Oxadiazole compound or salt thereof, agricultural/horticultural bactericide containing the same, and method for using the same
阅读说明：本技术 噁二唑化合物或其盐类及含有该化合物的农园艺用杀菌剂、以及其使用方法 (Oxadiazole compound or salt thereof, agricultural/horticultural bactericide containing the same, and method for using the same ) 是由 藤田直弥 山下真生 于 2018-12-27 设计创作，主要内容包括：在农业及园艺等作物的生产中,病害造成的损害依然很大,由于产生了对现有药物具有耐药性的病害等原因,期待开发一种新型的农园艺用杀菌剂。本发明提供一种以通式(I)表示的化合物或其盐类为有效成分的农园艺用杀菌剂、以及其的使用方法。式中,R<Sup>1</Sup>表示(a2)(C<Sub>1</Sub>-C<Sub>6</Sub>)烷基等。R<Sup>2</Sup>表示(b1)氢原子等。R<Sup>3</Sup>表示(c1)氢原子或(c2)(C<Sub>1</Sub>-C<Sub>6</Sub>)烷基等。R<Sup>4</Sup>表示(d2)(C<Sub>1</Sub>-C<Sub>6</Sub>)烷基等。X<Sup>1</Sup>、X<Sup>2</Sup>、X<Sup>3</Sup>及X<Sup>4</Sup>表示(e1)氢原子等。Y表示氧原子等。【化学式1】<Image he="329" wi="700" file="DDA0002555085380000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(In the production of crops such as agriculture and horticulture, damage due to diseases is still large, and development of a novel agricultural or horticultural fungicide is expected due to diseases that have resistance to conventional drugs. The present invention provides a pesticide for agricultural and horticultural use containing a compound represented by the general formula (I) or a salt thereof as an active ingredientMicrobial agents, and methods of use thereof. In the formula, R 1 Denotes (a2) (C 1 ‑C 6 ) Alkyl groups, and the like. R 2 Represents (b1) a hydrogen atom or the like. R 3 Represents (C1) a hydrogen atom or (C2) (C) 1 ‑C 6 ) Alkyl groups, and the like. R 4 Denotes (d2) (C 1 ‑C 6 ) Alkyl groups, and the like. X 1 、X 2 、X 3 And X 4 Represents (e1) a hydrogen atom or the like. Y represents an oxygen atom or the like. [ chemical formula 1])
1. A compound represented by the general formula (I) or a salt thereof,
[ chemical formula 1]
In the formula, R1Represents:
(a1) a hydrogen atom;
(a2)(C1-C6) An alkyl group;
(a3)(C2-C6) An alkenyl group;
(a4)(C2-C6) An alkynyl group;
(a5)(C3-C6) A cycloalkyl group;
(a6) halo (C)1-C6) An alkyl group;
(a7) halo (C)2-C6) An alkenyl group;
(a8) halo (C)2-C6) An alkynyl group; or
(a9) Halo (C)3-C6) A cycloalkyl group,
R2represents:
(b1) a hydrogen atom;
(b2)(C1-C6) An alkyl group;
(b3)(C2-C6) An alkenyl group;
(b4)(C2-C6) Alkynyl radical；
(b5)(C3-C6) A cycloalkyl group;
(b6) halo (C)1-C6) An alkyl group;
(b7) halo (C)2-C6) An alkenyl group;
(b8) halo (C)2-C6) An alkynyl group; or
(b9) Halo (C)3-C6) A cycloalkyl group,
R3represents:
(c1) a hydrogen atom;
(c2)(C1-C6) An alkyl group;
(c3)(C2-C6) An alkenyl group;
(c4)(C2-C6) An alkynyl group;
(c5)(C3-C6) A cycloalkyl group;
(c6)(C1-C6) An alkylcarbonyl group; or
(c7)(C1-C6) An alkoxycarbonyl group, a carbonyl group,
R4represents:
(d1) a hydrogen atom;
(d2)(C1-C6) An alkyl group;
(d3)(C2-C6) An alkenyl group;
(d4)(C2-C6) An alkynyl group;
(d5)(C3-C6) A cycloalkyl group;
(d6)(C1-C6) An alkoxy group;
(d7) halo (C)1-C6) An alkyl group;
(d8) halo (C)2-C6) An alkenyl group;
(d9) halo (C)2-C6) An alkynyl group;
(d10) halo (C)3-C6) A cycloalkyl group;
(d11) halo (C)1-C6) An alkoxy group;
(d12)Ra(Rb) N radical, in which RaAnd RbIndependently of one another represent hydrogen atom(C)1-C6) Alkyl, (C)3-C6) Cycloalkyl group, (C)3-C6) Cycloalkyl (C)1-C6) Alkyl, phenyl, (C)1-C6) Alkylcarbonyl or phenylcarbonyl;
(d13) an aryl group;
(d14) aryl having 1 to 8 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d15) a heteroaryl group;
(d16) heteroaryl having 1 to 3 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d17) aryl radical (C)1-C6) An alkyl group;
(d18) aryl having 1 to 8 substituents on the ring (C)1-C6) Alkyl, the substituents are respectively and independently selected from halogen atom, cyano, nitro and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d19) heteroaryl (C)1-C6) An alkyl group;
(d20) heteroaryl (C) having 1 to 3 substituents on the ring1-C6) Alkyl, the substituents are respectively and independently selected from halogen atom, cyano, nitro and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d21) (C) having 1 to 3 substituents on the chain1-C6) Alkyl, the substituents are respectively and independently selected from cyano, (C)1-C6) Alkoxy radical, Ra(Rb) N radical (in the formula, R)aAnd RbAs described above), (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl and (C)1-C6) Alkylsulfonyl groups; or
(d22) A 3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms in the ring,
X1、X2、X3and X4Each independently represents:
(e1) a hydrogen atom;
(e2) a halogen atom;
(e3) a cyano group;
(e4) a nitro group;
(e5)(C1-C6) An alkyl group;
(e6)(C3-C6) A cycloalkyl group;
(e7)(C1-C6) An alkoxy group;
(e8) halo (C)1-C6) An alkyl group;
(e9) halo (C)1-C6) An alkoxy group;
(e10) halo (C)3-C6) A cycloalkyl group;
(e11)(C1-C6) An alkylthio group;
(e12)(C1-C6) An alkylsulfinyl group;
(e13)(C1-C6) An alkylsulfonyl group;
(e14) halo (C)1-C6) An alkylthio group;
(e15) halo (C)1-C6) An alkylsulfinyl group; or
(e16) Halo (C)1-C6) An alkyl sulfonyl group, a carboxyl group,
y represents an oxygen atom; or a sulfur atom.
2. A compound or salt thereof according to claim 1,
R1comprises the following steps:
(a2)(C1-C6) An alkyl group, a carboxyl group,
R2comprises the following steps:
(b1) a hydrogen atom, and a nitrogen atom,
R3comprises the following steps:
(c1) a hydrogen atom;
(c2)(C1-C6) An alkyl group; or
(c5)(C3-C6) A cycloalkyl group,
R4comprises the following steps:
(d2)(C1-C6) An alkyl group;
(d3)(C2-C6) An alkenyl group;
(d4)(C2-C6) An alkynyl group;
(d5)(C3-C6) A cycloalkyl group;
(d6)(C1-C6) An alkoxy group;
(d7) halo (C)1-C6) An alkyl group;
(d12)Ra(Rb) N radical, in which RaAnd RbEach independently represents a hydrogen atom or (C)1-C6) Alkyl, (C)3-C6) Cycloalkyl group, (C)3-C6) Cycloalkyl (C)1-C6) Alkyl, phenyl, (C)1-C6) Alkylcarbonyl or phenylcarbonyl;
(d13) an aryl group;
(d14) aryl having 1 to 8 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d15) a heteroaryl group;
(d17) aryl radical (C)1-C6) An alkyl group;
(d21) (C) having 1 to 3 substituents on the chain1-C6) Alkyl, the substituents are respectively and independently selected from cyano, (C)1-C6) Alkoxy radical, Ra(Rb) N radical (in the formula, R)aAnd RbAs described above. ) (C)1-C6) An alkylthio group,(C1-C6) Alkylsulfinyl and (C)1-C6) Alkylsulfonyl groups; or
(d22) A 3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms in the ring,
X1、X2、X3and X4Independently from each other:
(e1) a hydrogen atom;
(e2) a halogen atom;
(e5)(C1-C6) An alkyl group;
(e7)(C1-C6) An alkoxy group;
(e11)(C1-C6) An alkylthio group;
(e12)(C1-C6) An alkylsulfinyl group; or
(e13)(C1-C6) An alkylsulfonyl group.
3. The compound or salt thereof according to claim 1or 2,
R3comprises the following steps:
(c1) a hydrogen atom; or
(c2)(C1-C6) An alkyl group, a carboxyl group,
X1、X2、X3and X4Independently from each other:
(e1) a hydrogen atom;
(e2) a halogen atom; or
(e7)(C1-C6) An alkoxy group,
y is an oxygen atom.
4. An agricultural or horticultural fungicide characterized by containing the compound according to any one of claims 1 to 3 or a salt thereof as an active ingredient.
5. A method for controlling a plant disease, characterized in that a plant or soil is treated with an effective amount of the agricultural or horticultural fungicide according to claim 4.
6. Use of the compound according to any one of claims 1 to 3 or a salt thereof as a bactericide for agricultural and horticultural use.
Technical Field
The present invention relates to a fungicide for agricultural and horticultural use containing an oxadiazole compound or a salt thereof as an active ingredient, and a method for using the same.
Background
Patent documents 1,2 and 3 describe that some kinds of oxadiazole derivatives have bactericidal activity against pathogenic bacteria of plant diseases.
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent application laid-open No. Sho 63-162680
[ patent document 2] pamphlet of International publication No. 2015/185485
[ patent document 3] pamphlet of International publication No. 2017/055473
Disclosure of Invention
Problems to be solved by the invention
In the production of crops such as agriculture and horticulture, damage due to diseases is still large, and development of a novel agricultural or horticultural fungicide is expected due to diseases that have resistance to conventional drugs.
Means for solving the problems
The present inventors have conducted extensive studies to develop a novel bactericide, and as a result, have found that a specific compound containing a hemiaminal (ヘミアミナール) structure in the structure of the compound or a salt thereof is useful as a bactericide for agricultural and horticultural use, and this is not described or suggested in any of the above known documents, and have completed the present invention.
Namely, the present invention relates to the following:
[1] a compound represented by the general formula (I) or a salt thereof,
[ chemical formula 1]
In the formula (I), the compound is shown in the specification,
R1represents:
(a1) a hydrogen atom;
(a2)(C1-C6) An alkyl group;
(a3)(C2-C6) An alkenyl group;
(a4)(C2-C6) An alkynyl group;
(a5)(C3-C6) A cycloalkyl group;
(a6) halo (C)1-C6) An alkyl group;
(a7) halo (C)2-C6) An alkenyl group;
(a8) halo (C)2-C6) An alkynyl group; or
(a9) Halo (C)3-C6) A cycloalkyl group,
R2represents:
(b1) a hydrogen atom;
(b2)(C1-C6) An alkyl group;
(b3)(C2-C6) An alkenyl group;
(b4)(C2-C6) An alkynyl group;
(b5)(C3-C6) A cycloalkyl group;
(b6) halo (C)1-C6) An alkyl group;
(b7) halo (C)2-C6) An alkenyl group;
(b8) halo (C)2-C6) An alkynyl group; or
(b9) Halo (C)3-C6) A cycloalkyl group,
R3represents:
(c1) a hydrogen atom;
(c2)(C1-C6) An alkyl group;
(c3)(C2-C6) An alkenyl group;
(c4)(C2-C6) An alkynyl group;
(c5)(C3-C6) A cycloalkyl group;
(c6)(C1-C6) An alkylcarbonyl group; or
(c7)(C1-C6) An alkoxycarbonyl group, a carbonyl group,
R4represents:
(d1) a hydrogen atom;
(d2)(C1-C6) An alkyl group;
(d3)(C2-C6) An alkenyl group;
(d4)(C2-C6) An alkynyl group;
(d5)(C3-C6) A cycloalkyl group;
(d6)(C1-C6) An alkoxy group;
(d7) halo (C)1-C6) An alkyl group;
(d8) halo (C)2-C6) An alkenyl group;
(d9) halo (C)2-C6) An alkynyl group;
(d10) halo (C)3-C6) A cycloalkyl group;
(d11) halo (C)1-C6) An alkoxy group;
(d12)Ra(Rb) N radical (in the formula, R)aAnd RbEach independently represents a hydrogen atom or (C)1-C6) Alkyl, (C)3-C6) Cycloalkyl group, (C)3-C6) Cycloalkyl (C)1-C6) Alkyl, phenyl, (C)1-C6) Alkylcarbonyl or phenylcarbonyl. ) (ii) a
(d13) An aryl group;
(d14) aryl having 1 to 8 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d15) a heteroaryl group;
(d16) heteroaryl having 1 to 3 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d17) aryl radical (C)1-C6) An alkyl group;
(d18) aryl having 1 to 8 substituents on the ring (C)1-C6) Alkyl, the substituents are respectively and independently selected from halogen atom, cyano, nitro and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d19) heteroaryl (C)1-C6) An alkyl group;
(d20) heteroaryl (C) having 1 to 3 substituents on the ring1-C6) Alkyl, the substituents are respectively and independently selected from halogen atom, cyano, nitro and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d21) (C) having 1 to 3 substituents on the chain1-C6) Alkyl, the substituents are respectively and independently selected from cyano, (C)1-C6) Alkoxy radical, Ra(Rb) N radical (in the formula, R)aAnd RbAs described above. ) (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl and (C)1-C6) Alkylsulfonyl groups; or
(d22) A 3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms in the ring,
X1、X2、X3and X4Each independently represents:
(e1) a hydrogen atom;
(e2) a halogen atom;
(e3) a cyano group;
(e4) a nitro group;
(e5)(C1-C6) An alkyl group;
(e6)(C3-C6) A cycloalkyl group;
(e7)(C1-C6) An alkoxy group;
(e8) halo (C)1-C6) An alkyl group;
(e9) halo (C)1-C6) An alkoxy group;
(e10) halo (C)3-C6) A cycloalkyl group;
(e11)(C1-C6) An alkylthio group;
(e12)(C1-C6) An alkylsulfinyl group;
(e13)(C1-C6) An alkylsulfonyl group;
(e14) halo (C)1-C6) An alkylthio group;
(e15) halo (C)1-C6) An alkylsulfinyl group; or
(e16) Halo (C)1-C6) An alkyl sulfonyl group, a carboxyl group,
y represents an oxygen atom; or a sulfur atom.
[2] The compound according to [1] or a salt thereof, wherein,
R1comprises the following steps:
(a2)(C1-C6) An alkyl group, a carboxyl group,
R2comprises the following steps:
(b1) a hydrogen atom, and a nitrogen atom,
R3comprises the following steps:
(c1) a hydrogen atom;
(c2)(C1-C6) An alkyl group; or
(c5)(C3-C6) A cycloalkyl group,
R4comprises the following steps:
(d2)(C1-C6) An alkyl group;
(d3)(C2-C6) An alkenyl group;
(d4)(C2-C6) An alkynyl group;
(d5)(C3-C6) A cycloalkyl group;
(d6)(C1-C6) An alkoxy group;
(d7) halo (C)1-C6) An alkyl group;
(d12)Ra(Rb) N radical (in the formula, R)aAnd RbIndependently represent hydrogenAtom, (C)1-C6) Alkyl, (C)3-C6) Cycloalkyl group, (C)3-C6) Cycloalkyl (C)1-C6) Alkyl, phenyl, (C)1-C6) Alkylcarbonyl or phenylcarbonyl. ) (ii) a
(d13) An aryl group;
(d14) aryl having 1 to 8 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d15) a heteroaryl group;
(d17) aryl radical (C)1-C6) An alkyl group;
(d21) (C) having 1 to 3 substituents on the chain1-C6) Alkyl, the substituents are respectively and independently selected from cyano, (C)1-C6) Alkoxy radical, Ra(Rb) N radical (in the formula, R)aAnd RbAs described above. ) (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl and (C)1-C6) Alkylsulfonyl groups; or
(d22) A cyclic 3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms,
X1、X2、X3and X4Independently from each other:
(e1) a hydrogen atom;
(e2) a halogen atom;
(e5)(C1-C6) An alkyl group;
(e7)(C1-C6) An alkoxy group;
(e11)(C1-C6) An alkylthio group;
(e12)(C1-C6) An alkylsulfinyl group; or
(e13)(C1-C6) An alkyl sulfonyl group, a carboxyl group,
y is an oxygen atom; or a sulfur atom.
[3] The compound according to [1] or [2], or a salt thereof,
R3comprises the following steps:
(c1) a hydrogen atom; or
(c2)(C1-C6) An alkyl group, a carboxyl group,
X1、X2、X3and X4Independently from each other:
(e1) a hydrogen atom;
(e2) a halogen atom; or
(e7)(C1-C6) An alkoxy group,
y is an oxygen atom.
[4] A bactericide for agricultural and horticultural use which is characterized in that,
the agricultural or horticultural fungicide contains the compound according to any one of [1] to [3] or a salt thereof as an active ingredient.
[5] A method for controlling plant diseases, which is characterized in that,
treating a plant or soil with an effective amount of the agricultural or horticultural fungicide according to [4 ]. And
[6] an application of the compound according to any one of [1] to [3] or a salt thereof as a bactericide for agricultural and horticultural use.
Effects of the invention
The compound of the present invention or a salt thereof has an excellent effect as a bactericide for agricultural and horticultural use.
Detailed Description
The terms used in the definition of the general formula (I) concerning the compound of the present invention are explained below.
"halogen" means "halogen atom" and means chlorine atom, bromine atom, iodine atom or fluorine atom.
“(C1-C6) The alkyl group "represents a linear or branched alkyl group having 1 to 6 carbon atoms, and includes, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, 2, 3-dimethyl-propyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, isohexyl, 2-hexyl, 3-hexyl, 2-methylpentyl, 3-methylpentyl, 1, 2-trimethylpropyl, 3-dimethylbutyl, and the like.
“(C2-C6) The "alkenyl group" represents a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, for example, a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, a 3, 3-dimethyl-1-butenyl group, or the like, "(C2-C6) The alkynyl group "represents a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, and examples thereof include an ethynyl group, a 1-propargyl group, a 2-propargyl group, a 1-butynyl group, a 2-butynyl group, a 3-methyl-1-propargyl group, a 2-methyl-3-propargyl group, a pentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, and a 3, 3-dimethyl-1-butynyl group.
“(C3-C6) Cycloalkyl "represents a cyclic alkyl group having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc." (C)1-C6) The alkoxy group "represents a linear or branched alkoxy group having 1 to 6 carbon atoms, for example, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentoxy group, an isopentoxy group, a tert-pentoxy group, a neopentoxy group, a2, 3-dimethylpropoxy group, a 1-ethylpropoxy group, a 1-methylbutoxy group, a n-hexoxy group, an isohexoxy group, a1, 1, 2-trimethylpropoxy group and the like.
“(C1-C6) The "alkylthio group" represents a straight-chain or branched alkylthio group having 1 to 6 carbon atoms, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, and isopentylAlkylthio, tert-pentylthio, neopentylthio, 2, 3-dimethyl-propylthio, 1-ethylpropylthio, 1-methylbutylthio, n-hexylthio, isohexylthio, 1, 2-trimethylpropylthio, and the like.
“(C1-C6) The "alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, n-pentylsulfinyl, isopentylsulfinyl, tert-pentylsulfinyl, neopentylsulfinyl, 2, 3-dimethyl-propylsulfinyl, 1-ethylpropylsulfinyl, 1-methylbutylsulfinyl, n-hexylsulfinyl, isohexylsulfinyl, and 1,1, 2-trimethylpropylsulfinyl.
“(C1-C6) The "alkylsulfonyl group" represents a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, a n-propylsulfonyl group, an isopropylsulfonyl group, a n-butylsulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, a n-pentylsulfonyl group, an isopentylsulfonyl group, a tert-pentylsulfonyl group, a neopentylsulfonyl group, a2, 3-dimethyl-propylsulfonyl group, a 1-ethylpropylsulfonyl group, a 1-methylbutylsulfonyl group, a n-hexylsulfonyl group, an isohexylsulfonyl group, a1, 1, 2-trimethylpropylsulfonyl group and the like.
“(C1-C6) The "alkylcarbonyl group" represents an alkylcarbonyl group having 2 to 7 carbon atoms, and includes, for example, acetyl, propionyl, butyryl, 2-methylpropionyl, pentanoyl, 2-methylbutyryl, 3-methylbutyryl, pivaloyl, hexanoyl, cyclopropylcarbonyl and the like having the above-mentioned (C)1-C6) Alkylcarbonyl of alkyl, and the like.
“(C1-C6) Alkoxycarbonyl "represents an alkoxycarbonyl group having 2 to 7 carbon atoms, and includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl and the like having the above-mentioned (C)1-C6) Alkoxycarbonyl groups of alkoxy groups, and the like.
In the above "(C)1-C6) Alkyl group "," (C)2-C6) Alkenyl "," (C)2-C6) Alkynyl "," (C)3-C6) Cycloalkyl group "," (C)1-C6) Alkoxy group "," (C)1-C6) Alkylthio groups "," (C)1-C6) Alkylsulfinyl "or" (C)1-C6) In the alkylsulfonyl "and the like, 1or 2 or more halogen atoms may be substituted at substitutable positions of each group, and when the number of the substituted halogen atoms is 2 or more, the halogen atoms may be the same or different. Groups obtained by substituting 1or 2 or more halogen atoms at substitutable positions of each group are each represented by "halo (C)1-C6) Alkyl "," halo (C)2-C6) Alkenyl "," halo (C)2-C6) Alkynyl "," halo (C)3-C6) Cycloalkyl "," halo (C)1-C6) Alkoxy "," halo (C)1-C6) Alkylthio "," halo (C)1-C6) Alkylsulfinyl "or" halo (C)1-C6) An alkylsulfonyl group ".
“(C1-C6)”、“(C2-C6)”、“(C3-C6) "and the like" indicate ranges of the number of carbon atoms of various substituents. Furthermore, the above definition can also be applied to the group to which the above substituent is attached, for example, "(C)1-C6) Alkoxy (C)1-C6) The alkyl group represents a group in which an alkoxy group having 1 to 6 carbon atoms, which is a straight chain or branched chain, is bonded to an alkyl group having 1 to 6 carbon atoms, which is a straight chain or branched chain.
The "aryl group" and "aryl group" represent an aromatic hydrocarbon group having 6 to 10 carbon atoms, and examples thereof include phenyl and naphthyl.
"heteroaryl group" and "heteroaryl" represent monocyclic aromatic heterocyclic groups, such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl, and the like.
The "3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms in the ring" means a non-aromatic heterocyclic group, and examples thereof include an oxirane group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group, a1, 3-dioxolanyl group, a1, 3-dioxanyl group, and a1, 4-dioxanyl group.
Examples of the salts of the compound represented by the general formula (I) of the present invention include salts with inorganic or organic base groups, for example, inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate and p-toluenesulfonate, sodium ion, potassium ion, calcium ion and trimethylammonium.
The compounds represented by the general formula (I) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula thereof, and may exist in two or more kinds of optical isomers and diastereomers, and the present invention includes each optical isomer and a mixture containing these optical isomers in an arbitrary ratio. In addition, the compound represented by the general formula (I) of the present invention and salts thereof may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, and the present invention includes each geometric isomer and a mixture containing the geometric isomers in an arbitrary ratio.
Among the compounds represented by the general formula (I) of the present invention, preferred embodiments are shown below.
As R1Preferably, the following components are used:
(a2)(C1-C6) An alkyl group.
As R2Preferably, the following components are used:
(b1) a hydrogen atom.
As R3Preferably, the following components are used:
(c1) a hydrogen atom;
(c2)(C1-C6) An alkyl group; or
(c5)(C3-C6) A cycloalkyl group,
more preferably:
(c1) a hydrogen atom; or
(c2)(C1-C6) An alkyl group.
As R4Preferably, the following components are used:
(d2)(C1-C6) An alkyl group;
(d3)(C2-C6) An alkenyl group;
(d4)(C2-C6) An alkynyl group;
(d5)(C3-C6) A cycloalkyl group;
(d6)(C1-C6) An alkoxy group;
(d7) halo (C)1-C6) An alkyl group;
(d12)Ra(Rb) N radical (in the formula, R)aAnd RbEach independently represents a hydrogen atom or (C)1-C6) Alkyl, (C)3-C6) Cycloalkyl group, (C)3-C6) Cycloalkyl (C)1-C6) Alkyl, phenyl, (C)1-C6) Alkylcarbonyl or phenylcarbonyl. ) (ii) a
(d13) An aryl group;
(d14) aryl having 1 to 8 substituents on the ring, wherein the substituents are independently selected from the group consisting of a halogen atom, a cyano group, a nitro group and (C)1-C6) Alkyl, (C)1-C6) Alkoxy group, (C)3-C6) Cycloalkyl, halo (C)1-C6) Alkyl, halo (C)1-C6) Alkoxy, halo (C)3-C6) Cycloalkyl group, (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl (C)1-C6) Alkylsulfonyl, halo (C)1-C6) Alkylthio, halo (C)1-C6) Alkylsulfinyl and halo (C)1-C6) Alkylsulfonyl groups;
(d15) a heteroaryl group;
(d17) aryl radical (C)1-C6) Alkane (I) and its preparation methodA group;
(d21) (C) having 1 to 3 substituents on the chain1-C6) Alkyl, the substituents are respectively and independently selected from cyano, (C)1-C6) Alkoxy radical, Ra(Rb) N radical (in the formula, R)aAnd RbAs described above. ) (C)1-C6) Alkylthio, (C)1-C6) Alkylsulfinyl and (C)1-C6) Alkylsulfonyl groups; or
(d22) A cyclic 3-to 6-membered non-aromatic heterocyclic group having 1 to 2 oxygen atoms.
As X1、X2、X3And X4Preferably, each independently is:
(e1) a hydrogen atom;
(e2) a halogen atom;
(e5)(C1-C6) An alkyl group;
(e7)(C1-C6) An alkoxy group;
(e11)(C1-C6) An alkylthio group;
(e12)(C1-C6) An alkylsulfinyl group; or
(e13)(C1-C6) An alkyl sulfonyl group, a carboxyl group,
further preferred are each independently:
(e1) a hydrogen atom;
(e2) a halogen atom; or
(e7)(C1-C6) An alkoxy group.
As Y, an oxygen atom is preferred; or a sulfur atom,
further preferably an oxygen atom.
The compounds of the present invention can be produced by, for example, the following production methods, but the compounds of the present invention and the production methods thereof are not limited thereto.
Production method 1
[ chemical formula 2]
(in the formula, R1、R4、X1、X2、X3、X4And Y is the same as for the group of formula (I). )
Among the compounds of the present invention, the compound represented by the general formula (I-1) can be produced by the following step [ a ] shown in the above scheme.
The step [ a ] is a step of reacting a compound represented by the general formula (1), a compound represented by the general formula (2), and a compound represented by the general formula (3) to produce a compound represented by the general formula (I-1).
Process [ a ]
The compound represented by the general formula (1) which can be produced by the method described in the pamphlet of International publication No. 2017/055473 can be reacted with the compound represented by the general formula (2) and the compound represented by the general formula (3) in the presence of an inert solvent to produce the compound represented by the general formula (I-1).
Examples of the compound represented by the general formula (3) that can be used in the present reaction (step [ a ]) include: the amount of titanium (IV) methoxide, titanium (IV) ethoxide, titanium (IV) n-propoxide, titanium (IV) isopropoxide, titanium (IV) n-butoxide, titanium (IV) tert-butoxide, etc., may be appropriately selected from the range of usually 1 to 5 times by mole with respect to the compound represented by the general formula (1).
The inert solvent used in the present reaction (step [ a ]) may be any solvent which does not significantly inhibit the progress of the present reaction, and examples thereof include: aliphatic hydrocarbons such as pentane, hexane, and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; esters such as ethyl acetate and propyl acetate; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (1).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be varied depending on the scale of the reaction and the reaction temperature, and usually may be within a range of several minutes to 48 hours. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and may be purified by recrystallization, column chromatography, or the like as necessary, thereby obtaining the target substance.
Production method 2
[ chemical formula 3]
(in the formula, R1、R3、R4、X1、X2、X3、X4And Y is the same as that described for the above formula (I), L represents a leaving group such as a halogen atom, a methanesulfonyl group, a toluenesulfonyl group, or a trifluoromethanesulfonate group. )
Among the compounds of the present invention, the compounds represented by the general formula (I-2) can be produced by the following steps [ b ] to [ e ] shown in the above schemes.
The step [ b ] is a step of reacting the compound represented by the general formula (4) with the compound represented by the general formula (2) and the compound represented by the general formula (3) to produce the compound represented by the general formula (5).
A step [ c ] of reacting the compound represented by the general formula (5) with the compound represented by the general formula (6) to produce a compound represented by the general formula (7).
The step [ d ] is a step of reacting the compound represented by the general formula (7) with hydroxylamine (8) to produce a compound represented by the general formula (9).
The step [ e ] is a step of reacting the compound represented by the general formula (9) with trifluoroacetic anhydride (10) to produce a compound represented by the general formula (I-2).
Step [ b ]]
The compound represented by the general formula (5) can be produced by reacting the compound represented by the general formula (4) with the compound represented by the general formula (2) and the compound represented by the general formula (3) in the presence of an inert solvent.
Examples of the compound represented by the general formula (3) that can be used in the present reaction include: the amount of titanium (IV) methoxide, titanium (IV) ethoxide, titanium (IV) n-propoxide, titanium (IV) isopropoxide, titanium (IV) n-butoxide, titanium (IV) tert-butoxide, etc., may be appropriately selected from the range of usually 1 to 5 times by mole with respect to the compound represented by the general formula (4).
The inert solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction, and examples thereof include: chain or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; esters such as ethyl acetate and propyl acetate; nitriles such as acetonitrile and propionitrile; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (4).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be varied depending on the scale of the reaction and the reaction temperature, and usually may be within a range of several minutes to 48 hours. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and may be purified by recrystallization, column chromatography, or the like as necessary, thereby obtaining the target substance.
Step [ c ]]
The compound represented by the general formula (7) can be produced by reacting the compound represented by the general formula (5) with the compound represented by the general formula (6) in the presence of a base and an inert solvent.
Examples of the base that can be used in the present reaction include: inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, and 1, 8-diazabicyclo [5.4.0] undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethyl-aminopyridine, and the amount thereof to be used may be appropriately selected from the range of usually 1 to 5 times by mole relative to the compound represented by the general formula (5).
The inert solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction, and examples thereof include: aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate, amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (5).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be usually within a range from several minutes to 48 hours depending on the scale of the reaction and the reaction temperature. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and may be purified by recrystallization, column chromatography, or the like as necessary, thereby obtaining the target substance.
Step [ d ]]
The compound represented by the general formula (9) can be produced by reacting the compound represented by the general formula (7) with hydroxylamine hydrochloride (8) in the presence of an inert solvent.
The inert solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction, and examples thereof include: alcohols such as methanol, ethanol, 1-propanol, and 2-propanol; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone; and inert solvents such as water, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (7).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be varied depending on the scale of the reaction and the reaction temperature, and usually may be within a range of several minutes to 48 hours. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and the target substance may be produced by purification such as recrystallization and column chromatography, if necessary.
Step [ e ]]
The compound represented by the general formula (I-2) can be produced by reacting a compound represented by the general formula (9) with trifluoroacetic anhydride (10) in the presence of a base and an inert solvent.
Examples of the base that can be used in the present reaction include: inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; tertiary amines such as triethylamine, diisopropylethylamine, and 1, 8-diazabicyclo [5.4.0] undec-7-ene; and nitrogen-containing aromatic compounds such as pyridine and dimethyl-aminopyridine, and the amount of the nitrogen-containing aromatic compounds to be used may be appropriately selected from the range of usually 1 to 5 times by mol based on the compound represented by the general formula (9).
The inert solvent that can be used in the present reaction is not particularly limited as long as it does not significantly inhibit the progress of the present reaction, and examples thereof include: aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (9).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be varied depending on the scale of the reaction and the reaction temperature, and usually may be within a range of several minutes to 48 hours. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and the target substance may be produced by purification such as recrystallization and column chromatography, if necessary.
Production method 3
[ chemical formula 4]
(in the formula, R1、R4、X2、X3、X4And Y is the same as for the group of formula (I), R5Is represented by (C)1-C6) An alkyl group, and n represents an integer of 1 to 2. )
Among the compounds of the present invention, the compounds represented by the general formulae (I-3) and (I-4) can be produced by the following steps [ f ] to [ g ] and [ f ] to [ h ] shown in the above schemes, respectively.
The step [ f ] is a step of reacting the compound represented by the general formula (1-2) with the compound represented by the general formula (10) to produce the compound represented by the general formula (1-3).
The step [ g ] is a step of reacting the compound represented by the general formula (1-3) with the compound represented by the general formula (3) and the compound represented by the general formula (2) to produce the compound represented by the general formula (I-3).
The step [ h ] is a step of oxidizing the compound represented by the general formula (I-3) to produce a compound represented by the general formula (I-4).
Step (f)]
The compound represented by the general formula (1-3) can be produced by reacting the compound represented by the general formula (1-2) with the compound represented by the general formula (10) in the presence of an inert solvent.
The inert solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction, and examples thereof include: aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as aprotic polar solvents such as dimethyl sulfoxide and 1, 3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or in a mixture of 2 or more. The amount of the compound to be used may be appropriately selected from the range of usually 0.1 to 100L per 1 mol of the compound represented by the general formula (1-2).
Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any reactant may be used in an excess amount. The reaction temperature is usually within a range from room temperature to the boiling point of the inert solvent used, and the reaction time may be varied depending on the scale of the reaction and the reaction temperature, and usually may be within a range of several minutes to 48 hours. After the reaction is completed, the target substance may be separated from the reaction system containing the target substance by a conventional method, and the target substance may be produced by purification such as recrystallization and column chromatography, if necessary.
Step [ g)]
The compound represented by the general formula (I-3) can be produced by reacting the compound represented by the general formula (1-3) with the compound represented by the general formula (2) and the compound represented by the general formula (3) according to the method described in the step [ a ] of the production method 1.
Procedure [ h]
The compound represented by the general formula (I-4) can be produced by oxidizing the compound represented by the general formula (I-3) by a method commonly used in chemical synthesis.
Representative examples of the compounds represented by the general formula (I) of the present invention will be illustrated in Table 1 below, but the present invention is not limited thereto.
In the table, "Me" represents a methyl group, "Et" represents an ethyl group, "n-Pr" represents an n-propyl group, "i-Pr" represents an isopropyl group, "c-Pr" represents a cyclopropyl group, "n-Bu" represents an n-butyl group, "i-Bu" represents an isobutyl group, "s-Bu" represents a sec-butyl group, "t-Bu" represents a tert-butyl group, "c-Pen" represents a cyclopentyl group, and "Ph" represents a phenyl group. The physical properties are a melting point (. degree. C.) or a refractive index nD(measurement temperature).
[ chemical formula 5]
[ TABLE 1]
TABLE 1
[ TABLE 2]
Table 1
[ TABLE 3]
Table 1
[ TABLE 4]
Table 1
[ TABLE 5]
Table 1
[ TABLE 6]
Table 1
1) Low polar diastereomer (high Rf value): compound No. 135 and Compound No. 138
2) Highly polar diastereomer (low Rf value): compound No. 136 and Compound No. 139
[ TABLE 7 ]
Table 1
The agricultural and horticultural fungicide containing as an active ingredient the compound represented by the general formula (I) of the present invention or a salt thereof is suitable for controlling diseases caused by grains, fruit trees, vegetables, other crops and flowers.
The target diseases include: filamentous diseases, bacterial diseases and viral diseases. Examples of the filamentous fungus diseases include: diseases caused by incomplete fungi (e.g., diseases of the genera Botrytis, Helminthosporium, Fusarium, Septoria, Cercospora, Pseudosporidium, Rhizoctonia, Pyricularia, Alternaria, etc.), Basidiomycetes (e.g., diseases of the genera Hemilelia, Rhizoctonia, Ustilago, Sarcophylla, Tyrophylla, and Hypocrea), diseases of the genera Hypocrea, Poctinia, Poecia, Poecium, Poecia, Poecium, and the genus Pseudosporium, Streptomyces (Monilinia) diseases, devilpox (uninula) diseases, and the like), other fungi (for example, Ascochyta (Ascochyta) diseases, Phoma (Phoma) diseases, Pythium (Pythium) diseases, corium (cornium) diseases, Pyrenophora (Pyrenophora) diseases, and the like). Examples of the bacterial diseases include: pseudomonas (Pseudomonas) diseases, Xanthomonas (Xanthomonas) diseases, Erwinia (Erwinia) diseases, and the like. Examples of the viral diseases include: for example, diseases caused by tobacco mosaic virus (Tabacco mosaic virus) and the like.
Specific examples of filamentous fungi diseases include: examples of the powdery mildew include powdery mildew of barley and wheat (Blumagarase), powdery mildew of cucumber (cucumber), powdery mildew of eggplant (eggplant), powdery mildew of barley and wheat (rye), powdery mildew of barley and wheat (wheat), wheat scab of wheat, wheat and wheat (wheat), wheat scab of wheat (wheat), wheat and wheat (wheat), wheat (wheat) rice blight of wheat and wheat (wheat), wheat (wheat) rice, wheat, gray mold of cucumber, strawberry, etc. (botrytis cinerea), sclerotinia sclerotiorum of tomato, cabbage, etc. (sclerotiorum), late blight of potato, tomato, etc. (Phytophthora infestans); and, as late blight of other plants, there are listed: scab of various plants such as cucumber scab (pseudoperonosporacus), grape scab (phytoparaviticola), apple scab (Venturia inaequalis), apple Alternaria leaf spot (Alternaria mali), eggplant black spot (Alternaria kikuchiana), citrus black spot (diaportrici), citrus scab (elsinoefaketta), beet brown spot (cercospora betanus), peanut brown spot (cercospora cordifolia), peanut black spot (cercospora personata), wheat leaf blight (septorii), wheat glume blight (leptospora nodorum), barley cross grain diseases (renophora), pyknoxia leaf diseases (pyrenosphaera), barley leaf blight (phytophthora graminis), barley leaf spot (sclerotiorhigo graminis), and sclerotiorhiza (sclerotiorum), wheat scab (sclerotiorhiza) and sclerotiorhiza (sclerotiorum), wheat scab (sclerotium spica), barley leaf spot (sclerotium spica) and sclerotium (sclerotium rot), barley leaf spot (sclerotium nigella, etc.
Specific examples of the bacterial diseases include: caused by the genus Pseudomonas, such as cucumber spot bacterial disease (Pseudomonas syringaepv. lachrymans), tomato bacterial wilt (Pseudomonas solanacearum) and rice bacterial blight (Pseudomonas glumae); caused by Xanthomonas, for example, cabbage black rot (Xanthomonas campestris), rice bacterial leaf blight (Xanthomonas oryzae) and citrus canker (Xanthomonas citri); and those caused by the genus Erwinia (Erwinia), such as cabbage soft rot (Erwinia carotovora).
Useful plants to which the compound represented by the general formula (I) or a salt thereof of the present invention can be applied are not particularly limited, and examples thereof include: cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, red bean, broad bean, pea, mung bean, peanut, etc.), fruit trees-fruits (apple, citrus, pear, grape, peach, plum, cherry, walnut, chestnut, apricot, rubber, etc.), leafy vegetables and fruits (cabbage, tomato, spinach, broccoli, lettuce, onion, shallot (chive, welsh onion), green pepper, eggplant, strawberry, hot pepper, okra, leek, etc.), root vegetables (carrot, potato, sweet potato, taro, white radish, turnip, lotus root, burdock, garlic, leek, etc.), processing crops (cotton, hemp, beet, hop, sugarcane, beet, olive, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, muskmelon, etc.), grazing herbs (fruit trees, sorghum, etc.), white sugar beet, corn, etc, Examples of the plants include plants such as cattail, alfalfa, etc.), lawns (beautiful lawn, pruned glume, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), timbers (ginkgo, cherry, mahogany, etc.), and woods (celosia cristata, ichthyosia cristata, pine, cypress, japanese cedar, japanese cypress, eucalyptus, etc.).
The "plant" also includes plants to which an HPPD inhibitor such as isoxaflutole has been added by a classical breeding method or a genetic recombination technique; ALS inhibitors such as imazethapyr and thifensulfuron; EPSP synthase inhibitors such as glyphosate; glutamine synthetase inhibitors such as glufosinate-ammonium; acetyl CoA carboxylase inhibitors such as sethoxydim; herbicide-resistant plants such as bromoxynil, dicamba, and 2, 4-D.
Examples of "plants" to which resistance has been imparted by a classical breeding method include: rape, wheat, sunflower and rice, which have resistance to imidazolinone ALS-inhibiting herbicides such as imazethapyr, have been sold under the trade name Clearfield (registered trademark). Soybeans having resistance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by a classical breeding method are sold under the trade name STS soybeans. SR corn is an example of a plant to which resistance to acetyl CoA carboxylase inhibitors such as trioxime herbicides and aryloxyphenoxypropionic acid herbicides has been similarly imparted by a conventional breeding method.
Plants to which resistance to acetyl CoA carboxylase inhibitors has been imparted are described in american academy of sciences (proc.natl.acad.sci.usa) volume 87, pages 7175 to 7179 (1990). In addition, the Weed society (Weed Science)53, 728-746 (2005) and the like have reported that a variant acetyl CoA carboxylase having resistance to an acetyl CoA carboxylase inhibitor can be produced by introducing a variant acetyl CoA carboxylase gene into a plant by using a gene recombination technique or introducing a variation related to the conferring of resistance into a plant acetyl CoA carboxylase to produce a plant having resistance to an acetyl CoA carboxylase inhibitor, and a base substitution variation represented by a chimeric repair technique (Gurat T.1999. reparig the Genome's selling Mistakes.science 285: 316-, the compound represented by the general formula (I) of the present invention or a salt thereof can also be used for these plants.
Further, examples of toxins expressed in recombinant plants include: an insecticidal protein from bacillus cereus or bacillus lacteus; endotoxin such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb 1or Cry9C derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3, and VIP 3A; insecticidal proteins from nematodes; animal-derived toxins such as scorpion toxin, spider toxin, bee toxin, or insect-specific neurotoxin; filamentous mycotoxins; a plant lectin; a lectin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, and papain inhibitor; ribosome Inactivating Proteins (RIP) such as lysine, corn-RIP, abrin, luffa, saporin, Briodin, etc.; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysone-UDP-glucosyltransferase, and cholesterol oxidase; an ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor plasma channel inhibitors; juvenile hormone esterase; a diuretic hormone receptor; a stilbene synthase; bibenzyl synthase; chitinase; dextranase and the like.
Further, as such toxins expressed in the gene recombinant plants, there are also included an endotoxin protein such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35 Ab; mixed toxins of insecticidal proteins such as VIP1, VIP2, VIP3, and VIP 3A; a toxin lacking a portion; a modified toxin. Mixed toxins are made by new combinations of different domains of these proteins using recombinant techniques. As a toxin in which a part of the amino acid sequence is deleted, Cry1Ab in which a part of the amino acid sequence is deleted is known. In the modified toxin, one or more of the amino acids of the native toxin are substituted.
Examples of such toxins and recombinant plants capable of synthesizing such toxins are described in EP-A-0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878, WO03/052073 and the like.
The agricultural or horticultural bactericide of the present invention can be used in combination with these techniques or can form a system with these techniques.
For the control of various diseases, the agricultural or horticultural fungicide of the present invention may be used as it is or in the form of an appropriate dilution or suspension with water or the like in an amount effective for the control of diseases for plants predicted to cause the diseases, and for example, for diseases caused in fruit trees, grains, vegetables and the like, seed treatments such as seed chemical impregnation, seed coating, Calper treatment and the like may be performed in addition to the spreading to the stem and leaf parts; the soil and the like are treated to be absorbed and used from the root, for example, soil full-layer mixing, street application, bed soil mixing, plug seedling treatment, planting hole treatment, plant base treatment, top dressing, rice seedling box treatment, water surface application and the like. In addition, the application of a drug to a nutrient solution in nutrient solution (hydroponics) cultivation, smoking, trunk injection, or the like may be performed.
The agricultural or horticultural fungicide of the present invention may be used in a place where the occurrence of a disease is predicted, as it is or in a form diluted or suspended with water or the like as appropriate, in an amount effective for controlling the disease.
Examples of the seed treatment method include: a method of impregnating a seed with a diluted or undiluted liquid or solid preparation in a liquid state to allow the seed to permeate the preparation, a method of mixing a solid preparation or a liquid preparation with a seed to perform a coating treatment to adhere the preparation to the surface of a seed, a method of mixing the preparation with an adhesive carrier such as a resin or a polymer to apply the mixture to a seed, a method of planting the seed while spreading the mixture in the vicinity of a seed, and the like.
The "seed" to be subjected to the seed treatment means a plant body at the initial stage of cultivation for propagation of a plant, and examples thereof include, in addition to the seed: bulbous roots, tubers, seed potatoes, plant buds, reproductive buds, bulbs, or vegetative propagation plant bodies for use in cuttage cultivation.
In the case of carrying out the method of use of the present invention, "soil" or "cultivation medium" of a plant means a support for cultivating a crop, particularly a support for rooting, and the material is not particularly limited as long as the plant can grow, and may be so-called soil, a mat for growing seedlings, water, or the like, and specific materials may be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, a gel-like material, a polymer material, rock wool, glass wool, wood chips, bark, or the like.
Examples of methods for applying the composition to the stem and leaf of a crop include: a method of diluting a liquid preparation such as an emulsion or a suspension or a solid preparation such as a wettable powder or a water-dispersible granule with water and then dispersing the diluted solution, a method of dispersing a powder, or smoking.
Examples of the method for applying the drug to the soil include: a method of applying the liquid preparation to the plant base or seedling bed of a plant, a method of spraying granules to the plant base or seedling bed of a plant, a method of spraying a powder, a wettable powder, a water-dispersible granule, a granule or the like to the whole soil before sowing or before transplanting, a method of spraying a powder, a wettable powder, a water-dispersible granule, a granule or the like to a planting hole, a street or the like before sowing or before planting a plant, or the like.
The formulation of the method for applying the pesticide to the seedling raising box of rice varies depending on the time of application such as application at the time of sowing, application at the time of greening, application at the time of transplantation, etc., but the pesticide may be applied in the form of a powder, a water-dispersible granule, a granule, etc. The application may also be by mixing with the ridging, which can be mixed with powders, water dispersible granules or granules, etc., for example, with the bed soil, with the casing soil, with the ridging as a whole, etc. The application of the formulation may also be carried out simply by alternating the formulation of the hills and the various formulations in layers.
As a method for applying the drug to paddy fields, solid preparations such as jumbo (jumbo) preparations, sacks, granules and water-dispersible granules, liquid preparations such as concentrated suspensions (フロアブル) and emulsions are generally spread over paddy fields in a flooded state. In addition, the appropriate preparation can also be scattered or injected into soil directly or after being mixed with fertilizer during the transplanting. In addition, chemical solutions such as emulsions and concentrated suspensions may be used from sources for inflow of water into paddy fields through outlets, irrigation devices, and the like, so that the chemicals can be easily applied along with water supply.
In the case of dry crops, seeds, cultivation carriers near plants, and the like can be treated from sowing to the stage of raising seedlings. For plants sown directly in dry land, it is preferable to treat the plant base of the plant being cultivated, in addition to the direct treatment of the seed. For example, a dispersion treatment using a granule or an irrigation treatment using a liquid agent diluted or not diluted in water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then to sow them.
As treatments for the seeding and seedling growing period of the cultivated plant to be transplanted, it is preferable to perform direct treatment of the seed, and further, irrigation treatment of a liquid chemical or dispersion treatment of granules on the seedling growing bed. In addition, it is also preferable to treat the planting hole with granules or to mix granules with a culture carrier near the place of transplantation at the time of planting.
The compound represented by the general formula (I) or a salt thereof of the present invention is usually used after being formed into a shape convenient for use according to a conventional method for agricultural chemical preparations.
That is, the compound represented by the general formula (I) or a salt thereof of the present invention may be used in a form of a suspension (suspension concentrate), emulsion, oil, liquid, wettable powder, water dispersible granule, powder, tablet, sachet, macrogranule, suspoemulsion, or the like, by mixing the compound or the salt thereof with an appropriate inert carrier or an auxiliary agent used as needed at an appropriate ratio, and then dissolving, separating, suspending, mixing, impregnating, adsorbing, or adhering the compound or the salt.
The agricultural or horticultural fungicide of the present invention may contain, in addition to the active ingredient, an additive ingredient which is generally used in pesticide preparations, as required. Examples of such additional components include: carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, adhesion imparting agents, tackifiers, colorants, extenders, spreaders, antifreezes, anticaking agents, disintegrants, disintegration inhibitors, and the like. Further, preservatives, plant pieces and the like may be used as the additive components as required. These additives may be used alone, or two or more of them may be used in combination.
Examples of the solid carrier include: natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicate, starch, cellulose, plant powder (such as sawdust, coconut shell, corn cob, tobacco stalk, etc.); plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), and the like. These may be used alone, or two or more of them may be used in combination.
Examples of the liquid carrier include: monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin, and polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and THF; aliphatic hydrocarbons such as normal paraffins, naphthenes, isoparaffins, kerosene, and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ -butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide and N-alkylpyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rape oil, cottonseed oil, and castor oil; and water and the like. These may be used alone, or two or more of them may be used in combination.
As the surfactant used as the dispersant or wet spreader, for example, there can be mentioned: sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene block polymer, alkylpolyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid diphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styrylphenyl ether, acetylene glycol, polyoxyalkylene addition acetylene glycol, polyoxyethylene ether type silicone, ester type silicone, fluorine type surfactant, polyoxyethylene castor oil, polyoxyethylene, Nonionic surfactants such as polyoxyethylene hardened castor oil, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, fatty acid salts, polycarboxylic acid salts, polyacrylic acid salts, sarcosinates of N-methyl-fatty acids, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkylamine salts including laurylamine hydrochloride, stearylpropylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethyl-benzalkonium chloride; and amphoteric surfactants such as amino acid type and betaine type. These surfactants may be used alone, or two or more of them may be used in combination.
Examples of the binder or the adhesion-imparting agent include: carboxymethylcellulose and its salt, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6000 to 20000, polyethylene oxide having an average molecular weight of 10 to 500 ten thousand, cellulose powder of a phospholipid (e.g., cephalin, lecithin, etc.), dextrin, and processed starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrene, (meth) acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylic acid salts, polyoxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol formalin condensates, synthetic resin emulsions, and the like.
Examples of the tackifier include: xanthan gum, guar gum, Diutan gum (Diutan gum), carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, and water-soluble polymer such as polysaccharide, and inorganic fine powder such as high-purity bentonite and fumed silica.
As the colorant, for example, there can be mentioned: inorganic pigments such as iron oxide, titanium dioxide, prussian blue; and organic dyes such as alizarin dyes, azo dyes, metal phthalocyanine dyes, and the like.
As the antifreeze, for example, there can be mentioned: and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
Examples of the auxiliary agent for preventing caking or promoting disintegration include: polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinyl pyrrolidone, fumed silica, ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, a copolymer of methacrylic acid, polyvinyl pyrrolidone, a polyaminocarboxylic acid chelate compound, a sulfonated styrene-isobutylene-maleic anhydride copolymer, a starch-polyacrylonitrile graft copolymer, and the like.
Examples of the decomposition inhibitor include: desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.
Examples of the preservative include potassium sorbate and 1, 2-benzothiazolin-3-one.
If necessary, other auxiliary agents such as a functional spreader, an activity enhancer such as a metabolic decomposition inhibitor such as piperonyl butoxide, an antifreeze such as propylene glycol, an antioxidant such as BHT, and an ultraviolet absorber may be further used.
The mixing ratio of the active ingredient compound may be increased or decreased as needed, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural or horticultural fungicide of the present invention, and for example, 0.01 to 50 parts by weight (0.01 to 50% by weight of the total weight of the herbicide) is suitable in the case of preparing a powder, granule, emulsion or wettable powder.
The amount of the compound represented by the general formula (I) or a salt thereof to be used in the present invention may be appropriately selected from the range of 0.001 to 10kg, preferably 0.01 to 1kg per 10 acres as the active ingredient compound according to the purpose, taking into consideration various factors such as the purpose, the target weeds, the growth and development conditions of crops, the tendency to generate weeds, weather and climate, environmental conditions, dosage forms, application methods, application places, and application time.
When a herbicide containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is used, it is diluted to an appropriate concentration and then spread or applied directly.
The agricultural or horticultural fungicide of the present invention may be used in combination with other agricultural or horticultural insecticides, acaricides, nematicides, fungicides, biological pesticides, etc., in order to extend the period of time required for controlling diseases or controlling the adaptive disease, or to reduce the amount of the pesticide, or may be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application. Representative compounds will be exemplified below, but are not limited thereto.
Examples of the agricultural or horticultural bactericide used for the above purpose include:
aureofungin (aureofungin), epoxiconazole (azaconazole), zearaln (azithiram), aprazacetam (acetolaces), activated ester (acibenzolar), activated ester-S-methyl (acibenzolar-S-methyl), azoxystrobin (azoxystrobin), dichlofluanid (anilazine), amisulbrom (amisulbrom), 1-aminopropyl phosphoric acid (ampropyfos), ametoctradin (ametoctradin), allyl alcohol (allylalcohol), allethrin (aldimorph), amobam (amobam), isotianil (isotianil), isoacetogenione (isovalene), isopyrazamide (isopyrazam), isoflunomide (isoprothiolane), isoprothiolane (isoprothiolane), isopyramide (isopyrazole), isopyramide (isoprothiolane), iprodione (iprodione), iprodione (isoproconazole (iprodione), iprodione (isoprothiolane (isoprocarb), iprazole (isopyrazole), iprazole (isoprocarb (iprazole), iprazole (isoproconazole (iprazole), iprazole (isofenpyroximine), isoproconazole (iprazole), iprazole (isoproconazole (iprazole), isoprocarb (iprazole), isoprocarb (iprazole), isoprocarb (isoprocarb), isoprocarb (isoproc, Clomazole (echlomezole), edifenphos (edifenphos), epoxiconazole (etaconazole), ethaboxam (ethaboxam), ethirimol (ethirimol), ethionamide (etem), ethoxyquin (ethloxyquin), hymexazol (etiodiazole), enestroburin (enestroburin), enoxastrobin (enoxastrobin), epoxiconazole (epoxiconazole), oxadixyl (oxadixyl), fluorothiazoleppirone (oxathipridin), oxathifludioxonil (oxathiprin), copper 8-hydroxyquinoline (copper-8-quinonolate), oxytetracycline (oxathicline), copperer-oxinate, imidazole (oxaprozolium), oxozolidone (oxozolidone), fumarone (oxozolidone-sodium), thifluxolone (sodium fumarate-octopirox), and the like,
Kasugamycin (kasugamycin), mycoparb (carbamorph), cyclopropanamide (carpropamide), carbendazim (carbendazim), carboxin (carboxin), carvone (carvone), quinoxalone (quinazamid), quinoxyfen (quinaxyofen), mefenoxam (chinomethianat), manomethione (quinomethionate), captafol (captafol), captan (captan), benalaxyl (miraxyl), quinconazol (quinconazol), quintozene (quintozene), iminoxyzoline (quintozole), quintozene (quintozene), iminoxyzoline (quintozene), iminoctadine (guazate), furamectin (guazatine), furametryn (prochloraz), pyricarb (cuproparb), coumoxystrobin (coumarone), chloroquindoxin (glyodin), chlorotetrazol (fenamidopropyl), chlorfenapyr (fenapyr), chlorfenapyr (chlorphenicolin), chlorfenapyr (chlorpheniramine), chlorfenamate), chlorfenapyr (chlorpheniramine), chlorpheniramine (chlorpheniramine), chlorpheniramine (chlorpheniramine), chlorpheniramine, Chlorpheniramine (chloroneb), salicylanilide (salicylanilide), cyazofamid (zarilamid), cyazofamid (cyazofamid), diethyl pyrocarbonate (diethyl pyrocarbonate), diethofencarb (diethofencarb), cyclanilide (cyflufamid), diclocyanide (dicymet), dichlozoline (dicholozoline), dichlorotriadimenol (diclosartan), benfluanide (dichlofluanid), cycloheximide (cycloheximide), diclomezine (diclomezine), niclosamide (dicloronan), dichlorophenol (dicholophen), dichloronaphthoquinone (dichloline), dithiodisulfam (pyrifos), pyridazone (dithinofos), dithianon (dithianon), dinicone (dinicone), dinicone (dinotefuran), dinotefuran (dinotefuran), dinotefuran (dinine (dinotefuran), dinotefuran (R-dinin (dinotefuran), dinotefuran (dinotefuran), dinone (dinotefuran), dinotefuran (dinone (dinotefuran), dinone (dinotefuran), dinotefuran (dinotefuran), dinone), dinotefuran (dinone (dinotefuran (dinone), dinotefuran (dinone), dinote, Primisum (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodinil), iprovalicarb (cyprofuran), cypenfluanid (cypendazole), simeconazole (simeconazole), dimethiol (dimethicol), dimethomorph (dimethomorph), cymoxanil (cymoxanil), dimoxystrobin (dimoxystrobin), ziram (ziram), silthiofam (silthiofam), streptomycin (strezomycin), spiroxamine (spiroxamine), pennisone (sultropen), cyprodinil (sedaxane), zoxamide (zoxamine), dazomethyl (dazomet), thifluzamide (fenpyrad), thifenpyrad (thifenpyrad), thifluzamide (thifenpyrad (thifluzamide), thifluzamide (thiocarb), thiuram (thiocarb), thiuracil (thiocarb), thiuram), thiuracil (thiocarb), thiuracil (thiocarb), thiuram), thiuracil (thiocarb), thiura, Thiram (tecoram), tetraconazole (tetraconazole), prochloraz (debacarb), dehydroacetic acid (dehydroacetic acid), tebuconazole (tebuconazole), isobutoxyquinoline (tebufloquin), doxycycline (dodicin), dodine (dodine), dodecyl benzene sulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph (dodemorph), hydralazone (drazoxolon), triadimenol (triadimirenol), triadimefon (triadimifon), butyltriazole (triazbutil), imidazoxazine (triazoxide), fenbuconazole (triamamihos), pyrimethanil (triafol), trichlamide (trichlamide), triclopyrimidine (triclopyr), tricyclazole (tricyclazole), sterilization (triticonazole), paraffin oil (butyloxime), trifloxystrobin (trifloxystrobin), trifloxystrobin (trin), trifloxystrobin (trifloxystrobin), trifloxystrobin (trin), trifloxystrobin, Phthalazinone (nitrothalopropyl), fluoropyrimidinol (nuarimol), cuppric nonyl phenolsulfonate (coppernylphenol sulfonate), quinolinyl acrylate (halaricine), validamycin (validamycin), valifenamide (valifenalate), hypersensitin (harpinprotein), picobactrazox, bixafen (bixafen), picoxystrobin (picoxystrobin), picobenzazamide, bithiophenol (bithionol), bitertanol (bitriazole), hymexazol (hydroxyisoxazole), isoxapyroxazole-potassium (hydroisoxazole-potassium), pyrane (binapacryl), biphenyl (biphenol), propidin (piperacillin), hymexazol (pyraclostrobin), pyrane (pyraclostrobin), pyrimethanil (pyraclostrobin (pyrimethanil), pyrimethanil (pyraclostrobin), pyrimethanil (pyraclostrobin), pyrimethanil (pyraclostrobin), pyrimethanil (pyraclostrobin), pyrimethanil (pyraclostrobin (, Chlorpyrifos (pyroxyfur), pyroquilon (pyroquilon), vinclozolin (vinclozolin), famoxadone (famoxadone), fenamidone (fenapanil), fenamidone (fenamidone), sodium diuron (fenaminosulf), fenamiprim (fenaminoquin), fenarimol (fenarimol), fenpropiram (fenpyrazone), fenoxanil (fenoxanil), pyrimethanil (fenoxaprop), pyrimethanil (fenpyrazone), pyrimethanil (fenpyrazamine), fenpropiconazole (fenpyrazamine), fenpyroxadine (fenpropidin), fenpropimorph (fenpropathrin), fenpyraclostrobin (fenpyrazamine), fenpyraclostrobin (fenpyrazamide), fenpropiconazole (fenpyrazamide), flufenamidone (fenpyrazone), flufenamidopropyl (flufenamidothiofen), pyrimethanil (fenpyraclostrobin), fenpropidin (fenpropidin), fenpropimorph (fenpropimorph), fenpropidin (fenpropidin), fenpropidin (flufenamide), fenpropidin (flufenamide), flufenamidothiofenamide (flufenacet), flufenamidothiofenadine), flufenamidone (flufen), flufen (flufen), flufen (flufen), flupyraclostrobin (fluopyram), flufenamide (fluoroimide), difuramide (furcarabanil), flupyraflufen (fluxapyroxad), fluquinconazole (fluquinconazole), furconazole (furconazol-cis), fludioxonil (fluxonil), flusilazole (flusilazole), flusulfamide (flusulfamide), flusulfamide (fluvalinate), flutriafol (flutriafol), furbenamide (flutolanil), flutriafol (flutriafol), furfural (furfurfurfurfurfurfurfurfurfurfurfurfurfurfurpyral), fenpropachlor (furbetulox), flufenamide (flufenamid), flumorph (flumorph), probenzoquinone (fluzid), prochloraz (prochloraz), prochloraz (cyromazine), propiconazole (propiconazole), propiconazole (propiconazole), propiconazole (propiconazole), propiconazole (propiconazole), propiconazole (propiconazole), propiconazole (propi, Benomyl (benomyl), pefurazoate (pefurazoate), quinoximes hydrazone (benzoquinone), penconazole (penconazol), benazolin (benzamorf), pencycuron (pencycuron), phenylhydroxamic acid (benzohydroxamic acid), benzovindiflupyr (benzovindifiupyrizer), bensulfuron (bentalcron), thiocyanobenzothiozole (benthiazole), benthiavalicarb-isopropyl (benthiavalicarb-isopropyl), penthiopyrad (penthiopyrad), penflufen (penflufen), boscalid (boscalid), phosophosphate (phosdipheny), fosetyl-Al (fosetyl-Al), polyoxins (polyoxins), milbemycin (milzianum), milnacipropyramid (fent), fenbuconazole (fenpropine), fenpropineb (fenpyr), pyrimethanil (fenpropineb), pyrimethanil (fenpyr), pyrimethanil (fenpropineb (propineb), pyrimethanil (fenpropiram), pyrimethanil (fenpropineb), pyrimethanil (propineb), pyrimethanil (fenpropineb), pyrimethanil (fenpropineb (propineb), pyrimethanil (fenpropineb (fenpropicarb (fen, Sulfocarb (methalosarb), metoclopramide (metazoxolon), metam (meta), metam (metham-sodium), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), metiram (metiram), methyl isothiocyanate (methythiocyate), mepiquat chloride (meptyl), metconazole (metconazol), thifluzamide (metsulfovax), furamex (methfuroxam), metominostrobin (metominobin), metrafenone (metrafenone), mepanipyrim (mepanipyrim), mefenoxam (mefenoxam), dinetoxazole (meptylum), diniconazole (meptyl), mefenoxam (meptyl), dinium chloride (meptyl), mefenamide (mepenil), iodomethane (iodomethane), pyrimethazole (metrafenone), silver (benzalkonium bromide), etc., basic cupric sulfate (copper sulfate), copper sulfate (copper chloride, etc.)
Sodium hypochlorite (sodium hypochlorite), copper hydroxide (copper hydroxide), hydrated sulfur agents (wet sulfur), lime sulfur agents (calcium polysulfides), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), inorganic sulfur (sulfur), anhydrous copper sulfate (copper sulfate), nickel dimethyl sulfate (nickel dimethyl carbonate), copper quinolinate (oxide copper) and other copper compounds, zinc sulfate (zinc sulfate), and copper pentahydrate (copper sulfate), and the like.
As the agricultural and horticultural insecticide, acaricide, nematicide used for the same purpose, for example, there can be exemplified:
3, 5-Dixylylmethylcarbamate (XMC), Bacillus thuringiensis azawai (Bacillus thuringiensis aizawai), Bacillus thuringiensis isalarcensis (Bacillus thuringiensis), Bacillus thuringiensis kurstaki, or Bacillus thuringiensis tenebrionis (Bacillus thuringiensis tenebrionis), Bacillus thuringiensis tenebrionis, Bacillus thuringiensis crystalline protein toxins produced by Bacillus thuringiensis, BPMC, Bt-toxin type insecticidal compounds, CBS (chlorophenylester), DCIP (dichlorodiisopropyl ester), D-propylene (1, 3-dichloropropylene), thiophosphoryl-4-dimethyl-O (DDO-4-dimethyl-O-4-thiophenyl-O-4-thiopropyl-O (DSP), thiophenyl-O-4-dimethyl-O-phenyl-O (4-phospho-4-dimethyl-O-phenyl-O-4-thioethyl-O (DSP), and N-phenyl-4-thiophenyl-O-phenyl-4-dimethyl-O-phosphate (DDO-4-thiophenyl-phenyl-4-dimethyl-O-phenyl-4-phenyl-O-4-thiophenyl-O-4-dimethyl-O-phenyl-O-O-4-O-, Tripropyl isocyanurate (TPIC), fluthrin (acrinathrin), azadirachtin (azadirachtin), bayphos (azinphos-methyl), acequinon (acequiylcyl), acetamiprid (acetamiprid), acetoprole (acetoprole), acephate (acephate), abamectin (abamectin), afidopyropen, abamectin-B (avermectin-B), sulphamethoprene (amifluumet), amitraz (amitraz), cotton boll (alanycarb), aldicarb (aldicarb), aldicarb (aldioxacarb), aldrin (aldrin), alpha-thiodan (pier-endosulfan), alpha-cypermethrin (alpha-cymethrin), benoxanthin (benazol), allethrin (isoproxylothrin), isoproxylothrin (isoprox), isoprothrin (isoprothrin-isoprothrin, isoprothrin (isoprofos), isoprothrin (isoprothrin, isoprothri, Indoxacarb (indoxacarb), S-fenvalerate (esfenvalerate), ethiofencarb (ethiofencarb), ethiofenphos (ethion), ethiprole (ethiprole), etoxazole (etoxazole), ethofenprox (ethofenprox), ethoprophos (ethoprophos), ethirimphos (ethymfos), emamectin (emamectin), emamectin benzoate (emamectin-benzoate), endosulfan (endosulfan), empenthrin (empenthrin), oxamyl (oxamyl), sufop (oxydemeton-methyl), isosulfothion (oxydemefos: ESP), oxibendazole (oxepidazole), flufencarbazide (oxfenthiuron), thiocyanofencarb (fenthion), thiocyanofencarb (fenpyrazone), Potassium oleate (potatonium), sodium oleate (sodium sulfofenthiocarb), thiocyanide (thiocarb (phenacylate), thiocyanine (phenazine), thiocyanide (phenazine), thiocarb (phenazine), thiocyanide (phenazine), thiocarb-methyl (phenazine), thiocyanide (phenazine), thiocarb-methyl-phenazine), bencarb-methyl-phenazine (phenazine), bencarb-methyl-phenazine (carbabencarb, Clofercarb, clothianidin (clothianidin), clofentezine (clofentezine), cyclopyramide (chromafenozide), chlorantraniliprole (chlorantraniliprole), phosphorus oxychloride (chlorethoxyfos), chlordimeform (chlorfenamate), chlorfenapyr (chlordane), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), chlorfenapyr (chlorphenapyr), chlorpyrifos (chlorpyrifos), chlorfenapyr (chlorofenphos), chlorpyrifos (1-fenthiuron), chlorfluazuron (chlorfluazuron), dicofol (chlorofenzine), chlorambucil (chlomethione), chlorfenapyr (chlorofenthion), chlorpyrifos (chlorpyrifos), chlorpyrifos (thiocyanofenpyrifos), thiocyanofenpyrifos (thiocyan), thiocyanofenprox (thiocyanofen), thiocyanofenprox (thiocyanide), thiocyanofen (thiocyanide), thiocyanide (thiocyanofen (thiocyanide), chlorpyrifos (chlorpyrifos), chlorpyrifos (thiocyanide), chlorpyrifos (chlorpyrifos), chlorpyri, Dichlorvos (DDVP), disulfoton (disulfofon), dinotefuran (dinotefuran), cyfluthrin (cyhalothrin), cyphenothrin (cyphenothrin), beta-cyfluthrin (cyfluthrin), diflubenzuron (diflubenzuron), cyflumetofen (cyfluthrin), flufenzine (diflufendazin), cyhexatin (cyhexatin), cypermethrin (cypermethrin), toxoplamethyl (dimetlvinphos), dimethoate (dimethofen), transfluthrin (dimefluthrin), silate (silafen), cyfluthrin (silate), spinetoram, dimethomozine (cyfluthrin), spinetoram (fluthrin), fluthrin (thiamethoxam), thiamethoxam (thiamethoxam), thiocyan (thiamethoxam), thiocyanin (thiamethoxam), dimethofen (tetramethrin), dimethofen), tetramethrin (tetramethrin), tetramethrin (tetramethrin), tetramethrin (tetramethrin), thiocyclam, thiodicap-sodium, fenamiphos, thiofenphos (thiometrin), deet (deet), dieldrin, methidathion (thiomethoprene), tefluthrin (tetraflumethrin), tetramethrin (tetramethrin), meprophos (tebufenofos), tebufenozide (tebufenozide), tebufenpyrad (tebufenpyrad), tefluthrin (tefluthrin), teflubenzuron (teflubenzuron), systemic phos-S-methyl (deuteron-S-methyl), thiothion (tefluthrin), deltamethrin (tefluthrin), tefluthrin (tefluthrin), thiopyrad (fluthrin), thiopyrafluthrin (tefluthrin), tefluthrin (fenpyrazone), tefluthrin (tefluthrin), tefluthrin (fenpyrazone), tefluthrin (fenpyrazone), tefluthrin (tefluthrin), tefluthrin (teflu, Thiacloprid (nicotinazine), nitenpyram (nitenpyram), novaluron (novaluron), noviflumuron (noviflumuron), hydroprene (hydroprene), fluoropyrazole (vanilloid), aphidicol (vamidothion), parathion (parathion), methylparathion (parathion-methyl), benzofenapyr (halfenprox), halofenozide (halofenozide), bistriflururon (bistriflururon), bisultap, hydramethylhydrazone (hydramethylnone), hydroxypropyl starch (hydropropyl), miticide (binapacryl), flukuroup, bifenazate (bifenazate), bifenthrin (bifenthrin), pymetrozine (pymetrozine), pyrazothion (pyriproxyfen), pyriproxyfen (pyridil), pyriproxyfen (pyridalyl), pyriproxyfen (pyriproxyfen), pyriproxyfen (pyradinil), pyriproxyfen (pyrad), pyriproxyfen (pyrad), pyriproxyfen, Fenazaquin (fenazaquin), fenamiphos (fenamiphos), fenisobrin (fenitrothion: MEP), fenoxycarb (fenoxycarb), fenoxycarb (fenothiocarb), phenothrin (phenothrin), fenobucarb (fenobucarb), fensulfothion (fensulfothion), fenthion (fenthion: MPP), phenthoate (phenoxate: PAP), fenvalerate (fenvalerate), fenpyroximate (fenpyroximate), fenpropathrin (fenpropathrin), fendazole (fenbendazole), fosthiazate (fosthiazate), varroamidine (formanate), temthion (butathyris), buprofezin (bufenzin), furacarb (furazarin), fenpyrafluthrin (flufenpyraflufen), flufenpyrazone (flufenpyrazothrin), flufenoxathion (flufenpyraflufen), flufenoxathion (flufenpyraflufenofos), flufenoxafen (flufenoxate (flufenoxathion), flufenoxathion (flufenoxafen), flufenoxafen (flufenoxafen), flufen), flufenoxafen (flufenoxafen), flufen (flufenoxafen), flufen (flufen), flufen (flufenoxafen), flufen (flufen), flufen (flufen), flufen (, Flufenzine (flufenzine), fluprophenyl ether (flufenprox), benzyl ether (fluproxyfen), fluflufluthrin (flucythrinate), fluhexfon (flubendiamide), flubendiamide (flubendiamide), flumethrin (fluethrin), flugimofen (flupirtine), profundum (prothiofos), propylphenthrin (prothifenbute), flonicamid (flonicamid), propaphos (propaphos), propargite (propagte: BPPS), profenofos (profenofos), fluthrin (proffluthrin), propoxur (propoxur: PHC), flumetquin (brofenpyroximate), bromopropylate (brofenpropathrin), benflumethrin (prothiofos), benflumethrin (prothromazine) (brofenpropathrin), bensultrin (fenthion), thiofenpyrazofenofos (fenthion), benflumethrin (fenthion) (benflumuron (fenthion), thifenpyrazofenox (thiofenthion), thifenpyrazofenofos (fenthiocarb) (1-2-benzothion (fenthiocarb), thifenpyrazone (fenthion) (chlorphos), thifenthion (fenthion) (bencarb (fenthion), thifenthiocarb) (bencarb (fenthion) (bencarb), thifenthiocarb (fenthiocarb (fenthion) (bencarb), thifenthiocarb (fenthiocarb) (bencarb), thifenthiocarb (bencarb), thifenthion (bencarb) (bencarb), thifenthiocarb), thifenthion, Phosphocarb (phoscarb), phosmet (phosmet: PMP), anti-mite complex (polynucleotides), varroamidine (formanate), thiophosphor (formothrion), phorate (phorate), machine oil (machine oil), malathion (malathion), milbemycin (milbemycin), milbemycin A (milbemycin-A), milbemycin (milbemectin), triazophos (mecarbam), methamidophos (methomyl), methomyl (methomyl), metaldehyde (metaldehyde), metaflumizone (metaflumizone), methamidophos (methamidophos), metam-ammonium (methomyl), metam-sodium (methomyl), methiocarb (methiocarb), methidathion (DMthion), methomyl (methyl ester), methomyl (methomyl) and methomyl (methyl chloride), methomyl (methomyl-methyl chloride), methomyl (methomyl) and methomyl (methomyl) are (methomyl), methomyl (methomyl) and methomyl (methomyl) are (methomyl) and methyl chloride (methyl chloride), methomyl (methyl chloride), methyl chloride (methyl chloride), methyl chloride (methyl chloride, methyl chloride, Metolcarb, meperfluthrin, mepalphos (mevinphos), monocrotophos (monocrotophos), bensultap (monosultap), momflurothrin, lambda-cyhalothrin (lambda-cyhalothrin), ryanodine (ryanodine), lufenuron (lufenuron), recalcure, resmethrin (resmethrin), lepimectin (lepimectin), rotenone (rotenone), levamisole hydrochloride (levansolhydrochloride), fenbutatin (fenbutatinoxide), methylthiopyrim tartrate (morantel tararate), methyl bromide (methyl bromide), tin (cytaxatin), calcium cyanamide (calcium cyanamide), sulfur (calcium sulfate), sulfur (ammonium sulfate), and nicotine (sulfatrifloxysulfate).
As herbicides used for the same purpose, for example, there can be exemplified: 1-naphthylacetamide (1-naphthylacetamide), 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPP, MCP, MCPA, 2 methyl 4 chloroethyl thioester (MCPA-thioethyl), MCPB, ioxynil (ioxynil), aclonifen (aclonifen), fentradinin (azafenidin), acifluorfen (acifluorfen), triazide (azinpropyrrone), sulfometuron (azimsulfuron), asulam (asulam), acetochlor (acetochlor), atrazine (atrazine), atrazine (), atrazine (atrazine), atrazine (asetron), isazosulfuron (acarone), cypermethrin (acarbon), pyrazofenon (acarbon), pyrazofenon (r), pyrazofenon (e), pyrazofenozide), pyrazofenon (a), pyrazofenox (a), pyrazofenozide (a), pyra, Amicarbazone (amicarbazone), amidosulfuron (amidosulfuron), fenflurazon (amicarbazone), pyrimethanil (amicarbazone), aminocyclopyrachlor (amicarbazone), aminopyralid (amicarbazone), terbutazone (amicarbazone), amicarbazone (amicarbazone), ametrdione (amicarbazone), ametryn (ametryn), alachlor (alachlor), dicloflufen (alloxydim), pentachlorothiac acid (alorac), imazapine (iofensulfuron), isoxauron (isouloron), cimetimide (isoxacarbazide), isoxaclozone (isoxapyrozone), isoxaflutole (isoxaflutole), isoxaflutole (isoxapyrozone), isoxaflutole (isoxaflutole), isoxaflutole (isoxapyrozone (isoxauron (isoxaprop (isoxauron), isoxapyroxaprop (isoxauron (isoxaprop (isoxapyroxaprop (isoxauron), isoxaprop (isoxapyroxaprop (isoxapyroxan), isoxapyroxaprop (isoxaprop (isofluroron)Grass (isopolinate), butazone (isomethiozin), trinexapac-ethyl (inabenfide), metribuzin (imazazine), fentrazole (ipfencarbazone), propadine (iprymepam), imazaquin (imazaquin), imazapic (imazapic), imazapyr (imazapyr), imazamethapyr (imazamethapyr), imazamethabenz (imazamethabenz z), imazamethabenz-methyl (imazamethabenz-methyl), imazamethabenz (imazamox), imazethapyr (imazethapyr), imazosulfuron (imazosulfuron), indoxazole (indofluam), indoxacin (indofluzone), indolebutyric acid (indobutrytacid), imazalil (uniconazole-P), imazaquin (imazapine), penoxsulam (bentazone), bentazone (imazachlor), bentazone (indomethabenzuron (bentazone), imazachlor (indomethabenzuron (bensulfuron), bensulam), indomethabenzuron (bensulfuron-P), indomethabenzuron (imazachlorMethyl acid (ethametsulfuron), ethametsulfuron (ethametsulfuron), dichlorfon (etholate), ethychlorozate ethyl, sulfothiouron (ethidimuron), nitrophenol (ethiofefen), ethephon (ethephon), ethoxysulfuron (ethysulfuron), fluroxypyr (ethoxyfen), pyrithiobac (ethofenprox), ethofenprox (ethofenprox), tebuconazole (epothiuron), endothio (ethoxysulfuron), oxaziclomefon (oxcarbazone), oxadiargyl (oxcarbazate), oxaziclodinate (oxcarbazone), carfentrazone (fentrazone), fentrazone (oxypyr), fentrazone (fentrazone), fentrazone (fentrazone), quizalofop (quizalofop), quizalofop-P (quizalofop-P), quizalofop-ethyl (quizalofop-ethyl), xylapplications (xylachlor), chloramphinine (quinocline), chloramphenical (quinonamide), quinclorac (quinmerac), cumyluron (cumuron), iodochlodinate (clodinate), glyphosate (glyphosate), glufosinate (glufosinate-P), pyriminophen (cremazine), clethodim (clethodim), cloethone (cloethydim), cloxacylic acid (cloxyfonac), clodinafop (clodinafop), clodinafop-propargyl (clopropargyl-pargyl), clomazone (clobetasol), cloclocloclocloclochlone (cloclocloclochlop-cloclin), clochlomethyl (clochlomethyl), clochlop (clochlomethyl), clofos (clochlomethyl (clochlo-clofos), clochlo-clofos (clochlo-clofos), clochlo-clofos (clochlo-P), clochlo (clo, Butachlor (chlorococcyl), chloramben (chloramben), cloransulam-methyl, chloraminophen (chlorandazol), chlorimuron-ethyl acid (chlorimuron), chlorimuron-ethyl, chlorsulfuron (chlorimuron), chlorophthalic acid (chlorimuron), chlorothioamide (chlorithiuramid), chlortoluron (chloritoluron), and grassesCumquat (chlororntroben), varroa (chlorofenac), avenate (chlorofenprox), chlorfluazuron (chloroflufam), fluocinonide (chlorofluzole), truthful alcohol (chloroflunol), chloranthus (chlorocarb), chlorpropham (chlorophen), chlormequat (chlorofluazuron), ethoxysulfuron (chlorotoluron), chlorfenapyr (chloroxynil), chlorsulfuron (chloroxuron), trichloropropionic acid (chlororopon), saflufenacil (saflufenacil), cyanazine (cyazone), cyanazine (cyhaloxyn), avena (ester-aluminate), diuron (diumuron), diethylcarbamquat (dimethylcarbam), dicamba (cyclocaryophyllum), diclocyclron (cyclosulfuron), propathron (2-sulfometuron (2-4-propathrin), diclofop (2-methyl-propathrin), diclofop (clofenapyr), diclofop (clodron-4-methyl-2, clodron, diclofop, diclofenoxaprop (clodron, clodron-2, diclofenoxuron, clodron-2, clodron (clodron, clodron-2, clodron, clo, Chlorsulfuron (dichloralurea), diquat (diquat), fluazuron (cisanilide), 2,4-d sodium sul-phur (disul), siduron (siduron), dithiopyr (dithiopyr), prodiamine (dinitramine), cinidon-ethyl (cinidon-ethyl), diniconazole (dinosam), cinolone (cinosulfuron), dinotefuran (dinoseb), tylenol (dinober), dinotefuran (dinofenate), trinitrop (dinoropp), cyhalofop-butyl (cyhalofop-butyl), diphenoxamide (diphenhydramide), cumyluron (difenoxypron), flupentenoic acid (difenoten), difenoswallowwort (difenoconazole), cybubutyne (cybutyne), cybutazine (cyhaloxyzine), cyhalofop (cyhalofop-butyl), cyhalofop-butyl (diclofen), pyriproxyfen (difenon), pyrimethanil (difenox), pyrimethanil (cyhalodinafuron (fenpyrad), pyrimethanil (cyhalodinil), pyrimethanil (cyhalodinafol (fenpyrazone), pyrimethanil (cyhalodinil), pyrimethanil (cyhalodinil), pyrimethanil (cyhalodinil), pyrimethanil (cyhalodinafbenbenbencarb (, Dimethenamid, simetryn, dimedone, dimehypo, metosulam, sulglycon, sulcotrione, fentrazine, sulfsultap, sulfentrazone, sulfsulsulfuron, sulfentrazone, sulfosulfuron, sulfometuron-methyl) Such as bensulfuron methyl, fenfluramine, bentazone, thifensulfuron methyl, thiofensulfuron methyl, thiofenpyrone, thifensulfuron methyl, thiofenpyrone, thifenpyrone, thifenuron methyl, thifensulfuron methyl, thifenpyromethyl, thifensulfuron methyl, terbutryn (terbutryn), topramezone (topramezone), tralkoxydim (trakoxydim), triaziflam (triaziflam), triasulfuron (triasulfuron), triafamone (triafamone), triallate (triallate), norflurazon (triallate), triclopyr (triclopyr), dichlorfon (triaphane), tribenuron (triallate), triflusulfuron (triasulfuron), triflusulfuron (triflusulfuron-methyl), trifluralin (trifluralin), trifloxysulfuron (triflusulfuron), tralkoxydim (triazone), trinitron (triasulfuron), trinuron (trinitrobenuron), bensulfuron (triflusuron), trinitron (trifluralol), trinitron (trifluralin), triflusulfuron (trifluralon-methyl), trifluralin (trifluralin), triflusulfuron (trinitron), trinitrotoluene (trifluralin), bensulfuron (trifluralin), bensulfuron (bensulfuron), bensultrinitron (bensulfuron), bensulfuron (bensultrinitron), bensulfuron (bensulfuron), bensultrinitron (bensulfuron), bensulfuron (bensultrinitron (trinitron), bensultrinitron), bensulfuron), bensultrinitron (bensultrin, Pyriclofenac (nipyraclofen), prosulfuron (neb), norflurazon (norflurazon), cudweed (norflurron), barban (barban), paclobutrazol (paclobutrazol), paraquat (paraquat), paraquat (paraflurron), haloperidol (haloxydine), halauxifen (free acid), haloxyfen (haloxyfop), haloxyfop (haloxyfop), and isoproxil (haloxyfop)haloxyfop-P, haloxyfop-methyl, fluoronifediamide (halosafen), halosulfuron-demethylate (halosulfuron), halosulfuron-methyl (halosulfuron-methyl), picloram (picloram), fluopyram (picolinafen), bicyclopyrone (bicyclophorone), bispyribac-sodium (bispyribac-sodium), pyrazosulfuron (pyradinon), pinoxaden (pinoxaden), bifenox (bifenox), piperophoron (piperophos), hymexazol (mexazol), pyraclonil (pyraclonil), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl), pyrazosulfuron-ethyl (pyrazosulfuron-4), pyrazosulfuron-methyl (pyrazosulfuron-methyl), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl), pyrazosulfuron-ethyl (pyrazosulfuron-methyl), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl-4), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl), pyrazosulfuron-ethyl (pyrazosulfuron-methyl), pyrazosulfuron-ethyl (pyrazosulfuron-4), pyrazosulfuron-ethyl (pyrazosulfuron-ethyl), pyrazosulfuron-ethyl (pyrazoethyl), pyrazosulfuron-2 (pyrazosulfuron-2), pyrazosulfuron-ethyl (pyrazoethyl-methyl), pyrazosulfuron-4, pyrazosulfuron-ethyl, pyrazoethyl, pyrazosulfuron-ethyl, pyrazoethyl, pyrithiobac-sodium (pyrithiobac), pyrithiobac-sodium (pyrithiobac-sodium), pyridate (pyridate), pyrithiobac-methyl (pyributicarb), pyribenzoxim (pyribenzoxim), pyrithiobac-sodium (pyrithiobac-methyl), pyrithiobac-methyl (pyribenzoxim), pyrithiobac-sodium (pyrithiobac-sodium), primisulfuron (primisulfuron), pyrithiobac-methyl (pyriminobac-methyl), pyrithiobac-sodium (pyroxasulfone), pyroxsulam (pyroxsulam), fenoxycarb (fenoxaprop-P), alantin (phenoxap), fenuron (fenoxaprop-P), isoxasulfone (fenoxasulfone), fenoxaprop-P (fenoxaprop-P), fenoxaprop-P (fenoxaprop-P), fenoxaprop-ethyl (fenoxaprop-P-ethyl), fenoxaprop-2 (fenoxaprop-P-ethyl), fenoxaprop-ethyl (fenoxaprop-P-5), fenoxaprop-ethyl (fenoxaprop-2, fenoxaprop-P-ethyl (fenoxaprop-3), fenoxaprop-P, fenoxaprop-5, fenoxaprop-P (fenoxaprop-P-ethyl, fenoxaprop-P, fenoxaprop-ethyl (fenoxaprop-2, fenoxaprop-5, fenoxaprop-P, fenoxaprop-2, fenoxaprop-ethyl (fenoxaprop-P, fenoxaprop, Butachlor (butachlor), butafenacil (butafenacil), butafosinate (butamifos), buthiuron (buthiuron), buthiuron (buthizole), buthiuron (buthylate), buthiuron (buturon), butachlor (buthyl), butafenacet (butroxydim), butralin (butralin), flazasulfuron (fluzasulfuron), flamprop (flamprop), furbensulfuron (furyloxyfen), propyzamide (prynachlor), primisulfuron-methyl (primisulfuron-methyl), fluazifop (fluzifop), fluazifop (fluazifop-P), fluazifop-P-ethyl-Butyl (fluzifop-butyl), pyriflufen-ethyl (fluazolate), fluroxypyr (fluoxypyr), fluometuron (fluorothiuron), fluometuron (fluometuron), fluoroglycofen (flutoluron), fluoroglycofen (fluoroglycofen), fluorone (fluorone), fentrazone (fludioxonil), fenpyr (fluidon), fluorone (flucarbazone), fluorone-sodium (flucarbazone-sodium), fluorozone (fluorofluralin), fluoropyrosulfuron (fluquindox), fluorosulfuron (fludioxonil), fluoropyrosulfuron (flusulfuron), fluorone (fluthiacet), fluoropyrenon (fluthiacet), fluoropyr-methyl (fluthiacet-methyl), fluoropyrsulfuron (flupyrsulfuron-methyl), fluoropyrsulfuron-methyl (flupyrenon), fluoropyrsulfuron (flupyrsulfuron), flufenacetron (flufenacet), flufenacet (fluroxypyr), flufenacetron (fluroxypyr), flufenacet (flufen), flufenacet (fluroxypyr), flufenacet (flufenacet), flufenacet (flufenacet), flufenacet (flufenacet), flufenacet, Flumetsulam (flumetsulam), fluazinone (fluridone), flurtamone (flurtamone), fluroxypyr (fluroxypyr), pretilachlor (pretilachlor), prometryn (proxan), ganbazine (proglinazine), cyazon (procyrazine), prodiamine (prodiamine), pinoxaden (prosulalin), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), propaquizab (prosulfocarb), oxadiargyl (propaquizafop), propachlor (propachlorchlorine), prometryne (propaquinolone), propamocarb (propaquinone), propyzamide (propyzamide), propyzamide (propaferin), propyzamide (propyzamide), propiconazole (propyzamide), jasmone (propafenone), propafenone (propafenone), propafenone (propaferin), propaferin (propiram), propaferin (propidium), propidium (fenpyr-methyl), propaferin (propiram), propaferin (propaferin), propidium (propaferin), propaferin (propaferin), propiram (propaferin), propiram), propaferin (prop, Bromophenol oxime (bromonoxim), bromobutyric acid amide (bromobutyride), furosemide (bromobonil), flutolanil (flurspreading), florpyrazauxifen, hexachloroacetone (hexachloroacetone), hexazinone (hexazinone), dimethenamid (pethoxamid), benazolin (benazolin), penoxsulam (penoxsulam), dichlord (petiolate), beflubutamid (beflubutut)amid), chlorfenapyr (vernolate), fomesafen (perfluidone), bencorarbazone, fenzadox (benzazadox), benethamine (benzzipam), benayl aminopurine (benzylammonirin), benzthiazuron (benzthiazuron), benfenamidone (benzfendazone), bensulide (bensulide), bensulfuron (bensuluron-methyl), neoyankeen (benzoxyprop), benzobicyclon (benzobicyclon), benzoxaflutole (benzofenanap), flumetsulam (benzofluor), bentazone (bentazone), mechlorfenchloramide (penoxsul), thiobensulam (benzofenamide), thiofanate (benthiacarb), pendimethalin (pendimethalin), pentoxazone (fenflurazone), ethazone (ethazone), butazone (fluroxypyr), trifloxysulfuron (2-methyl-ethyl), trifloxysulfuron (2 (sulfourea), sulfamuron (2 (thiofanyl), sulfamethoxide (2 (benfluroxypyr), bensularone (bensularone), sulfamuron (thiofanyl), bensularone (2 (thiofanuron (thiofanyl), bensularone (2 (thiofanyl), sulfamethoxide (bensularone), bensularone (bensularone), bensularone (bensularone ), bensulbensularone (bensularone (bensulbensulbensulbensulbensulbensulbensulbensulbensularone), bensul, Mesotrione (mesotrione), metribuzin (methoprene), metribuzin (methprotryne), metazachlor (metazachlor), metoxazole (methazole), metazosulfuron (metazosulfuron), methabenzthiazuron (methabenzthiazuron), metam (metamitron), metamifop (metam), metam (metam), fluroxypyr (methamphron), metoxuron (metham), metosulam (methamphetalin), metosulam (methzolin), methiocarb (methiobenzocarb), methimazone (methimazone), metoxuron (metoxuron), metosulam (metosulam), metosulron (metharon), metosulron (methazone), metosulron (metosuluron), metosuluron (metosuluron), metosultrin (metosultrin), metosultrin (metosultrin), metosultrin (metosultrin), metosultrin (, Linuron (monolinuron), molinate (molinate), varez (moramquat), iodosulfuron-methyl-amino acid (iodosulfuron), iodosulfuron-sodium (iodosulfuron-methyl-sodium), iodoxynil (iodobonil), iodomethane (iodomethane), lactofen (lactofen), linuron (Linuron),Rimsulfuron (rimsulfuron), lenacil (lenacil), sulfocyanetamide (rhodethanil), calcium peroxide (calcium peroxide), methyl bromide (methyl bromide), and the like.
Further, as the biopesticides, for example, microbial pesticides used as insecticides or nematicides such as Nuclear Polyhedrosis Viruses (NPV), Granulosis viruses (gravisis viruses, GV), Cytoplasmic Polyhedrosis Viruses (CPV), entomopox viruses (EPV), and other viral preparations, monacrosporium turcicola (monacrosporphragmatophagum), wireworms (steinernemacampas), insect parasitic nematodes (Steinernemakushidai), and punctured spore rods (pasteurianes); microbial pesticides used as bactericides, such as Trichoderma lignicolum (Trichoderma lignrum), agrobacterium radiobacter (agrobacterium radiobacter), nonpathogenic Erwinia carotovora (Erwinia carotovora), and bacillus subtilis (bacillus subtilis); and a biopesticide used as a herbicide such as Xanthomonas campestris (Xanthomonas campestris) can be used in combination, and the same effect can be expected.
Further, as the biopesticide, for example, natural enemies such as apis mellifera (encarsiamomosa), acanthomys columba (aphhidius coides), cecidomycosis erysipelas (aphhidolepis), イ pisum pellegeli (diglypisa), siberian bombesia cichorea (dacnusasibica), physeiidae persicae persimilis (phytoseiurus persimilis), amblyseius persimilieus persicae (amblyseius), orius cucumeris (oriussuritus), and orius donovatus (oriussuritus) may be added; microbial pesticides such as Beauveria brongniartii (Beauveria brongniartii); and pheromone agents such as (Z) -10-tetradecenyl ═ acetate, (E, Z) -4, 10-tetradecenyl ═ acetate, (Z) -8-dodecenyl ═ acetate, (Z) -11-tetradecenyl ═ acetate, (Z) -13-eicosa-10-one, and 14-methyl-1-octadecene.
Hereinafter, representative embodiments of the present invention will be illustrated, but the present invention is not limited thereto.
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