bで示される、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基としては、例えば、メトキシ基、トリフルオロメトキシ基、エトキシ基、2,2,2−トリフルオロエトキシ基、プロポキシ基、1−メチルエトキシ基、ブトキシ基、2−メチルプロポキシ基、1−メチルプロポキシ基及び1,1−ジメチルエトキシ基が挙げられる。 Examples of the C1-C4 alkoxy group optionally having one or more halogen atoms represented by R 1 , R 5a and R 5b include a methoxy group, a trifluoromethoxy group, an ethoxy group, 2,2, Examples include 2-trifluoroethoxy group, propoxy group, 1-methylethoxy group, butoxy group, 2-methylpropoxy group, 1-methylpropoxy group, and 1,1-dimethylethoxy group.

1で示される、1個以上のハロゲン原子を有していてもよいC1−C3アルキルスルファニル基としては、例えば、メチルスルファニル基、エチルスルファニル基、プロピルスルファニル基、イソプロピルスルファニル基、トリフルオロメチルスルファニル基、2,2,2−トリフルオロエチルスルファニル基及びペンタフルオロエチルスルファニル基が挙げられる。 Examples of the C1-C3 alkylsulfanyl group represented by R 1 which may have one or more halogen atoms include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, and trifluoromethylsulfanyl. Group, 2,2,2-trifluoroethylsulfanyl group and pentafluoroethylsulfanyl group.

2aとしては、例えば、6−フルオロ−3−ピリジル基、6−クロロ−3−ピリジル基、6−ブロモ−3−ピリジル基、6−メチル−3−ピリジル基、3−ピリジル基、2−ピリジル基が挙げられる。
2bとしては、例えば、2−フルオロ−5−チアゾリル基、2−クロロ−5−チアゾリル基、2−ブロモ−5−チアゾリル基、2−メチル−5−チアゾリル基、5−チアゾリル基が挙げられる。
2cとしては、例えば、5−ピリミジニル基が挙げられる。
Examples of R 2a include 6-fluoro-3-pyridyl group, 6-chloro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-methyl-3-pyridyl group, 3-pyridyl group, 2- A pyridyl group is mentioned.
Examples of R 2b include a 2-fluoro-5-thiazolyl group, a 2-chloro-5-thiazolyl group, a 2-bromo-5-thiazolyl group, a 2-methyl-5-thiazolyl group, and a 5-thiazolyl group. .
Examples of R 2c include a 5-pyrimidinyl group.

4aとしては、例えば、フェニル基、2−フルオロフェニル基、3−フルオロフェニル基、4−フルオロフェニル基、3−クロロフェニル基、4−クロロフェニル基、3−シアノフェニル基、4−シアノフェニル基、2,4−ジクロロフェニル基、2,5−ジフルオロフェニル基、2−フルオロ−4−シアノフェニル基、2−メチル−4−クロロフェニル基、4−クロロ−2−フルオロフェニル基、3−(トリフルオロメトキシ)フェニル基、4−(トリフルオロメチル)フェニル基、2−クロロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメトキシ)フェニル基、2−メチル−4−(トリフルオロメチル)フェニル基が挙げられる。
4bとしては、例えば、6−フルオロ−3−ピリジル基、6−クロロ−3−ピリジル基、2,6−ジクロロ−3−ピリジル基、4,6−ジクロロ−3−ピリジル基、6−トリフルオロメチル−3−ピリジル基が挙げられる。
Examples of R 4a include a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2,4-dichlorophenyl group, 2,5-difluorophenyl group, 2-fluoro-4-cyanophenyl group, 2-methyl-4-chlorophenyl group, 4-chloro-2-fluorophenyl group, 3- (trifluoromethoxy ) Phenyl group, 4- (trifluoromethyl) phenyl group, 2-chloro-4- (trifluoromethyl) phenyl group, 2-fluoro-4- (trifluoromethyl) phenyl group, 2-fluoro-5- (tri Fluoromethyl) phenyl group, 2-fluoro-5- (trifluoromethoxy) phenyl group, 2-methyl-4- (tri Ruoromechiru) phenyl group.
Examples of R 4b include 6-fluoro-3-pyridyl group, 6-chloro-3-pyridyl group, 2,6-dichloro-3-pyridyl group, 4,6-dichloro-3-pyridyl group, 6-tridyl group, and the like. A fluoromethyl-3-pyridyl group is mentioned.

本メソイオン化合物の態様としては、例えば次の化合物が挙げられる。
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基、トリフルオロメトキシ基又はトリフルオロメチルスルファニル基であり、R2が2−クロロ−5−チアゾリル基又は5−ピリミジニル基である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は5−ピリミジニル基である化合物;
式(I)において、nが1であり、R1がフッ素原子であり、R2が2−クロロ−5−チアゾリル基又は5−ピリミジニル基である化合物;
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基、トリフルオロメトキシ基又はトリフルオロメチルスルファニル基であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが1であり、R1がフッ素原子であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが1であり、R1が6−クロロ−3−ピリジル基、2,6−ジクロロ−3−ピリジル基又は6−トリフルオロメチル−3−ピリジル基であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、トリフルオロメトキシ基、6−クロロ−3−ピリジル基、2,6−ジクロロ−3−ピリジル基又は6−トリフルオロメチル−3−ピリジル基であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが1であり、R1がフェニル基、2,4−ジクロロフェニル基、2,5−ジフルオロフェニル基、4−クロロ−2−フルオロフェニル基、3−(トリフルオロメトキシ)フェニル基、4−(トリフルオロメチル)フェニル基、2−クロロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメトキシ)フェニル基又は2−メチル−4−(トリフルオロメチル)フェニル基であり、R2が2−クロロ−5−チアゾリル基である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、シアノ基、メチル基、メトキシ基、トリフルオロメチル基、トリフルオロメトキシ基、フェニル基、2,4−ジクロロフェニル基、2,5−ジフルオロフェニル基、4−クロロ−2−フルオロフェニル基、3−(トリフルオロメトキシ)フェニル基、4−(トリフルオロメチル)フェニル基、2−クロロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−4−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメチル)フェニル基、2−フルオロ−5−(トリフルオロメトキシ)フェニル基又は2−メチル−4−(トリフルオロメチル)フェニル基であり、R2が2−クロロ−5−チアゾリル基である化合物;
As an aspect of this mesoionic compound, the following compound is mentioned, for example.
In the formula (I), n is 1, R 1 is a fluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group, trifluoromethoxy group or trifluoromethylsulfanyl group, and R 2 Wherein 2- is a 5-chloro-5-thiazolyl group or a 5-pyrimidinyl group;
In the formula (I), n is 2, R 1 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound wherein 2 is a 2-chloro-5-thiazolyl group or a 5-pyrimidinyl group;
In the formula (I), a compound wherein n is 1, R 1 is a fluorine atom, and R 2 is a 2-chloro-5-thiazolyl group or a 5-pyrimidinyl group;
In the formula (I), n is 1, R 1 is a fluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group, trifluoromethoxy group or trifluoromethylsulfanyl group, and R 2 A compound wherein is a 2-chloro-5-thiazolyl group;
In the formula (I), n is 2, R 1 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound wherein 2 is a 2-chloro-5-thiazolyl group;
In the formula (I), a compound wherein n is 1, R 1 is a fluorine atom, and R 2 is a 2-chloro-5-thiazolyl group;
In the formula (I), n is 1, R 1 is a 6-chloro-3-pyridyl group, a 2,6-dichloro-3-pyridyl group or a 6-trifluoromethyl-3-pyridyl group, and R 2 A compound wherein is a 2-chloro-5-thiazolyl group;
In formula (I), n is 2, R 1 is the same as or different from each other, fluorine atom, chlorine atom, trifluoromethoxy group, 6-chloro-3-pyridyl group, 2,6-dichloro-3- A compound which is a pyridyl group or a 6-trifluoromethyl-3-pyridyl group and R 2 is a 2-chloro-5-thiazolyl group;
In the formula (I), n is 1, and R 1 is a phenyl group, 2,4-dichlorophenyl group, 2,5-difluorophenyl group, 4-chloro-2-fluorophenyl group, 3- (trifluoromethoxy) Phenyl group, 4- (trifluoromethyl) phenyl group, 2-chloro-4- (trifluoromethyl) phenyl group, 2-fluoro-4- (trifluoromethyl) phenyl group, 2-fluoro-5- (trifluoro) Methyl) phenyl group, 2-fluoro-5- (trifluoromethoxy) phenyl group or 2-methyl-4- (trifluoromethyl) phenyl group, and R 2 is a 2-chloro-5-thiazolyl group;
In formula (I), n is 2, R 1 is the same as or different from each other, fluorine atom, chlorine atom, cyano group, methyl group, methoxy group, trifluoromethyl group, trifluoromethoxy group, phenyl group, 2,4-dichlorophenyl group, 2,5-difluorophenyl group, 4-chloro-2-fluorophenyl group, 3- (trifluoromethoxy) phenyl group, 4- (trifluoromethyl) phenyl group, 2-chloro-4 -(Trifluoromethyl) phenyl group, 2-fluoro-4- (trifluoromethyl) phenyl group, 2-fluoro-5- (trifluoromethyl) phenyl group, 2-fluoro-5- (trifluoromethoxy) phenyl group Or a compound which is a 2-methyl-4- (trifluoromethyl) phenyl group and R 2 is a 2-chloro-5-thiazolyl group;

次に、本発明に用いられる本メソイオン化合物の具体例を示す。
式(I−a)で示される化合物;

Figure 2014024830
[式中、n及びR1の組合せは、[表1]、[表2]及び[表3]に示されるいずれかの組合せを表す。] Next, specific examples of the present mesoionic compound used in the present invention are shown.
A compound of formula (Ia);
Figure 2014024830
[Wherein, the combination of n and R 1 represents any combination shown in [Table 1], [Table 2] and [Table 3]. ]

Figure 2014024830
Figure 2014024830












Figure 2014024830
Figure 2014024830








Figure 2014024830
なお、[表1]、[表2]及び[表3]中のR1における「3−(CH=CH2)」及び「3−OCF3」等の「3−」との記載は、前記式(I−a)中のベンゼン環上の置換位置が3位であることを表す。
Figure 2014024830
In addition, the description of “3-” such as “3- (CH═CH 2 )” and “3-OCF 3 ” in R 1 in [Table 1], [Table 2] and [Table 3] It represents that the substitution position on the benzene ring in the formula (Ia) is the 3-position.

式(I−b)で示される化合物;

Figure 2014024830
[式中、n及びR1の組合せは、[表4]に示されるいずれかの組合せを表す。] A compound of formula (Ib);
Figure 2014024830
[Wherein, the combination of n and R 1 represents any combination shown in [Table 4]. ]

Figure 2014024830
なお、[表4]中のR1における「3−CF3」及び「3−OCF3」等の「3−」との記載は、前記式(I−b)中のベンゼン環上の置換位置が3位であることを表す。
Figure 2014024830
In Table 4, the description of “3-” such as “3-CF 3 ” and “3-OCF 3 ” in R 1 is the substitution position on the benzene ring in the formula (Ib). Represents the 3rd position.

本メソイオン化合物には、式(I)に示される構造のほかに、他の構造式で示されるイオン化の態様も存在し、それらの態様のいずれかが単独で又は2種以上が混合して存在し得るが、本メソイオン化合物はこれらを包含する。   In addition to the structure represented by formula (I), the present mesoionic compound also includes ionization embodiments represented by other structural formulas, and any of these embodiments is present alone or in admixture of two or more. However, the present mesoionic compounds include these.

本メソイオン化合物は、国際公開第2011/017342号に記載される方法により製造することができる。   This mesoionic compound can be produced by the method described in International Publication No. 2011/017342.

本発明に用いられるプロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンはいずれも公知の化合物であり、例えば「 The Pesticide Manual-15th edition(BCPC刊);ISBN 978−1−901396−18−8 」の927、1134、1163、840及び999ページ等に記載されている。これらの化合物は市販の製剤から得るか、公知の方法により製造することにより得られる。
本発明に用いられるイソチアニルは公知の化合物であり、例えば国際公開第99/024413号に記載された方法で製造することができる。
Probenazole, thiazinyl, tricyclazole, oryastrobine and pyroxylone used in the present invention are all known compounds, for example, “The Pesticide Manual-15th edition (BCPC); ISBN 978-1-901396-18-8” 927, 1134, 1163, 840, and 999 pages. These compounds can be obtained from commercially available preparations or produced by known methods.
Isotianil used in the present invention is a known compound and can be produced, for example, by the method described in International Publication No. 99/024413.

本発明において、本メソイオン化合物は、そのままで用いることもできるが、通常は、本メソイオン化合物と不活性担体とを混合し、必要に応じて界面活性剤やその他の製剤用補助剤を添加して、油剤、乳剤、フロアブル剤、水和剤、顆粒水和剤、粉剤、粒剤等に製剤化されて用いられる。
かかる本メソイオン化合物を含有する製剤における本メソイオン化合物の含有量は、通常0.01〜100重量%、好ましくは0.1〜90重量%、さらに好ましくは0.5〜70重量%である。
In the present invention, the mesoionic compound can be used as it is, but usually the mesoionic compound and an inert carrier are mixed, and a surfactant or other formulation adjuvant is added as necessary. , Oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like.
The content of the present mesoionic compound in the preparation containing the present mesoionic compound is usually 0.01 to 100% by weight, preferably 0.1 to 90% by weight, and more preferably 0.5 to 70% by weight.

本防除組成物は、本メソイオン化合物と本化合物Aとを単に混合したものでもよいが、通常は、本メソイオン化合物と本化合物Aと不活性担体とを混合し、必要に応じて界面活性剤やその他の製剤用補助剤を添加して、油剤、乳剤、フロアブル剤、水和剤、顆粒水和剤、粉剤、粒剤等に製剤化されて用いられる。
かかる本メソイオン化合物と本化合物Aとを含有する製剤における、本メソイオン化合物と本化合物Aの合計量は、通常0.1%〜100重量%、好ましくは0.1〜90重量%、さらに好ましくは0.5〜70重量%である。
The present control composition may be a simple mixture of the present mesoionic compound and the present compound A. Usually, the present mesoionic compound, the present compound A and an inert carrier are mixed, and if necessary, a surfactant or Other formulation adjuvants are added and formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like.
The total amount of the present mesoionic compound and the present compound A in the preparation containing the present mesoionic compound and the present compound A is usually 0.1% to 100% by weight, preferably 0.1 to 90% by weight, more preferably 0.5 to 70% by weight.

製剤化の際に用いられる不活性担体としては、固体担体、液体担体が挙げられる。前記の固体担体としては、例えばカオリンクレー、アッタパルジャイトクレー、ベントナイト、モンモリロナイト、酸性白土、パイロフィライト、タルク、珪藻土、方解石等の鉱物、トウモロコシ穂軸粉、クルミ殻粉等の天然有機物、尿素等の合成有機物、炭酸カルシウム、硫酸アンモニウム等の塩類、合成含水酸化珪素等の合成無機物等からなる微粉末あるいは粒状物が挙げられ、液体担体としては、例えばキシレン、アルキルベンゼン、メチルナフタレン等の芳香族炭化水素類、2−プロパノール、エチレングリコール、プロピレングリコール、エチレングリコールモノエチルエーテル等のアルコール類、アセトン、シクロヘキサノン、イソホロン等のケトン類、ダイズ油、綿実油等の植物油、石油系脂肪族炭化水素類、エステル類、ジメチルスルホキシド、アセトニトリル及び水が挙げられる。
界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルアリールスルホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエチレンアルキルアリールエーテルリン酸エステル塩、リグニンスルホン酸塩、ナフタレンスルホネートホルムアルデヒド重縮合物等の陰イオン界面活性剤及びポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルポリオキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル等の非イオン界面活性剤、及びアルキルトリメチルアンモニウム塩等の陽イオン界面活性剤が挙げられる。
その他の製剤用補助剤としては、例えばポリビニルアルコール、ポリビニルピロリドン等の水溶性高分子、アラビアガム、アルギン酸及びその塩、CMC(カルボキシメチルセルロ−ス)、ザンサンガム等の多糖類、アルミニウムマグネシウムシリケート、アルミナゾル等の無機物、防腐剤、着色剤及びPAP(酸性リン酸イソプロピル)、BHT(2,6−ジ−tert−ブチル−4−メチルフェノール)等の安定化剤が挙げられる。
Examples of the inert carrier used for formulation include a solid carrier and a liquid carrier. Examples of the solid carrier include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomite, calcite, and other natural organic substances such as corn cob powder and walnut shell powder, urea. Examples include synthetic organic materials such as calcium carbonate, ammonium sulfate, and the like, fine powders or granular materials made of synthetic inorganic materials such as synthetic silicon hydroxide, and liquid carriers include aromatic carbonization such as xylene, alkylbenzene, and methylnaphthalene. Hydrogens, alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons and esters Kind Sulfoxide, acetonitrile, and water.
Examples of surfactants include anionic interfaces such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like. Nonionic surfactants such as activators and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol Inorganic substances such as preservatives, coloring agents and stabilizers such as PAP (isopropyl acid phosphate) and BHT (2,6-di-tert-butyl-4-methylphenol).

本防除組成物における、本メソイオン化合物と本化合物Aとの含有量の比は、特に限定されないが、重量比で通常10:1〜1:100、好ましくは5:1〜1:50である。   The ratio of the content of the present mesoionic compound and the present compound A in the present control composition is not particularly limited, but is usually 10: 1 to 1: 100, preferably 5: 1 to 1:50 by weight.

本発明は、本メソイオン化合物又は本防除組成物を、イネの育苗地に施用することにより行われる。ここで、イネの育苗地とは、イネの播種後、移植時までの期間に苗が栽培される地を意味し、本田とは区別される。かかるイネの育苗地では、水田土、畑土、山土等の土壌、人工培土および人工成型培地等が用いられる。   The present invention is performed by applying the present mesoionic compound or the present control composition to rice seedlings. Here, the rice seedling place means a place where seedlings are cultivated during the period from seeding of rice to the time of transplanting, and is distinguished from Honda. In such rice seedlings, paddy soil, field soil, mountain soil, and the like, artificial culture soil, artificial molding media, and the like are used.

本発明において、さらに他の殺虫剤、殺菌剤を混用または併用することもできる。   In the present invention, other insecticides and fungicides can be used in combination or in combination.

本発明によって防除することができるウンカ類としては、例えば、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)及びヒメトビウンカ(Laodelphax striatellus)が挙げられる。   Examples of planthoppers that can be controlled according to the present invention include yellow planthopper (Nilaparvata lugens), white-spotted planthopper (Sogataella furcifera), and brown planthopper (Laodedelfax straellatus).

本発明によって、移植後のイネに対するウンカ類による加害を抑制することができる。かかるウンカ類による加害としては、イネの枯死やイネの分げつ数の減少等が挙げられる。   According to the present invention, it is possible to suppress damage caused by planthoppers on rice after transplantation. Examples of the damage caused by such planthoppers include the death of rice and the reduction of the number of rice tillers.

本メソイオン化合物又は本防除組成物をイネの育苗地に施用した後、イネを移植する。イネを移植する場所としては、水田等の湛水した土壌や乾田等が挙げられる。   After applying the present mesoionic compound or the present control composition to a rice nursery, the rice is transplanted. Examples of places where rice is transplanted include flooded soil such as paddy fields and dry rice fields.

本発明において、本メソイオン化合物又は本防除組成物を施用する時期は、イネの播種後から移植時までの期間であれば特に限定されないが、好ましくは移植5日前から移植2日前である。   In the present invention, the time for applying the present mesoionic compound or the present control composition is not particularly limited as long as it is a period from the sowing of rice to the time of transplantation, but preferably 5 days before transplantation and 2 days before transplantation.

本発明において、本メソイオン化合物又は本防除組成物の施用量は、防除対象であるウンカ類の種類や発生程度、製剤形態、気象条件等によって変化させ得るが、本メソイオン化合物量、又は、本メソイオン化合物と本化合物Aとの合計量として、イネの育苗地1m2あたり、通常0.01〜1000g、好ましくは0.1〜200gである。 In the present invention, the application amount of the present mesoionic compound or the present control composition can be changed depending on the type and degree of occurrence of the planthoppers to be controlled, the formulation form, weather conditions, etc., but the amount of the present mesoionic compound or the present mesoion The total amount of the compound and the present compound A is usually 0.01 to 1000 g, preferably 0.1 to 200 g, per 1 m 2 of rice seedlings.

本発明において、イネの育苗地がイネの育苗箱である場合の施用量は、本メソイオン化合物量、又は、本メソイオン化合物と本化合物Aとの合計量として、育苗箱1箱(横 約60cm、縦 約30cm)あたり通常0.01〜35g、好ましくは0.02〜20gである。   In the present invention, when the rice seedling is a rice seedling box, the application amount is the amount of the mesoionic compound or the total amount of the mesoionic compound and the compound A as one box (about 60 cm in width, It is usually 0.01 to 35 g, preferably 0.02 to 20 g per length (about 30 cm).

本発明において用いられる本メソイオン化合物又は本防除組成物の製剤形態が、粒剤、粉剤等の場合は、通常希釈することなくそのまま施用する。乳剤、水和剤、顆粒水和剤、フロアブル剤等の場合は、そのまま施用してもよいが、通常は水で希釈して施用する。この場合、本メソイオン化合物の濃度、または、本メソイオン化合物と本化合物Aとの合計での濃度は、通常0.00001〜10重量%、好ましくは0.0001〜5重量%である。   When the preparation form of the present mesoionic compound or the present control composition used in the present invention is a granule, a powder or the like, it is usually applied as it is without dilution. In the case of emulsions, wettable powders, granular wettable powders, flowable powders and the like, they may be applied as they are, but are usually diluted with water and applied. In this case, the concentration of the present mesoionic compound or the total concentration of the present mesoionic compound and the present compound A is usually 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight.

本発明において、イネの品種は特に限定されない。また、遺伝子組換え技術や交配による育種法によって、除草剤耐性、有害生物への耐性あるいは環境ストレス耐性が付与されたイネであってもよい。   In the present invention, rice varieties are not particularly limited. Moreover, the rice to which herbicide tolerance, pest tolerance, or environmental stress tolerance was imparted by genetic recombination techniques or breeding methods by crossing may be used.

以下、本発明を製剤例及び試験例にてさらに詳しく説明するが、本発明は以下の例のみに限定されるものではない。なお、以下の例において、部は特にことわりの無い限り重量部を表す。また、以下の例において『本メソイオン化合物(化合物No.1)』等の記載により特定される化合物とは、表1乃至表4中に記載の対応する「化合物No.」により特定された化合物と同じである。   Hereinafter, the present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified. In the following examples, the compound specified by the description such as “present mesoionic compound (Compound No. 1)” is the compound specified by the corresponding “Compound No.” described in Table 1 to Table 4. The same.

まず、製剤例を示す。   First, formulation examples are shown.

製剤例1(粒剤)
本メソイオン化合物(化合物No.1〜69)を4部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
Formulation Example 1 (Granule)
4 parts of this mesoionic compound (Compound Nos. 1 to 69), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 100 parts of kaolin clay residue are thoroughly ground and mixed, and water is added. After kneading well, granulation is dried to obtain granules.

製剤例2(粒剤)
本メソイオン化合物(化合物No.1〜69)を4部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
Formulation Example 2 (Granule)
4 parts of this mesoionic compound (Compound Nos. 1 to 69), 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 100 parts of kaolin clay residue are thoroughly ground and mixed. After adding water and kneading well, granulation is dried to obtain granules.

製剤例3〜9(粒剤)
イソチアニル2部に代えて、[表5]記載のそれぞれの化合物及び使用量で適用した以外は製剤例2と同様の操作を行い、それぞれの粒剤を得る。
Formulation Examples 3 to 9 (granule)
Instead of 2 parts of isotianil, the same operation as in Formulation Example 2 is carried out except that each compound and the amount used described in [Table 5] are applied to obtain each granule.

Figure 2014024830
Figure 2014024830

製剤例10(粒剤)
本メソイオン化合物(化合物No.1〜69)を1部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
Formulation Example 10 (Granule)
1 part of this mesoionic compound (Compound Nos. 1 to 69), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 100 parts of kaolin clay residue are thoroughly ground and mixed, and water is added. After kneading well, granulation is dried to obtain granules.

製剤例11(粒剤)
本メソイオン化合物(化合物No.1〜69)を1部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
Formulation Example 11 (Granule)
1 part of this mesoionic compound (Compound Nos. 1 to 69), 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 100 parts of kaolin clay residue are thoroughly ground and mixed. After adding water and kneading well, granulation is dried to obtain granules.

製剤例12〜18(粒剤)
イソチアニル2部に代えて、[表6]記載のそれぞれの化合物及び使用量で適用した以外は製剤例11と同様の操作を行い、それぞれの粒剤を得る。
Formulation Examples 12-18 (granule)
Instead of 2 parts of isotianil, the same operation as in Preparation Example 11 is carried out except that each compound and amount used described in [Table 6] are applied to obtain each granule.

Figure 2014024830
Figure 2014024830

製剤例19(水和剤)
本メソイオン化合物(化合物No.1〜69)10部を、ラウリル硫酸ナトリウム4部、リグニンスルホン酸カルシウム2部、合成含水酸化珪素微粉末20部及び珪藻土残部を混合した中に加え、よく攪拌混合して水和剤100部を得る。
Formulation Example 19 (wettable powder)
Add 10 parts of this mesoionic compound (Compound Nos. 1 to 69) into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and the remainder of diatomaceous earth and mix well. To obtain 100 parts of wettable powder.

製剤例20(水和剤)
本メソイオン化合物(化合物No.1〜69)10部及びイソチアニル2部を、ラウリル硫酸ナトリウム4部、リグニンスルホン酸カルシウム2部、合成含水酸化珪素微粉末20部及び珪藻土残部を混合した中に加え、よく攪拌混合して水和剤100部を得る。
Formulation Example 20 (wettable powder)
10 parts of this mesoionic compound (Compound Nos. 1 to 69) and 2 parts of isotianil were added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and the remainder of diatomaceous earth, Mix well and obtain 100 parts of wettable powder.

製剤例21〜25(水和剤)
イソチアニル2部に代えて、[表7]記載のそれぞれの化合物及び使用量で適用した以外は製剤例20と同様の操作を行い、水和剤100部を得る。
Formulation Examples 21 to 25 (wettable powder)
It replaces with 2 parts of isotianil, and except having applied with each compound and usage-amount of the [Table 7] description, operation similar to the formulation example 20 is performed, and a wettable powder 100 parts is obtained.

Figure 2014024830
Figure 2014024830

製剤例26(フロアブル剤)
本メソイオン化合物(化合物No.1〜69)5部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン30部及び水残部を混合した混合物100部を湿式粉砕法で微粉砕することにより、フロアブル剤を得る。
製剤例27(フロアブル剤)
本メソイオン化合物(化合物No.1〜69)5部、イソチアニル2部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン30部及び水残部を混合した混合物100部を湿式粉砕法で微粉砕することにより、フロアブル剤を得る。
Formulation Example 26 (Flowable)
By finely pulverizing 100 parts of a mixture obtained by mixing 5 parts of the present mesoionic compound (Compound Nos. 1 to 69), 30 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and the remainder of water by a wet pulverization method, Obtain a flowable agent.
Formulation Example 27 (Flowable)
Finely pulverize 100 parts of a mixture of 5 parts of this mesoionic compound (Compound Nos. 1 to 69), 2 parts of isotianil, 30 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and the remainder of the water by wet grinding. By doing so, a flowable agent is obtained.

製剤例28〜32(フロアブル剤)
イソチアニル2部に代えて、[表8]記載のそれぞれの化合物及び使用量で適用した以外は製剤例27と同様の操作を行い、それぞれのフロアブル剤を得る。
Formulation Examples 28-32 (Flowable)
Instead of 2 parts of isotianil, the same operation as in Formulation Example 27 was carried out except that each compound and the amount used described in [Table 8] were applied to obtain each flowable agent.

Figure 2014024830
Figure 2014024830

次に、本発明の効果を試験例にて示す。   Next, the effect of the present invention will be shown by test examples.

試験例1
本メソイオン化合物(化合物No.6)、本メソイオン化合物(化合物No.7)及びイソチアニルの所定量を、それぞれソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.6)又は本メソイオン化合物(化合物No.7)の水希釈液と、イソチアニルの水希釈液とを混合し、表9及び表10に記載の施用量となるように試験用薬液を調製した。
移植12日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種8日後、草丈7cm、1.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植5日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種15日後、草丈9cm、1.8葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種18日後、草丈11cm、2.1葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植当日、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種20日後、草丈13cm、2.4葉期)1株の株元土壌に前記試験用薬液0.5mlを施用した。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種20日後、草丈13cm、2.4葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表9及び表10に示す。
Test example 1
Acetone containing 5% (w / v) of Sorgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.) in a predetermined amount of the present mesoionic compound (Compound No. 6), the present mesoionic compound (Compound No. 7) and isotianil. After dissolving in 0.2 ml (manufactured by Kosei Pharmaceutical Co., Ltd.), it was diluted with water to a predetermined concentration.
The mesoionic compound (compound No. 6) or the mesoionic compound (compound No. 7) in water diluted with an aqueous solution of isothianyl is mixed and tested to give the application rates shown in Table 9 and Table 10. A medical solution was prepared.
Twelve days before transplanting, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 8 days after sowing, plant height 7 cm, 1.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
Five days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, variety: Hoshino Yume, 15 days after sowing, plant height 9 cm, 1.8 leaves). 5 ml was applied and placed in a greenhouse (23 ° C.).
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 18 days after sowing, plant height 11 cm, 2.1 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
On the day of transplantation, paper pot planted rice (Oryza sativa, cultivar: Hoshi no Yume, 20 days after sowing, plant height 13 cm, 2.4 leaf stage) 1 strain of stock solution 0.5 ml of the above test solution Applied.
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, without applying the test chemical, rice planted in a paper pot (20 days after sowing, plant height 13 cm, 2.4 leaf stage) was transplanted in the same manner as in the treated area, placed in a greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average values are shown in Tables 9 and 10.

式1);死虫率(%)=(供試虫数−生存虫数)/供試虫数×100   Formula 1); death rate (%) = (number of test insects−number of surviving insects) / number of test insects × 100

式2);補正死虫率(%)={(処理区死虫率−無処理区死虫率)/(100−無処理区死虫率)}×100   Formula 2); corrected mortality rate (%) = {(treatment area mortality rate−untreated area mortality ratio) / (100−untreated area mortality ratio)} × 100

式3);枯死茎率(%)=枯死茎数/供試茎数×100




































Formula 3); dead stem rate (%) = number of dead stems / number of test stems × 100




































Figure 2014024830
Figure 2014024830














Figure 2014024830
Figure 2014024830

試験例2
本メソイオン化合物(化合物No.6)及びオリサストロビンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.6)の水希釈液と、オリサストロビンの水希釈液とを混合し、表11に記載の施用量となるように試験用薬液を調製した。
移植5日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種17日後、草丈10cm、2葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種20日後、草丈12cm、2.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種22日後、草丈14cm、2.5葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、試験1と同様に、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表11に示す。
Test example 2
This mesoionic compound (compound No. 6) and orissastrobin are dissolved in 0.2 ml of acetone (manufactured by Wako Pure Chemical Industries, Ltd.) containing 5% (w / v) of Sorgen TW-20 (Daiichi Kogyo Seiyaku), respectively. After that, it was diluted with water to a predetermined concentration.
The mesoionic compound (Compound No. 6) in water and orisatrobin in water were mixed to prepare a test drug solution having the application rates shown in Table 11.
Five days before transplantation, paper pot planted rice with 6 stems (Oryza sativa, variety: Hoshi no Yume, 17 days after sowing, plant height 10 cm, 2-leaf stage) 0.5 ml of the above test chemical solution was added to the stock soil. Applied and placed in greenhouse (23 ° C.).
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 20 days after sowing, plant height 12 cm, 2.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, paperpot planted rice (22 days after sowing, plant height 14 cm, 2.5 leaf stage) without transplanting the test chemical was transplanted in the same manner as in the treated area, placed in the greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, as in Test 1, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average value is shown in Table 11.

Figure 2014024830
Figure 2014024830

試験例3
本メソイオン化合物(化合物No.7)及びオリサストロビンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.7)の水希釈液と、オリサストロビンの水希釈液とを混合し、表12に記載の施用量となるように試験用薬液を調製した。
移植12日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種8日後、草丈7cm、1.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植5日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種15日後、草丈9cm、1.8葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種18日後、草丈11cm、2.1葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植当日、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種20日後、草丈13cm、2.4葉期)1株の株元土壌に前記試験用薬液0.5mlを施用した。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種20日後、草丈13cm、2.4葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、試験1と同様に、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表12に示す。
Test example 3
The mesoionic compound (Compound No. 7) and orissastrobin are dissolved in 0.2 ml of acetone (manufactured by Wako Pure Chemical Industries, Ltd.) containing 5% (w / v) of Sorgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.) each in a predetermined amount. After that, it was diluted with water to a predetermined concentration.
The mesoionic compound (Compound No. 7) in water and orisatrobin in water were mixed to prepare a test drug solution having the application rates shown in Table 12.
Twelve days before transplanting, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 8 days after sowing, plant height 7 cm, 1.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
Five days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, variety: Hoshino Yume, 15 days after sowing, plant height 9 cm, 1.8 leaves). 5 ml was applied and placed in a greenhouse (23 ° C.).
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 18 days after sowing, plant height 11 cm, 2.1 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
On the day of transplantation, paper pot planted rice (Oryza sativa, cultivar: Hoshi no Yume, 20 days after sowing, plant height 13 cm, 2.4 leaf stage) 1 strain of stock solution 0.5 ml of the above test solution Applied.
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, without applying the test chemical, rice planted in a paper pot (20 days after sowing, plant height 13 cm, 2.4 leaf stage) was transplanted in the same manner as in the treated area, placed in a greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, as in Test 1, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average value is shown in Table 12.

Figure 2014024830
Figure 2014024830

試験例4
本メソイオン化合物(化合物No.6)、本メソイオン化合物(化合物No.7)及びプロベナゾールをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.6)又は本メソイオン化合物(化合物No.7)の水希釈液と、プロベナゾールの水希釈液とを混合し、表13に記載の施用量となるように試験用薬液を調製した。
移植12日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種8日後、草丈8cm、1.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植5日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種15日後、草丈10cm、1.8葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種18日後、草丈12cm、2.1葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種20日後、草丈13cm、2.4葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、試験1と同様に、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表13に示す。
Test example 4
This mesoionic compound (Compound No. 6), this mesoionic compound (Compound No. 7) and probenazole, respectively, acetone (Wako Pure), containing 5% (w / v) Sorgen TW-20 (Daiichi Kogyo Seiyaku). Yakuhin Kogyo Co., Ltd.) was dissolved in 0.2 ml and diluted with water to a predetermined concentration.
The mesoionic compound (Compound No. 6) or the aqueous mesoionic compound (Compound No. 7) in water and the aqueous solution of probenazole are mixed, and the test drug solution is prepared so that the application amount shown in Table 13 is obtained. Prepared.
Twelve days before transplanting, paper pot planted rice with 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 8 days after sowing, plant height 8 cm, 1.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
Five days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshino Yume, 15 days after sowing, plant height 10 cm, 1.8 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, variety: Hoshino Yume, 18 days after sowing, plant height 12 cm, 2.1 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, without applying the test chemical, rice planted in a paper pot (20 days after sowing, plant height 13 cm, 2.4 leaf stage) was transplanted in the same manner as in the treated area, placed in a greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, as in Test 1, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average value is shown in Table 13.

Figure 2014024830
Figure 2014024830

試験例5
本メソイオン化合物(化合物No.41)、本メソイオン化合物(化合物No.55)、イソチアニル、プロベナゾール及びオリサストロビンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.41)又は本メソイオン化合物(化合物No.55)の水希釈液と、イソチアニル、プロベナゾール又はオリサストロビンの水希釈液とを混合し、表14に記載の施用量となるように試験用薬液を調製した。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種20日後、草丈12cm、2.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種22日後、草丈14cm、2.5葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、試験1と同様に、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表14に示す。
Test Example 5
This mesoionic compound (Compound No. 41), this mesoionic compound (Compound No. 55), isothianyl, probenazole, and orissastrobin are each contained in a predetermined amount and 5% (w / v) Sorgen TW-20 (Daiichi Kogyo Seiyaku). After dissolving in 0.2 ml of acetone (manufactured by Wako Pure Chemical Industries), it was diluted with water to a predetermined concentration.
The mesoionic compound (compound No. 41) or the mesoionic compound (compound No. 55) in water diluted with an aqueous solution of isothianyl, probenazole, or orysastrobin so as to give the application rate shown in Table 14. A test chemical solution was prepared.
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 20 days after sowing, plant height 12 cm, 2.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, paperpot planted rice (22 days after sowing, plant height 14 cm, 2.5 leaf stage) without transplanting the test chemical was transplanted in the same manner as in the treated area, placed in the greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, as in Test 1, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average value is shown in Table 14.

Figure 2014024830
Figure 2014024830

試験例6
本メソイオン化合物(化合物No.10)、本メソイオン化合物(化合物No.16)、本メソイオン化合物(化合物No.21)、イソチアニル、プロベナゾール及びオリサストロビンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.2mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.10)、本メソイオン化合物(化合物No.16)又は本メソイオン化合物(化合物No.21)の水希釈液と、イソチアニル、プロベナゾール又はオリサストロビンの水希釈液とを混合し、表15〜表17に記載の施用量となるように試験用薬液を調製した。
移植5日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種17日後、草丈10cm、2葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
移植2日前、茎数を6本にしたペーパーポット植えイネ(Oryza sativa、品種:ほしのゆめ、播種20日後、草丈12cm、2.3葉期)1株の株元土壌に前記試験用薬液0.5mlを施用し、温室(23℃)に置いた。
前記試験用薬液を施用したペーパーポット植えイネを1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。イネの株元をプラスチック製カップで覆い、トビイロウンカの4齢幼虫と成虫を10頭ずつ放飼し、イネ全体とプラスチック製カップをナイロン製ネットで覆った。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずにペーパーポット植えイネ(播種22日後、草丈14cm、2.5葉期)を、処理区と同様に移植し、温室に置き、トビイロウンカの4齢幼虫と成虫を放飼した。これを無処理区と呼ぶ。
放飼10日後に供試した虫の生死とイネの茎の枯死数を観察した。その観察結果から、試験1と同様に、式1)によって死虫率、式2)によって補正死虫率、式3)によって枯死茎率を算出した。なお、試験は2反復で行った。その平均値を表15〜表17に示す。






























Test Example 6
The present mesoionic compound (Compound No. 10), the present mesoionic compound (Compound No. 16), the present mesoionic compound (Compound No. 21), isothianyl, probenazole, and orisatrobin are each given in a predetermined amount, Sorgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.). ) Was dissolved in 0.2 ml of acetone (manufactured by Wako Pure Chemical Industries) containing 5% (w / v), and then diluted with water to a predetermined concentration.
The present mesoionic compound (Compound No. 10), the present mesoionic compound (Compound No. 16) or the present mesoionic compound (Compound No. 21) in water diluted with an aqueous solution of isothianyl, probenazole or orisatrobin, The test chemical solution was prepared so that it might become the application rate of 15-Table 17.
Five days before transplantation, paper pot planted rice with 6 stems (Oryza sativa, variety: Hoshi no Yume, 17 days after sowing, plant height 10 cm, 2-leaf stage) 0.5 ml of the above test chemical solution was added to the stock soil. Applied and placed in greenhouse (23 ° C.).
Two days before transplantation, a paper pot planted rice having 6 stems (Oryza sativa, cultivar: Hoshi no Yume, 20 days after sowing, plant height 12 cm, 2.3 leaf stage) 1 strain of the above medicinal solution 0. 5 ml was applied and placed in a greenhouse (23 ° C.).
The rice planted with the paper pot to which the test chemical solution was applied was transplanted to the flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.). The rice stock was covered with a plastic cup, 10 4th instar larvae and adults of the brown planthopper were released, and the whole rice and the plastic cup were covered with a nylon net. This is called a processing zone.
On the other hand, paperpot planted rice (22 days after sowing, plant height 14 cm, 2.5 leaf stage) without transplanting the test chemical was transplanted in the same manner as in the treated area, placed in the greenhouse, and the 4th instar larvae and adults of the brown planthopper Was released. This is called an untreated section.
Ten days after release, the number of dead insects and the number of dead stems in rice were observed. From the observation results, as in Test 1, the mortality rate was calculated by Formula 1), the corrected mortality rate by Formula 2), and the dead stem rate by Formula 3). The test was repeated twice. The average values are shown in Table 15 to Table 17.






























Figure 2014024830
Figure 2014024830








Figure 2014024830
Figure 2014024830






Figure 2014024830
Figure 2014024830

Claims (8)

イネの移植栽培において、式(I)
Figure 2014024830
[式中、
1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、1個以上のハロゲン原子を有していてもよいC1−C3アルキルスルファニル基、シアノ基、ハロゲン原子又はR4を表し、
nは、0〜3のいずれかの整数を表し、
4は、以下の式で示されるR4a及びR4bのいずれかの基
Figure 2014024830
{式中、
5a及びR5bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基又はハロゲン原子を表し、
a及びZbは同一又は相異なり、0、1又は2を表し、
5a及びR5bがそれぞれ2個ある場合、それぞれのR5a及びR5bは同一又は相異なっていてもよい。}を表し、
2は、以下の式で示されるR2a、R2b及びR2cのいずれかの基
Figure 2014024830
{式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。}を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物の有効量を、イネの育苗地に施用する工程を有するウンカ類の防除方法。
In transplantation cultivation of rice, the formula (I)
Figure 2014024830
[Where:
R 1 has a C1-C4 alkyl group which may have one or more halogen atoms, a C2-C4 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C4 alkoxy group, an optionally substituted C1-C3 alkylsulfanyl group, a cyano group, a halogen atom or R 4 ;
n represents any integer of 0 to 3,
R 4 represents any group of R 4a and R 4b represented by the following formula:
Figure 2014024830
{Where,
R 5a and R 5b are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms, cyano Represents a group or a halogen atom,
Z a and Z b are the same or different and represent 0, 1 or 2,
When there are two R 5a and R 5b , each R 5a and R 5b may be the same or different. },
R 2 represents any group of R 2a , R 2b and R 2c represented by the following formula:
Figure 2014024830
{Where,
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. }.
Incidentally, when n is 2 or 3, a plurality of R 1 may be different from each other. ] The control method of the planthopper which has the process of applying the effective amount of the compound shown by this to the rice seedling nursery.
前記式(I)で示される化合物が、当該式(I)において、
2が、以下の式で示されるR2a及びR2bのいずれかの基
Figure 2014024830
[式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。]である化合物である請求項1に記載のウンカ類の防除方法。
In the formula (I), the compound represented by the formula (I) is
R 2 is any group of R 2a and R 2b represented by the following formula:
Figure 2014024830
[Where:
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. The method for controlling planthoppers according to claim 1, wherein
式(I)で示される化合物の有効量を、イネの移植5日前〜2日前に施用する請求項1又は2に記載のウンカ類の防除方法。   The method for controlling planthoppers according to claim 1 or 2, wherein an effective amount of the compound represented by the formula (I) is applied 5 to 2 days before the transplantation of rice. イネの移植栽培において、式(I)
Figure 2014024830
[式中、
1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、1個以上のハロゲン原子を有していてもよいC1−C3アルキルスルファニル基、シアノ基、ハロゲン原子又はR4を表し、
nは、0〜3のいずれかの整数を表し、
4は、以下の式で示されるR4a及びR4bのいずれかの基
Figure 2014024830
{式中、
5a及びR5bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基又はハロゲン原子を表し、
a及びZbは同一又は相異なり、0、1又は2を表し、
5a及びR5bがそれぞれ2個ある場合、それぞれのR5a及びR5bは同一又は互いに相異なっていてもよい。}を表し、
2は、以下の式で示されるR2a、R2b及びR2cのいずれかの基
Figure 2014024830
{式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。}を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物と、群(A)より選ばれる1種以上の化合物とを含有するウンカ類防除組成物の有効量を、イネの育苗地に施用する工程を有するウンカ類の防除方法。
群(A):イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンからなる群。
In transplantation cultivation of rice, the formula (I)
Figure 2014024830
[Where:
R 1 has a C1-C4 alkyl group which may have one or more halogen atoms, a C2-C4 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. An optionally substituted C1-C4 alkoxy group, an optionally substituted C1-C3 alkylsulfanyl group, a cyano group, a halogen atom or R 4 ;
n represents any integer of 0 to 3,
R 4 represents any group of R 4a and R 4b represented by the following formula:
Figure 2014024830
{Where,
R 5a and R 5b are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms, cyano Represents a group or a halogen atom,
Z a and Z b are the same or different and represent 0, 1 or 2,
When there are two R 5a and R 5b , each R 5a and R 5b may be the same or different from each other. },
R 2 represents any group of R 2a , R 2b and R 2c represented by the following formula:
Figure 2014024830
{Where,
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. }.
Incidentally, when n is 2 or 3, a plurality of R 1 may be different from each other. ] The control method of the planthopper which has the process of applying the effective amount of the planthopper control composition containing the compound shown by 1 and 1 or more types of compounds chosen from a group (A) to a rice seedling raising place.
Group (A): A group consisting of isothianyl, probenazole, thiazinyl, tricyclazole, orisatrobin and pyroxylone.
前記式(I)で示される化合物が、当該式(I)において、
2が、以下の式で示されるR2a及びR2bのいずれかの基
Figure 2014024830
[式中、
3a及びR3bは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又はハロゲン原子を表し、
a及びXbは同一又は相異なり、0又は1を表す。]である化合物である請求項4に記載のウンカ類の防除方法。
In the formula (I), the compound represented by the formula (I) is
R 2 is any group of R 2a and R 2b represented by the following formula:
Figure 2014024830
[Where:
R 3a and R 3b are the same or different and represent a C1-C4 alkyl group or a halogen atom which may have one or more halogen atoms,
X a and X b are the same or different and represent 0 or 1. The method for controlling planthoppers according to claim 4, wherein
式(I)で示される化合物と、群(A)より選ばれる1種以上の化合物との含有量の比が、重量比で10:1〜1:100であるウンカ類防除組成物を用いる請求項4又は5に記載のウンカ類の防除方法。   Claims using a planthopper control composition in which the ratio of the content of the compound represented by the formula (I) and one or more compounds selected from the group (A) is 10: 1 to 1: 100 by weight. Item 6. A method for controlling planthoppers according to Item 4 or 5. ウンカ類防除組成物の有効量を、イネの移植5日前〜2日前に施用する請求項4〜6のいずれかに記載のウンカ類の防除方法。   The method for controlling planthoppers according to any one of claims 4 to 6, wherein an effective amount of the planthopper control composition is applied 5 to 2 days before transplanting rice. ウンカ類が、トビイロウンカ、セジロウンカまたはヒメトビウンカである請求項1〜7のいずれかに記載のウンカ類の防除方法。   The planthopper is a brown planthopper, a white-spotted planthopper, or a common planter. The method for controlling planthoppers according to any one of claims 1 to 7.
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