PYRIMIDINE COMPOUND, HARMFUL ARTHROPOD CONTROL AGENT, USE OF THE PYRIMIDINE COMPOSITE AND METHOD OF

专利摘要:

公开号:BR112013013291B1
申请号:R112013013291-4
申请日:2011-11-30
公开日:2018-02-27
发明作者:Takahashi Masaki；Tanabe Takamasa；Nokura Yoshiniko
申请人:Sumitomo Chemical Co., Ltd.；
IPC主号:

专利说明:

(54) Title: PYRIMIDIN COMPOUND, HARMFUL ARTHROPOD CONTROL AGENT, USE OF PYRIMIDIN COMPOUND AND METHOD OF CONTROLLING HARMFUL ARTHROPODS (51) Int.CI .: A01N 43/54; A01N 43/76; A01N 43/90; C07D 403/04; C07D 413/04; C07D 413/14; C07D 471/04; C07D 487/04; C07D 498/04; A01P 7/00 (52) CPC: A01N 43/54, A01N 43/76, A01N 43/90, C07D 403/04, C07D 413/04, C07D 413/14, C07D 471/04, C07D 487/04, C07D 498/04 (30) Unionist Priority: 01/12/2010 JP 2010-268138 (73) Holder (s): SUMITOMO CHEMICAL CO., LTD.
(72) Inventor (s): MASAKI TAKAHASHI; TAKAMASA TANABE; YOSHINIKO NOKURA
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Invention Patent Descriptive Report for PYRIMIDIN COMPOUND, HARMFUL ARTHROPOD CONTROL AGENT, USE OF PYRIMIDIN COMPOUND AND METHOD OF CONTROLING HARMFUL ARTHROPODS.
Technical Field
The present invention relates to a pyrimidine compound and its use in pest control.
Background Technique
Compounds having pest control activity have been discovered and developed as an active ingredient in a pest control agent. Certain pyrimidine compounds are known (see, Patent Literature 1-2).
Citation List
Patent Literature
Patent Literature 1: US 4690926
Patent Literature 2: WO 2008/108958
Summary of the Invention
Technical problems
An object of the present invention is to provide a new compound having a pest control activity.
Solution to the Problem
The present inventors studied in order to discover a compound having a pest control activity and found that a pyrimidine compound of the following formula (1) has a pest control activity, thereby leading to the present invention.
That is, the present invention provides:
[1] A pyrimidine compound of the formula (1):
R ³ R ²
R ¹ (1) where:
R ¹ represents hydrogen or halogen,
Following is sheet 1a / 85
Petition 870170090485, of 11/23/2017, p. 4/13
1a / 85
Petition 870170090485, of 11/23/2017, p. 5/13
2/85 optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, one C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C1-C6 alkylamino group optionally having one or more halogens, a C2-C8 dialkylamino group optionally having one or more halogens , a C2-C6 alkylcarbonylamino group optionally having one or more halogens, a C2-C6 alkoxycarbonylamino group optionally having one or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2-C6 alkoxycarbonyl group optionally having one or more halogens, a C2-C6 alkylcarbamoyl group optionally having one or more halogens, a C2-C8 dialkylcarbamoyl group optionally having one or more halogens, a g C2-C6 alkoxyalkyl group optionally having one or more halogens, a C2-C6 alkylthioalkyl group optionally having one or more halogens, a phenyl group optionally having one or more atoms or groups selected from Group a, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group a, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group, a cyano group, or a formyl group,
R ⁴ and R ⁵ can be the same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C1-C6 alkylamino group optionally having one or more halogens, a C2-C8 dialkylamino group optionally having one or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2-C6 alkoxycarbonyl group optionally having one or more halogens, one phenyl group optionally having one or more atoms or groups selected from Group a, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected those in Group a, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group, a cyano group, or a formyl group, provided that both R ⁴ and R ⁵ are not hydrogen; or R ⁴ and R ⁵ can together with the atoms to which they are attached form a 5- or 6-membered ring having one or more halogens,
X represents nitrogen or = CR ⁶ - where R ⁶ represents hydrogen or halogen,
Y represents nitrogen or = CR ⁷ - where R ⁷ represents hydrogen or halogen,
Z represents oxygen or -NR ⁸ - where R ⁸ represents a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, or hydrogen; and Group α consists of a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1- alkylsulfinyl group C3 optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, halogen, a cyano group, and a nitro group (hereinafter referred to as the present compound);
[2] The pyrimidine compound according to the above [1] where R ¹ is hydrogen, and R ² is hydrogen;
[3] The pyrimidine compound according to the above [1] or [2] wherein R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having a or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen;
4/85 [4] The pyrimidine compound according to the above [1] or [2] wherein R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having a or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen;
[5] The pyrimidine compound according to the above [1] or [2] wherein R ³ is a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens , or a C1-C3 alkylsulfonyl group optionally having one or more halogens;
[6] The pyrimidine compound according to any one of the above [1] - [5] wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen;
[7] The pyrimidine compound according to any of the above mentioned a20 [1] - [5] wherein R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluoro, a C1-C3 alkylthio group having one or more fluoro, chloro, or bromo, and R ⁵ is hydrogen;
[8] The pyrimidine compound according to any of the above [1] - [7] where Z is oxygen, X is = CR ⁶ -, and R ⁶ is hydrogen;
[9] The pyrimidine compound according to any of the above [1] - [7] where Z is -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, and R ⁶ is hydrogen ;
[10] The pyrimidine compound according to any of the above [1] - [9] where Y is nitrogen;
[11] A pest control agent comprising the pyrimidine compound according to any of the above [1] - [10] and an inert vehicle;
5/85 [12] Use of the pyrimidine compound according to any of the above [1] - [10] to control pests;
[13] A method of controlling pests that comprises the step of applying an effective amount of the pyrimidine compound according to any of the above [1] - [10] to pests or pest habitats.
Description of Modalities
In the present compound, examples of the halogen include fluorine, chlorine, bromine, and iodine.
Here, for example, the C2-C6 part in a C2-C6 alkoxycarbonyl group represents that the number of carbon atoms in the entire alkoxycarbonyl group is within a range of 2 to 6.
In the present compound, examples of the C1-C6 chain hydrocarbon group include, for example, a C1-C6 alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group , a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a tercpentyl group, a neopentyl group, a hexyl group, and an isohexyl group;
a C2-C6 alkenyl group such as a vinyl group, a
2-propenyl, a 2-butenyl group, a 3-butenyl group, a 2-methyl-2propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group, and a 2hexenyl group; and a C2-C6 alkynyl group such as an ethynyl group, a group
2-propynyl, a 2-butynyl group, and a 3-butynyl group.
In the present compound, examples of the C1-C6 chain hydrocarbon group optionally having one or more halogens include, for example, a C1-C6 alkyl group optionally having one or more halogens such as a methyl group, an ethyl group, a propyl group , an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,26 / 85 trichlorethyl group, a pentafluoroethyl group, a group perfluoropropyl, a perfluorobutyl group, and a perfluoroexyl group;
a C2-C6 alkenyl group optionally having one or more halogens such as a vinyl group, a 2-propenyl group, a 3-chloro2-propenyl group, a 2-chloro-2-propenyl group, a 3,3-dichloro-group 2-propenyl, a 2-butenyl group, a 3-butenyl group, a 2-methyl-2-propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group, and a 2-hexenyl group; and a C2-C6 alkynyl group optionally having one or more halogens such as an ethynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-chloro-2-propynyl group, and a 3bromo- group 2-propynyl.
In the present compound, examples of the C3-C8 cycloalkyl group optionally having one or more halogens include, for example, a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a cyclobutyl, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
In the present compound, examples of the C1-C6 alkoxy group optionally having one or more halogens include, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2trifluoroethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.
In the present compound, examples of the C1-C6 alkylthio group optionally having one or more halogens include, for example, a methylthio group, a trifluoromethylthio group, an ethylthio group, a 2,2,2trifluoroethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.
In the present compound, examples of the C1-C6 alkylsulfinyl group optionally having one or more halogens include, for example, a methylsulfinyl group, a trifluoromethylsulfinyl group, an ethylsulfinyl group, a
7/85 2,2,2-trifluoroethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a isobutylsulfinyl group, a secbutylsulfinyl group, a tert-butylsulfinyl group, a pentylsulfinyl group, and a hexylsulfinyl group.
In the present compound, examples of the C1-C6 alkylsulfonyl group optionally having one or more halogens include, for example, a methylsulfonyl group, a trifluoromethylsulfonyl group, and an ethylsulfonyl group.
In the present compound, examples of the C1-C6 alkylamino group optionally having one or more halogens include, for example, a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, a propylamino group, an isopropylamino group, a butylamino group, a pentylamino group, and a hexylamino group.
In the present compound, examples of the C2-C8 dialkylamino group optionally having one or more halogens include, for example, a dimethylamino group, a diethylamino group, a bis (2,2,2-trifluoroethyl) amino group, and a dipropylamino group.
In the present compound, examples of the C2-C6 alkylcarbonylamino group optionally having one or more halogens include, for example, an acetylamino group, a propionylamino group, a butanoylamino group, a pentanoylamino group, a trifluoroacetylamino group, and a trichloroacetylamino group.
In the present compound, examples of the C2-C6 alkoxycarbonylamino group optionally having one or more halogens include, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a propoxycarbonylamino group, a tert-butoxycarbonylamino group, and a 2,2,2trichloroethoxycarbonylamino group.
In the present compound, examples of the C2-C6 alkylcarbonyl group optionally having one or more halogens include, for example, an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, and a trifluoroacetyl group.
In the present compound, examples of the C2-C6 alkoxycarbonyl group optionally having one or more halogens include, for example, a
8/85 methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, and a tert-butoxycarbonyl group.
In the present compound, examples of the C2-C6 alkylcarbamoyl group optionally having one or more halogens include, for example, a methylcarbamoyl group, an ethylcarbamoyl group, and a 2,2,2trifluoroethylcarbamoyl group.
In the present compound, examples of the C2-C8 dialkylcarbamoyl group optionally having one or more halogens include, for example, a dimethylcarbamoyl group, a diethylcarbamoyl group, and a dipropyl10 carbamoyl group.
In the present compound, examples of the C2-C6 alkoxyalkyl group optionally having one or more halogens include, for example, a methoxymethyl group, an ethoxymethyl group, a 1-methoxyethyl group, and a 1 - (2,2,2-trifluoroethoxy) group ethyl.
In the present compound, examples of the C2-C6 alkylthioalkyl group optionally having one or more halogens include, for example, a methylthiomethyl group, an ethylthiomethyl group, a 1-methylthioethyl group, and a trifluoromethylthiomethyl group.
In the present compound, examples of the phenyl group optionally having one or more atoms or groups selected from Group a include, for example, a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a group 2 -cyanophenyl, a 3-cyanophenyl group, a 4-cyanophenyl group, a 2-nitrophenyl group, a 3-nitrophenyl group, a 4nitrophenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 425 methylphenyl group, a 425 methylphenyl group 2- (trifluoromethyl) phenyl, a 3- (trifluoromethyl) phenyl group, a 4- (trifluoromethyl) phenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, a 4-methoxyphenyl group, a 2- (methylthio) phenyl group, a 2- (ethylthio) phenyl group, a 2- (ethylsulfinyl) phenyl group, a 2- (ethylsulfonyl) phenyl group, and a 4- (trifluoromethoxy) phenyl group.
In the present compound, examples of the 5-6 membered aromatic heterocyclic group include a 5 membered aromatic heterocyclic group and a 6 membered aromatic heterocyclic group such as a group
9/85
2- pyrrolyl, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a group
3-thienyl, a 5-pyrazolyl group, a 4-pyrazolyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a pyrazinyl group, a 1pyrrolyl group, and a 1-pyrazolyl group.
In the present compound, examples of the 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group a include a 5 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group α and a heterocyclic group aromatic 6-member optionally having one or more atoms or groups selected from Group α such as a 1-methyl-2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5bromo-2-furyl group, a 5-nitro-2-furyl group, a 2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a 2,4-dimethyl-3-furyl group, a 2-thienyl group, a 3-thienyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a group
1-methyl-3-trifluoromethyl-5-pyrazolyl, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 2methyl- 3-pyridinyl, a 6-methyl-3-pyridinyl group, a 2-chloro-3-pyridinyl group, a 6-chloro-3-pyridinyl group, a pyrazinyl group, a 1-pyrrolyl group, a 1,2 group, 4-triazole-1-yl, and a 1-pyrazolyl group.
In the present compound, examples of the compound in which R ⁴ and R ⁵ can together with the atom to which they are attached form a 5- or 6-membered ring having one or more halogens include, for example, the compounds of the formulas: (a) - (j):
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[where R ¹ , R ² , R ³ , X, Y, and Z are as defined above].
In the present compound, examples of the C1-C3 alkyl group optionally having one or more halogens include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and a group
2,2,2-trifluoroethyl.
In the present compound, examples of the C1-C3 alkoxy group optionally having one or more halogens include, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2trifluoroethoxy group, a propyloxy group, and an isopropyloxy group .
In the present compound, examples of the C1-C3 alkylthio group optionally having one or more halogens include, for example, a methylthio group, a trifluoromethylthio group, an ethylthio group, a 2,2,2trifluoroethylthio group, a propylthio group, and an isopropylthio group .
In the present compound, examples of the C1-C3 alkylsulfinyl group optionally having one or more halogens include, for example, a methylsulfinyl group, a trifluoromethylsulfinyl group, an ethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a propylsulfinyl group, and a isopropylsulfinyl group.
In the present compound, examples of the C1-C3 alkylsulfonyl group optionally having one or more halogens include, for example, a methylsulfonyl group, a trifluoromethylsulfonyl group, and an ethylsulfonyl group.
In the present compound, examples of the C1-C3 alkyl group having one or more fluors include, for example, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, and a 2,2,225 trifluoroethyl group.
In the present compound, examples of the C1-C3 alkoxy group having
11/85 one or more fluorines include, for example, a trifluoromethoxy group, a 2,2,3,3-tetrafluoropropoxy group, and a 2,2,2-trifluoroethoxy group.
In the present compound, examples of the C1-C3 alkylthio group having one or more fluoro include, for example, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoroisopropylthio group, and a 2,2,2trifluoroethylthio group.
Examples of the present compound, for example, include the following pyrimidine compounds.
A pyrimidine compound of formula (1) in which R ¹ is hydrogen.
A pyrimidine compound of the formula (1) in which R ¹ is halogen.
A pyrimidine compound of the formula (1) in which R ² is hydrogen.
A pyrimidine compound of the formula (1) in which R ² is halogen.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, and R ² is hydrogen.
A pyrimidine compound of formula (1) wherein R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halo25 geniuses, a C1-C6 alkylsulfonyl group optionally having one or more halogens, an alkylamino group C1-C6 optionally having one or more halogens, a C2-C8 dialkylamino group optionally having one or more halogens, a C2-C6 alkylcarbonylamino group optionally having one or more halogens, a C2-C6 alkoxycarbonylamino group optionally having one or more halogens, one C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2-C6 alkoxycarbonyl group optionally having one or more halogens, an optional C2-C6 alkylcarbamoyl group12 / 85 o one or more halogens, a C2-C8 dialkylcarbamoyl group optionally having one or more halogens, a C2-C6 alkoxyalkyl group optionally having one or more halogens, a C2C6 alkylthioalkyl group optionally having one or more halogens, hydrogen, halogen, a hydroxyl group , a mercapto group, an amino group, a nitro group, a cyano group, or a formyl group.
A pyrimidine compound of the formula (1) wherein R ³ is a phenyl group optionally having one or more atoms or groups selected from Group a, or a 5-6 membered aromatic heterocyclic group optionally 10 having one or more atoms or groups selected Group a.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens 15, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C1-C6 alkylamino group optionally having one or more halogens, a C2 dialkylamino group -C8 optionally having one or more halogens, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group, or a cyano group.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, or a C1-C3 alkylsulfonyl group optionally having a or more halogens.
A pyrimidine compound of the formula (1) where R ³ is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, a propyloxy group, a trifluoromethoxy group, a group 2, 2-difluoroethoxy, a 2,2,2-trifluoroethoxy group, a 2,2, ΑΛΙ 5 tetrafluoropropoxy group, a methylthio group, an ethylthio group, a propylthio group, a trifluoromethylthio group, a 2,2,2-trifluoroethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a trifluoromethylsulfonyl group, a group
2,2,2-trifluoroethylsulfonyl, hydrogen, fluorine, chlorine, or bromine.
A pyrimidine compound of the formula (1) wherein R ³ is chlorine, an ethyl group, a 2,2,2-trifluoroethoxy group, an ethylthio group, an ethylsufinyl group, or an ethylsulfonyl group.
A pyrimidine compound of formula (1) in which R ³ is chlorine.
A pyrimidine compound of the formula (1) in which R ³ is an ethyl group.
A pyrimidine compound of the formula (1) wherein R ³ is a 2,2,2-trifluoroethoxy group.
A pyrimidine compound of formula (1) wherein R ³ is an ethylthio group, an ethylsulfinyl group, or an ethylsulfonyl group.
A pyrimidine compound of the formula (1) wherein R ³ is an ethylthio group.
14/85
A pyrimidine compound of the formula (1) wherein R ³ is an ethylsulfinyl group.
A pyrimidine compound of the formula (1) wherein R ³ is an ethylsulfonyl group.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, and R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens , a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, and R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens , hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, and R ³ is a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens , or a C1-C3 alkylsulfonyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, and R ³ is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, a propyloxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,225 trifluoroethoxy group, a 2,2,4,4-tetrafluoropropoxy group, a methylthio group, an ethylthio group, a propylthio group, a trifluoromethylthio group, a 2,2,2trifluoroethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a methylsulfonyl group, a ethylsulfonyl group, a propylsulfonyl group, a trifluoromethyl group a 2,2,2-trifluoroethylsulfonyl, hydrogen, fluorine, chlorine, or bromine group.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen15 / 85nio, R ² is hydrogen, R ³ is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group , a propyloxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2trifluoroethoxy group, a 2,2,4,4-tetrafluoropropoxy group, hydrogen, fluorine, chlorine, or bromine.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, and R ³ is a methylthio group, an ethylthio group, a propylthio group, a trifluoromethylthio group, a 2,2,2-trifluoroethylthio group , a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a trifluoro10-romethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a methylsulfonyl group, a ethylsulfonyl group, a propylsulfonyl group, a trifluoromethylsulfonyl group, or a 2.2 group , 2-trifluoroethylsulfonyl.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, R ² is hydrogen, and R ³ is chlorine, an ethyl group, or a 2,2,215 trifluoroethoxy group.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, and R ³ is an ethylthio group, an ethylsulfinyl group, or an ethylsulfonyl group.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, R ² is hydrogen, and R ³ is chlorine.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, R ² is hydrogen, and R ³ is an ethylthio group.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, R ² is hydrogen, and R ³ is an ethylsulfinyl group.
A pyrimidine compound of the formula (1) in which R ¹ is hydrogen, R ² is hydrogen, and R ³ is an ethylsulfonyl group.
A pyrimidine compound of the formula (1) wherein R ⁴ and R ⁵ can be the same or different, and independently represent, a C1-C6 chain hydrocarbon group optionally having one or more halo30 geniuses, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a
16/85 C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C1-C6 alkylamino group optionally having one or more halogens, a C2-C8 dialkylamino group optionally having a or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2-C6 alkoxycarbonyl group optionally having one or more halogens, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group, a cyan group, or a formyl group.
A pyrimidine compound of formula (1) in which R ⁴ and R ⁵ may be the same or different, and independently represent a phenyl group optionally having one or more atoms or groups selected from Group a, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group a, or hydrogen; or R ⁴ and R ⁵ can together with the atom to which they are attached form a 5- or 6-membered ring having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2- alkoxycarbonyl group C6 optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, a cyano group, or a formyl group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group,
17/85 or a cyan group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having a or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group.
A pyrimidine compound of formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkyl group thio optionally having a or more halogens, halogen, or a cyan group.
A pyrimidine compound of formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens or a C1-C3 alkoxy group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens.
A pyrimidine compound of formula (1) wherein R ⁴ is a C1-C3 alkoxy group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylthio group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C 1 -C 3 alkylsulfinyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylsulfonyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, a C1-C3 alkylthio group having one or more fluors, chlorine, or bromine.
A pyrimidine compound of the formula (1) wherein R ⁴ is a group of C1-C3 alkyl having one or more fluorines.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkoxy group having one or more fluorines.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylthio group having one or more fluorines.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylsulfinyl group optionally having one or more fluorines.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylsulfonyl group optionally having one or more fluorines.
A pyrimidine compound of the formula (1) in which R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a trifluoromethyl group, a group trifluoromethylsulfinyl, a trifluoromethylsulfonyl, chlorine, bromine, or iodine group.
A pyrimidine compound of formula (1) wherein R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
A pyrimidine compound of formula (1) wherein R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethyl group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a pentafluoroethyl group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethylthio group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethylsulfinyl group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethylsulfonyl group.
A pyrimidine compound of the formula (1) in which R ⁴ is hydrogen.
19/85
A pyrimidine compound of formula (1) wherein R ⁵ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2- alkoxycarbonyl group C6 optionally having one or more halogens, hydrogen, halogen, a hydroxyl group, a mercapto group, a nitro group, a cyano group, or a formyl group.
A pyrimidine compound of formula (1) wherein R ⁵ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyan group.
A pyrimidine compound of formula (1) wherein R ⁵ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group.
A pyrimidine compound of formula (1) wherein R ⁵ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, or a cyan group.
A pyrimidine compound of formula (1) wherein R ⁵ is a C1-C3 alkyl group optionally having one or more halogens or a C1-C3 alkoxy group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁵ is a group of C1-C3 alkyl optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C1-C3 alkoxy group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, a C1-C3 alkylthio group having one or more fluors, chlorine, or bromine.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C 1 -C 3 alkyl group having one or more fluorines.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C 1 -C 3 alkoxy group having one or more fluors.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C 1 -C 3 alkylthio group having one or more fluorines.
A pyrimidine compound of formula (1) wherein R ⁵ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine.
A pyrimidine compound of the formula (1) wherein R ⁵ is a trifluoromethyl group.
A pyrimidine compound of the formula (1) in which R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, or a C1-C3 alkylsulfonyl group optionally having one or more halogens, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hi21 / 85 hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is hydrogen, and R ⁵ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1 alkylthio group -C3 optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, a C1-C3 alkylthio group having one or more fluors, a C1-C3 alkylsulfinyl group having one or more fluorines, or a C1-C3 alkylsulfonyl group having one or more fluors, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, a C1-C3 alkylthio group having one or more fluors, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkyl group having one or more fluorines, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C 1 -C 3 alkylthio group having one or more fluorines, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) wherein R ⁴ is a C1-C3 alkylsulfinyl group having one or more fluorines, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a C1-C3 alkylsulfonyl group having one or more fluorines, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁵ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, a C1-C3 alkylthio group having one or more fluors, chlorine, or bromine, and R ⁴ is hydrogen.
A pyrimidine compound of formula (1) in which R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-difluoroethoxy group, a trifluoromethyl group, a trifluoromethyl group trifluoromethylsulfinyl, a trifluoromethylsulfonyl group, chlorine,
22/85 bromine, or iodine, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) wherein R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is a trifluoromethyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is a pentafluoroethyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is a trifluoromethylthio group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethylsulfinyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is a trifluoromethylsulfonyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which R ⁴ is iodine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine, and R ⁵ is hydrogen .
A pyrimidine compound of the formula (1) in which R ⁴ is hydrogen, and R ⁵ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine.
A pyrimidine compound of formula (1) wherein R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where X is nitrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, and R ⁶ is hydrogen or halogen.
23/85
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, and R ⁶ is hydrogen.
A pyrimidine compound of the formula (1) where X is nitrogen or = CR ⁶ -, and R ⁶ is hydrogen.
A pyrimidine compound of the formula (1) in which Y is nitrogen.
A pyrimidine compound of the formula (1) where Y is = CR ⁷ -, and R ⁷ is hydrogen or halogen.
A pyrimidine compound of the formula (1) where Y is = CR ⁷ -, and R ⁷ is hydrogen.
A pyrimidine compound of the formula (1) where Y is nitrogen or = CR ⁷ -, and R ⁷ is hydrogen.
A pyrimidine compound of the formula (1) where X is nitrogen, and Y is nitrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, and R ⁷ is hydrogen or halogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, and Y is nitrogen.
A pyrimidine compound of the formula (1) where X is nitrogen, Y is = CR ⁷ -, and R ⁷ is hydrogen or halogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, and R ⁶ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen or = CR ⁷ -, and R ⁷ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group having one or more fluorines, a
24/85 C1-C3 alkoxy group having one or more fluorine, a C1-C3 alkylthio group having one or more fluorine, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2- trifluoroethoxy, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having a or more fluorine, a C1-C3 alkylthio group having one or more fluorine, chlorine, or bromine, R ⁵ is hydrogen.
A pyrimidine compound of formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a group 2, 2,2-trifluoroethoxy, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen or halogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, R ⁵ it's hydrogen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen or halogen, R ⁴ is a C1-C3 alkyl group having one or more fluoro, a C1-C3 alkoxy group having one or more fluoro, a C1-C3 alkylthio group having one or more fluoro, chloro, or bromo, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) where X is = CR ⁶ -, R ⁶
25/85 is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen or halogen, R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine , or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which Z is oxygen.
A pyrimidine compound of the formula (1) wherein Z is -NR ⁸ -, R ⁸ is hydrogen, a C1-C6 chain hydrocarbon group optionally having one or more halogens, or a C3-C8 cycloalkyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) where Z is -NR ⁸ -, and R ⁸ is a C1-C6 chain hydrocarbon group optionally having one or more halogens.
A pyrimidine compound of the formula (1) where Z is -NR ⁸ -, and R ⁸ is a C1-C3 alkyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) where Z is -NR ⁸ -, and R ⁸ is a methyl group, an ethyl group, or a cyclopropyl group.
A pyrimidine compound of the formula (1) in which Z is -NR ⁸ -, and R ⁸ is a methyl group.
A pyrimidine compound of the formula (1) where Z is oxygen or -NR ⁸ -, and R ⁸ is a C1-C3 alkyl group optionally having one or more halogens.
A pyrimidine compound of the formula (1) in which Z is oxygen or -NR ⁸ -, and R ⁸ is a methyl group, an ethyl group, or a cyclopropyl group.
A pyrimidine compound of the formula (1) in which Z is oxygen or -NR ⁸ -, and R ⁸ is a methyl group.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, and Z is oxygen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen, and Z is oxygen.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, Z is -NR ⁸ -, and R ⁸ is a methyl group.
A pyrimidine compound of the formula (1) where X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen, Z is -NR ⁸ -, and R ⁸ is a methyl group.
26/85
A pyrimidine compound of the formula (1) where Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, and R ⁴ is an optionally C1-C3 alkyl group having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, and a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, R ⁴ is a C1 alkyl group -C3 optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyan group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ -, R ⁷ is hydrogen or halogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group , a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where Z is oxygen, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) where Z is -NR ⁸ -, R ⁸
27/85 is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, one C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) in which Z is oxygen, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having a or more fluoro, a C1-C3 alkylthio group having one or more fluoro, chloro, or bromo, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where Z is -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group having one or more fluoro, a C1-C3 alkoxy group having one or more fluoro, a C1-C3 alkylthio group having one or more fluoro, chloro, or bromo, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optionally C1-C6 alkylthio group having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, an optional C1-C6 alkylthio group28 / 85 having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, R ⁵ is hydrogen, X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen or = CR ⁷ -, R ⁷ is hydrogen, Z is oxygen or -NR ⁸ -, and R ⁸ is a C1-C6 chain hydrocarbon group optionally having one or more halogens.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens , a C1-C3 alkylthio group optionally having one or more
29/85 halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, Z is oxygen, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, Z is -NR ⁸ - , R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, one C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, a group propyloxy, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2trifluoroethoxy group, a 2,2,4,4-tetrafluoropropoxy group, a methylthio group, an ethylthio group, a propylthio group, a trifluoromethylthio group, a 2,2,2trifluoroethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a methylsulfonyl group, a ethylsulfonyl group, a propylsulfonyl group, a trifluoromethyl group a 2,2,2-trifluoroethylsulfonyl, hydrogen, fluorine, chlorine, or bromine group, Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group optionally having
30/85 one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group, a mercapto group, a nitro group, or cyan group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a C1-C3 alkyl group having one or more fluors, a C1-C3 alkoxy group having one or more fluors, one C1-C3 alkylthio group having one or more fluorines, chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) wherein R ¹ is hydrogen, R ² is hydrogen, R ³ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1-C3 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen, Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a trifluoromethyl group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group , chlorine, or bromine, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a methoxy group, an ethoxy group, a group propyloxy, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2trifluoroethoxy group, a 2,2,4,4-tetrafluoropropoxy group, a methylthio group, an ethylthio group, a propylthio group, a trifluoromethylthio group , a 2,2,2trifluoroethylthio group, a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group,
31/85 a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, hydrogen, fluorine, chlorine, or bromine, Z is oxygen or -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, R ⁶ is hydrogen, R ⁴ is a trifluoromethyl group, a toxic trifluorome group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, chlorine, or bromine , and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is an ethyl group, a 2,2,2-trifluoroethoxy group, an ethyl group, an ethyl sulfinyl group, an ethyl sulfonyl group, or chlorine, R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R ⁵ is hydrogen.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is an ethyl group, a 2,2,2-trifluoroethoxy group, an ethyl group, an ethyl sulfinyl group, an ethyl sulfonyl group, or chlorine, R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R ⁵ is hydrogen, X is = CR ⁶ -, R ⁶ is hydrogen, Y is = CR ⁷ - , R ⁷ is hydrogen, Z is -NR ⁸ -, and R ⁸ is a methyl group.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is an ethyl group, a 2,2,2-trifluoroethoxy group, an ethyl group, an ethyl sulfinyl group, an ethyl sulfonyl group, or chlorine, R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R ⁵ is hydrogen25, X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, Z is -NR ⁸ -, and R ⁸ is a methyl group.
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is an ethyl group, a 2,2,2-trifluoroethoxy group, or chlorine, R ⁴ is a trifluoromethyl group, a group pentafluoroethyl, a tri30 fluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R ⁵ is hydrogen, X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, Z is -NR ⁸ -, and R ⁸ is a group methyl.
32/85
A pyrimidine compound of the formula (1) where R ¹ is hydrogen, R ² is hydrogen, R ³ is an ethyl group, an ethylsulfinyl group, an ethylsulfonyl group, or chlorine, R ⁴ is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R ⁵ is hydrogen, X is = CR ⁶ -, R ⁶ is hydrogen, Y is nitrogen, Z is -NR ⁸ -, and R ⁸ is a methyl group.
The production method of the present compound is illustrated below.
The present compound can be produced, for example, according to the following production methods A-G.
(Production method A)
The present compound can be produced, for example, according to the following method:
R ³ R ² nA
R ’
Step CA — 2) (11) (12)
Step condensing agent (A-1)
Condensing agent
Dehydrating agent. Acid or base when needed
wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and Z are as defined above.
Step (A-1):
Compound (13) can be produced by reacting compound (11) with compound (12) in the presence of a condensing agent.
The reaction is carried out in the presence or absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF), and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene;
hydrocarbons such as toluene, benzene, and xylene; esters such as
33/85 ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as Ν, Ν-dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), 1,3-dimethyl2-imidazolidinone, and dimethylsulfoxide; aromatic compounds containing nitro5 genius such as pyridine and quinoline, and mixtures thereof.
Examples of the condensing agent to be employed in the reaction include carbodiimides such as 1-ethyl-3- (3dimethylaminopropyl) hydrochloride carbodiimide (hereinafter referred to as WSC) and 1,3dicyclohexylcarbodiimide.
A catalyst can be added to the reaction when needed.
Examples of the catalyst to be employed in the reaction include 1-hydroxybenzotriazole.
The amount of the compound (12) to be used in the reaction is normally 1 to 2 moles based on 1 mole of the compound (11). The amount of the condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of the compound (11). The amount of the catalyst to be used in the reaction is normally 0.01 to 0.2 moles based on 1 mol of the compound (11).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, Compound (13) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (13) can also be purified by recrystallization, chromatography, and the like (s).
Step (A-2)
The present compound can be produced by intramolecular condensation of the compound (13).
The reaction is usually carried out in the presence of a solvent.
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Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3dimethyl-2-imidazolidinone, and dimethylsulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
In the reaction, a dehydrating agent, acid or base can be used when necessary.
Examples of the dehydrating agent to be employed in the reaction include phosphorus oxychloride, acetic anhydride, trifluoroacetic anhydride, a mixture of triphenylphosphine, base, and carbon tetrachloride or carbon tetrabromide, and a mixture of triphenylphosphine and azodiesters such as diethyl azodicarboxylate.
Examples of the acid to be employed in the reaction include sulfonic acids such as para-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
Examples of the base to be employed in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU), and 1, 5-diazabicyclo [4,3,0] -5-nonene; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the condensing agent to be used in the reaction is normally 1 to 5 moles based on 1 mole of the compound (13). The amount of acid to be used in the reaction is 0.1 mois to 5 moles based on 1 mol of the compound (13). The amount of the base to be used in the reaction is from 1 mol to 5 mol based on 1 mol of the compound (13).
The reaction temperature of the reaction is normally within a range of 0 to 200 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
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Upon completion of the reaction, the present compound can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound can also be purified by recrystallization, chromatography, and the like).
Step (A-3)
Also, the present compound can be produced by reacting the compound (11) with the compound (12).
The reaction is carried out in the presence or absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3dimethyl-2-imidazolidinone, and dimethylsulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
Examples of the condensing agent to be employed in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide.
A catalyst can be added to the reaction when needed.
Examples of the catalyst to be employed in the reaction include 1-hydroxybenzotriazole.
The amount of the compound (12) to be used in the reaction is normally 1 to 2 moles based on 1 mole of the compound (11). The amount of the condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of the compound (11). The amount of the catalyst to be used in the reaction is normally 0.01 to 0.2 moles based on 1 mol of the compound (11).
The reaction temperature of the reaction is normally within
36/85 a range of 0 to 200 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound can also be purified by recrystallization, chromatography, and the like).
(Production method B)
The present compound can be produced, for example, according to the following method.

j
H (15)
Step (B-2)
Oxidizing agent
wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and Z are as defined above.
Step (B-1)
Compound (15) can be produced by reacting compound (11) with compound (14).
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be employed in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hidrocar37 / 85 bonetos such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; nitrogen-containing aromatics such as pyridine and quinoline;
and mixtures of these.
An acid or base can be added to the reaction when needed.
The reaction temperature of the reaction is normally within a range of 0 to 150 ° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.
Upon completion of the reaction, Compound (15) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (15) can also be purified by recrystallization, chromatography, and the like (s).
Step (B-2)
The present compound can be produced by oxidizing Compound (15)
The reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,
1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3dimethyl-2-imidazolidinone, and dimethylsulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
Examples of the oxidizing agent to be employed in the reaction include oxygen, metal oxidizing agents such as lead (IV) acetate and lead (IV) oxide, and organic periodides such as iodobenzene diacetate.
38/85
The reaction temperature of the reaction is normally within a range of 0 to 150 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound can also be purified by recrystallization, chromatography, and the like.
Step (B-3)
Also, the present compound can be produced by reacting compound (11) with compound (14).
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be employed in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
An acid or base can be added to the reaction when necessary.
The reaction temperature of the reaction is normally within a range of 0 to 200 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the
39/85 solids generated in the reaction mixture by filtration. The present isolated compound can also be purified by recrystallization, chromatography, and the like).
(Production method C)
The present compound can be produced, for example, according to the following method.
H nh ₂ z
I
H
R ³ R ²

(13) (11) base, as required Step (C-1)
dehydrating agent, acid or base, as needed
Step (C — 2)
wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and Z are as defined above.
Step (C-1)
Compound (13) can be produced by reacting compound 10 (11) with compound (16).
The reaction is carried out in the presence or absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 15 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3dimethyl-2-imidazolidinone, and dimethylsulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
A base can be added to the reaction when needed.
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Examples of the base to be employed in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline. 2,6lutidine, DBU, and 1,5-diazabicyclo [4,3,0] -5-nonene; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbone and sodium hydride.
The amount of the compound (16) to be used in the reaction is normally 1 to 2 mois based on 1 mole of compound (11). The amount of the base to be used in the reaction is normally 1 to 5 mois based on 1 mol of the compound (11).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, compound (13) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (13) can also be purified by recrystallization, chromatography, and the like (s).
Step (C-2)
The present compound can be produced from compound (13) by a method similar to that of Step (A-2) in Production Method A.
Step (C-3)
The present compound can be produced by reacting compound (11) with compound (16) according to step (C-1) in Production method C.
(Production method D)
Among the present compounds, the present compound (1-iii) in which R ³ is OR ^3a can be produced by reacting compound (1 -ii) with compound (17) in the presence of a base.
41/85
R ^3a OH (17) Base
R ^3a
OR ²
(1-iii) where R ¹ , R ² , R ⁴ , R ⁵ , X, Y, and Z are as defined above, L ¹ is a leaving group such as chlorine, bromine, iodine, para-toluenesulfonyloxy, and a methanesulfonyloxy group, and R ^3a is a C1-C6 alkyl group optionally having one or more halogens.
The reaction is usually carried out in the presence of a solvent, however a solvent amount of the compound (17) can be used.
Examples of the solvent to be employed in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
Examples of the base to be employed in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6lutidine, DBU, and 1,5-diazabicyclo [4,3,0] -5-nonene; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the compound (17) to be used in the reaction is normally 1 to 2 moles based on 1 mole of the compound (1-ii). The amount of the base to be used in the reaction is normally 1 to 5 mois based on 1 mol of the compound (1-ii).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound (1-iii) can
42/85 be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound (1-iii) can also be purified by recrystallization, chromatography, and the like (s).
(Production method E)
Among the present compounds, the present compound (1-iv) in which R ³ is SR ^3a can be produced by reacting the compound (1 -ii) with the compound (18) in the presence of a base.
(1-ii) (1-iv) where R ¹ , R ² , R ⁴ , R ⁵ , R ^3a , L ¹ , X, Y, and Z are as defined above.
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as
1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,320 dimethyl-2-imidazolidinone, and dimethyl sulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
Examples of the base to be employed in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6lutidine, DBU, and 1,5-diazabicyclo [4,3,0] -5-nonene; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the compound (18) to be used in the reaction is
43/85 usually 1 to 2 moles based on 1 mole of the compound (1 -ii). The amount of the base to be used in the reaction is normally 1 to 5 moles based on 1 mole of the compound (1 -ii).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound (1-iv) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound (1-iv) can also be purified by recrystallization, chromatography, and the like (s).
(Production method F)
Among the present compounds, the present compound (1-v) where R ³ is NR ^3b R ^3c can be produced by compound (1-ii) with compound (19) in the presence of a base.
(1-ü)
R ^3b
R ^3c -NH (19)
Base
R ³¹¹ _R 3c_ _n ' _r 2
(1-v) where R ¹ , R ² , R ⁴ , R ⁵ , L ¹ , X, Y, and Z are as defined above, R ^3b is a C1-C6 alkyl group optionally having one or more halogens,
R ^3c is a C1-C6 alkyl group optionally having one or more halogens or hydrogen, provided that the total number of carbon atoms in the R ^3b or R ^{3c group is} not more than 8.
The reaction is normally carried out in the presence of a solvent, however a solvent amount of the compound (19) can be used.
Examples of the solvent to be employed in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; hydro44 / 85 halogenated carbides such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; nitrogen-containing aromatics such as pyridine and quinoline; and mixtures of these.
Examples of the base to be employed in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6lutidine, DBU, and 1,5-diazabicyclo [4,3,0] -5-nonene; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the compound (19) to be used in the reaction is normally 1 to 2 mois based on 1 mol of the compound (1 -ii). The amount of the base to be used in the reaction is normally 1 to 5 mois based on 1 mol of the compound (1 -ii).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound (1-v) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound (1-v) can also be purified by recrystallization, chromatography, and the like (s).
(Production method G)
Among the present compounds, the present compound (1-vii) in which R ³ is R ^3d can be produced by reacting the present compound (1-vi) with a boronic acid compound of the compound (20) or a tin compound of compound (21) in the presence of a palladium compound and a base.
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R ~ Β (ΟΗ) ₂ (20)
or
R ^3d SnBu ₃ (21)
Rl
R ⁵ _R 3d
R ²
N
NK (1-vii) where R ¹ , R ² , R ⁴ , R ⁵ , X, Y, and Z are as defined above, L ² is bromine or iodine, and R ^3d is a phenyl group optionally having one or more atoms or groups selected from Group a, or a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group a.
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be employed in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, THF, and methyl tert-butyl ether; hydrocarbons such as toluene, benzene, and xylene; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; and mixtures of these.
Examples of the palladium compound to be employed in the reaction include palladium-carbon, palladium chloride, palladium acetate, tetracis (triphenylphosphine) palladium, {1,1'bis (diphenylphosphine) ferrocene} methylene chloride} dichloropalladium complex, and dichlorobisyl (triphenylphosphine) palladium (II).
Examples of the base to be employed in the reaction include sodium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium acetate, and tripotassium phosphate.
The reaction can be carried out in the presence of a phase transfer catalyst when necessary.
Examples of the phase transfer catalyst to be employed in the reaction include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium bromide.
The amount of the compound (20) or compound (21) to be used in the reaction is normally 1 to 2 mois based on 1 mole of the compound (1 -vi). The amount of the base to be used in the reaction is normally 1 to 5 mois based on 1 mol of the compound (1 -vi).
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The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the present compound (1-vii) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The present isolated compound (1-vii) can also be purified by recrystallization, chromatography, and the like (s).
The intermediates of the present invention can be produced, for example, by the following method.
(Reference production method 1)
Compound (11) can be produced, for example, by the following method.
^Κί γ ^Χ γ ^Ν θ2 _r5 X _y Á _z _ _h
Ύχ nh ₂
ZH (M1) (M2) (11) where R ⁴ , R ⁵ , X, Y, and Z are as defined above.
(Step 1)
The compound (M2) can be produced by nitriding the compound (M1) in the presence of a nitrating agent.
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be employed in the reaction include aliphatic halogenated hydrocarbons such as chloroform; acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
Examples of the nitration agent to be employed in the reaction include concentrated nitric acid.
The amount of the nitration agent is normally 1 to 3 mois based on 1 mol of the compound (M1).
The reaction temperature of the reaction is normally within a range of -10 to 100 ° C. The reaction time of the reaction is usually
47/85 within a range of 0.1 to 24 hours.
Upon completion of the reaction, the compound (M2) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (M2) can also be purified by recrystallization, chromatography, and the like (s).
(Step 2)
Compound (11) can be produced by reacting compound 10 (M2) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is normally carried out under 1 to 100 hydrogen atoms, usually in the presence of a solvent.
Examples of the solvent to be employed in the reaction include ethers such as THF and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the hydrogenation catalyst to be employed in the reaction include transition metal compounds such as palladium-carbon, palladium hydroxide, Raney ° 'R nickel, and platinum oxide.
The amount of hydrogen is normally 3 mois based on 20 1 mol of the compound (M2). The amount of the hydrogenation catalyst is normally from 0.001 to 0.5 mol based on 1 mol of the compound (M2).
An acid or base can be added to the reaction when needed.
The reaction temperature of the reaction is normally within a range of -20 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, compound (11) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (11) can also be purified by recrystallization, chromatography, and the like (s).
48/85 (Reference production method 2)
Compound (12) can be produced, for example, by the following method.
R ³ R ² R ³ R ²
R ³ R ²
(M3) (M4) (12) where R ¹ , R ² , and R ³ are as defined above.
(Step 1)
The compound (M4) can be produced by reacting the compound (M3) with 2-furylboronic acid in the presence of a palladium compound and a base.
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be employed in the reaction include water, ethers such as 1,4-dioxane, diethyl ether, THF, and methyl tert-butyl ether; hydrocarbons such as toluene, benzene, and xylene; nitriles such as acetonitrile; polar aprotic solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethyl sulfoxide; and mixtures of these.
Examples of the palladium compound to be employed in the reaction include palladium-carbon, palladium chloride, palladium acetate, tetracis (triphenylphosphine) palladium, {1,1bis (diphenylphosphine) ferrocene} methylene chloride} dichloropalladium complex, and dichlorobis (triphenylphosphine) ) palladium (II).
Examples of the base to be employed in the reaction include sodium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium acetate, and tripotassium phosphate.
The reaction can be carried out in the presence of a phase transfer catalyst when necessary.
Examples of the phase transfer catalyst to be employed in the reaction include, for example, quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium bromide.
The amount of 2-furylboronic acid to be used in the reaction is usually 1 to 2 moles based on 1 mole of the compound (M3). The amount of the base to be used in the reaction is normally 1 to 5 moles based on 1 mole of the compound (M3).
The reaction temperature of the reaction is normally within a range of 0 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, the compound (M4) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; adding the reaction mixture to the water, and collecting the solids generated by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated compound (M4) can also be purified by recrystallization, chromatography, and the like (s).
(Step 2)
Compound (12) can be produced by reacting compound (M4) with an oxidizing agent.
The reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be employed in the reaction include, for example, acetone, methyl isobutyl ketone, water, and mixtures thereof.
Examples of the oxidizing agent to be employed in the reaction include potassium permanganate.
The amount of the oxidizing agent to be used in the reaction is normally 1 to 10 moles based on 1 mole of the compound (M4).
The reaction temperature of the reaction is normally within a range of -20 to 100 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.
Upon completion of the reaction, compound (12) can be isolated by adding the reaction mixture to the water, extracting with an organic solvent, and concentrating the organic layer; or by adding the reaction mixture to the water, and collecting the solids generated by filtration. The isolated compound (12) can also be purified by recrystallization, chromatography, and the like (s).
Examples of the present compound are shown below.
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A compound of the formula (A):
R ³
where Y is = CH-, Z is oxygen, and R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables 1-11: Table 1
R ³ R ⁴ R ⁵ H cf ₃ H F cf ₃ H Cl cf ₃ H Br cf ₃ H I cf ₃ H ch ₃ cf ₃ H ch ₂ ch ₃ cf ₃ H ch ₂ ch ₂ ch ₃ cf ₃ H CH ₂ CH (CH ₃ ) ₂ cf ₃ H och ₃ cf ₃ H och ₂ ch ₃ cf ₃ H och ₂ ch ₂ ch ₃ LLO H OCH ₂ CH (CH ₃ ) ₂ cf ₃ H ocf ₃ cf ₃ H och ₂ cf ₃ cf ₃ H och ₂ chf ₂ cf ₃ H och ₂ cfh ₂ cf ₃ H och ₂ chfchf ₂ cf ₃ H och ₂ cf ₂ chfcf ₃ cf ₃ H sch ₃ cf ₃ H
Table 2
R ^J
SCH ₂ CH ₃
CF,
R ⁵
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sch ₂ ch ₂ ch ₃ cf ₃ H SCH ₂ CH (CH ₃ ) ₂ cf ₃ H scf ₃ cf ₃ H sch ₂ cf ₃ cf ₃ H sch ₂ chf ₂ cf ₃ H sch ₂ cfh ₂ cf ₃ H sch ₂ chfchf ₂ cf ₃ H sch ₂ cf ₂ chfcf ₃ cf ₃ H S (O) CH ₃ cf ₃ H S (O) CH ₂ CH ₃ cf ₃ H S (O) CH ₂ CH ₂ CH ₃ cf ₃ H S (O) CH ₂ CH (CH ₃ ) ₂ cf ₃ H S (O) CF ₃ cf ₃ H S (O) CH ₂ CF ₃ cf ₃ H S (O) CH ₂ CHF ₂ cf ₃ H S (O) CH ₂ CFH ₂ cf ₃ H S (O) CH ₂ CHFCHF ₂ cf ₃ H S (O) CH ₂ CF ₂ CHFCF ₃ cf ₃ H S (O) ₂ CH ₃ cf ₃ H
Table 3
R ³ R ⁴ R ⁵ S (O) ₂ CH ₂ CH ₃ cf ₃ H S (O) ₂ CH ₂ CH ₂ CH ₃ cf ₃ H S (O) ₂ CH ₂ CH (CH ₃ ) ₂ cf ₃ H S (O) ₂ CF ₃ cf ₃ H S (O) ₂ CH ₂ CF ₃ cf ₃ H S (O) ₂ CH ₂ CHF ₂ cf ₃ H S (O) ₂ CH ₂ CFH ₂ cf ₃ H S (O) ₂ CH ₂ CHFCHF ₂ cf ₃ H S (O) ₂ CH ₂ CF ₂ CHFCF ₃ cf ₃ H nhch ₃ cf ₃ H
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nhch ₂ ch ₃ cf ₃ H nhch ₂ ch ₂ ch ₃ cf ₃ H NHCH (CH ₃ ) ₂ cf ₃ H N (CH ₃ ) ₂ cf ₃ H N (CH ₂ CH ₃ ) ₂ cf ₃ H NHC (O) CH ₃ cf ₃ H NHC (O) OCH ₃ cf ₃ H C (O) CH ₃ cf ₃ H C (O) OCH ₃ cf ₃ H ch ₂ och ₃ cf ₃ H
Table 4
R ³ R ⁴ R ⁵ CH ₂ OCH ₂ CH ₃ cf ₃ H ch ₂ sch ₃ cf ₃ H ch ₂ sch ₂ ch ₃ cf ₃ H Phenyl cf ₃ H 2-SCH ₃ -phenyl cf ₃ H 2-SCH ₂ CH ₃ -phenyl cf ₃ H 1,2,4-triazole-1-yl cf ₃ H Pyrazol-14la cf ₃ H Pyridin-2-ila cf ₃ H Pyridin-3-ila cf ₃ H OH CF3 H SH CF3 H nh ₂ CF3 H CN CF3 H no ₂ CF3 H CHO CF3 H
Table 5
R ³ R ⁴ R ⁵ H H cf ₃
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F H cf ₃ Cl H cf ₃ Br H cf ₃ ch ₃ H cf ₃ ch ₂ ch ₃ H cf ₃ och ₃ H cf ₃ och ₂ ch ₃ H cf ₃ och ₂ cf ₃ H O"Πw och ₂ chf ₂ H cf ₃ sch ₃ H cf ₃ sch ₂ ch ₃ H cf ₃ S (O) CH ₃ H cf ₃ S (O) CH ₂ CH ₃ H cf ₃ S (O) ₂ CH ₃ H cf ₃ S (O) ₂ CH ₂ CH ₃ H cf ₃ nhch ₂ ch ₃ H cf ₃ N (CH ₂ CH ₃ ) ₂ H cf ₃
Table 6
R ³ R ⁴ R ⁵ H C (CH ₃ ) ₃ H F C (CH ₃ ) ₃ H Cl C (CH ₃ ) ₃ H Br C (CH ₃ ) ₃ H ch ₃ C (CH ₃ ) ₃ H ch ₂ ch ₃ C (CH ₃ ) ₃ H och ₃ C (CH ₃ ) ₃ H och ₂ ch ₃ C (CH ₃ ) ₃ H och ₂ cf ₃ C (CH ₃ ) ₃ H och ₂ chf ₂ C (CH ₃ ) ₃ H sch ₃ C (CH ₃ ) ₃ H sch ₂ ch ₃ C (CH ₃ ) ₃ H
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S (O) CH ₃ C (CH ₃ ) ₃ H S (O) CH ₂ CH ₃ C (CH ₃ ) ₃ H S (O) ₂ CH ₃ C (CH ₃ ) ₃ H S (O) ₂ CH ₂ CH ₃ C (CH ₃ ) ₃ H nhch ₂ ch ₃ C (CH ₃ ) ₃ H N (CH ₂ CH ₃ ) ₂ C (CH ₃ ) ₃ H
Table 7
R ³ R ⁴ R ⁵ H CHF ₂ H F chf ₂ H Cl chf ₂ H Br chf ₂ H ch ₃ chf ₂ H ch ₂ ch ₃ chf ₂ H och ₃ chf ₂ H OCH ₂ CH ₃ chf ₂ H OCH2CF3 chf ₂ H OCH ₂ CHF ₂ chf ₂ H sch ₃ chf ₂ H sch ₂ ch ₃ chf ₂ H S (O) CH ₃ chf ₂ H S (O) CH ₂ CH ₃ chf ₂ H S (O) ₂ CH ₃ chf ₂ H S (O) ₂ CH ₂ CH ₃ chf ₂ H nhch ₂ ch ₃ chf ₂ H N (CH ₂ CH ₃ ) 2 chf ₂ H
Table 8
R ³ R ⁴ R ⁵ H cf ₂ cf ₃ H F CF2CF3 H Cl CF2CF3 H
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Br cf ₂ cf ₃ H ch ₃ cf ₂ cf ₃ H ch ₂ ch ₃ cf ₂ cf ₃ H och ₃ cf ₂ cf ₃ H och ₂ ch ₃ cf ₂ cf ₃ H och ₂ cf ₃ CF2CF3 H och ₂ chf ₂ cf ₂ cf ₃ H sch ₃ cf ₂ cf ₃ H sch ₂ ch ₃ cf ₂ cf ₃ H S (O) CH ₃ cf ₂ cf ₃ H S (O) CH ₂ CH ₃ cf ₂ cf ₃ H S (O) ₂ CH ₃ cf ₂ cf ₃ H S (O) ₂ CH ₂ CH ₃ cf ₂ cf ₃ H nhch ₂ ch ₃ cf ₂ cf ₃ H N (CH ₂ CH ₃ ) ₂ cf ₂ cf ₃ H
Table 9
R ³ R ⁴ R ⁵ H scf ₃ H F scf ₃ H Cl scf ₃ H Br scf ₃ H ch ₃ scf ₃ H ch ₂ ch ₃ scf ₃ H och ₃ scf ₃ H och ₂ ch ₃ scf ₃ H och ₂ cf ₃ scf ₃ H och ₂ chf ₂ scf ₃ H sch ₃ scf ₃ H sch ₂ ch ₃ scf ₃ H S (O) CH ₃ scf ₃ H S (O) CH ₂ CH ₃ scf ₃ H
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S (O) ₂ CH ₃ scf ₃ H S (O) ₂ CH ₂ CH ₃ scf ₃ H nhch ₂ ch ₃ scf ₃ H N (CH ₂ CH ₃ ) ₂ scf ₃ H
Table 10
R ³ R ⁴ R ⁵ H S (O) CF ₃ H F S (O) CF ₃ H Cl S (O) CF ₃ H Br S (O) CF ₃ H ch ₃ S (O) CF ₃ H ch ₂ ch ₃ S (O) CF ₃ H och ₃ S (O) CF ₃ H och ₂ ch ₃ S (O) CF ₃ H och ₂ cf ₃ S (O) CF ₃ H och ₂ chf ₂ S (O) CF ₃ H sch ₃ S (O) CF ₃ H sch ₂ ch ₃ S (O) CF ₃ H S (O) CH ₃ S (O) CF ₃ H S (O) CH ₂ CH ₃ S (O) CF ₃ H S (O) ₂ CH ₃ S (O) CF ₃ H S (O) ₂ CH ₂ CH ₃ S (O) CF ₃ H nhch ₂ ch ₃ S (O) CF ₃ H N (CH ₂ CH ₃ ) ₂ S (O) CF ₃ H
Table 11
R ³ R ⁴ R ⁵ H S (O) ₂ CF ₃ H F S (O) ₂ CF ₃ H Cl S (O) ₂ CF ₃ H Br S (O) ₂ CF ₃ H ch ₃ S (O) ₂ CF ₃ H
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ch ₂ ch ₃ S (O) ₂ CF ₃ H och ₃ S (O) ₂ CF ₃ H och ₂ ch ₃ S (O) ₂ CF ₃ H och ₂ cf ₃ S (O) ₂ CF ₃ H och ₂ chf ₂ S (O) ₂ CF ₃ H sch ₃ S (O) ₂ CF ₃ H sch ₂ ch ₃ S (O) ₂ CF ₃ H S (O) CH ₃ s (O) ₂ cf ₃ H S (O) CH ₂ CH ₃ S (O) ₂ CF ₃ H S (O) ₂ CH ₃ S (O) ₂ CF ₃ H S (O) ₂ CH ₂ CH ₃ S (O) ₂ CF ₃ H nhch ₂ ch ₃ S (O) ₂ CF ₃ H N (CH ₂ CH ₃ ) ₂ S (O) ₂ CF ₃ H
A compound of the formula (A) in which Y is nitrogen, Z is oxygen, and R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables 111.
A compound of the formula (A) where Y is = C (CI) -, Z is oxygen, 5 R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables 1-11.
A compound of the formula (A) where Y is = CH-, Z is -N (CH ₃ ) -, R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables 1-11.
A compound of the formula (A) where Y is nitrogen, Z is N (CH ₃ ) -, R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables
1-11.
A compound of the formula (A) where Y is = C (CI) -, Z is -N (CH ₃ ) -, R ³ , R ⁴ , and R ⁵ represent a combination shown in Tables 1-11.
Examples of pests against which the present compound has an activity include harmful arthropods such as harmful insects and mites in harmful ones, and nematodes. In particular, examples of pests include the following.
Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, and Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens, and Empoasca onukii; Aphididae such as
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Aphis gossypii, Myzus persicae, Brevicoryne brassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus, and Hyalopterus pruni; Pentatomidae such as Nezara antennata, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, and mixed Halyomorpha; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, and Aleurocanthus spiniferus; Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, and Pseudaulacaspis pentagona; Tingidae; Scimps such as Cimex lectularius; and Psyllidae.
Lepidoptera: Piralidae such as Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Ostrinia fumarcalis, Hellula undalis, and Pediasia teterrellus; Noctuidae such as Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Thoricoplusia spp., Heliothis spp., And Helicoverpa spp .; Pieridae such as Pieris rapae; Tortrícidae such as Adoxophyes spp., Grapholita molesta, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai., Homona magnanima, Archips fuscocupreanus, and Cydia pomonella; Gracillariidae such as Caloptilia theivora and Phyllonorycter ringoneella; Carposinidae such as Carposina niponensis; Lyonetiidae such as Lyonetia spp .; Lymantriidae such as Lymantria spp. and Euproctis spp; Yponomeutidae such as Plutella xylostella; Gelechiidae such as Pectinophora gossypiella and Phthorímaea operculella; Arctiidae such as Hyphantria cunea; and Tineidae such as Tinea translucens and Tineola bisselliella.
Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, and Frankliniella intonsa.
Diptera: Culices such as Culex pipiens pallens, Culex tritaeniorhynchus, and Culex quinquefasciatus; Aedes spp. such as Aedes aegypti and Aedes albopictus; Anopheles spp. such as Anopheles sinensis; Chironomidae; Muscidae such as Musca domestica and Muscina stabulans; Calliphoridae; Sarcophagidae; Fanniidae; Anthomyiidae such as Delia platura and De59 / 85 lia antiqua; Agromyzidae such as Agromyza oryzae, Hydrellia griseola, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticol; Chloropidae such as Clorops oryzae; Tephritidae such as Dacus cucurbitae and Ceratitis capitata; Drosophilidae; Phoridae such as Megaselia spiracularis; Psycho5 didae such as Clogmia albipunctata; Simuliidae; Tabanidae such as Tabanus trigonus; and stable flies.
Coleoptera: Diabrotica spp. such as Diabrotica virgifera virgifera and Diabrotica undecimpunctata howardi; Scarabaeidae such as Anômala cuprea, Anômala rufocuprea, and Popillia japonica; weevils such as Sito10 philus zeamais, Lissorhoptrus oryzophiius, Caiiosobruchuys chienensis, Echinocnemus squameus, Anthonomus grandis, and Sphenophorus venatus; Tenebrionidae such as Tenebrio molitor and Tribolium castaneum; Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, and Leptinotarsa decemlineata; Dermestidae such as Anthrenus verbasci and Dermestes maculates; Anobiidae such as Lasioderma serricorne; Epilachna such as Epilachna vigintioctopunctata; Scolytidae such as Lyctus brunneus and Tomicus piniperda; Bostrychidae; Ptinidae; Cerambycidae such as Anoplophora malasiaca; Agriotes spp., And Paederus fuscipes.
Orthoptera: Migratory locust, Gryllotalpa africana, Oxya yezo20 ensis, Oxya japonica, and Gryllidae.
Hymenoptera: Formicidae such as Monomorium pharaosis,
Formica fusca japonica, Ochetellus glaber, Pristomyrmex pungens, Pheidole noda, Acromyrmex spp., And Solenopsis spp .; Vespidae; Betylidae; and Tenthredinidae such as Athalia rosae and Athalia japonica.
Nematoda: Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae, and Pratylenchus neglectus.
Blattodea: Blattella germanica, Periplaneta fuliginosa, Periplane30 ta americana, Periplaneta brunnea, and Blatta orientalis.
Acarina: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oligonychus spp .; Eri60 / 85 ophyidae such as Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus schlechtendali; Tarsonemidae such as Polyphagotarsonemus tatus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae; Ixodidae such as Haemaphysalis longicornis, Haemaphysalis fiava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophilus microplus, and Rhipicephalus sanguineus; Acaridae such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides ptrenyssnus; Cheyletidae such as Che10 yletus eruditus, Cheyletus malaccensis, and Cheyletus moorei; Dermanyssidae such as Ornithonyssus bacoti, Ornithonyssus sylvairum, and Dermanyssus gallinae: Trombiculidae such as Leptotrombidium akamushi; and Araneae such as Chiracanthium japonicum and Latrodectus hasseltii.
The pest control agent of the present invention contains the present compound and an inert vehicle. Generally, the pest control agent of the present invention is a formulation such as an emulsion, a solution in oil, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a fumigation agent, a poison bait, and a resin formulation which are obtained by mixing the present compound and an inert vehicle such as a solid vehicle, a liquid vehicle and a gaseous vehicle, and also adding a surfactant and another adjuvant for formulation, if necessary.
The pest control agent of the present invention normally contains the present compound in an amount of 0.01% to 95% by weight.
Examples of the solid carrier to be employed for formulation include a fine powder and a clay granule (such as kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay), synthetic hydrated silicon oxide, talc, ceramics, other minerals inorganic (such as, silica, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica) or chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride).
61/85
Examples of the liquid carrier include water, alcohols (such as methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, and phenoxyethanol), ketones (such as acetone, methyl ethyl ketone, and cyclohexanone) , aromatic hydrocarbons (such as toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylethylene, and methylnaphthalene), aliphatic hydrocarbons (such as hexane, cyclohexane, kerosene, and light oil), esters (such as ethyl acetate, butyl acetate, isopropyl milistate, ethyl oleate, diisopropyl adipate, diisopropyl adipate, and propylene glycol acetate monomethyl ether), nitriles (such as acetonitrile and isobutyronitrile), ethers (such as diisopropyl ether, 1,4 -dioxane, dimethyl ether ethylene glycol, dimethyl ether diethylene glycol, monomethyl ether diethylene glycol, monomethyl ether propylene glycol, monomethyl ether dipropylene glycol, and 3-methoxy-3methyl-1-butanol), acid amides (such as Ν, Ν- dimethylformamide and N, Ndi methylacetamide), halogenated hydrocarbons (such as dichloromethane, trichloroethane, and tetrachlorocarbon), sulfoxides (such as dimethyl sulfoxide), propylene carbonate, and vegetable oils (such as soybean oil and cottonseed oil).
Examples of the gaseous vehicle include fluorocarbons, butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.
Examples of the surfactant include nonionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, and polyethylene glycol fatty acid ester; and anionic surfactant such as salts of alkylsulfonic acid, salts of alkylbenzenesulfonic acid and salts of alkyl sulfonic acid.
Examples of the other formulation aid include binders, dispersants, colorants and stabilizers, and particularly, for example, casein, gelatin, polysaccharides (such as starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, polymers soluble in synthetic water (such as polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acid), PAP (acid isopropyl phosphate), BHT (2,6-di-t-butyl-4-methylphenol), and BHA (a mixture of 2-t-butyl- 4-methoxyphenol and 3-t-butyl-4methoxyphenol).
The method for controlling pests of the present invention is to apply
62/85 an effective amount of the present compound to pests directly and / or pest habitats (such as plant, soil, at home, and in the body of animals). The present compound is normally employed as the pest control agent of the present invention in the pest control method of the present invention.
When the pest control agent of the present invention is employed for pest control in agriculture, the amount of application is normally from 1 to 10,000 g as the present compound of 10,000 m ² . When the pest control agent of the present invention is a formulation of emulsions, wettable or flowable powders, it is usually applied after dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm. When the pest control agent of the present invention is a formulation of granules or powders, it is normally applied as such.
Formulations and dilute aqueous solutions of the formulation can be sprayed directly onto the plant to be protected from pests, or can be applied to the soil to control pests living in a soil.
In addition, resin formulations in the form of coatings or strips can be applied by a method such as ventilating around the plants, distending around the plants, and depositing on the soil surface at the base of the plant.
When the pest control agent of the present invention is employed for pest control at home, the amount of application is normally 0.01 to 1,000 mg as the present compound of 1 m ² in the case of application to a flat surface, and from 0.01 to 500 mg as the present compound of 1 m ³ in the case of application by area. When the pest control agent of the present invention is a formulation of emulsions, wetted or flowable powders, they are usually applied after dilution with water to have an active ingredient concentration of 0.1 to 1,000 ppm. When the pest control agent of the present invention is a formulation of solutions in oil, aerosols, fumigation agents and poison baits, they are normally applied as such.
63/85
The pest control agent of the present invention can be used on farmland plots on which crops shown below are grown.
Agriculture crops: corn, rice, wheat, barley, rye, oats, 5 sorghum, cotton, soybeans, peanuts, sarrazine, beets, rapeseed, sunflower, sugar cane, and tobacco;
Vegetables: Solanaceae vegetables (such as eggplant, tomato, green pepper, hot pepper, and potato), Cucurbitaceae vegetables (such as cucumber, pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (such as Japanese radish, turnip, horseradish , kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli and cauliflower), Compositae vegetables (such as burdock, chrysanthemum wreath, artichoke, and lettuce), Liliaceae vegetables (such as Welsh onion, onion, garlic, and asparagus ), Umbelliferae vegetables (such as carrots, parsley, celery, and parsnips), Chenopodiaceae vegetables (such as spinach, and Swiss chard), Labiatae vegetables (such as Japanese basil, mint, and basil), strawberry, sweet potatoes, yams, and aroid;
Fruit trees: pomegranate fruits (such as apple, common pear, Japanese pear, Chinese quince, and quince), fleshy fruit of the rooster (such as peach, plum, nectarine, Japanese plum, cherry, apricot, and prune), plants citrus (such as mandarin Satsuma, orange, lemon, lime and grapefruit), nuts (such as chestnut, walnut, hazelnut, almond, pistachio, cashew, and macadamia nut), soft fruits (such as blueberry species , cranberry, blackberry and raspberry), grape, persimmon, olive oil, loquat, banana, coffee, date, coconut tree, and oil palm;
Trees other fruit trees: tea, blackberry, flowering trees (such as azalea, camellia, hydrangea, sasanqua, lllicium anisatum, cherry, tulip poplar, crepe myetle, and orange osmanthus), street trees (such as ash tree , birch, dogwood, eucalyptus, ginco, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, flat tree, zelkova, Japanese life-tree, pine tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm and horse chestnut), sweet viburnum, Podocar64 / 85 pus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, and Chainese howthorn.
Lawn: emerald (such as Japanese lawn grass and mascarene grass), Bermuda grass (such as Cynodon dactylon), curved grass (such as low curved grass, Agrostis stolonifera, and Agrostis tenuis), field grass (such as grass Kentucky field and rugged field grass), twig (such as sheep grass, chewing twig, and creeping twig), ryegrass (such as perennial ryegrass and chaff), rooster foot, and timothy grass;
Others: flowers (such as rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners, gypsophila, gerbera, vase marigold, sage, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamene, orchid, lily of the valley, lavender, stem, ornamental cabbage, primrose, poinsttia, gladiolus, cattleya, daisy, cymbidium, and begonia), biofuel plants (such as Jatropha curcas, saffron, Camelina alyssum, switchgrass, miscanthus, yellow grass, Arundo dona , kenaf, cassava, willow, and seaweed), and foliage plant.
The crops include genetically modified crops.
The pest control agent of the present invention can be used as a mixture with or with other insecticides, mites, nematocides, fungicides, plant growth regulators, herbicides, and synergists. Examples of the active ingredients of the insecticide, acaricide, nematocide, fungicide, plant growth regulator, herbicide, and synergistic are shown below.
Active ingredients of insecticides:
(1) Organic phosphorus compounds:
Acephate, aluminum phosphide, butathiophes, cadusafes, chlorethoxyphos, chlorphenvenins, chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP, DCIP (diazinone, dichlorodi-isopropyl ether), diclofention: ECP, dichlorvos: DDVP, dichloride, dimethoxy , etion, etoprofos, etrimfos, fention: MPP, fenitrotion: MEP, fostiazato, formotion, hydrogen phosphide, isofenfos, isoxation, malation, mesulfenfos, metidation: DMTP, monocrotofos, naled: BRP, oxidepro65 / 85 fos: ESP, paration, fosalone, fosmet: PMP, pirimiphos-methyl, pyridafention, quinalfos, phentoate: PAP, profenofos, propafos, protiofos, pirachlorfos, salition. sulprofos, tebupirimfos, temefos, tetrachlorvinfos, terbufos, tiometon, triclorfon: DEP, vamidotion, forato, and cadusafos.
(2) Carbamate Compounds:
Alanicarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloetocarb, etiofencarb, phenobucarb, fenotiocarb, fenoxicarb, furatiocarb, isoprocarb: MIPC, metolcarb, metomila, metiocarb, NAC, oxam, piram, xylilcarb, and aldicarb.
(3) Pyrethroid Compounds:
Acrinatrin, aletrine, benflutrin, beta-cyfluthrin, bifenthrin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, sphenopherrin, etofenprox, flufenetrin, flufethrin, flufethin, flufenetrin, flufethrine, flufethetrine, flufethin, flufethetrine, flufethrine, flufethin, sigma-cypermethrin, silafluofen, teflutrin, tralometrine, transflutrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambdacialotrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate (methlutrin, , 3RS; 1RS, 3SR) 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl, -2,2-dimethyl-3-prop-1enylcyclopropanecarboxylate, (EZ) - (1 RS, 3RS; 1 RS, 3,5R) 2,3,5,6-tetrafluoro-4-methylbenzyla -2,2-dimethyl-3-prop-1 -enylcyclopropanecarboxylate, and (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- 2,3,5,6-tetrafluoro-4 (methoxymethyl) benzyl (2methyl-1-propenyl) cyclopropanecarboxylate.
(4) Nereistoxin Compounds:
Cartap, bensultap, tiocyclam, monosultap, and bissultap.
(5) Neonicotinoid compounds:
Imidacloprid, nitenpiram, acetamipride, thiamethoxam, thiacloprid, dinotefuran, and clothianidin.
(6) Benzoylurea Compounds:
Chlorfluazuron, bistrifluron, diafentiuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron.
66/85 (7) Phenylpyrazole Compounds:
Acetoprol, etiprol, fipronil, vaniliprol, pyriprol, and pirafluprol.
(8) Bt Toxins:
Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;
(9) Hydrazine compounds:
Chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
(10) Organic chlorine compounds:
Aaldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
(11) Other insecticidal active ingredients:
Machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorfenapyr, cyantraniliprol, ciromazine, DD (1,3Dichloropropene), emamectin-benzoate, phenazaquin, flupirazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, pyrimidine, pyrimethoxine, pyrimethoxine, pyrimethoxine, pyrimethoxine, pyrimethoxine, pyrimethoxidine , tolfenpirade, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerin, flonicamide, flurinfen, formethanate, metam-ammonium, metam-sodium, metho-sodium, bromide potassium, protrifenbute, spiromesifene, sulfoxaflor, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, espinetoram, chlorantraniliprol, tralopyril, cyantraniliprol, A compound of the following formula (K):
on what:
R ¹⁰⁰ is chlorine, bromine, or a trifluoromethyl group, R ²⁰⁰ is chlorine, bromine, or a methyl group, and R ³⁰⁰ is chlorine, bromine, or a cyano group, and a compound of the following formula (L):
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on what:
R ¹⁰⁰⁰ is chlorine, bromine, or iodine.
Acaricide active ingredients:
Acequinocyl, amitraz, benzoxime, biphenate, bromopropylate, 5 quinomethionate, chlorobenzylate, CPCBS (chlorfenson), clofentezine, ciflumetofen, Kelthane (dicofol), ethoxyzol, fenbutatin oxide, phenothiocarb, propoxyxy, fluoxyoxy, fluoxyoxy, fluoxyoxy, fluoxyoxy , pyridaben, pyrimidiphene, tebufenpirade, tetradifon, spirodiclofen, spiromesifene, spirotetramat, amidoflumet, and cyienopirafen.
Nematocide active ingredients:
DCIP, fosthiazate, levamisole hydrochloride (levamisole), methylisothiocyanate, morantel tartrate, and imiciafos.
Active fungicide ingredients:
Azol fungicidal compounds such as propiconazole, protioco15 nazol, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, diphenoconazole, cyproconazole, metconazole, triflumizol, hexazol, tincanazol, methanol, tracetone , and flutriafol;
Cyclic amine fungicidal compounds such as fenpropimorph, tridemorph, and phenpropidin;
Benzimidazole fungicidal compounds such as carbendezin, benomyl, thiabendazole, and thiophanate-methyl;
Procimidone; cyprodinil; pyrimethanil; dietofencarb; tiuram; fluazinam; mancozeb; iprodione; vinclozoline; chlorothalonil; captano; mepanipi25 kidney; fenpiclonil; fludioxonil; diclofluanide; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; piribencarb; spiroxamine; quinoxyphene; fenhexamide; famoxadone; fenamidone; zoxamide; etaboxam; amisulfon; iprovalicarb; bentiavali68 / 85 carb; cyzofamide; mandipropamide; boscalide; pentiopyrade; metrafenone; fluopyran; bixafen; cyflufenamide; proquinazide; isothianyl, and thiadinyl.
Active herbicide ingredients:
(1) Phenoxygraxic acid herbicidal compounds:
2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide.
(2) Benzoic acid herbicidal compounds:
2,3,6-TBA, dicamba, clopyralide, picloram, aminopyralide, quinclorac, and quinmerac.
(3) Urea herbicidal compounds:
Diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebutiuron, metabenztiazuron, cumiluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds:
Atrazine, ametorin, cyanazine, simazine, propazine, simetrin, dimetametrin, prometrin, metribuzin, triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compounds:
Paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compounds:
Bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compounds:
Pendimethalin, prodiamine, and trifluralin.
(8) Herbicide compounds of organic phosphorus:
Amiprofos-methyl, butamiphos, bensulide, piperophos, anilophos, glyphosate, glufosinate, glufosinate-P, and bialafos.
(9) Carbamate herbicidal compounds:
Di-alate, tri-alate, EPTC, butylate, bentiocarb, esprocarb, molinate, dimepiperate, swep, chlorprofam, fenmedipham, phenisofam, pyributicarb, and asulam.
(10) Acidic amide herbicidal compounds:
Propanyl, propizamide, bromobutide, and etobenzanide.
(11) Chloroacetanilide herbicidal compounds:
Acetochlor, alachlor, butachlor, dimetenamide, propachlor, metaza69 / 85 chlor, metolachlor, pretilachlor, tenilchlor, and petoxamide.
(12) Diphenylether herbicidal compounds;
Acifluorfen-sodium, bifenox, oxyfluorfen, lactofene, fomesafene, clomethoxyynyl, and aclonifene.
(13) Herbicidal cyclic imide compounds;
Oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentila, flumioxazin, piraflufen-ethyl, oxadiargyl, pentoxazone, flutiacet-methyl, butafenacil, benzfendizone, bencarbazone, and saflufenacil.
(14) Pyrazole herbicidal compounds;
Benzofenap, pyrazolate, pyrazoxifene, topramezone, and pyrasulfotol.
(15) Trichetone herbicidal compounds;
Isoxaflutol, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuriltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compounds:
Clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, phenoxaprop-ethyl, fluazifop-butyl, haloxifop-methyl, quizalofop-ethyl, and metamifop.
(17) Trioneoxime herbicidal compounds:
Aloxidim-sodium, setoxidim, butroxidim, cletodim, cloproxidim, cicloxidim, tepraloxidim, tralcoxidim, and profoxidim.
(18) Sulphonylurea herbicidal compounds;
Chlorosulfurone, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfurone, bensulfuron-methyl, tifensulfuronmethyl, pyrazosulfuron-ethyl, primisulfuron-methyl, nicosulfurone, aminosulfurone, aminosulfurone, prosinosulfurone, kosulfurone, kosulfurone, kosulfurone, kosulfurone, kosulfuron, methyl, triflussulfuron-methyl, flazasulfurone, cyclosulfamuron, flupirsulfurone, sulfosulfurone, azinsulfurone, ethoxysulfurone, oxassulfurone, iodosulfuron-methyl-sodium, foransulfurone, mesosulfuron-methyl, trifloxysulfone, trifloxysulfone, trifloxysulfone, trifloxysulfone, trifloxysulfone.
(19) Imidazolinone herbicidal compounds:
Imazametabenz-methyl, imazametapyr, imazamox, imazapyr, ima70 / 85 zaquin, and imazetapyr.
(20) Sulfonamide herbicidal compounds:
Flumetsulam, metosulam, diclosulam, florasulam, chloransulammethyl, penoxsulam, and pyroxsulam.
(21) Pyrimidinyloxybenzoic acid herbicidal compounds:
Piritiobac-sodium, bispiribac-sodium, piriminobac-methyl, pyribenzoxim, pyriftalide, and pirimisulfan.
(22) Other herbicidal compounds:
Bentazon, bromacila, terbacila, chlortiamide, isoxaben, dinoseb, amitrol, cinmetilina, tridifano, dalapon, diflufenzopyr-sodium, dithiopir, tiazopir, flucarbazone-sodium, propoxycarbazone-sodium, mefenacetam, flafenacetam, fenacetam, flefacetam, fefenacetam, flafenacetam, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamide, clomazone, amicarbazone, pinoxaden, pyraclonyl, pyroxassulfone, thiencarbazone-methyl, aminocyclopyrachlor, ipfencarzoline and meth.
Active synergistic ingredients:
Piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10trinorborn-5-ene-2,3-dicarboxyimide (MGK 264), N-decliimidazole, WARFantiresistente, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), tphenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.
Examples
The present invention is described in more detail by the Production Examples, Formulation Examples and Test Examples, however the present invention is not limited to these Examples.
First, the Production Examples of the present compound are shown below.
Production Example 1
A mixture of N ¹ -methyl-4-trifluoromethyl-benzene-1,2-diamine (1.14 g), 5-chloro-pyrimidine-4-carboxylic acid (1.14 g), WSC (1.02 g) , and pyridine (12 ml) was stirred at 115 ° C for 3 hours. After resting to cool to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate
71/85 magnesium, and concentrated under reduced pressure. To the resulting residue, para-toluenesulfonic acid monohydrate (3.42 g) and xylene (12 ml) were added, and the reaction mixture was stirred at 140 ° C for 3 hours with the removal of water using a Dean- Stark. After resting to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.40 g of the compound of the formula:
Production Example 2
To a mixture of sodium ethyl mercaptanate (0.16 g) and DMF (4 ml), 2- (5-chloropyrimidin-4-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (Compound 14) ( 0.40 g) was added under ice cooling, and the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.39 g of the compound of the formula:
Production Example 3
To a mixture of 2- (5-ethylthiopyrimidin-4-yl) -1-methyl-5-trifluoromethyl1 H-benzimidazole (Compound 7) (0.29 g) and chloroform (4 ml), 69-75% acid 3 -chloroperbenzoic (0.28 g) was added under ice cooling. After stirring the reaction mixture at room temperature for 0.5 hour, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the reaction mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.18 g of the compound of the formula:
and 0.11 g of the compound of the formula:
θ ^Η 3 (Compound 9).
Production Example 4
A mixture of 4,6-dichloro-5-ethylpyrimidine (10 g), 2-furylboronic acid (6.33 g), tetracis (triphenylphosphine) palladium (1.94 g), dimethoxyethane (100 ml), and sodium carbonate solution (2 mol / l) (60 ml) was stirred at 70 ° C for 2 hours and at 80 ° C for 2 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 6.06 g of 4-chloro-5-ethyl-6- (furan-2-yl) -pyrimidine.
4-chloro-5-ethyl-6- (furan-2-yl) -pyrimidine:
¹ H-NMR (CDCI ₃ ) δ: 1.31 (3H, t), 3.14 (2H, q), 6.62 (1H, dd), 7.33 (1 H, dd), 7.68 (1H, dd), 8.76 (1H, s).
A mixture of 4-chloro-5-ethyl-6- (furan-2-yl) -pyrimidine (3.0 g), hydrazine monohydrate (3.0 g), triethylamine (3.0 g), and THF ( 20 ml) was stirred at reflux for 2 hours. To the mixture, hydrazine monohydrate (1 g) was added, and stirred under reflux for 3 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water
73/85 was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to provide 2.85 g of [5-ethyl-6- (furan-2-yl) -pyrimidin-4-yl] -hydrazine.
[5-ethyl-6- (furan-2-yl) -pyrimidin-4-yl] -hydrazine:
hn-nh ₅ ¹ H-NMR (CDCb) δ: 1.26 (3H, t), 2.77 (2H, q), 4.09 (2H, brs), 6.22 (1H, brs), 6 , 56 (1 H, dd), 7.11 (1 H, dd), 7.60 (1H, dd), 8.58 (11-1, s).
To a mixture of [5-ethyl-6- (furan-2-yl) -pyrimidin-4-yl] -hydrazine (2.85 g), acetonitrile (50 ml), and para-toluenesulfonyl chloride (2.86 g), pyridine (2.37 g) was added under ice cooling, and the reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture, water (50 ml) was added, and precipitated solids were collected by filtration. The solid was sequentially washed with water (20 ml) and acetonitrile (20 ml), and dried. To the resulting solid, sodium hydroxide (8.1 g), ethylene glycol (100 ml), and water (50 ml) were added, and stirred under reflux for 3 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 2.03 g of 5-ethyl-4-furan-2-yl-pyrimidine.
5-ethyl-4- (furan-2-yl) -pyrimidine:
¹ H-NMR (CDCb) δ: 1.31 (3H, t), 2.99 (2H, q), 6.61 (1H, dd), 7.29 (1 H, dd), 7.67 ( 1 H, dd), 8.59 (1H, s), 9.04 (1H, s).
A mixture of 5-ethyl-4- (furan-2-yl) -pyrimidine (2.03 g), acetone (70 ml), and water (35 ml) was stirred at 50 ° C, potassium permanganate (15 g ) was added to it over 15 minutes, and the reaction mixture was stirred under reflux for 1 hour. After standing to cool the reaction mixture to room temperature, to the reaction mixture, hydro carbonate solution25
74/85 saturated aqueous sodium genius was added, and extracted with tert-butyl methyl ether. To the resulting aqueous layer, hydrochloric acid was added, and extracted with methyl tert-butyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to provide 1.14 g of 5-etH-pyrimidine-4-carboxylic acid.
5-ethyl-pyrimidine-4-carboxylic acid:
¹ H-NMR (CDCI ₃ ) δ: 1.33 (3H, t), 3.22 (2H, q), 8.90 (1H, s), 9.18 (1H, s).
To a mixture of 3-amino-5-trifluoromethylpyridin-2-ol (0.27 g), WSC (0.58 g), and pyridine (10 ml), 5-ethyl-pyrimidine-4-carboxylic acid was added under ice-cooling, and the reaction mixture was stirred at 80 ° C for 10 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.26 g of 5-ethyl-N- (2-hydroxy-5-trifluoromethyl-pyridin-3-yl) pyrimidine-4-carboxamide.
5-ethyl-N- (2-hydroxy-5-trifluoromethyl-pyridin-3-yl) -pyrimidine-4carboxamide:
To a mixture of 5-ethyl-N- (2-hydroxy-5-trifluoromethyl-pyridin-3-yl) pyrimidine-4-carboxamide (0.26 g), triphenylphosphine (0.24 g), and THF (20 ml ), diethyl azodicarboxylate (40% toluene solution) (0.41 ml) was added under ice cooling, and the reaction mixture was stirred at 50 ° C for 10 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ace25
75/85 ethyl touch. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to provide 0.19 g of the formula:
A mixture of N ¹ -methyl-4-trifluoromethyl-benzene-1,2-diamine (0.29 g), pyrimidine-4-carbaldehyde (0.20 g), sodium sulfite (0.48 g), and DMF (8 ml) was stirred at 80 ° C for 2 hours, then at 100 ° C for 2.5 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.20 g of the compound of the formula:
^ch 3 (Compound 2).
Production Example 6
To a mixture of N ² -methyl-5-trifluoromethylpyridine-2,3-diamine (2.65 g), WSC (2.66 g), 4-dimethylaminopyridine (0.10 g), THF (10 ml), and pyridine (10 ml), 5-chloropyrimidine-4-carboxylic acid was added under ice-cooling, and the reaction mixture was stirred at 50 ° C for 8 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 1.77 g of 5-chloro-N- (2-methylamino-5-trifluoromethyl-pyridin-3-yl) -pyrimidine-425 carboxamide.
5-chloro-N- (2-methylamino-5-trifluoromethyl-pyridin-3-yl) -pyrimidine-4carboxamide:
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ch ₃ ¹ H-NMR (CDCI ₃ ) δ: 9.47-9.39 (1H, m), 9.19 (1H, s), 9.00 (1H, s), 8.39 (1H, s ), 7.89 (1H, s), 5.02-4.88 (1H, m), 3.10 (3H, d).
To a mixture of 5-chloro-N- (2-methylamino-5-trifluoromethyl-pyridin3-yl) -pyrimidine-4-carboxamide (1.77 g) and xylene (100 ml), para-toluenesulfonic acid monohydrate (2 , 23 g) was added at room temperature, and the reaction mixture was stirred at 170 ° C for 2 days. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.79 g of the compound of the formula:
Production Example 7
To a mixture of 60% sodium hydride (in oil) (0.04 g) and
DMF (6 ml), 2,2,2-trifluoroethanol (0.05 g) was added dropwise under ice cooling, and the reaction mixture was stirred for 5 minutes. After Compound 13 (0.12 g) was added, the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.14 g of the compound of the formula:
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f ₃ c
ch ₃ (Compound 3).
Production Example 8
To a mixture of compound 13 (0.36 g) and DMF (20 ml), sodium ethyl mercaptanate (0.34 g) was added under ice cooling, and the reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, water was added, and precipitated solids were collected by filtration. The solid was washed with water, and dried to provide 0.35 g of the compound of the formula;
Production Example 9
To a mixture of compound 4 (0.24 g) and chloroform (20 ml), 6975% 3-chloroperbenzoic acid (0.28 g) was added under ice cooling, and the reaction mixture was stirred at room temperature for 3 ,5 hours. Then, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.09 g of the compound of the formula:
and 0.13 g of the compound of the formula:
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F, C
(Compound 6).
Production Example 10
A mixture of 2-amino-4-trifluoromethyl-phenol (0.27 g), 5-ethyl-pyrimidine-4-carboxylic acid (0.27 g), WSC (0.25 g), and pyridine (5 ml) was stirred at 80 ° C for 1 hour, at 100 ° C for 1.5 hour, and at 115 ° C for 0.5 hour. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel to provide 0.34 g of 5-ethyl-N- (2-hydroxy-5-trifluoromethyl-phenyl) pyrimidine-4-carboxamide.
5-ethyl-N- (2-hydroxy-5-trifluoromethyl-phenyl) -pyrimidine-4-carboxamide:
¹ H-NMR (CDCb) δ: 10.52 (1H, brs), 9.18 (1H, s), 8.87 (1H, s), 7.64 (1 H, d), 7.43 ( 1 H, dd), 7.13 (1 H, d), 3.26 (2H, q), 1.35 (3H, t).
The Compound (0.21 g) of the formula:
F, C
(Compound 10) was produced according to Production Example 4, replacing 5-ethyl-N- (2-hydroxy-5-trifluoromethyl-pyridin-3-yl) -pyrimidine-4-carboxamide with 5-ethyl-N- (2-hydroxy-5-trifluoromethyl-phenyl) -pyrimidine-4-carboxamide.
The compounds produced by a Production Method similar to the Production Examples above are shown in the following table.
The compound of formula (1):
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where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Y, and Z represent a combination shown in Tables 12-13.
Table 12
Compound R ¹ R ² R ³ R ⁴ R ⁵ X Y Z 1 H H H cf ₃ H = CH- = CH- 0 2 H H H cf ₃ H = CH- = CH- -N (CH ₃ ) - 3 H H OCH2CF3 cf ₃ H = CH- N -N (CH ₃ ) - 4 H H SCH ₂ CH ₃ cf ₃ H = CH- N -N (CH ₃ ) - 5 H H S (O) CH ₂ CH ₃ cf ₃ H = CH- N -N (CH ₃ ) - 6 H H S (O) ₂ CH ₂ CH ₃ cf ₃ H = CH- N -N (CH ₃ ) - 7 H H sch ₂ ch ₃ cf ₃ H = CH- = CH- -N (CH ₃ ) 8 H H S (O) CH ₂ CH ₃ cf ₃ H = CH- = CH- -N (CH ₃ ) - 9 H H S (O) ₂ CH ₂ CH ₃ cf ₃ H = CH- = CH- -N (CH ₃ ) - 10 H H ch ₂ ch ₃ cf ₃ H = CH- = CH- 0 11 H H ch ₂ ch ₃ cf ₃ H = CH- N -N (CH ₃ ) - 12 H H ch ₂ ch ₃ cf ₃ H = CH- = CH- -N (CH ₃ ) - 13 H H Cl cf ₃ H = CH- N -N (CH ₃ ) - 14 H H Cl cf ₃ H = CH- = CH- -N (CH ₃ ) - 15 H H ch ₂ ch ₃ cf ₃ H = CH- N 0
Table 13
Compound R ¹ R ² R ³ R ⁴ R ⁵ X Y Z 16 H H Cl SCF ₃ H = CH- N -N (CH ₃ ) - 17 H H SCH ₂ CH ₃ scf ₃ H = CH- N -N (CH ₃ ) - 18 H H S (O) CH ₂ CH ₃ scf ₃ H = CH- N -N (CH ₃ ) - 19 H H S (O) ₂ CH ₂ CH ₃ scf ₃ H = CH- N -N (CH ₃ ) - 20 H H Cl cf ₂ cf ₃ H = CH- N -N (CH ₃ ) - 21 H H SCH ₂ CH ₃ cf ₂ cf ₃ H = CH- N -N (CH ₃ ) - 22 H H S (O) CH ₂ CH ₃ cf ₂ cf ₃ H = CH- N -N (CH ₃ ) -
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23 H H S (O) ₂ CH ₂ CH ₃ cf ₂ cf ₃ H = CH- N -N (CH ₃ ) - 24 H H och ₂ ch ₃ cf ₃ H = CH- = CH- -N (CH ₃ ) -
The ¹ H-NMR data for the compounds listed in Tables 12-13 are shown below.
Compound 1 ¹ H-NMR (CDCIs) δ: 7.78 (1H, d), 7.83 (1H, d), 8.18 (1H, s), 8.31 (1H, dd), 9.05 (1H, d), 9.49 (1H, d).
Compound 2 ¹ H-NMR (CDCI ₃ ) δ: 9.35 (1H, d), 8.93 (1H, d), 8.42-8.40 (1H, m), 8.15-8.14 (1H, m), 7.66-7.63 (1H, m), 7.57 (1H, d), 4.40 (3H, s).
Compound 3 ¹ H-NMR (CDCl3) δ: 9.19 (1H, s), 8.81 (1H, s), 8.79 (1H, m), 8.41 (1H, m), 4.72 -4.66 (2H, m), 4.15 (3H, s).
Compound 4 ¹ H-NMR (CDCl3) δ: 9.12 (1H, s), 8.85 (1H, s), 8.79 (1H, m), 8.46 (1H, m), 4.23 (3H, s), 3.10 (2H, q), 1.43 (3H, t).
Compound 5 ¹ H-NMR (CDCl3) δ: 9.59 (1H, s), 9.48 (1H, s), 8.83 (1H, m), 8.40 (1H, m), 4.45 (3H, s), 3.70-3.65 (1H, m), 3.25-3.20 (1H, m), 1.54-1.48 (3H, m).
Compound 6 ¹ H-NMR (CDCl3) δ: 9.60 (1H, s), 9.52 (1H, s), 8.81 (1H, d), 8.36 (1 H, d), 4, 04 (3H, s), 4.04-3.99 (2H, m), 1.45 (3H, t).
Compound 7 ¹ H-NMR (CDCl3) δ: 9.09 (1H, s), 8.81 (1H, s), 8.24-8.22 (1H, m), 7.67-7.63 ( 1H, m), 7.56 (1H, d), 4.13 (3H, s), 3.07 (2H, q), 1.41 (3H, t).
Compound 8 ¹ H-NMR (CDCb) δ: 9.55 (1H, s), 9.43 (1H, s), 8.15-8.13 (1H, m), 7.72-7.68 ( 1H, m), 7.62 (1H, d), 4.39 (3H, s), 3.77-3.67 (1H, m), 3.28-3.18 (1H, m), 1 , 52 (3H, t).
Compound 9 ¹ H-NMR (CDCb) δ: 9.57 (1H, s), 9.49 (1H, s), 8.13-8.10 (1H, m), 7.70-7.66 ( 1H, m), 7.59 (1 H, d), 4.05 (2H, q), 3.95 (3H, s), 1.44 (3H, t).
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Compound 10 ¹ H-NMR (CDCI ₃ ) δ: 9.32 (1H, s), 8.90 (1H, s), 8.21-819 (1H, m), 7.83 (1 H, d), 7 , 78-7.74 (1H, m), 3.37 (2H, q), 1.40 (3H, t).
Compound 11 ¹ H-NMR (CDCl3) δ: 9.25 (1H, s), 8.88 (1H, s), 8.77 (1H, m), 8.38 (1H, m), 4.15 (3H, s), 3.13 (2H, q), 1.29 (3H, t)
Compound 12 ¹ H-NMR (CDCl3) δ: 9.22 (1H, s), 8.85 (1H, s), 8.16-8.14 (1H, m), 7.67-7.63 ( 1H, m), 7.56 (1 H, d), 4.04 (3H, s), 3.11 (2H, q), 1.25 (3H, t).
Compound 13 ¹ H-NMR (CDCl3) δ: 9.29 (1H, s), 9.02 (1H, s), 8.81 (1H, d), 8.45 (1H, d), 4.13 (3H, s).
Compound 14 ¹ H-NMR (CDCl3) δ: 9.26 (1H, s), 8.99 (1H, s), 8.23-8.20 (1H, m), 15 7.70-7.65 (1H, m), 7.58 (1 H, d), 4.03 (3H, s).
Compound 15 ¹ H-NMR (CDCl3) δ: 9.35 (1H, s), 8.93 (1H, s), 8.82 (1H, d), 8.49 (1H, d), 3.33 (2H, q), 1.41 (3H, t).
Compound 16 ¹ H-NMR (CDCb) δ: 9.28 (1H, s), 9.02 (1H, s), 8.75 (1H, d), 8.51 (1H, d), 4.11 (3H, s).
Compound 17 ¹ H-NMR (CDCl3) δ: 9.11 (1H, s), 8.84 (1H, s), 8.72 (1H, s), 8.52 (1H, s), 4.21 (3H, s), 3.10 (2H, q), 1.43 (3H, t).
Compound 18 ¹ H-NMR (CDCb) δ: 9.58 (1H, s), 9.47 (1H, s), 8.77 (1H, d), 8.47 (1 H, d), 4, 43 (3H, s), 3.74-3.60 (1H, m), 3.30-3.17 (1H, m), 1.50 (3H, t).
Compound 19 ¹ H-NMR (CDCb) δ: 9.59 (1 H, s), 9.51 (1H, s), 8.75 (1H, d), 8.42 30 (1 H, d), 4.07-3.97 (5H, m), 1.45 (3H, t)
Compound 20 ¹ H-NMR (CDCb) δ: 9.29 (1H, s), 9.02 (1H, s), 8.75 (1H, d), 8.43
82/85 (1H, d), 4.13 (3H, s).
Compound 21 ¹ H-NMR (CDCb) δ: 9.12 (1H, s), 8.85 (1H, s), 8.73 (1H, s), 8.44 (1 H, s), 4, 23 (3H, s), 3.19-3.03 (2H, m), 1.48-1.38 (3H, m).
Compound 22 ¹ H-NMR (CDCb) δ: 9.59 (1H, s), 9.48 (1H, s), 8.78 (1H, s), 8.37 (1 H, s), 4, 45 (3H, s), 3.74-3.61 (1H, m), 3.31-3.18 (1H, m), 1.53-1.46 (3H, m).
Compound 23 ¹ H-NMR (CDCb) δ: 9.60 (1H, s), 9.52 (1H, s), 8.76 (1 H, d), 8.33 (1 H, d), 4 , 06-3.97 (5H, m), 1.45 (3H, t).
Compound 24 ¹ H-NMR (CDCb) δ: 9.14 (1H, s), 8.75 (1H, s), 8.15-8.13 (1H, m), 7.66-7.62 ( 1H, m), 7.55-7.53 (1H, m), 4.63 (2H, q), 4.04 (3H, s).
Formulation examples are shown below. The part is based on weight.
Formulation Example 1
Any of Compounds 1-24 (10 parts) is dissolved in a mixture of xylene (35 parts) and N, N-dimethylformamide (35 parts), and to the mixture is added polyoxyethylene styrene phenyl ether (14 parts) and dodecylben20 zenosulfonate calcium (6 parts), and stirred to provide emulsions of each compound.
Formulation Example 2
Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), synthetic hydrated silicone oxide powder (20 parts) and diatomite (54 parts) are mixed, then any of the Compounds 1 is added to the mixture -24 (20 parts), and mixed to provide wetting powders for each compound.
Formulation Example 3
To any of Compounds 1-24 (2 parts) is added synthetic hydrated silicone oxide powder (1 part), calcium lignin sulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts) , and mixed. Then, an appropriate amount of
83/85 water, also stirred, granulated with a granulator, and air-dried to provide granules of each compound.
Formulation Example 4
Any of Compounds 1-24 (1 part) is dissolved in an appropriate amount of acetone. To the mixture is added synthetic hydrated silicone oxide powder (5 parts), PAP (0.3 part), and Fubasami clay (93.7 parts), and well stirred. Then, acetone is removed by evaporation to provide the powders of each compound.
Formulation Example 5
A mixture (weight ratio = 1: 1) of ammonium salt of polyoxyethylene alkyl ether sulfate and white carbon (35 parts), any of Compounds 1-24 (10 parts), and water (55 parts) are mixed , sprayed by a wet grinding method to provide the formulations for each compound.
Formulation Example 6
Any of Compounds 1-24 (0.1 part) is dissolved in xylene (5 parts) and trichloroethane (5 parts), and mixed with deodorized kerosene (89.9 parts) to provide oil solutions of each compound.
Formulation Example 7
Any of Compounds 1-24 (10 mg) is dissolved in acetone (0.5 ml). The mixture is added to the solid powdered animal feed (solid powder for breeding, CE-2, from CLEA Japan, Inc.), (5 g) and mixed evenly. Then, acetone is removed by evaporation to provide poison baits for each compound.
Formulation Example 8
Any of Compounds 1-24 (0.1 part) and Neothiosol (Chuo
Kasei Co. Ltd.) (49.9 parts) are loaded into an aerosol container. After an aerosol valve is connected to the container, dimethyl ether (25 parts) and LPG (25 parts) are loaded into the container. The container is vibrated, and a trigger is activated to provide oily aerosols of each compound. Formulation Example 9
Any of Compounds 1-24 (0.6 part), BHT (2,6-di-tert84 / 85 butyl-4-methylphenol) (0.01 part), xylene (5 parts), deodorized kerosene (3.39 parts), and an emulsifier (Atmos 300 (a trade name registered by Atmos Chemical Ltd.)) (1 part) are mixed and dissolved. The mixture and distilled water (50 parts) are loaded into an aerosol container, and a valve is turned on. Then, the propellant (LPG) (40 parts) is pressure loaded into the container through the valve to provide aqueous aerosols of each compound.
The effects of the present pest control compounds are shown in the Test Examples.
Test Example 1
After spraying, the number of surviving Aphis gossypii parasitized on cucumber leaves was examined, and a control value was calculated according to the following equation:
Control value (%) = {1 - (Cb x Tai) / (Cai x Tb)) x 100 15 where the symbols represent as follows:
Cb: the number of insects in an untreated section before treatment,
Cai: the number of insects in an untreated section under observation,
Tb: the number of insects in a section treated before treatment,
Tai: the number of insects in a section treated under observation. As a result, in the treated section of the test spray solution for each of Compounds 1-13 and 15-24, the control value of 90% or 25 plus was shown.
Test Example 2
Test spray solutions were prepared by diluting the formulations of each of Compounds 2-13 and 15-24 obtained in Formulation Example 5 with water to provide 500 ppm of an active ingredient concentration.
On the other hand, Bemisia tabaci adult was released in a tomato seedling (the third stage of the true leaf) planted in a glass of
85/85 polyethylene, and prepared to lay eggs for about 24 hours. The tomato seedling was kept in a greenhouse for 8 days. When the instar larvae hatched from the eggs, the test spray solution above was sprayed in the amount of 10 ml / cup. The cup was kept in an oven at 25 ° C. After storage for 7 days, the number of instar larvae to survive on tomato leaves was examined, and a control value was calculated according to the following equation:
Control Value (%) = {1 - (Cb x Tai) / (Cai x Tb)) x 100 where the symbols represent as follows:
Cb: the number of pests in an untreated section before treatment,
Cai: the number of pests in an untreated section under observation,
Tb: the number of pests in a section treated before treatment,
Tai: the number of pests in a section treated under observation. As a result, in the treated section of the spray test solution of each of Compounds 2-13 and 15-24, the control value of 90% or more was shown.
Industrial Applicability
The present compound has a pest control effect and is useful as an active ingredient in a pest control agent.
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权利要求:
Claims (13)
[1]
1. Pyrimidine compound, characterized by the fact that it has the formula (1):
R ¹ (1) where:
R ¹ represents hydrogen or halogen,
R ² represents hydrogen or halogen,
R ³ represents a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group
10 optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, an alkylamino group C1-C6 optionally having one or more halogens, a C2-C8 dialkylamino group
Optionally having one or more halogens, a C2-C6 alkylcarbonylamino group optionally having one or more halogens, a C2-C6 alkoxycarbonylamino group optionally having one or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, an alkoxycarbonyl group C2-C6 optionally having one or more
20 halogens, a C2-C6 alkylcarbamoyl group optionally having one or more halogens, a C2-C8 dialkylcarbamoyl group optionally having one or more halogens, a C2-C6 alkoxyalkyl group optionally having one or more halogens, a C2-C6 alkylalkyl group optionally having one or more halogens, a phenyl group optionally having one or
25 more atoms or groups selected from Group α, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group α, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a group nitro, a cyan group, or a formyl group,
Petition 870170090485, of 11/23/2017, p. 6/13
[2]
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R ⁴ and R ⁵ can be the same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having
5 one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, a C1- alkylamino group C6 optionally having one or more halogens, a C2-C8 dialkylamino group optionally having a
10 or more halogens, a C2-C6 alkylcarbonyl group optionally having one or more halogens, a C2-C6 alkoxycarbonyl group optionally having one or more halogens, a phenyl group optionally having one or more atoms or groups selected from Group α, a heterocyclic group aromatic 5-6 member optionally having one or more atoms or
15 groups selected from Group α, hydrogen, halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group, a cyano group, or a formyl group, provided that both R ⁴ and R ⁵ are not hydrogen; or R ⁴ and R ⁵ can together with the atom to which they are attached form a 5- or 6-membered ring having one or more halogens,
20 X represents nitrogen or = CR ⁶ - where R ⁶ represents hydrogen or halogen,
Y represents nitrogen or = CR ⁷ - where R ⁷ represents hydrogen or halogen,
Z represents oxygen or -NR ⁸ - where R ⁸ represents a group
25 of C1-C6 chain hydrocarbon optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, or hydrogen; and Group α consists of a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having
30 one or more halogens, halogen, a cyano group, and a nitro group.
2. Pyrimidine compound according to claim 1, characterized by the fact that R ¹ is hydrogen, and R ² is hydrogen.
Petition 870170090485, of 11/23/2017, p. 7/13
[3]
3/4
Pyrimidine compound according to claim 1 or 2, characterized in that R ³ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens , a C1-C6 alkylthio group
5 optionally having one or more halogens, a C1-C6 alkylsulfinyl group optionally having one or more halogens, a C1-C6 alkylsulfonyl group optionally having one or more halogens, hydrogen, or halogen.
[4]
Pyrimidine compound according to claim 1 or 2, characterized in that R ³ is an optionally C 1 -C ³ alkyl group
10 having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, a C1 alkylsulfonyl group -C3 optionally having one or more halogens, hydrogen, or halogen.
15
[5]
A pyrimidine compound according to claim 1 or 2, characterized in that R ³ is a C1-C3 alkylthio group optionally having one or more halogens, a C1-C3 alkylsulfinyl group optionally having one or more halogens, or one C1-C3 alkylsulfonyl group optionally having one or more halogens.
20
[6]
A pyrimidine compound according to any one of claims 1 to 5, characterized in that R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, a C1-C3 alkylthio group optionally having one or more halogens, halogen, a hydroxyl group,
25 a mercapto group, a nitro group, or a cyano group, and R ⁵ is hydrogen.
[7]
Pyrimidine compound according to any one of claims 1 to 5, characterized in that R ⁴ is a C1-C3 alkyl group having one or more fluores, a C1-C3 alkoxy group having one or more fluores, a group C1-C3 alkylthio having one or more fluores, chloro or bromo, ₅
30 and R ⁵ is hydrogen.
[8]
8. Pyrimidine compound according to any one of claims 1 to 7, characterized in that Z is oxygen, X is = CR ⁶ -,
Petition 870170090485, of 11/23/2017, p. 8/13
4/4 and R ⁶ is hydrogen.
[9]
A pyrimidine compound according to any one of claims 1 to 7, characterized in that Z is -NR ⁸ -, R ⁸ is a methyl group, X is = CR ⁶ -, and R ⁶ is hydrogen.
[10]
10. Pyrimidine compound according to any one of claims 1 to 9, characterized by the fact that Y is nitrogen.
[11]
11. Harmful arthropod control agent, characterized by the fact that it comprises the pyrimidine compound as defined in any one of claims 1 to 10, and an inert vehicle.
[12]
12. Use of the pyrimidine compound as defined in any of claims 1 to 10, characterized by the fact that it is to control harmful arthropods.
[13]
13. Method of controlling harmful arthropods, characterized in that it comprises the step of applying an effective amount of the pyrimidine compound as defined in any one of claims 1 to 10, to harmful arthropods or habitats of harmful arthropods.
Petition 870170090485, of 11/23/2017, p. 9/13

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JP5790440B2|2015-10-07|

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法律状态:
2017-08-29| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

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2018-01-02| B15K| Others concerning applications: alteration of classification|Ipc: A01N 43/54 (1980.01), A01N 43/76 (1980.01), A01N 4 |

---

2018-01-16| B09A| Decision: intention to grant|

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2018-02-27| B16A| Patent or certificate of addition of invention granted|

优先权:

---

申请号 | 申请日 | 专利标题

---

JP2010-268138|2010-12-01|

---

JP2010268138|2010-12-01|

---

PCT/JP2011/078229|WO2012074135A1|2010-12-01|2011-11-30|Pyrimidine compound and use for pest control thereof|

---