CN104024222A - Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide - Google Patents

Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide Download PDF

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Publication number
CN104024222A
CN104024222A CN201280053503.4A CN201280053503A CN104024222A CN 104024222 A CN104024222 A CN 104024222A CN 201280053503 A CN201280053503 A CN 201280053503A CN 104024222 A CN104024222 A CN 104024222A
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alkyl
alkoxy
halogenated
carbonyl
group
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Inventor
松崎义广
中尾勇美
安河内英二
御所佳典
远西正范
诹访明之
犬饲佳代
中野元文
藤冈伸祐
三原纯
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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Abstract

The present invention relates to a phthalamide derivative represented by general formula (I) or a salt thereof. [In the formula, X1 represents a halogen atom or the like; X2 represents a halogen atom or the like; m represents 0, 1, 2 or 3; Y1 and Y2 independently represent a hydrogen atom, a halogen atom, an alkyl group or the like; n represents 0, 1 or 2; Z1, Z2 and Z3 may be the same as or different from one another and independently represent a nitrogen atom, CH, C-Y2 or C-A-Q (wherein at least one of Z1, Z2 and Z3 represents C-A-Q); A represents a linear or branched (C1-C8)alkylene group; Q represents a specific condensed heterocyclic group containing a nitrogen atom; R1 represents a (C1-C8)alkylthio-(C1-C8)alkyl group or the like; and R2 and R3 independently represent a hydrogen atom or the like.

Description

Phthaloyl amide derivatives and containing the derivative agricultural and horticultural pesticide and its application method
Technical field
The present invention relates to using the new phthaloyl amide derivatives or its esters containing annelated heterocycles base as the agricultural and horticultural pesticide and its application method of effective component.
Background technique
So far, although developing various agriculturals and horticultural pesticide, but in the production of agricultural and the crops such as gardening because of pest etc. caused by damage it is still serious so far, in addition, there is also generate to have the problems such as pest of repellence to previous medicament, therefore, it is desirable to develop a kind of new agricultural and horticultural pesticide.In addition, also seeking always while the aging due to agriculture pursuer seeks various labour-saving method of administration with the agricultural of the characteristic suitable for these method of administration and the exploitation of horticultural pesticide.
It is described in patent document 1,2,3 and 4 and certain phthaloyl amide derivatives is used separately as insecticide.It remains desirable, however, that exploitation has the new agricultural and horticultural pesticide of the system of more high activity and/or broader spectrum of insecticidal spectrum.
Existing technical literature
Patent document
Patent document 1: International Publication No. 2004-080984 pamphlet
Patent document 2: International Publication No. 2005-095351 pamphlet
Patent document 3: International Publication No. 2006-053643 pamphlet
Patent document 4: International Publication No. 2010-012442 pamphlet
Summary of the invention
Subject to be solved by the invention
Therefore, problem of the present invention is that, a kind of noval chemical compound for novel agricultural and horticultural pesticide is provided.
The means to solve the problem
The inventors of the present invention are furtherd investigate repeatedly in view of the above subject, as a result, it has been found that, the excellent feature not having in phthaloyl amide derivatives or its esters unknown so far with previous similar compound, further progress research, so far completes the present invention.
That is, the present invention relates to the inventions of at least following [1]~[6] item:
[1] lead to phthaloyl amide derivatives or its esters that formula (I) indicates:
[chemical formula 1]
In formula, X1It indicates
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；
(a12)(C1-C8) halogenated alkyl sulfonyl；
(a13) carbamoyl；
(a14) amino；
(a15)(C1-C8) alkyl amino；
(a16)(C3-C8) cycloalkyl amino；
(a17)(C3-C8) naphthenic base (C1-C8) alkyl amino；
(a18)(C1-C8) alkoxy (C1-C8) alkyl amino；
(a19) bis- (C1-C8) alkyl amino (alkyl may be the same or different)；
(a20) Formylamino；
(a21)(C1-C8) alkyl-carbonyl-amino；
(a22)(C1-C8) alkoxycarbonyl amino；
(a23) phenyl；
(a24) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenyl；
(a25) phenoxy group；Or
(a26) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenoxy group,
X2It may be the same or different,
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；
(b6)(C1-C8) halogenated alkoxy；
(b7) carbamoyl；
(b8) amino；
(b9)(C1~C8) alkyl amino；
(b10)(C3~C8) cycloalkyl amino；
(b11)(C3~C8) naphthenic base (C1~C8) alkyl amino；
(b12)(C1~C8) alkoxy (C1~C8) alkyl amino；
(b13) bis- (C1~C8) alkyl amino (alkyl may be the same or different)；
(b14) Formylamino；
(b15)(C1~C8) alkyl-carbonyl-amino；
(b16)(C1~C8) alkoxycarbonyl amino；
(b17) phenyl；
(b18) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenyl；
(b19) phenoxy group；Or
(b20) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenoxy group,
M indicates 0,1,2 or 3,
Y1It indicates
(c1) hydrogen atom；
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c5)(C1-C8) halogenated alkyl；
(c6)(C1-C8) alkoxy；
(c7)(C1-C8) halogenated alkoxy；
(c8)(C1-C8) alkylthio group；
(c9)(C1-C8) halogenated alkylthio；
(c10)(C1-C8) Alkylsulfinyl；
(c11)(C1-C8) haloalkylsulfinyl；
(c12)(C1-C8) alkyl sulphonyl；Or
(c13)(C1-C8) halogenated alkyl sulfonyl,
Y2It may be the same or different, indicate
(d2) halogen atom；
(d3)(C1-C8) alkyl；
(d4)(C1-C8) halogenated alkyl；
(d5)(C1-C8) alkoxy；
(d6)(C1-C8) halogenated alkoxy；
(d7)(C1-C8) alkylthio group；
(d8)(C1-C8) halogenated alkylthio；
(d9)(C1-C8) Alkylsulfinyl；
(d10)(C1-C8) haloalkylsulfinyl；
(d11)(C1-C8) alkyl sulphonyl；Or
(d12)(C1-C8) halogenated alkyl sulfonyl,
N indicates 0,1 or 2,
Z1、Z2And Z3It may be the same or different, indicate nitrogen-atoms, CH, C-Y2Or C-A-Q (wherein, in logical formula (I), C-A-Q can also only with Z1、Z2And Z3Any of bonding),
(the C of A expression linear chain or branched chain1-C8) alkylidene,
Q indicates annelated heterocycles base selected from the following,
[chemical formula 2]
In formula, it is bonded with the part that symbol " " marks with A,
W1It may be the same or different, indicate
(e1) hydrogen atom；
(e2) halogen atom；
(e3) cyano；
(e4) formoxyl；
(e5) cyano (C1-C8) alkyl；
(e6)(C1-C8) alkyl；
(e7)(C2-C8) alkenyl；
(e8)(C2-C8) alkynyl；
(e9)(C2-C8) halogenated alkenyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e16)(C3-C8) halogenated cycloalkyl；
(e17)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e20)(C1-C8) alkyl sulphonyl；
(e21)(C1-C8) alkylthio group (C1-C8) alkyl；
(e22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(e23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(e24)(C1-C8) halogenated alkylthio；
(e25)(C1-C8) haloalkylsulfinyl；
(e26)(C1-C8) halogenated alkyl sulfonyl；
(e27)(C1-C8) alkoxy carbonyl；
(e28)(C2-C8) allyloxycarbonyl；
(e29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(e30)(C1-C8) alkyl-carbonyl；
(e31)(C3-C8) naphthene base carbonyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；Heterocycle with identical or different is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(e34)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(e35)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(e36)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(e37)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above, R5It is same or different to each other)；
(e38) aryl；
(e39) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(e40) aryloxycarbonyl epoxide；
(e41) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryloxycarbonyl epoxide of 1~5 substituent group in phenoxy group；
(e42) aryl (C1-C8) alkyl；
(e43) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e44) heterocycle；
(e45) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group；
(e46) heterocycle (C1-C8) alkyl；Or
(e47) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl,
W2、W2a、W2bAnd W2cIt may be the same or different, indicate
(f1) hydrogen atom；
(f2)(C1-C8) alkyl；
(f3) work as W2And W2aOr W2bAnd W2cWhen being bonded on same carbon atom, > C=O base；
(f4) work as W2And W2aOr W2bAnd W2cWhen being bonded on same carbon atom, > C=N-R6Base (wherein, R6Indicate cyano, (C1-C8) alkyl or (C1-C8) alkoxy)；
(f5) in Q18 or Q27, W2And W3It can also be bonded and form 5~8 yuan of saturation nitrogen-containing heterocycles containing 1 nitrogen-atoms；
(f6) halogen atom；
(f7)(C1-C8) alkoxy；Or
(f8)W2bAnd W2cCarbon atom that is bonding and being bonded with them is formed together unsubstituted 5~8 yuan of saturated or unsaturated aliphatic rings, which contains 0~2 oxygen atom,
W3And W3aIt may be the same or different, indicate
(m1) hydrogen atom；
(m2) cyano；
(m3) formoxyl；
(m4) cyano (C1-C8) alkyl；
(m5)(C1-C8) alkyl；
(m6)(C2-C8) alkenyl；
(m7)(C2-C8) alkynyl；
(m8)(C2-C8) halogenated alkenyl；
(m9)(C3-C8) naphthenic base；
(m10)(C1-C8) alkoxy (C1-C8) alkyl；
(m11)(C1-C8) halogenated alkyl；
(m12)(C3-C8) halogenated cycloalkyl；
(m13)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(m14)(C1-C8) alkylthio group (C1-C8) alkyl；
(m15)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(m16)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(m17)(C1-C8) alkoxy carbonyl；
(m18)(C2-C8) allyloxycarbonyl；
(m19)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(m20)(C1-C8) alkyl-carbonyl；
(m21)(C3-C8) naphthene base carbonyl；
(m22)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(m23)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(m24)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(m25)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(m26)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above)；
(m27) aryl；
(m28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(m29) aryl (C1-C8) alkyl；
(m30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(m31) heterocycle；
(m32) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group；
(m33) heterocycle (C1-C8) alkyl；Or
(m34) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g3) cyano；
(g4) formoxyl；
(g5) cyano (C1-C8) alkyl；
(g6)(C1-C8) alkyl；
(g7)(C2-C8) alkenyl；
(g8)(C2-C8) alkynyl；
(g9)(C2-C8) halogenated alkenyl；
(g10)(C3-C8) naphthenic base；
(g11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(g12)(C1-C8) alkoxy；
(g13)(C1-C8) alkoxy (C1-C8) alkyl；
(g14)(C1-C8) halogenated alkyl；
(g15)(C1-C8) halogenated alkoxy；
(g16)(C3-C8) halogenated cycloalkyl；
(g17)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(g18)(C1-C8) alkylthio group；
(g19)(C1-C8) Alkylsulfinyl；
(g20)(C1-C8) alkyl sulphonyl；
(g21)(C1-C8) alkylthio group (C1-C8) alkyl；
(g22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(g23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(g24)(C1-C8) halogenated alkylthio；
(g25)(C1-C8) haloalkylsulfinyl；
(g26)(C1-C8) halogenated alkyl sulfonyl；
(g27)(C1-C8) alkoxy carbonyl；
(g28)(C2-C8) allyloxycarbonyl；
(g29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(g30)(C1-C8) alkyl-carbonyl；Or
(g31)(C3-C8) naphthene base carbonyl,
P indicates 0,1 or 2,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h4)(C3-C8) naphthenic base；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h6) hydroxyl (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h11) aryl；
(h12) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
(h13) arylthio (C1-C8) alkyl；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h15) aryl (C1-C8) alkylthio group (C1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl；
(h17) aryl (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h19) aryloxy group (C1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h21) aryl (C1-C8) alkoxy (C1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h23) aryl (C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h25) aryl carbonyl epoxide (C1-C8) alkyl；
(h26) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl carbonyl epoxide (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h27) aryl methylene imino group oxygroup (C1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h29) aryl (C1-C8) Alkoximino (C1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl；
(h31)R4(R5) N carbonyl oxygroup (C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(h32)R4(R5) N carbonyl (C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(h33)R4(R5) N carbonyl (R4)N(C1-C8) alkyl (in formula, R4And R5It is as defined above, R4It is same or different to each other)；
(h34) heterocycle (C1-C8) alkyl；Or
(h35) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) (C2-C8) 1~5 substituent group in alkynyl heterocycle (C1-C8) alkyl；Or
Indicate substituent group below (part marked with symbol " " and nitrogen atom bonding),
[chemical formula 3]
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j2)(C1-C8) alkyl；
(j3) cyano；
(j4)(C1-C8) alkyl-carbonyl；
(j5)(C1-C8) halogenated alkyl carbonyl；
(j6)(C1-C8) alkoxy carbonyl；
(j7) aryl；
(j8) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
(j9) aryl sulfonyl；Or
(j10) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl sulfonyl of 1~5 substituent group in phenoxy group,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；
(k2)(C1-C8) alkyl；
(k3)(C3-C8) naphthenic base；Or
(k4)(C3-C8) naphthenic base (C1-C8) alkyl；Or
(k5)R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom；
R3It indicates
(l1) hydrogen atom；
(l2)(C1-C8) alkyl；
(l3)(C3-C8) naphthenic base；Or
(l4)(C3-C8) naphthenic base (C1-C8) alkyl.
[2] phthaloyl amide derivatives or its esters as described in above-mentioned [1], wherein X1For
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；
(a12)(C1-C8) halogenated alkyl sulfonyl,
X1Substituent group in addition is as defined in [1].
[3] phthaloyl amide derivatives or its esters as described in above-mentioned [1], wherein X2For
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；
(b6)(C1-C8) halogenated alkoxy,
X2Substituent group in addition is as defined in [1].
[4] phthaloyl amide derivatives or its esters as described in above-mentioned [1], wherein X1For
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；
(a12)(C1-C8) halogenated alkyl sulfonyl,
X2For
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；
(b6)(C1-C8) halogenated alkoxy,
X1And X2Substituent group in addition is as defined in [1].
[5] phthaloyl amide derivatives or its esters as described in above-mentioned [1], wherein X1It indicates
(a1) hydrogen atom；
(a2) halogen atom；
(a7)(C1-C8) alkylthio group；
(a9)(C1-C8) Alkylsulfinyl；Or
(a11)(C1-C8) alkyl sulphonyl,
X2It indicates
(b2) halogen atom,
M indicates 0 or 1,
Y1It indicates
(c1) hydrogen atom；
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
Y2It indicates
(d2) halogen atom；
(d3)(C1-C8) alkyl；
(d4)(C1-C8) halogenated alkyl；
(d5)(C1-C8) alkoxy；Or
(d6)(C1-C8) halogenated alkoxy,
N indicates 0 or 1,
Q indicates Q1, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q16, Q18, Q19, Q21, Q23, Q24, Q25, Q26, Q27, Q28, Q29, Q30 or Q31, wherein
W1It may be the same or different, indicate
(e1) hydrogen atom；
(e4) formoxyl；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e21)(C1-C8) alkylthio group (C1-C8) alkyl；
(e22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(e23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(e27)(C1-C8) alkoxy carbonyl；
(e29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, heterocycle, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(e34)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(e35)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(e36)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(e37)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above, R5It is same or different to each other)；
(e38) aryl；
(e39) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(e44) heterocycle；Or
(e46) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；
(g14)(C1-C8) halogenated alkyl；Or
(g27)(C1-C8) alkoxy carbonyl；
P indicates 0；
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h12) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl；
(h17) aryl (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h26) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl carbonyl epoxide (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl；
(h31)R4(R5) N carbonyl oxygroup (C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(h32)R4(R5) N carbonyl (C1-C8) alkyl (in formula, R4And R5It is as defined above)；Or
(h33)R4(R5) N carbonyl (R4)N(C1-C8) alkyl (in formula, R4And R5It is as defined above, R4It is same or different to each other)
(h34) heterocycle (C1-C8) alkyl；
Or
Indicate substituent group below (part marked with symbol " " and nitrogen atom bonding),
[chemical formula 4]
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j2)(C1-C8) alkyl；
(j3) cyano；
(j4)(C1-C8) alkyl-carbonyl；
(j5)(C1-C8) halogenated alkyl carbonyl；
(j6)(C1-C8) alkoxy carbonyl；
(j8) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
Or
(j10) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl sulfonyl of 1~5 substituent group in phenoxy group,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl；
(k5) or R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3It indicates
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl.
[6] phthaloyl amide derivatives or its esters as described in above-mentioned [1], wherein
X1It indicates
(a2) halogen atom,
M indicates 0,
Y1It is identical or different, it indicates
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
N indicates 0,
Z2Indicate C-A-Q,
Q indicates Q1, Q8 or Q18, wherein
W1It indicates
(e1) hydrogen atom；
(e4) formoxyl；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e27)(C1-C8) alkoxy carbonyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；Heterocycle with identical or different is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(e34)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(e35)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(e36)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(e37)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above, R5It is same or different to each other)；
(e38) aryl；
(e44) heterocycle, or
W2、W2aAnd W2bIt may be the same or different, indicate
(f1) hydrogen atom；
(f2)(C1-C8) alkyl；Or
(f3) work as W2And W2aWhen being bonded on same carbon atom, > C=O base,
W3And W3aIt may be the same or different, indicate
(m1) hydrogen atom；
(m2) cyano；
(m4) cyano (C1-C8) alkyl；
(m5)(C1-C8) alkyl；
(m6)(C2-C8) alkenyl；
(m7)(C2-C8) alkynyl；
(m8)(C2-C8) halogenated alkenyl；
(m9)(C3-C8) naphthenic base；
(m10)(C1-C8) alkoxy (C1-C8) alkyl；
(m11)(C1-C8) halogenated alkyl；
(m14)(C1-C8) alkylthio group (C1-C8) alkyl；
(m15)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(m16)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(m17)(C1-C8) alkoxy carbonyl；
(m18)(C2-C8) allyloxycarbonyl；
(m19)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(m20)(C1-C8) alkyl-carbonyl；
(m21)(C3-C8) naphthene base carbonyl；
(m23)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(m24)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(m25)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(m26)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above)；
(m27) aryl；
(m28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(m29) aryl (C1-C8) alkyl；
(m31) heterocycle；Or
(m33) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；Or
(g14)(C1-C8) halogenated alkyl,
P indicates 0,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl；
(h34) heterocycle (C1-C8) alkyl；
Alternatively, indicate substituent group below (part marked with symbol " " and nitrogen atom bonding),
[chemical formula 5]
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j3) cyano；Or
(j5)(C1-C8) halogenated alkyl carbonyl,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl；
(k5) or R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3It indicates
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl.
[7] agricultural and horticultural pesticide, which is characterized in that contain phthaloyl amide derivatives described in any one of [1] to [6] or its esters as effective component.
[8] application method of agricultural and horticultural pesticide described in above-mentioned [7], which is characterized in that use a effective amount of agricultural and horticultural pesticide processing plant or soil.
[9] animal parasite agent for preventing and eliminating, which is characterized in that contain phthaloyl amide derivatives described in any one of [1] to [6] or its esters as effective component.
Invention effect
Phthaloyl amide derivatives or its esters of the invention have the structure feature including annelated heterocycles base not available for previous compound.By the way that with this structure feature, the compound of the present invention not only shows brilliant effect to lepidoptera pest, but also also shows that brilliant effect to Thysanoptera, coleoptera, Diptera and the pest of Semiptera.Above compound especially of the invention has insecticidal effect to Thysanoptera, and it is advantage not available for previous similar compound that this point, which is not both disclosed in the prior art or is not implied,.
In addition, above compound of the invention also shows effect to the pest colonized in the domestic animals such as the pet animals such as dog or cat or ox or sheep.
Specific embodiment
In definition of the meaning of following term for each substituent group in the logical formula (I) of phthaloyl amide derivatives of the present invention in the specification and claims, it is suitable for corresponding term.
" halogen " refers to that " halogen atom " refers to such as fluorine atom, chlorine atom, bromine atom or iodine atom, " (C1-C8) alkyl " refer to such as methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tert-butyl, n-pentyl, isopentyl, tertiary pentyl, neopentyl, 2; 3- dimethyl propyl, 1- ethyl propyl, 1- methyl butyl, n-hexyl, isohesyl, 1; 1; 2- thmethylpropyl, 3; alkyl of the carbon number 1~8 of the linear chain or branched chains such as 3- dimethylbutyl, heptyl, octyl, " (C2-C8) alkenyl " refer to such as vinyl, allyl, isopropenyl, 1- cyclobutenyl, 2- cyclobutenyl, 2- methyl -2- acrylic, 1- methyl -2- acrylic, 2- methyl-1-propylene base, pentenyl, 1- hexenyl, 3; alkenyl of the carbon number 2~8 of linear chain or branched chains such as 3- dimethyl -1- cyclobutenyl, heptenyl, octenyl
“(C2-C8) alkynyl " and refer to the linear chain or branched chain such as acetenyl, 1- propinyl, 2-propynyl, 1- butynyl, 2- butynyl, 3- butynyl, 3- methyl-1-propinyl, 2- methyl-3- propinyl, pentynyl, 1- hexin base, 3,3- dimethyl-1- butynyl, heptynyl, octynyl carbon number 2~8 alkynyl.
“(C3-C8) naphthenic base " refer to the cyclic alkyl of the carbon number 3~8 such as cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, suberyl, cyclooctyl, " (C1-C8) alkoxy " refer to such as methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isoamoxy, tertiary amoxy, neopentyl oxygen, 2; 3- dimethyl propylene oxygroup, 1- ethylpropoxy, 1- methyl butoxy, positive hexyloxy, dissident's oxygroup, 1; 1; alkoxy of the carbon number 1~8 of the linear chain or branched chains such as 2- trimethyl propoxyl group, oxygroup in heptan, octyloxy, " (C2-C8) alkenyloxy group " and refer to the linear chain or branched chain such as propenyloxy group, butenyloxy, amylene oxygroup, hexene oxygroup, heptene oxygroup, octene oxygroup carbon number 2~8 alkenyloxy group, " (C2-C8) alkynyloxy group " and refer to the linear chain or branched chain such as propargyl alcoholate, butine oxygroup, pentyne oxygroup, hexin oxygroup, heptyne oxygroup, octyne oxygroup carbon number 2~8 alkynyloxy group.
“(C1-C8) alkylthio group " refer to such as methyl mercapto, ethylmercapto group, positive rosickyite base, isopropyisulfanyl, positive butylthio, secondary butylthio, tertiary butylthio, positive penta sulfenyl, isopentylthio, tertiary penta sulfenyl, new penta sulfenyl, 2; 3- dimethyl propylene sulfenyl, 1- ethyl rosickyite base, 1- methylbutylthio, just own sulfenyl, isohexylthio, 1; 1; alkylthio group of the carbon number 1~8 of linear chain or branched chains such as 2- trimethyl rosickyite base, sulfenyl in heptan, pungent sulfenyl, " (C1-C8) Alkylsulfinyl " refer to such as methyl sulfinyl, ethylsulfinyl-1 base, n-propyl sulfinyl, isopropyl sulfinyl, normal-butyl sulfinyl, sec-butyl sulfinyl, tert-butyl sulfinyl, n-pentyl sulfinyl, isopentyl sulfinyl, tertiary pentyl sulfinyl, neopentyl sulfinyl, 2, 3- dimethyl propyl sulfinyl, 1- ethyl propyl sulfinyl, 1- methyl butyl sulfinyl, n-hexyl sulfinyl, isohesyl sulfinyl, 1, 1, 2- thmethylpropyl sulfinyl, heptyl sulfinyl, the Alkylsulfinyl of the carbon number 1~8 of the linear chain or branched chains such as octyl sulfinyl, " (C1-C8) alkyl sulphonyl " refer to such as methyl sulphonyl, ethylsulfonyl, n-propyl sulfonyl, isopropelsulfonyl, normal-butyl sulfonyl, sec-butylsulfonyl, tert. butylsulfonyl, n-pentyl sulfonyl, isopentyl sulfonyl, tertiary pentyl sulfonyl, neopentyl sulfonyl, 2; 3- dimethyl propyl sulfonyl, 1- ethyl propyl sulfonyl, 1- methyl butyl sulfonyl, n-hexyl sulfonyl, isohesyl sulfonyl, 1; alkyl sulphonyl of the carbon number 1~8 of the linear chain or branched chains such as 1,2- thmethylpropyl sulfonyl, heptyl sulfonyl, octyl sulfonyl.
“(C2-C8) alkenylthio group " and refer to the linear chain or branched chain such as propylene sulfenyl, butylene sulfenyl, amylene sulfenyl, hexene sulfenyl, heptene sulfenyl, octene sulfenyl carbon number 2~8 alkenylthio group, " (C2-C8) alkynes sulfenyl " and refer to the linear chain or branched chain such as propine sulfenyl, butine sulfenyl, pentyne sulfenyl, hexin sulfenyl, heptyne sulfenyl, octyne sulfenyl carbon number 2~8 alkynes sulfenyl.
“(C2-C8) alkenylsulfinyl " and refer to the linear chain or branched chain such as acrylic sulfinyl, cyclobutenyl sulfinyl, pentenyl sulfinyl, hexenyl sulfinyl, heptenyl sulfinyl, octenyl sulfinyl carbon number 2~8 alkenylsulfinyl, " (C2-C8) alkynylsulfinyl " and refer to the linear chain or branched chain such as propinyl sulfinyl, butynyl sulfinyl, pentynyl sulfinyl, hexin base sulfinyl, heptynyl sulfinyl, octynyl sulfinyl carbon number 2~8 alkynylsulfinyl.
“(C2-C8) alkenylsufonyl " and refer to the linear chain or branched chain such as acrylic sulfonyl, cyclobutenyl sulfonyl, pentenyl sulfonyl, hexenyl sulfonyl, heptenyl sulfonyl, octenyl sulfonyl carbon number 2~8 alkenylsufonyl, " (C2-C8) alkynylsulfonyl " and refer to the linear chain or branched chain such as propinyl sulfonyl, butynyl sulfonyl, pentynyl sulfonyl, hexin base sulfonyl, heptynyl sulfonyl, octynyl sulfonyl carbon number 2~8 alkynylsulfonyl.
In above-mentioned " (C1-C8) alkyl ", " (C2-C8) alkenyl ", " (C2-C8) alkynyl ", " (C3-C8) naphthenic base ", " (C1-C8) alkoxy ", " (C2-C8) alkynyloxy group ", " (C3-C8) naphthenic base ", " (C1-C8) alkoxy " and can be replaced by 1 or 2 or more halogen atom on substituted position, substituted halogen atom be 2 or more when, halogen atom may be the same or different, and respectively indicate " halogenated (C1-C8) alkyl ", " halogenated (C2-C8) alkenyl ", " halogenated (C2-C8) alkynyl ", " halogenated (C3-C8) naphthenic base ", " halogenated (C1-C8) alkoxy ", " halogenated (C1-C8) alkylthio group ", " halogenated (C1-C8) Alkylsulfinyl ", " halogenated (C1-C8) alkyl sulphonyl ", " halogenated (C3-C8) naphthenic base ".
" aryl " refers to the aromatic hydrocarbyl of the carbon number 6~10 such as phenyl, 1- naphthalene, 2- naphthalene.
In addition, " (C1-C8)”、“(C2-C8)”、“(C3-C8) " etc. statements indicate the carbon number ranges of various substituent groups.In turn, above-mentioned definition can also be expressed as the group that above-mentioned substituent group is connected, for example, in " (C1-C8) alkoxy (C1-C8) alkyl " in the case where, indicate that the alkoxy of the carbon number 1~8 of linear chain or branched chain is bonded to the alkyl of the carbon number 1~8 of linear chain or branched chain.In addition, for example, in " ((C1-C8) alkoxy) ((C3-C8) naphthenic base) (C1-C8) alkyl " in the case where, the cyclic alkyl of the alkoxy and carbon number 3~8 that indicate the carbon number 1~8 of linear chain or branched chain is bonded to the alkyl of the carbon number 1~8 of linear chain or branched chain.
“(C1-C8) alkylidene ", such as can enumerate: methylene, ethylidene, propylidene, isopropylidene, butylidene etc..
As W2And W3Bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 member heterocyclic ring containing nitrogen selected from oxygen atom, nitrogen-atoms and sulphur atom, can enumerate: pyrrolidines, piperidines, morpholine, thiomorpholine, piperazine etc..
As " heterocycle " and " heterocycle ", can enumerate: in addition to the carbon atom as ring atom, containing 1 to 4 selected from oxygen atom, heteroatomic 5 or 6 unit monocycle formula aromatic heterocyclic radicals of sulphur atom and nitrogen-atoms or 3 to 6 unit monocycle formula non-aromatic heterocycles and aromatics as the monocyclic or non-aromatic heterocyclic and phenyl ring annelated heterocycles base made of condensed or the aromatics as the monocyclic or non-aromatic heterocyclic annelated heterocycles base made of (heterocycle can also be different) is condensed each other.
As " aromatic heterocyclic radical ", such as can enumerate: furyl, thienyl, pyridyl group, pyrimidine radicals, pyridazinyl, pyrazinyl, pyrrole radicals, imidazole radicals, pyrazolyl, thiazolyl, isothiazolyl,It is oxazolyl, differentOxazolyl,The monocyclics aromatic heterocyclic radical such as di azoly, thiadiazolyl group, triazolyl, tetrazole radical, triazine radical；Quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, benzofuranyl, benzothienyl, benzoOxazolyl, benzisoxaAromatic condensed heterocyclic radicals such as oxazolyl, benzothiazolyl, benzimidazolyl, benzotriazole base, indyl, indazolyl, Pyrrolopyrazine base, imidazopyridyl, Imidazopyrazines base, pyrazolo pyrrolidinyl, pyrazolo thienyl, method for preparation of pyrazolotriazine base etc..
As " non-aromatic heterocycle ", such as can enumerate: oxirane base (oxylanyl), thiirane base (thiiranyl), aziridinyl, oxetanyl (oxetanyl), Thietane base (thietanyl), azetidinyl (azethydinyl), pyrrolidinyl, piperidyl, morpholinyl, thio-morpholinyl, piperazinyl, hexamethyleneimino,Oxazolidinyl, thiazolidinyl, imidazolidinyl,Oxazoline base, thiazolinyl, imidazolinyl, dioxolyl, dioxolanyl, dihydroDi azoly, 2- oxo -1,3-Oxazolidine -5- base, pyranose, THP trtrahydropyranyl, thiapyran base, tetrahydro thiapyran base, 1- aoxidize tetrahydro thiapyran base, 1,1- titanium dioxide tetrahydro thiapyran base, tetrahydrofuran base, twoThe monocyclics non-aromatic heterocycles such as alkyl, pyrazolidinyl, pyrazolinyl, tetrahydro-pyrimidine base, dihydro triazolyl, tetrahydro triazolyl；Non-aromatic annelated heterocycles bases such as indolinyl, dihydro-iso indolyl, dihydro benzo furyl, dihydrobenzo dioxine base (dihydrobenzodioxynyl), dihydrobenzo Diazesuberane base (dihydrobenzodioxepinyl), tetrahydrochysene benzfuran base, chromene base, dihydroquinoline base, tetrahydric quinoline group, dihydro-isoquinoline base, tetrahydro isoquinolyl, dihydro phthalazinyl (phtharazine) etc..
It as " heterocycle ", such as can enumerate: isoquinolyl, tetrazole radical, quinolyl, differentOxazolyl, pyrimidine radicals, pyrazinyl, pyridyl group, pyrazolyl, benzimidazolyl, 2,3- dioxoisoindole base, tetrahydrofuran base, oxirane base, thienyl, pyridazinyl etc..
As the salt for the phthaloyl amide derivatives that logical formula (I) of the invention indicates, such as can illustrate: the organic acid salts and sodium ion, potassium ion, calcium ion, trimethyl ammonium etc. such as the inorganic acids such as hydrochloride, sulfate, nitrate, phosphate salt, acetate, fumarate, maleate, oxalates, mesylate, benzene sulfonate, tosilate are inorganic or organic base between salt.
The phthaloyl amide derivatives and its salt that logical formula (I) of the invention indicates have one or more asymmetric centers sometimes in its structural formula, sometimes there is also optical isomer of more than two kinds and diastereoisomer, the present invention also includes whole various optical isomers and contains mixture made of them with arbitrary proportion.In addition, sometimes there is also 2 kinds of geometric isomers from carbon-to-carbon or carbon-to-nitrogen double bond in its structural formula, the present invention also includes whole various geometric isomers and contains mixture made of them with arbitrary proportion the phthaloyl amide derivatives and its salt that logical formula (I) of the invention indicates.
In the phthaloyl amide derivatives and its salt that logical formula (I) of the invention indicates, as a preferred option, scheme below can be illustrated:
X1It indicates
(a1) hydrogen atom；
(a2) halogen atom；
(a7)(C1-C8) alkylthio group；
(a9)(C1-C8) Alkylsulfinyl；Or
(a11)(C1-C8) alkyl sulphonyl,
X2It indicates
(b2) halogen atom,
M indicates 0 or 1,
Y1It indicates
(c1) hydrogen atom；
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
Y2It indicates
(d2) halogen atom；
(d3)(C1-C8) alkyl；
(d4)(C1-C8) halogenated alkyl；
(d5)(C1-C8) alkoxy；Or
(d6)(C1-C8) halogenated alkoxy,
N indicates 0 or 1,
Q indicates Q1, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q16, Q18, Q19, Q21, Q23, Q24, Q25, Q26, Q27, Q28, Q29, Q30 or Q31, wherein W1It may be the same or different, indicate
(e1) hydrogen atom；
(e2) halogen atom；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e21)(C1-C8) alkylthio group (C1-C8) alkyl；
(e22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(e23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(e27)(C1-C8) alkoxy carbonyl；
(e29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, heterocycle, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(e34)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(e35)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(e36)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(e37)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above, R5It is same or different to each other)；
(e38) aryl；Or
(e39) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(e44) heterocycle；Or
(e46) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；
(g14)(C1-C8) halogenated alkyl；Or
(g27)(C1-C8) alkoxy carbonyl,
P indicates 0,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h12) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl；
(h17) aryl (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h26) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl carbonyl epoxide (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl；
(h31)R4(R5) N carbonyl oxygroup (C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(h32)R4(R5) N carbonyl (C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(h33)R4(R5) N carbonyl (R4)N(C1-C8) alkyl (in formula, R4And R5It is as defined above, R4It is same or different to each other)；Or
(h34) heterocycle (C1-C8) alkyl,
Alternatively, indicating
Substituent group (part marked with symbol " " and nitrogen atom bonding) below,
[chemical formula 6]
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j2)(C1-C8) alkyl；
(j3) cyano；
(j4)(C1-C8) alkyl-carbonyl；
(j5)(C1-C8) halogenated alkyl carbonyl；
(j6)(C1-C8) alkoxy carbonyl；
(j8) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl of 1~5 substituent group in phenoxy group；
Or
(j10) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl sulfonyl of 1~5 substituent group in phenoxy group,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl；Or
(k5)R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3For
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl.
Scheme more preferably can illustrate scheme below:
X1It indicates
(a2) halogen atom,
M indicates 0,
Y1It is identical or different, it indicates
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
N indicates 0,
Z2Indicate C-A-Q,
Q indicates Q1, Q8 or Q18, wherein
W1It indicates
(e1) hydrogen atom；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e27)(C1-C8) alkoxy carbonyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, heterocycle, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl (in formula, R4And R5It is as defined above)；
(e34)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(e35)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(e36)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(e37)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above, R5It is same or different to each other)；
(e38) aryl；Or
(e44) heterocycle,
W2And W2aIt may be the same or different, indicate
(f1) hydrogen atom；
(f2)(C1-C8) alkyl；Or
(f3) work as W2And W2aWhen being bonded on same carbon atom, > C=O base,
W3It indicates
(m1) hydrogen atom；
(m2) cyano；
(m4) cyano (C1-C8) alkyl；
(m5)(C1-C8) alkyl；
(m6)(C2-C8) alkenyl；
(m7)(C2-C8) alkynyl；
(m8)(C2-C8) halogenated alkenyl；
(m9)(C3-C8) naphthenic base；
(m10)(C1-C8) alkoxy (C1-C8) alkyl；
(m11)(C1-C8) halogenated alkyl；
(m14)(C1-C8) alkylthio group (C1-C8) alkyl；
(m15)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(m16)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(m17)(C1-C8) alkoxy carbonyl；
(m18)(C2-C8) allyloxycarbonyl；
(m19)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(m20)(C1-C8) alkyl-carbonyl；
(m21)(C3-C8) naphthene base carbonyl；
(m23)R4(R5) NCO- base (in formula, R4And R5It is as defined above)；
(m24)R4(R5) NCOO- base (in formula, R4And R5It is as defined above)；
(m25)R4(R5)NSO2Base (in formula, R4And R5It is as defined above)；
(m26)R4(R5)NCON(R5)-base (in formula, R4And R5It is as defined above)；
(m27) aryl；
(m28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(m29) aryl (C1-C8) alkyl；
(m31) heterocycle；Or
(m33) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；Or
(g14)(C1-C8) halogenated alkyl；
P indicates 0,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl (in formula, R4And R5It is as defined above) and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl；
(h34) heterocycle (C1-C8) alkyl；
Alternatively, indicating
Substituent group (part marked with symbol " " and nitrogen atom bonding) below,
[chemical formula 7]
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j3) cyano；Or
(j5)(C1-C8) halogenated alkyl carbonyl,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl；
(k5) or R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3For
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl.
As particularly preferred scheme, each scheme below can be illustrated:
·X1Indicate (a2) halogen atom,
M indicates 0,
·Y1It is identical or different, indicate (c4) (C1-C8) alkyl,
N indicates 0,
·Z2Indicate that C-A-Q, Q indicate Q8, wherein W3Indicate (m5) (C1-C8) alkyl, (m9) (C3-C8) naphthenic base or (m11) (C1-C8) halogenated alkyl,
W4、W5、W6And W7It may be the same or different, indicate (g1) hydrogen atom or (g14) (C1-C8) halogenated alkyl；
·R1Indicate (h8) (C1-C8) alkylthio group (C1-C8) alkyl；(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；Or (h10) (C1-C8) alkyl sulphonyl (C1-C8) alkyl,
·R2For (k1) hydrogen atom, R3For (l1) hydrogen atom.
In addition, above-mentioned or following preferred embodiment or the compound with each substituent group possessed by 1 or 2 or more particular compound are preferred.
The representative preparation method for the phthaloyl amide derivatives that logical formula (I) of the invention described below indicates, but the present invention is not limited to this.
Preparation method 1.
[chemical formula 8]
(in formula, X1、X2、Y1、Y2、Z1、Z2、Z3、A、Q、R1、R2、R3, m and n it is as defined above.M indicates the leaving groups such as halogen atom, sulfonyloxy methyl oxygroup or tosyloxy)
Make according to Japanese Unexamined Patent Publication 11-240857 bulletin, Japanese Unexamined Patent Publication 2001-131141 bulletin, the general formula (II-1) or (II-2) different imide derivative for indicating for the method preparation recorded in Japanese Unexamined Patent Publication 2002-326989 bulletin in the presence of acids and bases or in the absence of the amine derivative that is indicated with logical formula (III) or logical formula (IV) reacted in atent solvent, thus the phthaloyl amide derivatives that general formula (I-1) or (I-2) are indicated can be prepared, the general formula (I-1) or (I-2) phthaloyl amide derivatives indicated are separated or are not separated, in the presence of base, the compound indicated in atent solvent with logical formula (V) or (VI) reacts, thus it is derivative that the phthalic amide that logical formula (I) indicates can be prepared Object.
1-1. general formula (II-1) or general formula (II-2) → general formula (I-1) or general formula (I-2)
As atent solvent used in this reaction, as long as halogenated aromatics hydro carbons, ether, two such as the progress of this reaction will not be significantly inhibited, such as can illustrate the halogenated hydrocarbons such as the aromatic hydrocarbons such as benzene,toluene,xylene, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, dichloro-benzenes, fluorobenzeneAcids, dimethyl sulfoxide, 1 such as amides, the acetic acid such as the esters such as the chains such as alkane, tetrahydrofuran or ring-type ethers, ethyl acetate, dimethylformamide, dimethyl acetamide, the atent solvents such as 3- dimethyl-2-imidazolinone, these atent solvents can be used alone or are mixed with two or more.
Since this reaction is reaction with same mole, it, can also be excessively using logical formula (III) or the amine of logical formula (IV) expression as long as equimolar uses each reactant.Reaction temperature can carry out in the boiling point region of room temperature to used atent solvent, and the reaction time changes according to reaction scale, reaction temperature, carry out in the range of several minutes to 48 hours.After reaction, as long as separating from the reaction system containing purpose object by conventional method, further according to needing to be refined by recrystallization, column chromatography etc., purpose object can thus be prepared.Alternatively, it is also possible to not from separated in reaction system and directly for in reaction process below.
1-2. general formula (I-1) or general formula (I-2) → logical formula (I)
As atent solvent used in this reaction, as long as the progress of this reaction will not be significantly inhibited, such as halogenated aromatics hydro carbons, methyl tertiary butyl ether(MTBE), ether, 1, the 2- dimethoxy-ethane, two such as can illustrate the aromatic hydrocarbons such as benzene,toluene,xylene, chlorobenzene, dichloro-benzenes, fluorobenzeneThe atent solvents such as amides, the 1,3-Dimethyl-2-imidazolidinone such as the esters such as the chains such as alkane, tetrahydrofuran or ring-type ethers, ethyl acetate, dimethylformamide, dimethyl acetamide, these atent solvents can be used alone or are mixed with two or more.
It as alkali used in this reaction, such as can illustrate: alkali alcoholates class, the butyl lithium such as metal hydride alkalines species, sodium methoxide, sodium ethoxide, the potassium tert-butoxide such as inorganic bases, lithium hydride, sodium hydride, the hydrofining such as the organic bases such as triethylamine, pyridine, potassium carbonate, sodium bicarbonate, sodium carbonate, sodium hydroxide etc..As long as its usage amount is suitable for selecting use in the range of from equimolar to molar excess relative to general formula (I-1) or (I-2) phthaloyl amide derivatives indicated.
Since this reaction is reaction with same mole, as long as the compound that equimolar is indicated using logical formula (V) or (VI), can also excessively use any reactant.Reaction temperature can carry out under room temperature to the reflux temperature of used atent solvent, and the reaction time changes according to reaction scale, reaction temperature etc., as long as in the range of several minutes to 48 hours being suitable for selection.After reaction, as long as separating from the reaction system containing purpose object by conventional method, further according to needing to be refined by recrystallization, column chromatography etc., purpose object can thus be prepared.
In turn, in logical formula (I), the R of (I-1) and (I-2)1Definition in, indicate (C1-C8) alkylthio group (C1-C8) thus the compound of alkyl can prepare R for example, being aoxidized with oxidants such as metachloroperbenzoic acid, hydrogen peroxide by the common method of those skilled in the art1Indicate (C1-C8) Alkylsulfinyl (C1-C8) alkyl or (C1-C8) alkyl sulphonyl (C1-C8) alkyl compound.It can also be carried out similarly additionally, there are the sulphur atom in Q26 and Q30 and be oxidized and prepare sulfurous acyloxy (sulfoxy) derivative, sulfone derivative.
Preparation method 2-1.
The derivative species that logical formula (III) indicates are new compound, for example, can by make general formula (III-1) (in formula, Y1、Y2、Z1、Z2、Z3, n, A and M it is as defined above) indicate compound and logical formula (VII) indicate derivative reacted in the presence of a base, in atent solvent, come prepare general formula (III-2) expression compound.
[chemical formula 9]
H-Q  (VII)
(in formula, Q is identical as above-mentioned Q).
As atent solvent workable in this reaction, as long as the progress of this reaction will not be significantly inhibited, such as the chains such as pentane, hexane, hexamethylene or cricoid aliphatic hydrocarbon can be illustrated；Petroleum ether, ligroin, ether, methyl tertiary butyl ether(MTBE), isopropyl ether, butyl ether, twoChains or the ring-type ethers such as alkane, dimethoxy-ethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM)；The halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride；The aromatic hydrocarbons such as benzene,toluene,xylene；The halogenated aromatics hydro carbons such as chlorobenzene, fluorobenzene, dichloro-benzenes；The ketones such as acetone, butanone (MEK), methyl isopropyl Ketone, methyl iso-butyl ketone (MIBK) (MIBK)；The nitriles such as acetonitrile, propionitrile；The esters such as ethyl acetate, butyl acetate；The atent solvent of the amides such as dimethylformamide (DMF), dimethyl acetamide (DMA), N-Methyl pyrrolidone, 1,3-Dimethyl-2-imidazolidinone, these atent solvents can be used alone or are mixed with two or more.
As alkali workable in this reaction, sodium bicarbonate can be illustrated, saleratus, sodium carbonate, carbonate and bicarbonate of the alkali metal such as potassium carbonate etc., lithium hydroxide, sodium hydroxide, potassium hydroxide, the hydroxide etc. of the alkalies and alkaline earths such as calcium hydroxide, lithium amide, Sodamide, alkali metal amino compounds such as potassamide etc., lithium hydride, sodium hydride, alkali metal hydrides such as hydrofining etc., sodium methoxide, sodium ethoxide, alkali alcoholates such as potassium tert-butoxide etc., triethylamine, 1, 1, 4, 4- tetramethylethylenediamine (TMEDA), N, accelerine, N, N- diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), 1, 4- diazabicyclo [2, 2, 2] octane (DABCO) and 1, 8- diazabicyclo [5, 4, 0] 11-7- The organic bases such as alkene (DBU).
The usage amount can be suitable for selection in the range of from 1 molar equivalent to 10 molar equivalents relative to the compound that general formula (III-1) indicates.
In addition, phase transfer catalyst can be used in this reaction, for example, can illustrate the quaternary ammonium ions classes such as 4 bromide, 4-propyl bromide, tetrabutylammonium bromide, the tetrabutyl double ammonium sulfate, tetrabutylammonium iodide, tri-n-octyl methyl ammonium chloride, benzyl triethyl ammonium bromide, butyl pyridinium bromide, heptyl pyridinium bromide, benzyltriethylammoinium chlorides,；The crown ether-likes such as dibenzo-18 crown-6, dicyclohexyl -18- crown- 6,18- crown- 6；[2.2.2]-cave ether, [2.1.1]-cave ether, [2.2.1]-cave ether, [2.2.B]-cave ether, [2O2O2S]-cave ether, [3.2.2]-cave cave Mi Deng ethers.
The usage amount can be suitable for selection in the range of from 0.001 molar equivalent to 1 molar equivalent relative to the compound that general formula (III-1) indicates.
Since this reaction is reaction with same mole, as long as equimolar uses each reactant, it can also excessively use any one of the derivative of general formula (III-1) or the expression of logical formula (VII).Reaction temperature can carry out in the boiling point region of room temperature to used atent solvent, and the reaction time changes according to reaction scale, reaction temperature, carry out in the range of several minutes to 48 hours.After reaction, as long as separating from the reaction system containing purpose object by conventional method, further according to needing to be refined by recrystallization, column chromatography etc., purpose object can thus be prepared.Alternatively, it is also possible to not from separated in reaction system and directly for in reaction process below.
Wherein, the compound of above-mentioned general formula (III-1) is Chem.Abstr.58 volumes of known publication, 3444e (1963)；Bull.Soc.Chim.Fr. (1934), 539-545 pages；J.Chem.Res.Miniprint, volume 8 (1987), 2133-2139 pages；J.Chem.Soc.B, (1967), 1154-1158 pages；J.Chem.Soc. (1961), 221-222 pages；The known compound recorded in J.Amer.Chem.Soc.111 volumes, 1989,5880-5886 pages etc..As concrete example, 4- nitro benzyl chloride (commercially available) can be illustrated, 4- bromine benzyl chloride (commercially available), the chloro- 4- nitro benzyl chloride of 2-, 2- methyl -4- nitro benzyl chloride, 2- methoxyl group -4- nitro benzyl chloride, the chloro- 4- nitro benzyl chloride of 3-, 3- methyl -4- nitro benzyl chloride, 3- methoxyl group -4- nitro benzyl chloride, methanesulfonic acid 4- nitrobenzyl ester, the chloro- 4- nitrobenzyl ester of methanesulfonic acid 2-, methanesulfonic acid 2- methyl -4- nitrobenzyl ester, methanesulfonic acid 2- methoxyl group -4- nitrobenzyl ester, the chloro- 4- nitrobenzyl ester of methanesulfonic acid 3-, methanesulfonic acid 3- methyl -4- nitrobenzyl ester, methanesulfonic acid 3- methoxyl group -4- nitrobenzyl ester, methanesulfonic acid 1- (the chloro- 4- nitro-phenyl of 3-)-ethyl ester, methanesulfonic acid 1- (3- methyl -4- nitro-benzene Base)-ethyl ester, methanesulfonic acid 1- (3- methoxyl group -4- nitro-phenyl)-ethyl ester etc..
In addition, benzoic acids and its esters that the nitro of the raw material of the derivative as your general formula (III-1) expression replaces are, for example, Chem.Ber.52 volumes, 1919, page 1083；Bull.Soc.Chim.Fr. (1962), 2255-2261 pages；Tetrahedron, (1985), 115-118 pages；Chem.Pharm.Bull., volume 41, (1993), substance well known to the document recorded in 894-906 pages etc. can according to circumstances be prepared by method that the document is recorded or based on its method.
[chemical formula 10]
(in formula, Y1、Y2、Z1、Z2、Z3, n, A and Q it is as defined above) derivative that indicates of the general formula (III-2) that is obtained by above-mentioned reaction for example can be by also being prepared the anil of general formula (III-3) expression according to the method recorded in " new experimental chemistry lecture 14 aoxidizes and reduction [II] (Wan Shan Co., Ltd.) " originally.
In addition, the amine derivative that logical formula (IV) indicates can for example be prepared according to the method recorded in International Publication No. 2001-23350 pamphlet.
Then, the representative preparation method for the condensed heterocyclic derivates that general formula Q of the invention is indicated is shown, but it's not limited to that for preparation method of the invention.
The preparation method of preparation method 3-1.Q1'
[chemical formula 11]
(in formula, W1、W4、W5、W6And W7It is as defined above).
For general formula Q1'(W1=CF3) indicate derivative species, such as the 4- hepta-fluoroiso-propyl -1 that can will be recorded in Japanese Unexamined Patent Publication 2001-122836,2- phenylenediamine (Qa), according to J.Am.Chem.Soc., volume 75, (nineteen fifty-three), the method recorded in page 1292, to prepare 5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole.
For general formula Q1'(W1=NH2) compounds, such as can be similarly according to J.Chem.Soc., nineteen sixty, the method recorded in page 2369 is prepared 2- amino -5- hepta-fluoroiso-propyl -1H- benzimidazole by Qa.
For general formula (Q1':W1=EtO) derivative species, such as can be similarly according to J.Heterocycl.Chem., volume 28, (1991), the method recorded in page 933 is prepared 2- ethyoxyl -5- hepta-fluoroiso-propyl -1H- benzimidazole by Qa.
The preparation method of preparation method 3-2.Q2', Q3', Q4'
[chemical formula 12]
(in formula, W1、W4、W5、W6And W7It is as defined above).
Similarly, for the derivative species that general formula Q2', Q3', Q4' are indicated, such as imidazopyridine can be prepared by the diamino-pyridine class (Qb, Qc, Qd) replaced by hepta-fluoroiso-propyl based on method shown in preparation method 2-1.
The preparation method of preparation method 3-3.Q8'
[chemical formula 13]
(in formula, W3、W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q8'), it can be according to J.Heterocycl.Chem., volume 2, (nineteen sixty-five), the method recorded in page 41,5- (hepta-fluoroiso-propyl) benzimidazoline -2- ketone is prepared by 4- hepta-fluoroiso-propyl -1,2- phenylenediamine (Qa).In addition, by can be based on the N for the method preparation recorded in Japanese Unexamined Patent Publication 2001-1228361Fluoro- 5- hepta-fluoroiso-propyl -1, the 2- phenylenediamine (Qa') of cyclopropyl -4- similarly prepares 1- cyclopropyl -5- fluoro- 6- (hepta-fluoroiso-propyl) benzimidazoline -2- ketone.
The preparation method of preparation method 3-4.Q9', Q10'
[chemical formula 14]
(in formula, W3、W4、W5、W6And W7It is as defined above).
Similarly, imidazopyridine (Q9', Q10') can be prepared by diamino-pyridine class Qb', Qd' replaced by hepta-fluoroiso-propyl based on the preparation method recorded in preparation method 2-3.
The preparation method of preparation method 3-5.Q6'
[chemical formula 15]
(in formula, W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q6'), such as it can be according to Org.Synth.20 volumes, (1940), the method recorded in page 73 is prepared 5- hepta-fluoroiso-propyl -1H- indazole by 2- methyl -4- (hepta-fluoroiso-propyl) aniline (Qe) recorded in Japanese Unexamined Patent Publication 2001-122836.
The preparation method of preparation method 3-6.Q18', Q19'
[chemical formula 16]
(in formula, W2、W2a、W3、W4、W5、W6And W7It is as defined above.R indicates C1~6Alkyl, Hal indicate halogen atom).
The derivative species indicated for general formula (Q18'), such as it can be by 2- chloromethyl -4- (hepta-fluoroiso-propyl) methyl phenyl carbamate (Qf) and 2- methoxyethyl amine recorded in Japanese Unexamined Patent Publication 2001-342186, to prepare 3- (2- methoxy ethyl) -6- hepta-fluoroiso-propyl -3,4- dihydro -1H- quinazoline -2- ketone.
Similarly, for general formula (Q19':W1=Me, W2,W3=O) indicate derivative species, it can be according to J.Heterocycl.Chem., volume 7, (1970), the method recorded in page 1337, by the 2- amino -5- hepta-fluoroiso-propyl-N-methyl-benzamide (Qg) prepared by the method recorded in Japanese Unexamined Patent Publication 2001-122836 from 2- Amino-N-methyl benzamide, to prepare 6- hepta-fluoroiso-propyl -3- methyl-1 H, 3H- quinazoline -2,4- diketone.
The preparation method of preparation method 3-7.Q11'
[chemical formula 17]
(in formula, W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q11'), it can be according to J.Heterocycl.Chem., volume 2, (nineteen sixty-five), the method recorded in page 41, by the 2- amino -5- hepta-fluoroiso-propyl phenol (Qh) recorded in Japanese Unexamined Patent Publication 2001-122836, to prepare 6- (hepta-fluoroiso-propyl) benzoOxazoline -2- ketone.
The preparation method of preparation method 3-8.Q13'
[chemical formula 18]
(in formula, W4、W5And W6It is as defined above).
The derivative species that general formula (Q13') indicates can be prepared based on method disclosed in preparation method 2-7 by 2- amino -3- pyridone class (Qi).
The preparation method of preparation method 3-9.Q12'
[chemical formula 19]
(in formula, W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q12'), it can be according to J.Heterocycl.Chem., volume 2, (nineteen sixty-five), the method recorded in page 41, by the 2- amino -5- hepta-fluoroiso-propyl thiophenol (Qj) of the method recorded in Japanese Unexamined Patent Publication 2001-122836 preparation can be passed through, to prepare 6- (hepta-fluoroiso-propyl) benzothiazoline -2- ketone.
The preparation method of preparation method 3-10.Q5'
[chemical formula 20]
(in formula, W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q5'), such as it can be according to Org.Synth., volume 3, the method recorded in 106 (1955), by the 4- hepta-fluoroiso-propyl -1 recorded in Japanese Unexamined Patent Publication 2001-122836,2- phenylenediamine (Qa), to prepare 5- hepta-fluoroiso-propyl -1H- benzotriazole.
The preparation method of preparation method 3-11.Q24', Q29'
[chemical formula 21]
(in formula, W2、W2a、W2b、W4、W5、W6And W7It is as defined above).
The derivative species indicated for general formula (Q24'), it can be according to J.Heterocycl.Chem., volume 2, (nineteen sixty-five), the method recorded in page 41, by 2- amino -5- hepta-fluoroiso-propyl benzylalcohol (Qk) class of the method recorded in Japanese Unexamined Patent Publication 2001-122836 preparation can be passed through, to prepare 7- (hepta-fluoroiso-propyl) benzoPiperazine -3- ketone.Likewise it is possible to according to J.Heterocycl.Chem., volume 2, (nineteen sixty-five), the method recorded in page 41, by 2- amino -5- hepta-fluoroiso-propyl benzyl carbinol class (Ql), to prepare 8- (hepta-fluoroiso-propyl) benzo oxygen azepine- 4- ketone.
The preparation method of preparation method 3-12.Q26', Q30'
[chemical formula 22]
(in formula, W2、W2a、W2b、W4、W5、W6And W7It is as defined above.R indicates C1-C6Alkyl).
The derivative species indicated for general formula (Q26'), if 2- amino -5- hepta-fluoroiso-propyl phenyl thiacetate (Qm) class that can be prepared by 2- aminophenyl thioacetic acid esters according to the method recorded in Japanese Unexamined Patent Publication 2001-122836 is cyclized, 3- oxo -2H- benzo [Isosorbide-5-Nitrae] thiazide can then be prepared.Similarly, if 2- amino -5- hepta-fluoroiso-propyl phenyl thiopropionate (Qn) class is cyclized, 3- oxo -2H- benzo [Isosorbide-5-Nitrae] thiazide can be prepared.
The preparation method of preparation method 3-13.Q28'
[chemical formula 23]
(in formula, W4、W5、W6And W7It is as defined above).
For general formula (Q28') indicate derivative species, if such as by (Qa) of above-mentioned record and trifluoroacetone acid esters dehydration condense and be cyclized, 1H- quinoxaline -2- ketone can be prepared.
The preparation method of preparation method 3-14.Q14', Q15'
[chemical formula 24]
(in formula, W3、W4、W5、W6、W7It is as defined above with A).
The derivative species that general formula (Q14') indicates can be by according to J.Am.Chem.Soc., volume 75, (nineteen fifty-three), the method recorded in page 1292 condense (Qa) of above-mentioned record and 3- methyl -4- nitrophenyl acetate class to prepare.
The compounds that general formula (Q15') indicates can be by according to J.Am.Chem.Soc., volume 75, (nineteen fifty-three), the method recorded in page 1292 condense (Qh) of above-mentioned record and 3- methyl -4- nitrophenyl acetate class to prepare.
The preparation method of preparation method 3-15.Q7'
[chemical formula 25]
(in formula, W1、W4、W5、W6And W7It is as defined above).
For the derivative species that general formula (Q7') is indicated, can be prepared by the way that indole derivatives (Qo) are carried out hepta-fluoroiso-propyl using the method recorded in Japanese Unexamined Patent Publication 2001-122836.
The compound of Q16 can be prepared by method same as the preparation method of preparation method 3-10.Q5'.
The compound of Q17 can prepare corresponding phthalimide compound by reacting corresponding ditridecyl phthalate compound with ammonia.
The compound of Q21 can be prepared based on the preparation method of preparation method 3-3.Q8'.
Q23 can be prepared based on the preparation method of preparation method 3-1.Q1'.
The compound of Q25 and Q27 can be prepared based on the preparation method of preparation method 3-12.Q26'.
The compound of Q31 can be prepared based on the preparation method of preparation method 3-7.Q11' by corresponding carbamide compound.
Hereinafter, the typical example for the phthaloyl amide derivatives that logical formula (I) of the invention indicates is illustrated in the 1st table to the 31st table, but the present invention is not limited to this.
In table, " n- " is indicated just, and different " i- " indicates different, and " t- " indicates that uncle, " c- " indicate alicyclic type hydrocarbon, and " Ph " indicates that phenyl, " * " indicate S- enantiomer.Physical property shows fusing point (DEG C) or refractive index nD(measuring temperature；℃).In addition, the compound for describing " NMR " in one column of physics value is shown in the 32nd table1H-NMR data.
[table 1 (1)]
1st table
[table 1 (2)]
[table 1 (3)]
[table 1 (4)]
[table 1 (5)]
[table 1 (6)]
[table 1 (7)]
[table 1 (8)]
[table 1 (9)]
[table 1 (10)]
[table 1 (11)]
[table 1 (12)]
[table 1 (13)]
[table 1 (14)]
[table 1 (15)]
[table 1 (16)]
[table 1 (17)]
[table 1 (18)]
[table 1 (19)]
[table 1 (20)]
[table 1 (21)]
[table 1 (22)]
[table 1 (23)]
[table 1 (24)]
[table 1 (25)]
[table 1 (26)]
*: indicating S- enantiomer, A=CH2；W7=H；Y2=H；Q=Q1
[table 2]
2nd table
No. R1 R2 R3 X1 Y1 Z1 Z2 W1 W5 W6 m.p.℃
2-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CF3 CF(CF3)2 H  
2-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CF3 CF(CF3)2 H  
2-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CF3 CF(CF3)2 H  
2-4 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH CF3 CF(CF3)2 H 135-138
2-5 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH CF3 CF(CF3)2 H 189-191
2-6 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH CF3 CF(CF3)2 H 186-188
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2；W7=H；Q=Q2
[table 3]
3rd table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q3
[table 4]
4th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4=H；Q=Q4
[table 5]
5th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q5
[table 6 (1)]
6th table
[table 6 (2)]
6-30 C*H(CH3)CH2SO2 H H Cl CH3 CH C-A-Q l H CF(CF3)2 H 142-144
6-31 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q l H CF(CF3)2 H  
6-32 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q l H CF(CF3)2 H 178-180
6-33 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q l H CF(CF3)2 H 130-132
6-34 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 H  
6-35 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 H 135-137
6-36 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 H 216-218
6-37 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 H  
6-38 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 H 127-129
6-39 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 H 186-188
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q6
[table 7 (1)]
7th table
[table 7 (2)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, W1, Y2, W7=H；Q=Q7
[table 8 (1)]
8th table
[table 8 (2)]
[table 8 (3)]
[table 8 (4)]
[table 8 (5)]
[table 8 (6)]
[table 8 (7)]
[table 8 (8)]
[table 8 (9)]
[table 8 (10)]
[table 8 (11)]
[table 8 (12)]
[table 8 (13)]
[table 8 (14)]
[table 8 (15)]
[table 8 (16)]
[table 8 (17)]
[table 8 (18)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q8
[table 9]
9th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W3 W5 W6 m.p.℃
9-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 132-135
9-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 155-158
9-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 145-150
9-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q CH3 CF(CF3)2 H 144-146
9-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q CH3 CF(CF3)2 H 135-140
9-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q CH3 CF(CF3)2 H 125-130
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q9
[table 10]
10th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W3 W5 W6 m.p.℃
10-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 128-130
10-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 174-176
10-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CH3 H CF(CF3)2 166-168
10-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 178-180
10-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 180-182
10-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q CH3 H CF(CF3)2 133-135
10-7 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 140-142
10-8 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 165-167
10-9 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CH3 CF(CF3)2 H 147-149
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4=H；Q=Q10
[table 11]
11st table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4=H；Q=Q11
[table 12]
12nd table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q12
[table 13]
13rd table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2=H；Q=Q13
[table 14]
14th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q14
[table 15]
15th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W4 W5 W6 m.p.℃
15-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H H CF(CF3)2  
15-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H H CF(CF3)2  
15-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H H CF(CF3)2  
15-4 C(CH3)2CH2SCH3 H H l Cl CH C-A-Q H H CF(CF3)2 223-225
15-5 C(CH3)2CH2SOCH3 H H l Cl CH C-A-Q H H CF(CF3)2  
15-6 C(CH3)2CH2SO2CH3 H H l Cl CH C-A-Q H H CF(CF3)2  
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q15
[table 16]
16th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W4 W5 W6 m.p.℃
16-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H CF(CF3)2 H 137-139
16-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H CF(CF3)2 H 132-135
16-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H CF(CF3)2 H 112-114
16-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q H CF(CF3)2 H  
16-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q H CF(CF3)2 H  
16-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q H CF(CF3)2 H  
16-7 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH H CF(CF3)2 H 186-187
16-8 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH H CF(CF3)2 H 174-176
16-9 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH H CF(CF3)2 H 136-140
16-10 C(CH3)2CH2SCH3 H H l CH3 C-A-Q CH H CF(CF3)2 H 127-132
16-11 C(CH3)2CH2SOCH3 H H l CH3 C-A-Q CH H CF(CF3)2 H 148-153
16-12 C(CH3)2CH2SO2CH3 H H l CH3 C-A-Q CH H CF(CF3)2 H 195-196
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q16
[table 17]
17th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W4 W5 W6 m.p.℃
17-1 C*H(CH3)CH2SCH3 H H Cl H CH C-A-Q Cl H H 145
17-2 C*H(CH3)CH2SCH3 H H Cl H CH C-A-Q H Cl Cl 126
17-3 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H Br H 224
17-4 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H Br H  
17-5 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H Br H  
17-6 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H Cl Cl 231
17-7 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H Cl Cl  
17-8 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H Cl Cl  
17-9 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H CF3 H  
17-10 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H CF3 H  
17-11 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H CF3 H  
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q17
[table 18 (1)]
18th table
[table 18 (2)]
[table 18 (3)]
[table 18 (4)]
[table 18 (5)]
[table 18 (6)]
[table 18 (7)]
[table 18 (8)]
[table 18 (9)]
[table 18 (10)]
[table 18 (11)]
[table 18 (12)]
[table 18 (13)]
[table 18 (14)]
[table 18 (15)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, W4, Y2, W7=H；Q=Q18
[table 19 (1)]
19th table
[table 19 (2)]
[table 19 (3)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q19
[table 20]
21st table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q21
[table 21 (1)]
23rd table
[table 21 (2)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q23
[table 22]
24th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q24
[table 23 (1)]
25th table
[table 23 (2)]
25th table (Continued)
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4=H；Q=Q25
[table 24]
26th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；p=0；Q=Q26
[table 25]
27th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q27
[table 26 (1)]
28th table
[table 26 (2)]
28-31 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH H H H CF(CF3)2 134-136
28-32 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH H H H CF(CF3)2 172-174
28-33 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH H H H CF(CF3)2 148-150
28-34 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH H H CF(CF3)2 H 124-126
28-35 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH H H CF(CF3)2 H  
28-36 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH H H CF(CF3)2 H 136-138
28-37 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH CH3 H H CF(CF3)2 129-131
28-38 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH CH3 H H CF(CF3)2 161-163
28-39 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH CH3 H H CF(CF3)2 154-156
28-40 C(CH3)2CH2SCH3 H H l CH3 C-A-Q CH CH3 H H CF(CF3)2 152-154
28-41 C(CH3)2CH2SOCH3 H H l CH3 C-A-Q CH CH3 H H CF(CF3)2 155-157
28-42 C(CH3)2CH2SO2CH3 H H l CH3 C-A-Q CH CH3 H H CF(CF3)2 191-192
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q28
[table 27]
29th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W2 W2a W4 W5 W6 m.p.℃
29-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H H H CF(CF3)2 H 136-138
29-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H H H CF(CF3)2 H 149-151
29-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q H H H CF(CF3)2 H 153-155
29-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q H H H CF(CF3)2 H 127-129
29-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q H H H CF(CF3)2 H 147-150
29-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q H H H CF(CF3)2 H 135-140
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W2b, W7=H；Q=Q29
[table 28]
30th table
No. R1 R2 R3 X1 Y1 Z1 Z2 W2 W2a W5 W6 m m.p.℃
30-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q H H CF(CF3)2 H 0 135-138
30-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q H H CF(CF3)2 H 0 161-163
30-3 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q H H CF(CF3)2 H 0 136-139
30-4 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q H H CF(CF3)2 H 0 140-144
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W2b, W4, W7=H；P=0:Q=Q30
[table 29]
31st table
No. R1 R2 R3 X1 Y1 Z1 Z2 W3 W3a W4 W5 W6 m.p.℃
31-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q CH3 CH3 H H CF(CF3)2  
31-7 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 113-115
31-8 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 140-150
31-9 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 137-144
31-10 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 107-108
31-11 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 131-135
31-12 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q C2H5 CH3 H H CF(CF3)2 128-130
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W7=H；Q=Q31
[table 30 (1)]
32nd table NMR data
[table 30 (2)]
[table 30 (3)]
[table 30 (4)]
[table 30 (5)]
[table 30 (6)]
[table 30 (7)]
[table 30 (8)]
[table 30 (9)]
[table 30 (10)]
[table 30 (11)]
[table 30 (12)]
[table 31 (1)]
33rd table
[table 31 (2)]
[table 31 (3)]
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q33
[table 32]
34th table
No R1 R2 R3 X1 Y1 Z1 Z2 W5 W6 m.p.℃
34-1 C*H(CH3)CH2SCH3 H H Cl CH3 CH C-A-Q CF(CF3)2 H 105-109
34-2 C*H(CH3)CH2SOCH3 H H Cl CH3 CH C-A-Q CF(CF3)2 H 128-131
34-3 C*H(CH3)CH2SO2CH3 H H Cl CH3 CH C-A-Q CF(CF3)2 H 114-115
34-4 C(CH3)2CH2SCH3 H H l CH3 CH C-A-Q CF(CF3)2 H 128-131
34-5 C(CH3)2CH2SOCH3 H H l CH3 CH C-A-Q CF(CF3)2 H 124-126
34-6 C(CH3)2CH2SO2CH3 H H l CH3 CH C-A-Q CF(CF3)2 H  
34-7 C*H(CH3)CH2SCH3 H H Cl CH3 C-A-Q CH CF(CF3)2 H  
34-8 C*H(CH3)CH2SOCH3 H H Cl CH3 C-A-Q CH CF(CF3)2 H  
34-9 C*H(CH3)CH2SO2CH3 H H Cl CH3 C-A-Q CH CF(CF3)2 H  
34-10 C(CH3)2CH2SCH3 H H l CH3 C-A-Q CH CF(CF3)2 H  
34-11 C(CH3)2CH2SOCH3 H H l CH3 C-A-Q CH CF(CF3)2 H  
34-12 C(CH3)2CH2SO2CH3 H H l CH3 C-A-Q CH CF(CF3)2 H  
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q34
[table 33]
35th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W1, W4, W7=H；Q=Q35
[table 34]
36th table
*: indicating S- enantiomer, A=CH2；Z3=CH；X2, Y2, W4, W7=H；Q=Q36
Contain various agriculturals, gardening, grain storage pest or the insect-pest exterminatings such as sanitary insect pest or Nemata using the phthaloyl amide derivatives or its esters of logical formula (I) expression of the invention as the agricultural and horticultural pesticide of effective component suitable for injure rice, fruit tree, vegetables, other crops and flowers class.
As above-mentioned pest or Nemata etc., insects below can be illustrated:
As Lepidoptera (Lepidoptera) pest, such as it can enumerate: green cochlid (Parasa consocia), bridge noctuid (Anomis mesogona), Papilio xuthus (Papilio xuthus), Matsumuraesesazukivora (Matsumuraeses azukivora), shoulder bar open country snout moth's larva (Ostrinia scapulalis), Africa is greedy night pretty young woman (Spodoptera exempta), fall webworms (Hyphantria cunea), Ostrinia furnacalis (Ostrinia furnacalis), mythimna separata (Pseudaletia separata), webbing moth (T Inea translucens), bran point wing steinernema (Bactra furfurana), straight grain rice hesperiidae (Parnara guttata), rice shows the wild snout moth's larva (Marasmia exigua) of line brush palpus, straight grain rice hesperiidae (Parnara guttata), Sesamia inferens (Sesamia inferens), tricyclic brachmia triannuella (Brachmia triannulella), oriental moth (Monema flavescens), cabbage looper (Trichoplusia ni), beans pleura open country snout moth's larva (Pleuroptya ruralis), small dragonfly geometrid moth (Cystidia c Ouaggaria), wave hairstreak (Lampides boeticus) in long-tail, Cephonodes hylas (Cephonodes hylas), heliothis zea (Helicoverpa armigera), graceful oak silkworm boat moth (Phalerodonta manleyi), Claniapreyeri (Leech) (Eumeta japonica), Pieris brassicae (Pieris brassicae), malacosoma neustria (Malacosoma neustria testacea), persimmon lifts limb moth (Stathmopoda masinissa), the thin moth of persimmon (Cuphodes diospyrosella), Ash Huang rolls up moth (Archips xylosteanus), yellow cutworm (Agrotis segetum), sweet potato steinernema (Tetramoera schistaceana), north Asia Huang swallowtail butterfly (Papilio machaon hippocrates), peach macula lutea bat moth (Endoclyta sinensis), crazing lyonetid (Lyonetia prunifoliella), Phyllonorycterringoneella (Phyllonorycter ringoneella), Cydia kurokoi (Cydia kurokoi), the green steinernema of chestnut (Eucoenogenes aestuosa), it is fresh It eats grape steinernema (Lobesia botrana), nettle grub (Latoia sinica), Batang blackening snout moth's larva (Euzophera batangensis), Chinese arrow Cochylisspp (Phalonidia mesotypa), mulberry spot avenges moths attracted by lamplight (Spilosoma imparilis), mulberry thin,tough silk open country snout moth's larva (Glyphodes pyloalis), mulberry leaf roller (Olethreutes mori), Tineolabisselliella (Tineola bisselliella), noctule moth (Endoclyta excrescens), European rain moth (Nemapogon granel Lus), apple tabaniformis (Synanthedon hector), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), cnaphalocrocis medinalls guenee (Cnaphalocrocis medinalis), it eats into stem noctuid (Sesamia calamistis), yellow rice borer (Scirpophaga incertulas), bluegrass snout moth (Pediasia teterrellus), potato tuberworm (Phthorimaea operculella), apple ant boat moth (Stauropus fagi persimilis), Beanpod phycitid (Etiella zinckenella), beet armyworm (Spodoptera exigua), hickie bat moth (Palpifer sexnotata), lawn armyworm (Spodoptera mauritia), the white standing grain snout moth's larva of rice (Scirpophaga innotata), Xestia c nigrum (Xestia c-nigrum), Sidemia depravata (Spodoptera depravata), Anagasta kuehniella (Ephestia kuehniella), Lee geometrid moth (Angerona prunaria), Closteraanastomosis L. (Clostera anastomos Is), soybean ruler noctuid (Pseudoplusia includens), river beans steinernema (Matsumuraeses falcana), Heliothis assulta (Helicoverpa assulta), stain three-spotted plusia (Autographa nigrisigna), black cutworm (Agrotis ipsilon), euproctis pseudoconspersa (Euproctis pseudoconspersa), adoxophyes moth (Adoxophyes orana), Caloptiliatheivora (Caloptilia theivora), Homonamagnanima (Homona magnanima), tobacco powder sp (Ephes Tia elutella), tea avoids creditors moth (Eumeta minuscula), poplar caterpillar (Clostera anachoreta), flax noctuid (Heliothis maritima), pilleriana (Sparganothis pilleriana), the dry noctuid of corn (Busseola fusca), sub- Euproctis flava (Euproctis subflava), big hawk geometrid moth (Biston robustum), paddy reality noctuid (Heliothis zea), tired noctuid (Aedia leucomelas), pears Na slug moth (Narosoideus flavid Orsalis), pears sword line moth (Viminia rumicis), pear leafminer (Bucculatrix pyrivorella), oriental fruit months (Grapholita molesta), the thin moth of the shallow skin of pears (Spulerina astaurota), pears reality phycitid (Ectomyelois pyrivorella), striped rice borer (Chilo suppressalis), green onion leaf miner (Acrolepiopsis sapporensis), Plodiainterpunctella (Plodia interpunctella), Hellula undalis (Hellula undalis), gelechiid (Sit Otroga cerealella), Spodoptera litura (Spodoptera litura), mung bean sprouts moth (Eucosma aporema), strawberry Acleris spp (Acleris comariana), ball palpus slug moth (Scopelodes contractus), it revolves orgyia antiqua (Orgyia thyellina), fall army worm (Spodoptera frugiperda), Zha Shi stalk open country snout moth's larva (Ostrinia zaguliaevi), rice green caterpillar (Naranga aenescens), cluster caterpillar (Andraca bipunctata), grape clearwing moth (Pa Ranthrene regalis), unfilled corner hawkmoth (Acosmeryx castanea), grape leaf miner (Phyllocnistis toparcha), grape dish fruit moth (Endopiza viteana), ring needle list line moth (Eupoecillia ambiguella), pears beans noctuid (Anticarsia gemmatalis), tobacco cloud rolls up moth (Cnephasia cinereipalpana), gypsymoth (Lymantria dispar), dendrolimus spectabilis (Dendrolimus spectabilis), eating-core bean worm (Leguminivo Ra glycinivorella), bean-pod borer (Maruca testulalis), beans steinernema (Matsumuraeses phaseoli), the big thin moth of Tofu pudding (Caloptilia soyella), citrus leaf lyonetid (Phyllocnistis citrella), beans nibble leaf open country snout moth's larva (Omiodes indicatus), apricot yellow volume moth (Archips fuscocupreanus), three spot plussids (Acanthoplusia agnata), eurycyttarus nigriplaga (Bambalina sp.), peach fruit moth (Carposina niponensis) , peach eats into wild snout moth's larva (Conogethes punctiferalis), clearwing moth category (Synanthedon sp.), peach leafminer noth (Lyonetia clerkella), small macula lutea swallowtail butterfly (Papilio helenus), spot edge bean powder butterfly East Asia subspecies (Colias erate poliographus), Phalera flavescens (Phalera flavescens), cabbage butterfly Japan subspecies (Pieris rapae crucivora), the butterflies classes such as cabbage butterfly (Pieris rapae), it steals poison moth (Euproctis similis), Suzuki leaf miner (Acrolepiop Sis suzukiella), European corn borer (Ostrinia nubilalis), lopper worm (Mamestra brassicae), big bridging worm (Ascotis selenaria), wormwood leaf roller (Phtheochroides clandestina) thin greatly, sketch rolls up moth (Hoshinoa adumbratana), apple lappet moth (Odonestis pruni japonensis), apple sword Autographa spp (Triaena intermedia), adoxophyes moth (Adoxophyes orana fasciata), lessor apple-worm (Gra Pholita inopinata), spilonota lechriaspis (Spilonota ocellana), bud Eucosmaspp (Spilonota lechriaspis), pears leaf spot moth (Illiberis pruni), apple silver moth (Argyresthia conjugella), suddenly thin moth (Caloptilia zachrysa) is spent, pears Huang rolls up moth (Archips breviplicanus), small bridging worm (Anomis flava), Pectinophora gossypiella (Pectinophora gossypiella), cotton leafroller (Notarcha derogata), melon thin,tough silk Wild snout moth's larva (Diaphania indica), tobacco budworm (Heliothis virescens), Ji Dingdian spark (Earias cupreoviridis),
As Semiptera (Hemiptera) pest, such as it can enumerate: Nezaraantennata (Nezara antennata), chrysanthemum band fleahopper (Stenotus rubrovittatus), secret note red stinkbug is as (Graphosoma rubrolineatum), rice Ye Chixu fleahopper (Trigonotylus coelestialium) etc., carrot coried (Aeschynteles maculatus), pale meat fleahopper (Creontiades pallidifer), red cotton bug (Dysdercus cingulatus), dark brown Aspidiotus (Chrysomphalus fic Us), red kidney Aspidiotus (Aonidiella aurantii), big brown cicada (Graptopsaltria nigrofuscata), China bug (Blissusleucopterus), Iceryapurchasi (Icerya purchasi), extra large wall stinkbug (Piezodorus hybneri), long niphe elongata (Lagynotomus elongatus), yellow rice Erythroneura subrufa (Thaia subrufa), scotinophora lurida (Scotinophara lurida), Chinese rose aphid (Sitobion ibarae), the rugged stinkbug of rock (Stariodes iwasakii), Coconut palm Aspidiotus (Aspidiotus destructor), white tongue fur fleahopper (Taylorilygus pallidulus), plum tumor volume aphid (Myzus mumecola), li po's armored scale (Pseudaulacaspis prunicola), acyrthosiphum pisim (Acyrthosiphon pisum), big smelly coried (Anacanthocoris striicornis), Japanese flower garden fleahopper (Ectometopterus micantulus), Japanese two star stinkbugs (Eysarcoris lewisi), podophyll coried (Molipteryx fuliginosa), Green leaf hopper (Cicadella viridis), red abdomen Rhopalosiphum spp (Rhopalosophum rufiabdominalis), olive black bourch (Saissetia oleae), greenhouse whitefly (Trialeurodes vaporariorum), oak guilt jassids (Aguriahana quercus), Lygus Hahn (Lygus spp.), birch silk floss spot aphid (Euceraphis punctipennis), toothed oak pacifies armored scale (Andaspis kashicola), the soft a red-spotted lizard (Coccus pseudomagnoliarum) of tangerine ash, Cavelerius saccharivorus (Cave Lerius saccharivorus), chrysanthemum shellfish ridge lace bug (Galeatus spinifrons), the small Macrosiphus spp of chrysanthemum (Macrosiphoniella sanborni), yellow kidney Aspidiotus (Aonidiella citrina), Halyomorphamista (Halyomorpha mista), one spot is preced with lace bug (Stephanitis fasciicarina), camphor tree point wing wood louse (Trioza camphorae), middle Leptocorisa spp (Leptocorisa chinensis), oak wood louse (Trioza quercicola), yellow angle shoulder lace bug (Uhlerites Latius), grape is with Erythroneura spp (Erythroneura comes), chinch bug (Paromius exiguus), three-bristle cudrania pomegranate bicircular armored scale (Duplaspidiotus claviger), two rice green leafhoppers (Nephotettix nigropictus), east flower garden fleahopper (Halticiellus insularis), the flat plant hopper in sugarcane angle (Perkinsiella saccharicida), apple psylla (Psylla malivorella), mulberry sucker (Anomomeura mori), Kang Shi mealybug (Pseudococcus lon Gispinis), white mulberry scale (Pseudaulacaspis pentagona), mulberry silk floss lecanium (Pulvinaria kuwacola), green plant bug (Apolygus lucorum), brachypterism ball chest chinch bug (Togo hemipterus), tangerine sound aphid (Toxoptera aurantii), Icing Sugar a red-spotted lizard (Saccharicoccus sacchari), sugarcane root aphid (Geoica lucifuga), bottle volume plant hopper (Numata muiri), Comstockaspisperniciosa (COMSTOCKASPIS perniciosa), tangerine unaspis shield kuwana (Unaspis ci Tri), eggplant ditch is without net aphid (Aulacorthum solani), wide two stars stinkbug (Eysarcoris ventralis), Bemisia argentifolii (Bemisia argentifolii), rice white leafhopper (Cicadella spectra), ivy Aspidiotus (Aspidiotus hederae), grain coried (Liorhyssus hyalinus), the black small wood louse (Calophya nigridorsalis) of back, white backed planthopper (Sogatella furcifera), tumor is prominent to repair tail aphid (Megoura crassicauda), brevicoryne brassicae (Brevico Ryne brassicae), soybean aphid (Aphis glycines), big Leptocorisa spp (Leptocorisa oratorius), nephotettix bipunctatus (Nephotettix virescens), lettuce refers to pipe aphid (Uroeucon formosanum), tobacco fleahopper (Cyrtopeltis tennuis), sweet potato whitefly (Bemisia tabaci), European peach heavily fortified point a red-spotted lizard (Lecanium persicae), sifting tea armored scale (Parlatoria theae), camphor tree stern net armored scale (Pseudaonidia paeoniae), smaller green leaf hopper (Empo is passed through greatly Asca onukii), Si Shi amber stinkbug (Plautia stali), the western rounded tail aphid of lily (Dysaphis tulipae), potato aphid (Macrosiphum euphorbiae), analog pear crown network pentatomidae (Stephanitis pyrioides), ceroplastes (Ceroplastes ceriferus), camellia piece shield rank (Parlatoria camelliae), beautiful fleahopper (Apolygus spinolai) afterwards, rice green leafhopper (Nephotettix cincticeps), light acrosternumhilare (Glaucias subpunctatus), the miscellaneous hair of Chenopodiaceae Fleahopper (Orthotylus flavosparsus), corn Rhopalosiphum spp (Rhopalosiphum maidis), popcorn wing plant hopper (Peregrinus maidis), two star stinkbug of wedge angle (Eysarcoris parvus), bed bug (Cimex lectularius), linden pine lice (Psylla abieti), brown paddy plant hopper (Nilaparvata lugens), cigarette wood louse (Psylla tobirae), Yunnan cabbage bug (Eurydema rugosum), Schizaphis piricola (Schizaphis piricola), pear psyllid (Psylla Pyricola), pears star piece armored scale (Parlatoreopsis pyri), pear crown network pentatomidae (Stephanitis nashi), Chinese wistaria ash mealybug (Dysmicoccus wistariae), pears a red-spotted lizard (Lepholeucaspis japonica), pears rounded tail aphid (Sappaphis piri), radish aphid (Lipaphis erysimi), green onion aphid (Neotoxoptera formosana), lotus Rhopalosiphum spp (Rhopalosophum nymphaeae), rose leafhopper (Edwardsiana rosae), lily and armored scale (Pinn Aspis aspidistrae), alder wood louse (Psylla alni), the long leafhopper of alder (Speusotettix subfusculus), omnivorousness leafhopper (Alnetoidia alneti), broomcorn millet white backed planthopper (Sogatella panicicola), alfalfa plant bug (Adelphocoris lineolatus), miscellaneous red cotton bug (Dysdercus poecilus), parlatoria zizyphus (Parlatoria ziziphi), chestnut lace bug (Uhlerites debile), small brown rice planthopper (Laodelphax striatellus), Hebei cabbage bug (Eurydema pulchrum), long shoulder spine coried (Cletus trigonus), punctum shovel head froghopper (Clovia punctata), Empoasca flavescens (Empoasca sp.), wide food Coccushesperidum (Coccus hesperidum), nutgrass flatsedge drum chest chinch bug (Pachybrachius luridus), rattan stern line mealybug (Planococcus kraunhiae), two spot fleahopper of timothy grass (Stenotus binotatus), grape leafhopper (Arboridia apicalis), two leafhoppers (Macrosteles fascifrons), Dolycoris baccarum (Dolycoris baccarum), tricyclic lucerne stinkbug (Adelphocoris triannulatus), grape phylloxera (Viteus vitifolii), cherry tumor coried (Acanthocoris sordidus), big Leptocorisa spp (Leptocorisa acuta), the huge section chief stinkbug of bamboo class (Macropes obnubilus), rice spiny coreid (Cletus punctiger), Riptortusclavetus (Riptortus clavatus), potato wood louse (Paratrioza cockerelli), willow rib point chest froghopper (Aphrophora cost Alis), Japanese lygus bug (Lygus disponsi), East Asia lygus bug (Lygus saundersi), pine tree pure white mealybug (Crisicoccus pini), loose jassids (Empoasca abietis), walnut pure white mealybug (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), garden stinkbug (Megacopta punctatissimum), two star stinkbugs (Eysarcoris guttiger), purple Lepidosaphesspp (Lepidosaphes beckii), tangerine wood louse (Diaphorina citri), Toxopteracitricidus (Toxoptera citricidus), tangerine stern line mealybug (Planococcus citri), citrus aleyrodid (Dialeurodes citri), tangerine pierces aleyrodid (Aleurocanthus spiniferus), the small mealybug of tangerine (Pseudococcus citriculus), small tangerine tower leafhopper (Zyginella citri), the small giant coccid of tangerine (Pulvinaria citricola), the soft a red-spotted lizard of papaya (Coccus discrepans), camphor tree net armored scale (Pseudaonidia duplex), tangerine giant coccid (Pulvinaria aur Antii), Ou Guojian ball a red-spotted lizard (Lecanium corni), green rice bug (Nezara viridula), wheat fleahopper (Stenodema calcaratum), rhopalosiphum padi (Rhopalosiphum padi), corn Rhopalosiphum spp (Sitobion akebiae), green bugs (Schizaphis graminum), wheat greenweed leafhopper (Sorhoanus tritici), Lee's short-tail aphid (Brachycaudus helichrysi), purple samara stinkbug (Carpocoris purpureipennis), black peach aphid (Myzus persicae ), mealy plum aphid (Hyalopterus pruni), two tail aphid of willow (Aphis farinose yanagicola), flint lace bug (Metasalis populi) after willow, unaspis shield kuwana (Unaspis yanonensis), yellow rose of Sharon wood louse (Mesohomotoma camphorae), different spiraea aphid (Aphis spiraecola), apple aphid (Aphis pomi), oystershell scale (Lepidosaphes ulmi), apple sucker (Psylla mali), yellow foot apple capsid (Heterocordylus flavipes), apple leaf curling aphid (Myz Us malisuctus), apple aphid (Aphidonuguis mali), apple Erythroneura spp (Orientus ishidai), apple aphid (Ovatus malicolens), eriosoma lanigerum (Eriosoma lanigerum), red ceroplastes floridensis (Ceroplastes rubens) and cotten aphid (Aphis gossypii)
As coleoptera (Coleoptera) pest, such as it can enumerate: Xystrocera Globosa (Xystrocera globosa), malicious rove beetle (Paederus fuscipes), golden-rimmed blue and white cockchafer (Eucetonia roelofsi), Callosobruchus chinensis (Callosobruchus chinensis), sweet potato is as (Cylas formicarius), alfalfa leaf is as (Hypera postica), Echinocnemussquameus (Echinocnemus squameus), Oulema oryzae (Oulema oryzae), long leg waterleaf first (Donacia provosti), Lissorhoptrusoryzophilus (Li Ssorhoptrus oryzophilus), colasosoma dauricum (Colasposoma dauricum), western India sweet potato weevil (Euscepes postfasciatus), mexican bean ladybird (Epilachna varivestis), acanthoscelides obtectus (Acanthoscelides obtectus), corn root leaf A (Diabrotica virgifera), Li Lan volumes as (Involvulus cupreus), aulacophora femoralis (Aulacophora femoralis), pea weevil (Bruchus pisorum), potato bug (Epilac Hna vigintioctomaculata), ridge chest nitidulid (Carpophilus dimidiatus), Cassida nebulosa (Cassida nebulosa), it is thick to carry on the back few hair flea beetle (Luperomorpha tunebrosa), Phyllotreta striolata (Phyllotreta striolata), Psacothea hilaris (Psacothea hilaris), golden suede glistens longicorn (Aeolesthes chrysothrix), Mongolian oak is as (Curculio sikkimensis), pineapple bug (Carpophilus hemipterus), Small blue and white cockchafer (Oxycetonia jucunda), 12 asterophyllite first of pumpkin (Diabrotica spp.), blackish green coloured silk rutelian (Mimela splendens), sitophilus zea-mais (Sitophilus zeamais), red flour beetle (Tribolium castaneum), rice weevil (Sitophilus oryzae), sub- flat powder steals (Palorus subdepressus), Japanese gill cockchafer (Melolonthajaponica), Anoplophoramalasiaca (Anoplophora malasiaca), quasi- mealworm (Neatus picipes) a little louder, potato leaf First (Leptinotarsa decemlineata), 11 asterophyllite first of cucumber (Diabrotica undecimpunctata howardi), long beak is hunted as (Sphenophorus venatus), ten four scotellaris (Crioceris quatuordecimpunctata), plum ball neck is as (Conotrachelus nenuphar), curculio davidi (Ceuthorhynchidius albosuturalis), daicon leaf beetle (Phaedon brassicae), tobacco death watch beetle (Lasioderma serricorne ), Japanese root nodule is as (Sitona japonicas), spot beak rutelian (Adoretus tenuimaculatus), Cabot's Tragopan (Tenebrio molitor), it is chrysomelid (Basilepta balyi) to have angle chest, small clover leaf is as (Hypera nigrirostris), the recessed shin flea beetle of knotweed (Chaetocnema concinna), Anomalacuprea (Anomala cuprea), seven gill cockchafer of pitch (Heptophylla picea), ladybug of eggplant 28 stars (Epilachna vigintioctopunctata), northern corn root-worm (Diabr Otica longicornis), brevitarsis (Eucetonia pilifera), wireworm click beetle (Agriotes spp.), black wool khapra beetle (Attagenus unicolor japonicus), spot sheath beans are chrysomelid (Pagria signata), polychrome different beetle (Anomala rufocuprea), a Ji intends powder and steals (Palorus ratzeburgii), Alphitobius (Alphitobius laevigatus), Anthrenus verbasci (Anthrenus verbasci), Lyctus brunneus Stephens (Lyctus brunneus), confused flour beetle (Tri Bolium confusum), secret note wheat firefly is chrysomelid (Medythia nigrobilineata), grape ridge tiger longicorn (Xylotrechus pyrrhoderus), US Potato flea beetle (Epitrix cucumeris), vertical pit cutting pin small moth (Tomicus piniperda), Monochamus alternatus (Monochamus alternatus), Japan popillia flavosellata fairmaire (Popillia japonica), beans Yuan is green (Epicauta gorhami), sitophilus zea-mais (Sitophilus zeamais), Japanese grass tiger is as (Rhynchites heros ), vegetables as (Listroderes costirostris), Callosobruchus maculatus (Callosobruchus maculatus), apple frost greenery leaf as (Phyllobius armatus), apple flower as (Linaeidea aenea) chrysomelid in (Anthonomus pomorum), verdigris and Anthonomusgrandis (Anthonomus grandis)
As Diptera (Diptera) pest, such as it can enumerate: Culex pipiens pallens (Culex pipiens pal lens), spinach spring fly (Pegomya hyoscyami), pea liriomyza bryoniae (Liriomyza huidobrensis), housefly (Musca domestica), rice straw fly (Chlorops oryzae), rice hair eye ephydrid (Hydrellia sasakii), Japanese rice maggot (Agromyza oryzae), barley hair eye ephydrid (Hydrellia griseola), barley hair eye ephydrid (Hydrellia griseola), malanagromyza phaseoli (O Phiomyia phaseoli), melon widow's hair on the neck trypetid (Dacus cucurbitae), cherry fruit fly (Drosophila suzukii), the peppery trypetid (Rhacochlaena japonica) of Japan, false stable fly (Muscina stabulans), the eye flys classes such as the different eye fly in East Asia (Megaselia spiracularis), moth fly (Clogmia albipunctata), Tipula spp (Tipula aino), it lies prostrate fly (Phormia regina), Culex tritaeniorhynchus (Culex tritaeniorhynchus), Anopheles sinensis (Anoph Eles sinensis), cabbage fly (Hylemya brassicae), soybean pod gall-midge (Asphondylia sp.), delia platura (Delia platura), green onion ground Hylemyia Platura Meigen (Delia antiqua), Rhagoletis cerasi (Rhagoletis cerasi), Culex molestus (Culex pipiens molestus Forskal), Mediterranean fruitfly (Ceratitis capitata), open up fruit fly (Bradysia agrestis) in library, Xiao's Chenopodiaceae spring fly (Pegomya cunicularia), vegetable leafminer (Liriomyza Sativae), melon liriomyza bryoniae (Liriomyza bryoniae), pea coloured silk dives fly (Chromatomyia horticola), Biological habit (Liriomyza chinensis), Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), aedes albopictus (Aedes albopictus), Liriomyza trifolii (Liriomyza trifolii), vegetable leafminer (Liriomyza sativae), tangerine fruit fly (Dacus dorsalis), orangery widow's hair on the neck trypetid (Dacus tsuneon Is), wheat midge (Sitodiplosis mosellana), America straw hippelates flavipes (Meromuza nigriventris), Mexico are by trypetid (Anastrepha ludens) and apple around trypetid (Phagoletis pomonella)
As Hymenoptera (Hymenoptera) pest, such as it can enumerate: crosspointer ant (Pristomyrmex pungens), aptery bee class (wingless wasp), kitchen ant (Monomorium pharaohnis), width section major part ant (Pheidole noda), cabbage sawfly (Athalia rosae), chestnut gall wasp (Dryocosmus kuriphilus) etc., mercerising ant (Formica fusca japonica), Hornet (giant hornet), Athalia infumata, Agre papana Panz (Arge pagana), Japan Cabbage sawfly (Athalia japonica), leaf cutting ant (Acromyrmex spp.), Solenopsis (Solenopsis spp.), three section sawfly of apple (Arge mali) and hairless recessed smelly ant (Ochetellus glaber)
As Orthoptera (Orthoptera) pest, such as it can enumerate: tip grass Zhong (Homorocoryphus lineosus), Gryllotalpa spp (Gryllotalpa sp.), smaller grasshopper (Oxya hyla intricata), Oxyayezoensis (Oxya yezoensis), migratory locusts (Locusta migratoria), O. japonica (Oxya japonica), rice Zhong (Homorocoryphus jezoensis) and Teleogryllus emma (Teleogryllus emma)
As Thysanoptera (Thysanoptera) pest, such as it can enumerate: red tape moon thrips (Selenothrips rubrocinctus), rice thrips (Stenchaetothrips biformis), haplothrips aculeatus (Haplothrips aculeatus), persimmon pipe thrips (Ponticulothrips diospyrosi), golden thistle horse (Thrips flavus), maize stays thrips (Anaphothrips obscurus), camphor tree pipe is sliding thrips (Liothrips floridensis), calamus thrips (Thrips simplex), jasmine black wool Ji Horse (Thripsnigropilosus), greenhouse thrips (Heliothrips haemorrhoidalis), pseudo- rod Phellinus linteus (Pseudodendrothrips mori), chrysanthemum microcephaly thrips (Microcephalothrips abdominalis), mangrove bark thrips (Leeuweniapasanii), evergreen chinquapin rate value skin thrips (Litotetothrips pasaniae), mandarin orange reality thrips (Scirtothrips citri), Chinese single tube thrips (Haplothrips chinensis), soybean surprise bacterium thrips (Mycterothrip S glycines), coarse wool thrips (Thrips setosus), the yellow hard thrips (Scirtothrips dorsalis) of tea, Michaelis rod thrips (Dendrothrips minowai), black single tube thrips (Haplothrips niger), onion thrips (Thrips tabaci), onion thrips (Thrips alliorum), yellow chest thrips (Thrips hawaiiensis), Ku Shi single tube thrips (Haplothrips kurdjumovi), sleeve refers to thrips (Chirothrips manicatus), beautiful flower thrips (Fankliniella Intonsa), color thrips (Thrips coloratus), Frankliniella occidentalis (Franklinella occidentalis), palm thrips (Thrips palmi), lily flower thrips (Frankliniella lilivora) and lily bulb are sliding thrips (Liothrips vaneeckei)
As Acarina (acari) pest, such as it can enumerate: leptotrombidium akamushi (Leptotrombidium akamushi), Dermacentor variabilis (Dermacentor variabilis), the perverse mite of Bai Shi fowl (Ornithonyssus bacoti), demodicidosis (Demodex canis), the ticks classes such as brown dog tick (Rhipicephalus sanguineus), Lushi tetranychid (Tetranychus ludeni), Mite (Tetranychus truncatus), tetranychus viennensis (Tetranychus viennensis), Shenmu-Yanan railway (Tetr Anychus kanzawai), Cheyletusmoorei (Cheyletus malaccensis), tyrophagus putrescentiae (Tyrophagus putrescentiae), dust mite (Dermatophagoides farinae), red back spider (Latrodectus hasseltii), dermacentor taiwanensis (Dermacentor taiwanicus), tea point leaf segment tick (Acaphylla theavagrans), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus), the perverse skin goitre mite of tomato (Aculops lycopersici) , northern fowl mite (Ornithonyssus sylvairum), Tetranychus urticae (Tetranychus urticae), Chinese goitre mite (Eriophyes chibaensis), Sarcoptes scabiei hominis (Sacroptes scabiei), haemaphysalis longicornis (Haemaphysalis longicornis), black foot castor bean tick (Ixodes scapularis), like food junket mite (Tyrophagus similis), Cheyletus eruditus (Cheyletus eruditus), panonychus citri (Panonychus citri), Mohs cheyletid mite (Cheyletus Moorei), purplish red short hairs mite (Brevipalpus phoenicis), ear itching mite (Octodectes cynotis), dermatophagoides pteronyssinus (Dermatophagoides ptrenyssnus), Haemaphysalis japonica (Haemaphysalis japonica), ixodes ovatus (Ixodes ovatus), citrus reticulata pediculus (Phyllocoptruta citri), the perverse goitre mite of steinman pin (Aculus schlechtendali), panonychus ulmi (Panonychus ulmi), lone star tick (Amblyomma americanum) and the perverse mite of cock skin ( Dermanyssus gallinae),
As Isoptera (Isopteran) pest, such as can enumerate: drift chest reticulitermes flavipe (Reticulitermes miyatakei), Workers of Coptotermes formosanus Shiraki (Coptotermes formosanus), the wet carpented ant (Hodotermopsis japonica) of Japan, Reticulitermes (Reticulitermes sp.), yellow limb reticulitermes flavipe (Reticulitermes flaviceps amamianus), goes here and there this termite (Glyptotermes kushimensis), Guangzhou formosanes (Coptoterme at small principal columns of a hall termite (Incisitermes minor) S guangzhoensis), permanent spring new termite (Neotermes koshunensis), Kodak U.S. tree termite (Glyptotermes kodamai), red tree termite (Glyptotermes satsumensis), Cryptotermes domesticus (Cryptotermes domesticus), Odontotermes formosanus (Odontotermes formosanus), middle island tree termite (Glyptotermes nakajimai), it is close to turn round termite (Pericapritermes nitobei) and eastern subterranean termite (Reticulitermes sp Eratus),
As cockroach mesh (blattodea) pest, such as it can enumerate: Peroplaneta fluligginosa (Periplaneta fuliginosa), Groton bug (Blattella germanica), oriental cockroach (Blatta orientalis), Periplanetabrunnea (Periplaneta brunnea), quasi- Groton bug (Blattella Iituricollis), the big Lian (Periplaneta japonica) of Japan and American cockroach (Periplaneta americana)
It as Siphonaptera (Siphonaptera) pest, such as can enumerate: Pulex irritans (Pulex irritans), cat flea (Ctenocephalides felis) and fowl c. leaf flea (Ceratophyllus gallinae)；
As Nemata (nematodes) pest, such as it can enumerate: Nothotylenchusacris (Nothotylenchus acris), aphelenchoides besseyi (Aphelenchoides besseyi), Cobb root (Pratylenchus penetrans), M hapla (Meloidogyne hapla), Meloidogyne incognita (Meloidogyne incognita), globodera rostochiensis (Globodera rostochiensis), javanese root knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycin Es), coffee pot handle (Pratylenchus coffeae), unsuccessful Pratylenchidae (Pratylenchus neglectus) and half puncture nematode (Tylenchus semipenetrans) and
It as mollusc, such as can enumerate: Pomacea canaliculata (Pomacea canaliculata), Africangiant snail (Achatina fulica), two-wire slug (Meghimatium bilineatum), Valencia column slug (Lehmannina valentiana), yellow slug (Limax flavus) and Okinawa thin skin snail (Acusta despecta sieboldiana).
In addition, agricultural and horticultural pesticide of the invention also has stronger insecticidal effect to the Liriomyza brponiae (Tuta absoluta) as other pests.
In addition, Animal Parasitic mite as one of the control object of animal parasite agent for preventing and eliminating of the invention, such as it can enumerate: boophilus microplus (Boophilus microplus), brown dog tick (Rhipicephalus sanguineus), haemaphysalis longicornis (Haemaphysalis longicornis), haemaphysalis flava (Haemaphysalis flava), haemaphysalis campanulata (Haemaphysalis campanulata), haemaphysalis conicinna (Haemaphysalis concinna), Haemaphysalis japonica (Haemaphysalis japonica), northern hilllock blood tick (Ha Emaphysalis kitaokai), this blood tick (Haemaphysalis ias) of clothing Asia, ixodes ovatus (Ixodes ovatus), Ixodes japonensis (Ixodes nipponensis), ixodes persulcatus (Ixodes persulcatus), tortoise shape flower tick (Amblyomma testudinarium), big lancing tick (Haemaphysalis megaspinosa), dermacentor reticulatus (Dermacentor reticulatus), the ticks classes such as dermacentor taiwanensis (Dermacentor taiwanesis)；The perverse mite of cock skin (Dermanyssus gallinae), the perverse mite of woods fowl (Ornithonyssus sylviarum), capsule fowl pierces birds mite class such as mite (Ornithonyssus bursa), the true trombiculid of Wei Shi (Eutrombicula wichmanni), leptotrombidium akamushi (Leptotrombidium akamushi), leptotrombidium pallidium (Leptotrombidium pallidum), leptotrombidium fuji (Leptotrombidium fuji), Leptotrombidium tosa, tetranychus autumnalis (Neotrombicula autumnal Is), eutrombicula alfreddugesi (Eutrombicula alfreddugesi), Gong Chuanhe takes turns trombiculids classes such as trombiculid (Helenicula miyagawai), Ya Shi Ji chela mite (Cheyletiella yasguri), rabbit Ji chela mite (Cheyletiella parasitivorax), the meat mite class such as cheyletiella blakei (Cheyletiella blakei), rabbit scabies mite (Psoroptes cuniculi), psoroptes bovis (Chorioptes bovis), dog ear mite (Otodectes cynotis), Sarcoptes scabiei hominis (Sarcoptes scabiei), Vermiform mites class such as the itch mites classes such as cat scab mite (Notoedres cati) and demodicidosis (Demodex canis) etc..Wherein, the preventing and kill off effectively to tick class etc. of the animal parasite agent for preventing and eliminating containing the compounds of this invention.
The flea class of other control objects as animal parasite agent for preventing and eliminating of the invention, it such as can enumerate: belong to the aptery insect of ectoparasitism of Siphonaptera (Siphonaptera), can more specifically enumerate: belonging to the flea class of Pulicidae (Pulicidae) and european mouse flea section (Ceratephyllus) etc..It as belonging to the flea class of Pulicidae, such as can enumerate: dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), Pulex irritans (Pulex irritans), Sticktight (Echidnophaga gallinacea), Xanthopsyllacheopis (Xenopsylla cheopis), leptopsylla musculi (Leptopsylla segnis), ceratophyllus fasciatus (Nosopsyllus fasciatus) and ceratophyllus anisus (Monopsyllus anisus) etc..Animal parasite agent for preventing and eliminating containing the compounds of this invention is prevented and kill off effectively to the flea class for wherein belonging to Pulicidae, especially dog flea, cat flea etc..
The ectoparasitism mite of another control object as animal parasite agent for preventing and eliminating of the invention, such as it can enumerate: haematopinus eurysternus (Haematopinus eurysternus), haematopinus asina (Haematopinus asini), sheep lice (Dalmalinia ovis), Linognathus vituli (Linognathus vituli), haematopinus suis (Haematopinus suis), the louse class such as crab louse (Phthirus pubis) and head louse (Pediculus humanus capitis), and dog nibbles mao lice etc. and stings lice class, horsefly (Tabanus trigonus), flowerfly (anthomyiid F ) and the blood sucking Diptera pest such as buffalo gnat (Simulium ornatum) etc. ly.In addition, animal parasite agent for preventing and eliminating of the invention is also effective to endoparasite, it as this endoparasite, such as can enumerate: protozoans such as Trematodas and coccidia, plasmodium, enteral sarcocystis, toxoplasma and Cryptosporidium such as tapeworms, blood fluke, the piece fluke such as Nematas, bothriocephalus linguloides, fish tapeworm, Taenia elliptica, multiceps, Echinococcus granulosus, the Echinococcus multilocularis such as lung worm, whipworm, nodositas nematode, stomach entozoa, roundworm and filaria class etc..
Since the phthaloyl amide derivatives indicated using the logical formula (I) of the present invention are the agricultural of effective component and horticultural pesticide to damage wet crop, dry crop, fruit tree, vegetables, the above-mentioned pest of other crops and flowers etc. has significant preventive effect, therefore, the period occurred according to prediction pest, there is preceding or confirmation emerging time point in pest, by with it to culture facility, paddy field, dry land, fruit tree, vegetables, other crops, the seed of flowers etc., the water in paddy field, the cultivation carrier etc. of cauline leaf or soil etc. is handled, to realize the expected effect of agricultural and horticultural pesticide of the invention.Wherein, the cultivation water etc. in plant hole soil, crop root, irrigation water, hydroponic culture when to the nursery soil of crop, flowers etc., transplanting is handled, through or be not through soil, from root absorption the compounds of this invention, that is, being preferred embodiment using metastatic application is permeated.
The useful plant that agricultural and horticultural pesticide of the invention can be used is not particularly limited, such as it can enumerate: cereal (such as, rice, barley, wheat, rye, oat, corn etc.), beans (soybean, red bean, semen viciae fabae, pea, Kidney bean, peanut etc.), Tree Fruit class (apple, citrus, pears, grape, peach, plum, cherry, English walnut, chestnut, almond, banana etc.), leaf fruit vegetables (wild cabbage, tomato, spinach, broccoli, lettuce, onion, shallot, green pepper, eggplant, strawberry, capsicum, gumbo etc.), root vegetables (carrot, potato, sweet potato, taro, radish, turnip, lotus root, fructus arctii, garlic etc.), crop (cotton is used in processing, fiber crops, beet, hops, sugarcane, beet, olive, rubber, coffee, tobacco, tea etc.), melon (pumpkin, cucumber, watermelon , muskmelon, muskmelon etc.), herbage class (orchard grass, sorghum, timothy grass, clover, alfalfa etc.), lawn plant class (Koryo sesame grass, bent grass etc.), fragrance (lavender, rosemary, thyme, parsley, pepper, ginger etc.), flowers class etc. it is ornamental with the plants such as crop (chrysanthemum, rose, carnation, orchid etc.), front yard wood (ginkgo, oriental cherry class, green wood etc.), forest (fir class, silver fir class, conifer, cypress, China fir, Chinese juniper, eucalyptus etc.).
Above-mentioned " plant " further includes due to traditional breeding method or gene recombination technology and to differentThe acetyl-CoA carboxylase inhibitors such as the glutamine synthetase inhibitors such as the epsp synthases inhibitor such as the ALS inhibitor such as the HPPD inhibitors such as azoles humulone (isoxaflutole), imazethapyr (imazethapyr), thifensulfuronmethyl (thifensulfuron-methyl), glyphosate (glyphosate), glufosinate-ammonium (glufosinate), sethoxydim (sethoxydim), Brominal (bromoxynil), dicamba (dicamba), 2, the herbicides such as 4- drop (2,4-D) impart the plant of resistance.
Example as " plant " for having been assigned resistance due to traditional breeding method, such as have the rape resistant to the imidazolones such as imazethapyr system ALS suppressive herbicide, wheat, sunflower, rice, sold with the trade name of Clearfield (registered trademark).Similarly, there is due to traditional breeding method and impart to the sulfonylureas ALS suppressive herbicide such as thifensulfuronmethyl the soybean of resistance, sold with the trade name of STS soybean.Similarly, as due to traditional breeding method and to the example of the resistant plants of acetyl-CoA carboxylase inhibitors such as triketone oximes, aryloxyphenoxypropionic class herbicide, there is SR corn etc..
In addition, the plant resistant to acetyl-CoA carboxylase inhibitor is recorded in Proc.Natl.Acad.Sci.USA, in volume 87, page 7175~7179 (nineteen ninety) etc..In addition, in Weed Science, volume 53, it has been reported that the mutation acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitor in page 728~746 (2005) etc., by the way that such mutation acetyl-coA carboxylase gene is introduced into plant using gene recombination technology, or the mutation for providing resistance is introduced into the acetyl-CoA carboxylase of plant, the plant resistant to acetyl-CoA carboxylase inhibitor can be produced.In turn, by with chimeraplasty (GuraT.1999.Repairing the Genome's Spelling Mistakes.Science, 285:316-318.) for representative, base substitution mutation nucleic acid is introduced into plant cell, method in acetyl-coA carboxylase gene or als gene to which the mutation of the amino acid replacement of site specific to be introduced into plant etc., the plant resistant to acetyl-CoA carboxylase inhibitor or ALS inhibitor etc. can be produced, these plants could be used that with agricultural and horticultural pesticide of the invention.
In turn, it as the toxin expressed in genetically modified plants, can enumerate: the pesticidal albumen from Bacillus cercus (Bacillus cereus) or Japanese beetle bacillus (Bacillus popilliae)；The insecticidal proteins such as delta-endotoxins, VIP1, VIP2, VIP3 or VIP3A such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C from bacillus thuringiensis (Bacillus thuringiensis)；Insecticidal proteins from nematode；The toxin that scorpion venom, spider venom, bee venom or insect-specific neurotoxin etc. are generated by animal；Hyphomycetes toxin；Phytolectin；Agglutinin；The protease inhibitors such as trypsin inhibitor, serpin, potato tuber-specific storage protein (patatin), cystatin, antipain；The ribosome inactivating proteins (RIP) such as glycine betaine (lycine), corn-RIP, abrin, soft melon albumen, Saponaria officinalis toxalbumin, briodin；The steroid metabolisms enzymes such as 3- hydroxy steroid oxidizing ferment, ecdysteroid-UDP- glucosyltransferase, cholesterol oxidase；Ecdysone inhibitor；HMG-CoA reductase；Sodium channel inhibitor, ockers plasma channel inhibitor；JH esterase；Diuretic hormone receptor；Stilbene synthase；Bibenzyl synthases；Chitinase；Dextranase etc..
In addition, it further include the hybrid toxins of the insecticidal proteins such as the delta-endotoxin proteins such as CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, Cry9C, Cry34Ab or Cry35Ab, VIP1, VIP2, VIP3 or VIP3A, the toxin of excalation, modified toxin as the toxin expressed in such genetically modified plants.Hybrid toxins are that the different structure territory of these albumen is carried out new combination by using gene recombination technology and is prepared.Toxin as excalation, it is known to lack the CrylAb of a part of amino acid sequence.As modified toxin, one or more amino acid of natural toxin are replaced.
The example of such toxin and the recombinant plant that can synthesize such toxin describe in EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878, WO03/052073 etc..
The toxin for including in these recombinant plants be especially can to plant assign to coleopteran pest, Hemipteran pest, Diptera pest, lepidoptera pest, Nemata resistance.Agricultural of the invention and horticultural pesticide can be used with these technologies and use or architecture.
Agricultural of the invention prevents and kill off various pests with horticultural pesticide, it can be directly or with acceptable diluents such as water, or effective amount is prevented and kill off for the plant use of prediction generation pest and nematode is for pest or nematode in the form of suspension, such as in fruit tree, cereal, the pest and nematode generated in vegetables etc., other than being dispersed in leaves and stems, it can also carry out impregnating in seed in a medicament, seed is coated, the seed treatments such as calper processing, it is mixed into whole soil layers, arrangement application, it is mixed with bed soil, rice transplanting processing, plant hole processing, crop root processing, top dressing, the nursery box of rice is handled, the processing to soil etc. of immersion treatment etc. and be allowed to from root absorption.Alternatively, it is also possible to by application, sootiness in the nutrient solution into nutrient solution (water plough) cultivation or be injected into the medium mode of trunk come using.
In turn, the place of the pest prediction can also occurs directly or with acceptable diluents such as water or in the form of suspension using preventing and kill off effective amount for pest in agricultural of the invention and horticultural pesticide, such as, other than interspersing among grain storage pest, house pest, sanitary insect pest, injurious forest-insect etc., it can be also used for being coated residential building material or as fumigant, bait formulation etc..
The method that as the method for seed treatment, such as can be enumerated: impregnate seed in a liquid state in the case where dilution or undiluted liquid or solid pharmaceutical preparation and permeate medicament；Solid or liquid preparation are mixed with seed, the method for handling and it being made to be attached to the surface of the seed is coated to seed；Solid or liquid preparation are mixed with adhesions carriers such as resin, polymer and it is made to be coated on the method on seed；Solid or liquid preparation are interspersed among to the method near seed while sowing.
" seed " for carrying out the seed treatment refers to the plant that initial stage is cultivated used in the growth of plant.For example, can also enumerate the plant of bulb, stem tuber, kind block, strain bud, aerial tuber, bulb or cuttage cultivation nourished and generated other than seed.
" soil " or " cultivation carrier " when implementing application method of the present invention refers to the support for cultivated crop, especially make the support of root growth, its material is not particularly limited, as long as the material of plant growth can be made, it can be soil, nursery pad, water etc., it as specific material, such as can be sand, float stone, vermiculite, diatomite, agar, spawn, polymer substance, asbestos, mineral wool, sawdust and bark.
As the method spread into crop leaves and stems or grain storage pest, house pest, sanitary insect pest or injurious forest-insect etc., the method for spreading the solid pharmaceutical preparations such as the liquid preparations such as emulsion, suspending agent or wettable powder or granular water-dispersible agent with water acceptable diluent, the method for spreading pulvis or sootiness etc. can be enumerated.
It as the method for administration to soil, such as can enumerate: water dilution or undiluted liquid preparation are applied to the method for the root or nursery seedbed etc. of plant；Granula is spread into the root of plant or the method in the seedbed that is used for nursery etc.；The method that pulvis, wettable powder, granular water-dispersible agent, granula etc. are spread and be incorporated into entire soil before sowing or transplanting；Pulvis, wettable powder, granular water-dispersible agent, granula etc. are spread into the method in planting hole, plant row etc. prior to seeding or before planting plants body.
As the method for administration of the nursery box to rice, dosage form for example can be different according to the difference of the Dressing dates such as application when application, greening phase apply, transplant when sowing, can be applied with dosage forms such as pulvis, granular water-dispersible agent, granulas.The blending earthed up with pulvis, granular water-dispersible agent or granula etc. can also can be carried out, such as bed soil blends, earthing blends and whole blending etc. of earthing up by apply with ridging blending.Ridging simply can also be alternatively formed stratiform with various preparations to apply.
As the method for administration to paddy field, usually the liquid preparations such as solid pharmaceutical preparations, suspending agent, the emulsions such as big granula, packaging agent, granula, granular water-dispersible agent are interspersed among on the paddy field of Riddled Condition.In addition, in rice transplanting, preparation appropriate directly or after blending with fertilizer etc. can be interspersed among or injected soil.Alternatively, it is also possible to utilize the medical fluids such as emulsion, suspending agent at the inflow source of the water in the paddy fields such as water inlet or irrigation rig, so that the supply with water is effortlessly applied.
In dry crop, from nursery stage is seeded into, the cultivation carrier etc. close to seed or plant can be handled.In the plant for being directly seeded in dry land, other than directly handling seed, preferably the root of the plant in cultivation is handled.Granula can be used to carry out spreading processing or dilution or the undiluted medicament in water are irrigated processing etc. with liquid.It is sowed again after cultivation carrier before granula and sowing is blended also as preferred processing.
As the sowing of the cultivated plant transplanted, the processing of nursery stage, in addition to directly handling seed, the perfusion processing or the distribution of granula for the medicament being preferably in a liquid state to nursery with seedbed are handled.In addition, being also preferred processing in the cultivation carrier for planting hole being handled or being blended in transplanting proximal site with granula in field planting.
Agricultural and horticultural pesticide of the invention is used generally according to the conventional method preparation of pesticidal preparations at the good shape for being suitable for using.
I.e., as long as derivative or its esters that logical formula (I) of the invention indicates are supported in inert carrier appropriate or are used cooperatively in appropriate proportions together with adjuvant as needed, is dissolved, is separated, is suspended, is mixed, is impregnated with, is adsorbed or is adhered to and preparation is suitable dosage form, such as suspending agent, emulsion, liquor, wettable powder, granular water-dispersible agent, granula, pulvis, tablet, packaging agent carrys out use.
Composition (agricultural and horticultural pesticide or animal parasite agent for preventing and eliminating) of the invention, can also be as needed containing commonly used in the adding ingredient in pesticidal preparations or animal parasite agent for preventing and eliminating in addition to effective component.It as the adding ingredient, can enumerate: the carriers such as solid carrier, liquid-carrier, surfactant, dispersing agent, wetting agent, adhesive, tackifier, thickener, colorant, spreading agent (extender), spreader-sticker (spreader), antifreezing agent, anticaking agent, disintegrating agent, decomposing inhibitor etc..Further, it is also possible to use preservative, plant piece etc. as adding ingredient as needed.These adding ingredients can be used alone, two or more can also be applied in combination.
As solid carrier, such as it can enumerate: quartz, clay, kaolin, pyrophyllite, sericite, talcum, bentonite, Emathlite, attapulgite, zeolite, the natural mineral matter class such as diatomite, calcium carbonate, ammonium sulfate, sodium sulphate, the inorganic salts such as potassium chloride, synthetic silicic acid, synthetic silicate, starch, cellulose, plant powder (such as sawdust, coconut husk, corncob, tobacco stem etc.) etc. organic solids carrier, polyethylene, polypropylene, the plastic carriers such as Vingon, urea, inorganic hollow body, plastic hollow body, fumed silica (fumed silica, White Carbon black) etc..They may be used singly or in combination of two or more.
As liquid-carrier, such as can enumerate: the unary alcohols such as methanol, ethyl alcohol, propyl alcohol, isopropanol, butanol, and/or, alcohols as the polyalcohols such as ethylene glycol, diethylene glycol (DEG), propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerol, ketones, ether, two such as the polyols such as propylene glycol species, acetone, butanone, methyl iso-butyl ketone (MIBK), diisobutyl ketone, cyclohexanoneAlkane, ethylene glycol monoethyl ether, dipropyl ether, the ethers such as tetrahydrofuran, n-alkane, cycloalkane, isoparaffin, kerosene, the aliphatic hydrocarbons such as mineral oil, benzene, toluene, dimethylbenzene, solvent naphtha, the aromatic hydrocarbons such as alkylnaphthalene, methylene chloride, chloroform, the halogenated hydrocarbons such as carbon tetrachloride, ethyl acetate, phthalic acid diisopropyl ester, dibatyl phithalate, dioctyl phthalate, the esters such as dimethyl adipate, the lactones such as gamma-butyrolacton, dimethylformamide, diethylformamide, dimethyl acetamide, the amides such as N- alkyl pyrrolidone, the nitriles such as acetonitrile, the sulphur compounds class such as dimethyl sulfoxide, soybean oil, rapeseed oil, cottonseed oil, the vegetable oil such as castor oil, water etc..They may be used singly or in combination of two or more.
As the surfactant for being used as dispersing agent or wet spreader, such as it can enumerate: sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl organic ether, polyoxyethylene alkyl phenyl ether formaldehyde condensation products, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkyl amine, Polyoxyethylene fatty acid amides fatty acid ester, polyoxyethylene fatty acid xenyl ether, polyalkylene benzyl phenyl ether, polyoxy alkylidene styrylphenyl ether, acetylenediol, polyoxy alkylidene addition acetylenediol, Polyoxyethylene Ether The nonionic surface active agent such as organosilicon, ester type organosilicon, fluorine system surfactant, Emulsifier EL-60, Crodaret,
Alkyl sulfate, polyoxyethylene alkyl ether sulfate salt, polyoxyethylene alkylphenyl ether sulfate salt, polyoxyethylene styrylphenyl ether sulfate, alkylbenzene sulfonate, alkylaryl sulfonates, lignosulfonates, alkyl sulfo succinate, naphthalene sulfonate, alkylnaphthalene sulfonate, the salt of naphthalene sulfonic acid-formaldehyde condensation product, the salt of alkyl naphthalene sulfonic acid formaldehyde condensation products, fatty acid salt, polycarboxylate, polyacrylate, N- methyl-fatty acid sarcosinates, resinate, ether phosphates, the anionic surfactant such as polyoxyethylene alkyl phenyl ether phosphate,
The cationic surface active agents such as the alkylamine salts such as laurylammonium chloride, stearyl amine hydrochloride, oleyl amine hydrochloride, stearyl amine acetate, stearyl propylamine acetate, alkyl trimethyl ammonium chloride, benzalkonium chloride,
Amphoteric surfactantes such as amino acid pattern or betaine type etc..
These surfactants can be used alone, alternatively, it is also possible to which two or more is applied in combination.
As adhesive or tackifier, such as it can enumerate: carboxymethyl cellulose or its salt, dextrin, water soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, Sodium Polyacrylate, the polyethylene glycol of average molecular weight 6000~20000, the polyethylene oxide of average molecular weight 100,000~5,000,000, phosphatide (such as cephalin, lecithin etc.) cellulose powder, dextrin, producing starch, polyaminocarboxylic acid complex compound, crosslinked polyvinylpyrrolidone, the copolymer of maleic acid and phenylethylene, (methyl) acrylic acid series copolymer, the half ester that polymer and dicarboxylic anhydride containing polyalcohol are formed, the water soluble salt of polystyrolsulfon acid, paraffin, terpenes, polyamide, polyacrylate, polyoxyethylene, wax, it is poly- Vinyl alkyl ethers, alkylphenol formaldehyde condensation product, synthetic resin emulsion etc..
As thickener, such as it can enumerate: inorganic micro powders such as the water soluble polymers such as xanthan gum, guar gum, enlightening spy glue (Diutan gum), carboxymethyl cellulose, polyvinylpyrrolidone, carboxy vinyl polymer, acrylic acid series polymeric compounds, starch derivatives, polysaccharide, high-purity bentonite, fumed silica (fumed silica, White Carbon black) etc..
It as colorant, such as can enumerate: organic dyestuff such as the inorganic pigments such as iron oxide, titanium oxide, Prussian blue, alizarin dyes, azo dyes, metallized phthalocyanine dye etc..
It as antifreezing agent, such as can enumerate: polyalcohols such as ethylene glycol, diethylene glycol (DEG), propylene glycol, glycerol etc..
As for preventing the adjuvant for agglomerating or promoting disintegration, such as it can enumerate: the polysaccharides such as starch, alginic acid, mannose, galactolipin, polyvinylpyrrolidone, fumed silica (fumed silica, White Carbon black), ester gum, Petropols, sodium tripolyphosphate, calgon, Metallic stearates, cellulose powder, dextrin, the copolymer of methacrylate, polyvinylpyrrolidone, polyaminocarboxylic acid's complex compound, sulfonated phenylethylene-isobutyiene-maieic anhydride copolymer, S-PAN graft copolymer etc..
It as decomposing inhibitor (stabilizer), such as can enumerate: ultraviolet absorbing agents such as antioxidants, salicylic acid compound, the benzophenone cpd such as the desiccant such as zeolite, quick lime, magnesia, phenolic compounds, amine compounds, sulphur compound, phosphate cpd etc..
It as preservative, such as can enumerate: potassium sorbate, 1,2-[4-morpholinodithio quinoline -3- ketone etc..
It can also be further as needed using other adjuvants such as antioxidants, the ultraviolet absorbing agents such as antifreezing agents, the BHT such as metabolic breakdowns inhibitor isoreactivity reinforcing agent, the propylene glycol such as functional spreader-sticker, piperonyl butoxide.
The mixing ratio of effective component compound can adjust as needed, relative to agricultural of the invention and 100 parts by weight of horticultural pesticide, it is suitable for selecting use in the range of 0.01~90 parts by weight, such as in the case where pulvis, granula, emulsion or wettable powder, effective component is preferably 0.01~50 parts by weight (that is, being 0.01~50 weight % relative to agricultural and the total weight of horticultural pesticide).
Noxious organism control agent, particularly agricultural of the invention and the usage amount of horticultural pesticide are depending on various factors, such as purpose, object pest, the upgrowth situation of crop, the occurence tendency of pest, weather, environmental condition, dosage form, method of administration, application place, Dressing date etc. and change, it is suitable for selection in the range of every 10 acres of 0.001g~10kg, preferably 0.01g~1kg according to purpose as effective component compound.
The object pest and disease damage prevented and kill off for further expansion extends and prevents and kill off period or in order to lower Pesticide use amount, noxious organism control agent of the invention, particularly agricultural and horticultural pesticide can also be used in mixed way with other agriculture and horticultural pesticide, acaricide, nematicide, fungicide, biological pesticides etc., alternatively, it is also possible to be used in mixed way according to opportunity is used with herbicide, plant growth regulator, fertilizer etc..
As other agriculturals and horticultural pesticide, acaricide, nematicide for the above purpose, such as can illustrate as follows:
Destroyed (XMC), Dipel Aizawa subspecies (Bacillus thuringienses aizawai), Bacillus thuringiensis subsp. israelensis (Bacillus thuringienses israelensis), Dipel Japan subspecies (Bacillus thuringienses japonensis), Dipel Kurstaki (Bacillus thuringienses kurstaki), Dipel intends walking first subspecies (Bacillus thuringienses tenebrionis), by Dipel (Bacillus thur Ingienses) the crystalline toxin generated, BPMC, Bt toxin system insecticidal compound, CPCBS (chlorfenizon), DCIP (nemamort), D-D (1, 3- dichloropropylene), DDT, NAC, O-4- dimethylsulfamoylphenyl O, O- systox (DSP), thiophosphin (EPN), three propyl ester of isocyanuric acid (TPIC), acrinathrin (acrinathrin), nimbin (azadirachtin), azinphos-methyl (azinphos-methyl), acequinocyl (acequinocyl), Acetamiprid (acetamiprid), acetyl worm nitrile (acetoprole), orthene (acepha Te), avermectin (abamectin), avermectin B (avermectin-B), horizontal amine mite ester (amidofIumet), Amitraz (amitraz), alanycarb (alanycarb), Aldicarb (aldicarb), aldoxycarb (aldoxycarb), drinox (aldrin), α -5a,6,9,9a-hexahydro-6,9-methano-2,4 (alpha-endosulfan), alphamethrin (alpha-cypermethrin), albendazole (albendazole), allethrin (allethrin), isazofos (isazofos), isamidofos, isoamidofos,Azoles phosphorus (isoxathion), isofenphos (isofenphos), Mobucin (isoprocarb:MIPC), ivermectin (ivermectin), imicyafos, imidacloprid (imidacloprid), Imiprothrin (imiprothrin), indoxacarb (indoxacarb), S- fenvalerate (esfenvalerate), ethiofencarb (ethiofencarb), Ethodan (ethion), ethiprole (ethiprole), etoxazole (etoxazole), ethofenprox (ethofenprox), phonamiphos (ethoprophos), etrimfos (etr Imfos), methylamino avilamycin (emamectin), emamectin-benzoate (emamectin-benzoate), 5a,6,9,9a-hexahydro-6,9-methano-2,4 (endosulfan), empenthrin (empenthrin), oxamyl (oxamyl), oxydemeton_methyl (oxydemeton-methyl), Thiometan (oxydeprofos:ESP), oxibendazole (oxibendazole), oxfendazole (oxfendazole), potassium oleate (Potassium oleate), enuatrol (sodium oleate), cadusafos (cadusafos), cartap (cartap), carbaryl (carbaryl), carbosulfan (carbosulfan), carbofuran (carbofuran), smart gamma cyhalothrin (gamma-cyhalothrin), Meobal (xylylcarb), quinalphos (quinalphos), kinoprene (kinoprene), chinomethionat (chinomethionat), cloethocarb (cloethocarb), clothianidin (clothianidin), clofentezine (clofentezine), ring tebufenozide (chromafenozide), Rynaxypyr (chlorantraniliprole), chlorethoxyfos (chloretho Xyfos), Spanon (chlordimeform), Niran (chlordane), chlopyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), bromine worm is clear (chlorphenapyr), chlorfenizon (chlorfenson), chlorfenviphos (chlorfenvinphos), chlorfluazuron (chlorfluazuron), chlorobenzilate (chlorobenzilate), chlorobenzoic acid ester (chlorobenzoate), Mitigan (dicofol: dicofol), salithion (salithion), cynock (cyanophos:C YAP), diafenthiuron (diafenthiuron), Nellite (diamidafos), cyanogen insect amide (cyantraniliprole), beta-cypermethrin (theta-cypermethrin), gram (dienochlor) everywhere, nitrile pyrrole mite ester (cyenopyrafen), salithion (dioxabenzofos), difenolan (diofenolan), σ-cypermethrin (sigma-cypermethrin), dichlofenthion (dichlofenthion:ECP), cycloprothrin (cycloprothrin), DDVP (dichlorvos:DDVP ), disulfoton (disulfoton), dinotefuran (dinotefuran), lambda-cyhalothrin (cyhalothrin), phenyl ether Cyano chrysanthemate (cyphenothrin), cyfloxylate (cyfluthrin), diflubenzuron (diflubenzuron), cyflumetofen (cyflumetofen), fluorine mite ester (diflovidazin), plictran (cyhexatin), cypermethrin (cypermethrin), dimethylvinphos (dimethylvinphos), Rogor (dimethoate), dimefluthrin (dimefluthrin), silafluofene (silafluof En), cyromazine (cyromazine), ethyl pleocidin (spinetoram), pleocidin (spinosad), Envidor (spirodiclofen), spiral shell worm ethyl ester (spirotetramat), Spiromesifen (spiromesifen), sulfluramid (sulfluramid), sulprofos (sulprofos), sulfoxaflor (sulfoxaflor), ζ-cypermethrin (zeta-cypermethrin), diazinon (diazinon), taufluvalinate (tau-fluvalinate), dazomet (dazomet), thiacloprid (thiacloprid), thiophene Worm piperazine (thiamethoxam), thiodicarb (thiodicarb), thiocyclam (thiocyclam), Cupric sulfate (thiosultap), dimehypo (thiosultap-sodium), thionazin (thionazin), thiometon (thiometon), Metadelphene (deet), dieldrite (dieldrin), Ravap (tetrach1orvinphos), tetradiphon (tetradifon), etrafluorine ethofenprox (tetramethylfluthrin), tetramethrin (tetramethrin), butyl pyrimidine phosphorus (tebupirimfos), tebufenozide (te Bufenozide), tebufenpyrad (tebufenpyrad), Tefluthrin (tefluthrin), fluorobenzene urea (teflubenzuron), demeton-methyl (demeton-S-methyl), Swebate (temephos), decis (deltamethrin), terbufos (terbufos), bromine band pyrrole carbonitrile (tralopyril), tralomethrin (tralomethrin), transfluthrin (transfluthrin), triaguron (triazamate), triazuron, trichlamide (trichlamide), metrifonate (trichlorphon : DEP), triflumuron (triflumuron), Tolfenpyrad (tolfenpyrad), 2-dichloroethylk dimethyl phosphate (naled:BRP), Nithiazine (nithiazine), Nitenpyram (nitenpyram), novaluron (novaluron), noviflumuron (noviflumuron), hydroprene (hydroprene), fluorine pyrazoles worm (vaniliprole), vamidothion (vamidothion), parathion (parathion), parathion-methyl (parathion-methyl), halfenprox (halfenprox), chlorine tebufenozide (halofenozide), double difluoros Worm urea (bistrifluron), dimehypo (bisultap), hydramethylnon (hydramethylnon), hydroxypropul starch (hydroxypropyl starch), binapacryl (binapacryl), Bifenazate (bifenazate), Biphenthrin (bifenthrin), pymetrozine (pymetrozine), pyraclofos (pyraclorfos), pyrafluprole, pyridaphethione (pyridafenthion), pyridaben (pyridaben), pyridine worm ether (pyridalyl), pyrifluquinazon, pyriprole, pyrrole third Ether (pyriproxyfen), Aphox (pirimicarb), pyrimidifen (Pyrimidifen), pirimiphos-methyl (pirimiphos-methy1), pyrethrin (pyrethrins), Fipronil (fiproni1), fenazaquin (fenazaquin), fenamiphos (fenamiphos), fenisobromolate (bromopropylate), fenifrothion (fenitrothion:MEP), fenoxycarb (fenoxycarb), fenothiocarb (fenothiocarb), phenyl ethofenprox (phenothrin), Bassa (fenobucarb), fensulfothion (fens Ulfothion), Entex (fenthion:MPP), phenthoate dimephenthoate cidial (phenthoate:PAP), fenvalerate (fenvalerate), fenpyroximate (fenpyroximate), Fenpropathrin (fenpropathrin), Fenbendazole (fenbendazole), fosthiazate (fosthiazate), Carzol (formetanate), special Pyrimitate (butathiofos), Buprofezin (buprofezin), furathiocarb (furathiocarb), prallethrin (prallethrin), fluacrypyrim (fluacrypyrim), fluazinam (flu Azinam), fluazuron (fluazuron), fluorine thiophene worm sulfone (fluensulfone), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), taufluvalinate (fluvalinate), pyrrole fluorine phosphine sulfide (flupyrazofos), phonetic worm amine (flufenerim), flufenoxuron (flufenoxuron), flufenzine (flufenzine), trifluoro ethofenprox (flufenoprox), halfenprox (fluproxyfen), brofluthrinate (flubrocythrinate), Flubendiamide (flubendiamide), flumethrin (f Lumethrin), flurimfen, Toyodan (prothiofos), protrifenbute, flonicamid (flonicamid), Kayaphos (propaphos), propargite (propargite:BPPS), Profenofos (profenofos), third Flumethrin (profluthrin), arprocarb (propoxur:PHC), fenisobromolate (bromopropylate), betacyfluthrin (beta-cyfluthrin), flubenzuron (hexaflumuron), Hexythiazox (hexythiazox), heptenophos (heptenophos), chlorine chrysanthemum Ester (permethrin), benclothiaz,Worm prestige (bendiocarb), bensultap (bensu1tap), Citrazon (benzoximate), Benfuracard micro (benfuracarb), phoxim (phoxim), Phosalone (phosalone), lythidathion (fosthiazate), fosthietan (fosthietan), phosphamidon (phosphamidon), phosphorus worm prestige (phosphocarb), phosmet (phosmet:PMP), Liuyang rhzomorph (polynactins), Carzol (formetanate), formothion (formothion), thimet (phorate), machine oil (machi Ne oil), malathion (malathion), milbemycin (milbemycin), milbemycin A (milbemycin-A), milbemectin (milbemectin), Afos (mecarbam), first oxydemeton_methyl (mesulfenfos), Methomyl (methomyl), the methaldehyde (metaldehyde), metaflumizone (metaflumizone), acephatemet (methamidophos), Carbam NCS (metam-ammonium), metham-sodium (metam-sodium), methiocarb (methiocarb), methidathion (methidathion:D MTP), oppose line ester (methyl isothiocyanate), methyl decyl amide (methyl neodecanamide), parathion-methyl (methyl parathion),Worm ketone (metoxadiazone), methoxychlor (methoxychlor), methoxyfenozide (methoxyfenozide), metofluthrin (metofluthrin), methoprene (methoprene), MTMC (metolcarb), fluorine chlorine ether pyrethroids (meperfluthrin), Menite (mevinphos), Azodrin (monocrotophos), Cupric sulfate (monosultap), gamma cyhalothrin (lambda-cyhalothrin), Ryanicide (ryanodine), lufenuron (lufenuron), resmethrin (resmethri N), rayperidin (lepimectin), rotenone (rotenone), levamisol (levamisol), fenbutatin oxide (fenbutatin oxide), Morantel Tartrate (morantel tartarate), bromomethane (Methyl bromide), plictran (cyhexatin), nitrolim (Calcium cyanamide), lime sulfur (Calcium polysulfide), the agricultural such as sulphur (Sulfur) and nicotine sulphate (nicotine-sulfate) and horticultural pesticide, acarus-killing, nematicide.
As the agricultural and horticultural bactericides used with same purpose, such as it can illustrate: aureofungin (aureofungin), oxygen ring azoles (azaconazole), azithiram (azithiram), acypetacs, Acibenzolar (acibenzolar), Acibenzolar (acibenzolar-S-methyl), Fluoxastrobin (azoxystrobin), anilazine (anilazine), amisulbrom (amisulbrom), ammonia propyl-phosphine is sour (ampropylfos), azoles mepanipyrim (ametoctradin), allyl alcohol (allyl alcohol), 4- dodecyl -2, 6- thebaine ( Aldimorph), ambam (amobam), isotianil (isotianil), isovaledione, isopyrazam (isopyrazam), Isoprothiolane (isoprothiolane), kind bacterium azoles (ipconazole), iprodione (iprodione), iprovalicarb (iprovalicarb), different rice blast net (iprobenfos), imazalil (imazalil), iminoctadine (iminoctadine), three octyl benzene sulfonate (iminoctadine-albesilate) of biguanides, iminoctadine triacetate (iminoctadine-triace Tate), glyoxalin (imibenconazole), uniconazole P (uniconazole), uniconazole P-P (uniconazole-P), kobam (echlomezole), edifenphos (edifenphos), etaconazole (etaconazole), Guardian (ethaboxam), ethirimol (ethirimol), Ethisul (etem), ethoxyquin (ethoxyquin), Grandox fumigant (etridiazole), Enestroburin (enestroburin), epoxiconazole (epoxiconazole),White spirit (oxadixyl), oxidation wither pound clever (oxycarboxin), copper 8-quinolinolate (copper-8-quinolinolate), terramycin (oxytetracycline), copper-oxinate,Imidazoles (oxpoconazole),Oxpoconazole fumarate (oxpoconazole-fumarate), oxolinic acide (oxolinic acid), octhilinone (octhilinone), ofurace (ofurace), orysastrobin (orysastrobin), the soil fungicides such as metham-sodium (metam-sodium), kasugarnycin (kasugamycin), carbamorph (carbamorph), ring propionyl bacterium amine (carpropamid), carbendazim (carbendazim), carboxin (carboxin), carvol (carvone), quinazamid (quinazamid), quinacetol, quinoxyfen (quino Xyfen), chinomethionat (quinomethionate), difoltan (captafol), captan (captan), smart M 9834 (kiralaxyl), quinconazole, pentachloronitrobenzene (quintozene), iminoctadine (guazatine), cufraneb (cufraneb), cuprobam (cuprobam), glyodin (glyodin), griseofulvin (griseofulvin), Climbazole (climbazole), cresols (cresol), kresoxim-methyl (kresoxim-methyl), chlozolinate (chlozolinate), clotrimazole (clotrima Zole), pest of going out azoles (chlobenthiazone), Imugan (chloraniformethan), Spergon (chloranil), four chloro-quinoxalines (chlorquinox), chloropicrin (chloropicrin), chlorfenazole, chlorine nitre naphthalene (chlorodinitronaphthalene), Bravo (chlorothalonil), chloroneb (chloroneb), zarilamid (zariIamid), salicylanilide (salicylanilide), cyazofamid (cyazofamid), pyrocarbonic acid diethyl ester (diethyl pyroca Rbonate), diethofencarb (diethofencarb), ring furoamide (cyclafuramid), double chlorine zarilamid (diclocymet), sclex (dichlozoline), diclobutrazol (diclobutrazol), dichlofluanid (dichlofluanid), cycloheximide (cycloheximide), diclomezin (diclomezine), botran (dicloran), antiphen (dichlorophen), dichlone (dichlone), disulfiram (disulfiram), Plondrel (ditalimfos), dithianon (dithian On), olefin conversion (diniconazole), R- olefin conversion (diniconazole-M), zineb (zineb), dinitrocrotonate (dinocap), dinocton-O (dinocton), nitre monooctyl ester (dinosulfon), dinoterbon (dinoterbon), dinobuton (dinobuton), the pentyl ester that disappears (dinopenton), double pyrrole sulphur(dipyrithione), diphenylamines (diphenylamine), phenyl ether methyl cyclic-azole (difenoconazole), ring fluorine benzyl bacterium amine (cyfIufenamid), fluorine mepanipyrim (difIumetorim), ciproconazole (cyproconazole), cyprodinil (cyprodinil), the phenyl amides based compounds such as cyprofuram (cyprofuram), cypendazole (cypendazole), simeconazoles (simeconazole), dimethirimol (dimethirimol), dimethomorph (dimethomorph), cymoxanil (cymoxanil), dimoxystrobin (dimoxys Trobin), bromomethane (methyl bromide), Fu Meixin (ziram), Silthiopham (silthiofam), streptomysin (streptomycin), volution bacterium amine (spiroxamine), sultropen (sultropen), sedaxane, zoxamide (zoxamide), dazomet (dazomet), milneb (thiadiazin), tiadinil (tiadinil), thiadifluor, probenazole (thiabendazole), tioxymid, thiochlorfenphim, thiophanate (thiophanate), thiophanate-methyl (th Iophanate-methyl), thicyofen (thicyofen), Eradex (thioquinox), chinomethionat (chinomethionat), thifluzamide (thifluzamide), thiram (thiram), decafentin (decafentin), tecnazene (tecnazene), tecloftalam (tecloftalam), thiram joins (tecoram), tetraconazole (tetraconazole), debacarb (debacarb), dehydroactic acid (dehydroacetic acid), Tebuconazole (tebuconazole), tebufloquin, dodicin (dodicin), dodine (dodine), dodecyl benzene sulfonic acid bis ethylene diamine mantoquita (II) (DBEDC), dodemorph (dodemorph), drazoxolon (drazoxolon), Triadimenol (triadimenol), triazolone (triadimefon), butrizol (triazbutil), triazoxide (triazoxide), triamiphos (triamiphos), triarimol (triarimol), trichlamide (trichlamide), tricyclazole (tricyclazole), triticonazole (triticonazole), tridemorph (tridemorph), tributyl Tin oxide (tributyltin oxide), fluorine bacterium azoles (triflumizole), trifloxystrobin (trif1xystrobin), triforine (triforine), Tolylfluanid (tolylfluanid), tolelofos-methyl (tolclofos-methyl), natamycin (natamycin), Dithane A40 (nabam), nitrothalisopropyl (nitrothal-isopropyl), nitrostylene (nitrostyrene), nuarimol (nuarimol), nonyl benzene copper phenolsulfonate (copper nonylphenol sulfonate), halacrinate (halac Rinate), jinggangmeisu (validamycin), valifenalate, super quick albumen (harpin protein), biphenyl pyrrole bacterium amine (bixafen), ZEN 90160 (picoxystrobin), fluopicolide (picobenzamide), Bithionol (bithionol), bitertanol (bitertanol), hydroxyisoxazole (hydroxyisoxazole), hydroxyisoxazole potassium (hydroisoxazole-potassium), binapacryl (binapacryl), biphenyl (biphenyl), disease spends clever (piperalin),Mould spirit (hymexazol), pyraoxystrobin (pyraoxystrobin), pyracarbolin (pyracarbolid), pyraclostrobin (pyraclostrobin), pyrazophos (pyrazophos), azoles amine bacterium ester (pyrametostrobin), pyriofenone, pyridinitril (pyridinitril), pyrifenox (pyrifenox), pyribencarb, pyrimethanil (pyrimethanil), pyroxychlor, chlorine pyrrole furan ether (pyroxyfur), pyroquilon (pyroquilon), vinclozolin (vinclozolin),Cycloheximide triazole (famoxadone), fenapanil (fenapanil), Fenamidone (fenamidone), fenaminosulf (fenaminosulf), Fenarimol (fenarimol), kind clothing ester (fenitropan), fenoxanil (fenoxanil), ferimzone (ferimzone), fervam (ferbam), fentin (fentin), fenpiclonil (fenpiclonil), amine benzene pyrrole bacterium ketone (fenpyrazamine), benzoxazole (fenbuconazole), fenfuram (fenfuram), fenpropidin (fenpropidin), butadiene morpholine (fenpropi Morph), fenhexamid (fenhexamid), Rabcide (phthalide), buthiobate (buthiobate), butylamine (butylamine), bupirimate (bupirimate), furidazol (fuberidazole), blasticidin-S (blasticidin-S), furametpyr (furametpyr), furalaxyl (furalaxyl), fluacrypyrim (fluacrypyrim), fluazinam (fluazinam), fluoxastrobin (fluoxastrobin), fluotrimazole (fluotrimazole), fluopicolide (fluopicolide), fluopyram (fluopyram), fluoromide (fluoroimide), furcarbanil (furcarbanil), fluxapyroxad (fluxapyroxad), Fluquinconazole (fluquinconazole), furconazole (furconazole), furconazole_cis (furconazole-cis), fludioxonil (fludioxonil), Flusilazole (flusilazole), flusulfamide (flusulfamide), flutianil, flutolanil (flutolanil), Flutriafol (flutriafol), furfural (furfural), it dresses seed amine (furmecyclox) , fluorine acyl bacterium amine (flumetover), flumorph (flumorph), the third oxygen quinoline (proquinazid), Prochloraz (prochloraz), procymidone (procymidone), prothiocarb (prothiocarb), prothioconazoles (prothioconazole), Propamocarb (propamocarb), propiconazole (propiconazole), Propineb (propineb), furan first thiophanate (furophanate), probenazole (probenazole), bromuconazole (bromuconazole), hexachlorobutadiene (hexachlorobutadiene), Hexaconazole (hexaconazole), hexamethylene sulphur phosphorus (hexylthiofos), bethoxazin, M 9834 (benalaxyl), smart M 9834 (benalaxyl-M), benodanil (benodanil), benomyl (benomyl), pefurazoate (pefurazoate), benquinox (benquinox), penconazole (penconazole), Benzene (benzamorf), Pencycuron (pencycuron), benzohydroxamic acid (benzohydroxamic acid), third azoles grass is grand (bentaluron), benthiozole (benthiazole), benzene thiophene bacterium Amine ester (benthiavalicarb-isopropyl), pyrrole metsulfovax (penthiopyrad), fluorine azoles bacterium aniline (penflufen), niacinamide (boscalid), phosdiphen (phosdiphen), triethylphosphine acid (fosetyl), phosethyl-Al (fosetyl-Al), Polyoxin (polyoxins), polyoxin (polyoxorim), Polycarbamate (polycarbamate), folpet (folpet), formaldehyde (formaldehyde), machine oil (machine oil), maneb (maneb), Mancozeb (mancozeb), double alkynes acyls Bacterium amine (mandipropamid), myclozolin (myclozolin), nitrile bacterium azoles (myclobutanil), midolthromycin (mildiomycin), milneb (milneb), miaow card disease is western (mecarbinzid), methasulfocarb (methasulfocarb), m-chloro drazoxolon (metazoxolon), metham-sodium (metam), metham-sodium (metam-sodium), metalaxyl (metalaxyl), Metalaxyl-M (metalaxyl-M), Carbatene (metiram), methyl-isorhodanate (methyl isothiocyanate), nitre benzene bacterium ester (mepthyl Dinocap), metconazole (metconazole), metsulfovax (metsulfovax), methuroxam (methfuroxam), SSF 126 (metominostrobin), metrafenone (metrafenone), mepanipyrim (mepanipyrim), Metalaxyl-M (mefenoxam), dinitro crotonates (meptyldinocap), mebenil (mepronil), mebenil (mebenil), iodomethane (iodomethane), pyrrole imidazoles (rabenzazole), benzalkonium chloride (benzalkonium chloride), basic copper chloride (ba Sic copper chloride), basic copper sulfate (basic copper sulfate), the inorganic fungicides such as metallic silver (silver), sodium hypochlorite (sodium hypochlorite), Kocide SD (cupric hydroxide), wettable sulphur (wettable sulfur), lime sulfur (calcium polysulfide), saleratus (potassium hydrogen carbonate), sodium bicarbonate (sodium hydrogen carbonate), inorganic sulfur (sulfur), anhydrous cupric sulfate (copper Sulfate anhydride), organic nickel (nickel dimethyldithiocarbamate), agricultural and the horticultural bactericides such as copper systems compound, zinc sulfate (zinc sulfate), the cupric sulfate pentahydrate (copper sulfate) such as organic copper (oxine copper).
Similarly, as herbicide, such as it can illustrate: 1- naphthaleneacetamide (1-naphthylacetamide), 2,4-PA, 2,3,6-TBA, 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-CPA (4-chlorophenoxyacetic acid), 4-CPB, 4-CPP, MCP, MCPA, 2 first, 4 chlorine thioethyl ester (MCPA-thioethyl), MCPB, MCPB, ioxynil (ioxynil), aclonifen (aclonifen), azoles benzofenap (azafenid In), acifluorfen (acifluorfen), aziprotryn (aziprotryne), azimsulfuron (azimsulfuron), sulphur grass is clever (asulam), Acetochlor (acetochlor), atrazine (atrazine), atraton, dredge grass grand (anisuron), anilofos (anilofos), tetraestrone (aviglycine), S- lures antiacid (abscisic acid), amicarbazone (amicarbazone), amidosulfuron (amidosulfuron), Amrol (amitrole), Ciamexone acid (aminocyclopyrachlor), It is chlorine Fampridine sour (aminopyralid), special careless piperazine ketone (amibuzin), amiprophos-methyl (amiprophos-methyl), special saliva ketone (ametridione), ametryn (ametryn), alachlor (alachlor), allidochlor (allidochlor), alloxydimsodium (alloxydim), pentachloro- oxopentanoic acid (alorac), differentIt is grand (isouron), fourth miaow quinoline ketone (isocarbamid), differentIt is chlorine humulone (isoxachlortole), differentIt is careless ether (isoxapyrifop), differentIt is azoles humulone (isoxaflutole), differentAcyl grass amine (isoxaben), isoprocil (isocil), isonoruron (isonoruron), isoproturon (isoproturon), isopropalin (isopropalin), isopolinate, isomethiozin (isomethiozin), inabenfide (inabenfide), ipazine (ipazine), halobenzene amine azoles (ipfencarbazone), third grass is fixed (iprymidam), imazaquin (imazaquin), AC 263222 (imazapic), imazapyr (imazapyr), imazamethapyr, imazamethabenz, miaow Oxalic acid (imazamethabenz-methyl), methoxy imazethapyr (imazamox), imazethapyr (imazethapyr), pyrazoles Sulfometuron Methyl (imazosulfuron), indaziflam grass amine (indaziflam), indanofan (indanofan), indolebutyric acid (indolebutyric acid), uniconazole P-P (uniconazole-P), Radix Glycyrrhizae saliva (eglinazine), esprocarb (esprocarb), ethametsulfuron (ethametsulfuron), ethametsulfuron (ethametsulfuron-methyl), ethalfluralin (ethal Fluralin), ethiolate (ethiolate), 'Inshuzhi ' (ethychlozate ethyl), ethidimuron (ethidimuron), etinofen (etinofen), ethephon (CEPHA),2-(chloroethyl) phosphonic acid (ethephon), ethoxysulfuron (ethoxysulfuron), ethoxyfenethyl (ethoxyfen), ethamine grass ether (etnipromid), ethofumesate (ethofumesate), ethobenzanid (etobenzanid), triazole sulphur (epronaz), erbon (erbon), endothal (endothal),Humulone (oxadiazon), propineHumulone (oxadiargyl),Metribuzin (oxaziclomefone), oxasulfuron (oxasulfuron), grass rattles away loose (oxapyrazon), Oxyfluorfen (oxyfluorfen), oryzalin (oryzalin), orthosulfamuron (orthosulfamuron), orbencarb (orbencarb), cafenstrole (cafenstrole), kecaoan ester (cambendichlor), kappa grass is clever (carbasulam), azoles humulone (carfentrazone), carfentrazone (carfentrazone-ethyl), karbutilate (karbutilate), carbetamide (carbetami De), specialAzoles prestige (carboxazole), quizalofop-ethyl (quizalofop), Quizalotop-ethyl (quizalofop-P), quizalofop-ethyl (quizalofop-ethyl), xylachlor (xylachlor), quinoclamine (quinoclamine), quinone duckweed amine (quinonamid), dichloro quinolinic acid (quinclorac), quinmerac (quinmerac), cumyluron (cumyluron), iodine chlorine pyridine ester (cliodinate), glyphosate (glyphosate), glufosinate-ammonium (glufosinate), smart glufosinate-ammonium (glufosinate-P), ether grass ether (credazin E), clethodim (clethodim), cloxyfonac (cloxyfonac), free alkynes oxalic acid (clodinafop), alkynes oxalic acid (clodinafop-propargyl), chlortoluron (chlorotoluron), clopyralid (clopyralid), hexamethylene clethodim (cloproxydim), adjust tartaric acid (cloprop), be bromax (chlorbromuron), clofop, differentCareless pine (clomazone), chlomethoxynil (chlomethoxyni1), chlomethoxyfen (chlomethoxyfen), clomeprop (clomeprop), chloroazifoppropynyl (chlorazifop), chlorazine (chlorazine), cloransulammethyl (cloransulam), chloranocryl (chloranocryl), chloramben (chloramben), chloromethyl ester sulphur grass amine (cloransulam-methyl), chloridazon (chloridazon), chlorimuronethyl (chlorimuron), chlorimuronethyl (chlorimuron-ethyl), chlorsulfuron (chlors Ulfuron), chlorthal (chlorthal), chlorthiamide (chlorthiamid), chlortoluron (chlortoluron), Mo 9 granular (chlornitrofen), Fenac (chlorfenac), chlorfenprop, chlorbufam (chlorbufam), chlorflurazole (chlorflurazole), chloroflurenol (chlorflurenol), grass loses dead (chlorprocarb), chlorpropham (chlorpropham), cycocel (chlormequat), ethoxy benzene is grand (chloreturon), chloroxynil (chloroxynil), it is withered Careless grand (chloroxuron), chloropon (chloropon), benzene flumetsulam (saflufenacil), cyanazine (cyanazine), cyanatryn (cyanatryn), Avadex (di-allate), diuron (diuron), diethyl weeding is bis- (diethamquat), dicamba (dicamba), Alipur-O (cycluron), cycloate (cycloate), cycloxydim (cycloxydim), diclosulam (diclosulam), cypromisulfuron (cyclosulfamuron), 2, 4- drop propionic acid (dichlorprop), essence 2, 4- drop propionic acid ( Dichlorprop-P), dichlobenil (dichlobenil), diclofop-methyl (diclofop), diclofop-methyl (diclofop-methyl), dichlormate (dichlormate), dichloral urea (dichloralurea), diquat dibromide (diquat), cisanilide (cisanilide), disul, Tupersan (siduron), dithiopyr (dithiopyr), dinitramine (dinitramine), cinidon-ethyl (cinidon-ethyl), dinosam (dinosam), cinosulfuron (cinosulfuron), dinoseb (dinoseb), dinoterb (dino Terb), ground is happy special (dinofenate), dinoprop (dinoprop), cyhalofop-butyl (cyhalofop-butyl), diphenamide (diphenamid), difenoxuron (difenoxuron), penta taste diclofop-methyl (difenopenten), difenzoquat (difenzoquat), cybutryne, cyprazine (cyprazine), tricyclic matches careless amine (cyprazole), diflufenican (diflufenican), diflufenzopyr (diflufenzopyr), dipropetryn (dipropetryn), cypromid (cypromid), fast (the cyperqua of herbage T), gibberellin (gibberellin), Simanex (simazine), dimexan (dimexano), dimethachlor (dimethachlor), careless pyridazone (dimidazon), isoamyl saliva (dimethametryn), dimethenamid (dimethenamid), symetryne (simetryn), Gesadrual (simeton), dimepiperate (dimepiperate),Azoles is grand (dimefuron), cinmethylin (cinmethylin), swep (swep), a word used for translation sulphur in heptan ester (sulglycapin), sulphur humulone (sulcotrione), sulfallate (sulfallate), sulfentrazone (sulfentrazone), Sulfosulfuron (sulfosulfuron), first ethyl methyl (sulfometuron), sulfometuronmethyl (sulfometuron-methyl), Zhong Dingtong (secbumeton), sethoxydim (sethoxydim), another fourth saliva (sebuthylazine), terbacil (terbacil), daimuron (daimuron) , dazomet (dazomet), Dalapon (dalapon), thiazfluron (thiazafluron), thrizopyr (thiazopyr), thiencarbazone, thiophene ketone sulphur is grand (thiencarbazone-methyl), tiocarbazil (tiocarbazil), phonetic grass amine (tioclorim), benthiocarb (thiobencarb), thiadiazoles grass amine (thidiazimin), Thidiazuron (thidiazuron), thifensulfuron methyl (thifensulfuron), thifensulfuronmethyl (thifensulfuron-methyl), desmedipham (desmedipham), desmetryn (desmetryn), four fluon (tetrafluron), P DimethenamidP (thenylchlor), tebutam (tebutam), tebuthiuron (tebuthiuron), Te Dingtong (terbumeton), tepraloxydim (tepraloxydim), tefuryltrione, tembotrions (tembotrione), delachlor (delachlor), terbacil (terbacil), terbucarb (terbucarb), terbuchlor (terbuchlor), Garagard (terbuthylazine), terbutryn (terbutryn), benzene pyrazoles humulone (topramezon E), tralkoxydim (tralkoxydim), triaziflam (triaziflam), triasulfuron (triasulfuron), tri-allate (tri-allate), trietazine (trietazine), tricamba (tricamba), trichlopyr (triclopyr), tridiphane (tridiphane), tritac (tritac), tritosulfuron (tritosulfuron), triflusulfuronmethyl (triflusulfuron), triflusulfuronmethyl (triflusulfuron-methyl), trefanocide (trifluralin), trifloxysulfuron (trifloxysulf Uron), indenes oxalyl (tripropindan), tribenuron-methyl (tribenuron-methyl), tribenuron-methyl (tribenuron), trifluoromethoxy phenoxy propionic acid (trifop), trifluoro dogstail oxime (trifopsime), trimeturon (trimeturon), quinclorac (naptalam), naproanilide (naproanilide), napropamide (napropamide), nicosulfuron (nicosulfuron), nitralin (nitralin), nitrofen (nitrofen), fluoroform grass ether (nitrofluorfen), nipyralofen (nipyraclofen), neburea (neburon), norflurazon (norflurazon), herban (noruron), oatax (barban), paclobutrazol (paclobutrazol), paraquat (paraquat), to fluon (parafluron), halozydine (haloxydine), haloxyfop-P-methyl (haloxyfop), haloxyfop-r-methyl (haloxyfop-P), haloxyfop-P-methyl (haloxyfop-methyl), fluorine nitre sulfonamide (halosafen), halosulfuronmethyl (halosulfuron), halosulfuronmethyl (halosulfuron-methyl), picloram (piclora M), fluorine pyrrole acyl grass amine (picolinafen), bicyclopyrone, bispyribac-sodium (bispyribac), bispyribac-sodium (bispyribac-sodium), than up to agriculture (pydanon), pinoxaden (pinoxaden), formic acid nitrofen (bifenox), piperophos (piperophos),Mould spirit (hymexazol), pyraclonil (pyraclonil), sulphonyl grass pyrazoles (pyrasulfotole), pyrazoxyfen (pyrazoxyfen), pyrazosulfuron (pyrazosulfuron), pyrazosulfuron (pyrazosulfuron-ethyl), pyrazolate (pyrazolate), bilanafos (bilanafos), pyraflufen-ethyl (pyraflufen-ethyl), phenolate trichloropyridine (pyriclor), pyridafol, pyrithiobac-sodium (pyrithiobac), pyrithiobac-sodium (pyrithiobac-sodium), pyridate (pyridate), ring Ester grass ether (pyriftalid), pyributicarb (pyributicarb), pyribenzoxim (pyribenzoxim), pyrimisulfan, primisulfuronmethyl (primisulfuron), KIH 6127 (pyriminobac-methyl), pyroxasulfone, pyroxsulam (pyroxsulam), acyl benzene sulphur prestige (fenasulam), phenisopham (phenisopham), fenuron (fenuron), fenoxasulfone,Azoles diclofop-methyl (fenoxaprop), essenceAzoles diclofop-methyl (fenoxaprop-P),Azoles diclofop-methyl (fenoxaprop-ethyl), phenothiol (phenothiol), 2, 4, 5- tears propionic acid (fenoprop), phenobenzuron (phenobenzuron), diclofop-methyl thiazole (fenthiaprop), chlorophenoxyethanol (fenteracol), fentrazamide (fentrazamide), phenmedipham (phenmedipham), phenmedipham (phenmedipham-ethyl), butachlor (butachlor), butafenacil (butafenacil), butamifos (butamifos), tebuthiuron (buthiuron), fourth Anthelvet ketone (buthidazo Le), butylate (butylate), buturon (buturon), butenachlor (butenachlor), butroxydim (butroxydim), butralin (butralin), butroxydim (butroxydim), flazasulfuron (flazasulfuron), wheat straw fluorine (flamprop), furyloxyfen (furyloxyfen), prynachlor (prynachlor), primisulfuronmethyl (primisulfuron-methyl), fluazifop (fluazifop), efficient fluazifop (fluazifop-P), fluazifop (fluazifop-butyl) , fluazolate (fluazolate), fluroxypyr (fluroxypyr), fluorine sulphur is grand (fluothiuron), fluometuron (fluometuron), fluoroglycofen-ethyl (fluoroglycofen), fluorochloridone (flurochloridone), trifluoro fluorodifen (fluorodifen), fluoronitrofen (fluoronitrofen), ethofumesate (fluoromidine), flucarbazonesodium (flucarbazone), flucarbazone (flucarbazone-sodium), fluchloraline (fluchloralin), flucetosulfuron (flucetosulfur On), KIH 9201 (fluthiacet), fluthiacet (fluthiacet-methyl), flupyrsulfuron-methyl-sodium (flupyrsulfuron), flufenacet (flufenacet), fluorobenzene pyridine is careless (flufenican), flufenpyrethyl (flufenpyr), flupropacil, tetrafluoro propionic acid (flupropanate), flupoxam (flupoxam), flumioxazin (flumioxazin), Flumiclorac pentyl (flumiclorac) Flumiclorac pentyl (flumiclorac-pentyl), alkynes grass amine (flumipropyn), trifluoroPiperazine (flumezin), fluometuron (fluometuron), Flumetsulam (flumetsulam), fluridone (fluridone), flurtamone (flurtamone), fluroxypyr (fluroxypyr), pretilachlor (pretilachlor), proxan, proglinazine (proglinazine), cyclopropylniitrile saliva (procyazine), prodiamine (prodiamine), first sulphur nitralin (prosulfalin), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), oxalate (propaquizafop), propachlor (pr Opachlor), propazine (propazine), propanil (propanil), alkynes Phenacylamine (propyzamide), propisochlor (propisochlor), jasmone (prohydrojasmon), piperazine imidazoles Sulfometuron Methyl (propyrisulfuron), Chem hoe (propham), profluazol (profluazol), profluralin (profluralin), Prohexadione calcium (prohexadione-calcium), procarbazone (propoxycarbazone), procarbazone (propoxycarbazone-sodium), clefoxidim (pro Foxydim), bromacil (bromacil), bromine grass is quick (brompyrazon), prometryn (prometryn), prometon (prometon), Brominal (bromoxynil), bromofenoxim (bromofenoxim), bromobutide (bromobutide), chaff oxalic acid dinitrile (bromobonil), florasulam (florasulam), hexachloroacetone (hexachloroacetone), hexazinone (hexazinone), pethoxamid (pethoxamid), benazolin (benazolin), penoxsuam (penoxsulam), pebulate (peb Ulate), beflubutamid (beflubutamid), vernolate (vernolate), yellow grass lies prostrate (perfluidone), bencarbazone, benzadox (benzadox), benzyl grass amine (benzipram), benzylaminopurine (benzylaminopurine), benzthiazuron (benzthiazuron), benzfendizone (benzfendizone), bensulide (bensulide), bensulfuron-methyl (bensulfuron-methyl), suffer (benzoylprop), benzobicylon (benzobicyclon), benzofenap (benzofe Nap), fluorine straw colour (benzofluor), bentazone (bentazone), pentanochlor (pentanochlor), benthiocarb (benthiocarb), pendimethalin (pendimethalin), ring pentaHumulone (pentoxazone), benfluralin (benfluralin), benfuresate (benfuresate), creeping weed phosphorus (fosamine), fomesafen (fomesafen), formamido group Sulfometuron Methyl (foramsulfuron), chloropyuril (forchlorfenuron), maleic hydrazide (maleic hydrazide), Vi par (mecoprop), mecopropP (mecoprop-P), medinoterb acetate (medinoterb), mesosulfuron (mesosulfuron), mesosulfuron (mesosulfuron-methyl), mesotrione (me Sotrione), green bristlegrass of going out saliva (mesoprazine), lattice grass net (methoprotryne), metazachlor (metazachlor), methazole (methazole), bis ether halosulfuronmethyl (metazosulfuron), methabenzthiazuron (methabenzthiazuron), metamitron (metamitron),Azole amide (metamifop), metham-sodium (metam), methalpropalin, methiuron (methiuron), thiamazole (methiozolin), first sulphur benzene prestige (methiobencarb), methyldymron (methyldymron), metoxuron (metoxuron), metosulam (metosulam), metsulfuron-methyl (metsulfuron), metsulfuron-methyl (metsulfuron-methyl), fluorine rattles away careless (metflurazon), metobromuron (metobromuron), metobenzuron (metobenzuron), methometon (methometon) , isopropyl methoxalamine (metolachlor), metribuzin (metribuzin), first piperazine(mepiquat-chloride), mefenacet (mefenacet), mefluidide (mefluidide), monalide (monalide), monisouron, telvar (monuron), monochloroacetic acid (monochloroacetic acid), afesin (monolinuron), molinate (molinate), Ceroxone (morfamquat), iodine sulphur is grand (iodosulfuron), iodosulfuron-methyl-sodium (iodosulfuron-methyl-sodium), iodine oxalic acid dinitrile (iodobonil), iodomethane (iodomethan E), the herbicides such as lactofen (lactofen), linuron (linuron), rimsulfuron (rimsulfuron), lenacil (lenacil), rodethanii (rhodethanil), calper calcium peroxide (calcium peroxide), bromomethane (methylbromide).
In addition, as biological pesticide, such as by with nuclear polyhedrosis virus (Nuclear polyhedrosis virus, NPV), PuGV (Granulosis virus, GV), cytoplasmic polyhedrosis virus (Cytoplasmic polyhedrosis virus, CPV), entomopoxvirus (EntomopoXI virus, the virus formulations such as EPV), tumor catches genus monacrosporium (Monacrosporium phymatophagum), nematode Steinernema carpocapsae (Steinernema carpocapsae), entomiasis prototype Steinernema Carpocapsae (Steinernema kushid Ai), puncture the microbial pesticide that pasteurellaceae bud bacterium (Pasteuria penetrans) etc. is used as desinsection or nematicide, Trichoderma lignorum (Trichoderma lignorum), radioactivity Agrobacterium (Agrobacterium radiobactor), the carrot soft rot Erwinia (Erwinia carotovora) of avirulence, bacillus subtilis (Bacillus subtilis) etc. is used as the microbial pesticide of fungicide, the biological pesticide etc. that xanthomonas campestris (Xanthomonas campestris) etc. is used as herbicide is used in mixed way, it can be expected that same effect.
In turn, as biological pesticide, such as it can also be with the even whip aphid chalcid fly of aleyrodid (Encarsia formosa), Ke Liemaa Bradley chalcid fly (Aphidius colemani), it eats aphid cecidomyiia (Aphidoletes aphidimyza), Diglyphus isaea (Diglyphus isaea), Dacnusa sibirica (Dacnusa sibirica), Phyloseiulus nersimilis (Phytoseiulus persimilis), Amblyseius cucumeris (Amblyseius cucumeris), the natural enemies such as mulberry minute pirate bugs (Orius sauteri) biology, muscardine (Beauveria bro Ngniartii) microbial pesticides, acetic acid (Z)-10- tetradecene ester, acetic acid (E such as, Z) pheromones such as-4,10- tetradecadiene ester, acetic acid (Z)-8- laurylene ester, acetic acid (Z)-11- tetradecene ester, (Z)-13- icosa alkene-10- ketone, 14- methyl-1-octadecylene are used in combination.
In the following, showing the embodiment about the preparation embodiment of the compounds of this invention and the preparation of insecticide of the present invention and insecticidal effect, but the present invention is not limited to these embodiments.
[embodiment]
Embodiment 1-1
[chemical formula 26]
1,2- phenylenediamine 10g, seven fluoro- 2- iodopropane 32.7g, sodium carbonate 14.6g and 4-butyl ammonium hydrogen sulfate 1g are added sequentially in the mixed liquor of ethyl acetate 100ml and water 100ml.Under stirring at room temperature, sodium dithionite 16g was successively added through 30 minutes on a small quantity.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 4- hepta-fluoroiso-propyl -1,2- phenylenediamine 24.3g.
1H-NMR(CDCl3, ppm): 3.46 (2H, brs), 3.61 (2H, brs), 6.74 (1H, d), 6.91 (1H, d), 6.95 (1H, s)
Embodiment 1-2
[chemical formula 27]
4- hepta-fluoroiso-propyl -1,2- phenylenediamine 2.76g is dissolved in trifluoroacetic acid 5ml, is reacted within 3 hours being heated to reflux lower progress.After reaction, excessive trifluoroacetic acid is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 3.1g.Physical property: m.p.132-133 DEG C.
Embodiment 1-3
[chemical formula 28]
5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 2.12g and 3- methyl -4- nitrobenzyl bromide 1.38g is dissolved in acetonitrile 20ml, potassium carbonate 1.25g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, it is refined residue obtained with silica gel column chromatography, thus obtains 5- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- Trifluoromethyl-1 H- benzimidazole 1.5g (physical property: m.p.95 DEG C) and 6- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- Trifluoromethyl-1 H- benzimidazole 0.9g (physical property: m.p.96 DEG C).
Embodiment 1-4
[chemical formula 29]
5- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- Trifluoromethyl-1 H- benzimidazole 1.0g is dissolved in ethyl alcohol 20ml, ammonium chloride 0.53g, iron powder 0.56g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 0.94g.
1H-NMR(CDCl3, ppm): 2.03 (3H, s), 3.62 (2H, brs), 5.41 (2H, s), 6.62 (1H, d), 6.86 (1H, d), 6.90 (1H, s), 7.43 (1H, d), 7.55 (1H, d), 8.19 (1H, s)
[chemical formula 30]
Similarly, 1- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 0.84g is obtained by 6- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- Trifluoromethyl-1 H- benzimidazole 0.9g.
1H-NMR(CDCl3, ppm): 2.10 (3H, s), 3.66 (2H, brs), 5.43 (2H, s), 6.61 (1H, d), 6.86 (1H, d), 6.90 (1H, s), 7.57 (1H, d), 7.62 (1H, s), 7.99 (1H, d)
Embodiment 1-5. (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.1-289) and (S)-N1{ 4- [(6- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.1-146)
[chemical formula 31]
The 1- prepared in embodiment 1-4 (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 0.71g and the iodo- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.60g are dissolved in acetonitrile 5ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.1-289) 1.08g.
1H-NMR(CDCl3, ppm): 1.26 (3H, d), 1.94 (3H, s), 2.28 (3H, s), 2.56 (2H, m), 4.31 (1H, m), 5.52 (2H, s), 6.07 (1H, d), 6.98 (1H, s), 7.03 (1H, d), 7.22 (1H, t), 7.40 (1H, d), 7.58 (1H, d), 7.80 (1H, d), 7.97 (1H, d), 8.18 (1H, d), 8.22 (1H, s), 8.31 (1H, s)
[chemical formula 32]
Similarly, (S)-N is obtained by 1- (4- amino -3- the methylbenzyl) -6- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole 0.71g prepared in embodiment 1-41{ 4- [(6- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.1-146) 0.70g.
1H-NMR(CDCl3, ppm): 1.22 (3H, d), 1.92 (3H, s), 2.26 (3H, s), 2.57 (2H, m), 4.29 (1H, m), 5.53 (2H, s), 6.16 (1H, d), 6.97 (1H, s), 7.01 (1H, d), 7.20 (1H, t), 7.59-7.64 (2H, m), 7.78 (1H, d), 7.96 (1H, d), 8.03 (1H, d), 8.17 (1H, d), 8.31 (1H, s)
Embodiment 2. (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.1-290), and
(S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.1-291)
[chemical formula 33]
By (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.83g is dissolved in chloroform 5ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.35g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.1-290) 0.4g and (S)-N1{ 4- [(5- hepta-fluoroiso-propyl -2- Trifluoromethyl-1 H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl } iodo- N of -3-2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.1-291) 0.4g.
(compound N is o.1-290)1H-NMR(CDCl3, ppm): 1.32 (3H, d), 2.18 (3H, s), 2.24 (3H, s), 2.78 (2H, m), 4.35 (1H, m), 5.52 (2H, s), 6.97 (1H, s), 6.99 (1H, d), 7.13 (1H, t), 7.45 (1H, d), 7.60 (2H, d), 7.77 (1H, d), 7.89 (1H, d), 8.03 (1H, d), 8.23 (1H, s), 8.43 (1H, s)
(compound N is o.1-291)1H-NMR(CDCl3, ppm): 1.44 (3H, d), 2.23 (3H, s), 2.71 (3H, s), 3.22 (2H, m), 4.52 (1H, m), 5.51 (2H, s), 6.90 (1H, d), 6.95-6.98 (2H, m), 7.12 (1H, t), 7.45 (1H, d), 7.60-7.63 (2H, m), 7.88 (2H, d), 8.19 (1H, s), 8.23 (1H, s)
Embodiment 3-1.
[chemical formula 34]
4- hepta-fluoroiso-propyl -1, the 2- phenylenediamine 2.76g synthesized according to the preparation method of embodiment 1-1 is dissolved in the mixed liquor of acetic acid 10ml and water 3ml, the water 2ml solution of sodium nitrite 0.76g is added dropwise under ice-cold stirring.After completion of dropwise addition, after being warming up to 80 DEG C and stirring 1 hour, ice water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 5- hepta-fluoroiso-propyl -1H- benzotriazole 2.3g.Physical property: m.p.151-152 DEG C.
Embodiment 3-2.
[chemical formula 35]
5- hepta-fluoroiso-propyl -1H- benzotriazole 1.3g and 3- methyl -4- nitrobenzyl bromide the 1.04g synthesized according to the preparation method of embodiment 3-1 is dissolved in acetonitrile 20ml, potassium carbonate 0.7g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, it is refined residue obtained with silica gel column chromatography, thus obtains 5- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -1H- benzotriazole 0.62g (physical property: m.p.80-81 DEG C), 6- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -1H- benzotriazole 0.59g (physical property: m.p.55-58 DEG C) and 5- hepta-fluoroiso-propyl -2- (3- methyl -4- nitrobenzyl) -2H- benzotriazole 0.32g (NMR data).
1H-NMR(CDCl3, ppm): 2.61 (3H, s), 5.94 (2H, s), 7.40 (1H, d), 7.41 (1H, s), 7.60 (1H, d), 7.96 (1H, d), 7.97 (1H, d), 8.24 (1H, s)
Embodiment 3-3.
[chemical formula 36]
5- hepta-fluoroiso-propyl-the 1- synthesized according to the preparation method of embodiment 3-2 (3- methyl -4- nitrobenzyl) -1H- benzotriazole 0.62g is dissolved in ethyl alcohol 12ml, ammonium chloride 0.37g, iron powder 0.38g and water 6ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -1H- benzotriazole 0.57g.
1H-NMR(CDCl3, ppm): 2.15 (3H, s), 3.66 (2H, brs), 5.73 (2H, s), 6.63 (1H, d), 7.09 (1H, d), 7.20 (1H, s), 7.45 (1H, d), 7.91 (1H, d), 8.20 (1H, s)
The chloro- N of embodiment 3-4. (S) -3-1{ 4- [(5- hepta-fluoroiso-propyl -1H- benzotriazole -1- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.5-10)
[chemical formula 37]
The 1- synthesized according to the preparation method of embodiment 3-3 (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -1H- benzotriazole 0.53g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.39g are dissolved in acetonitrile 5ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(5- hepta-fluoroiso-propyl -1H- benzotriazole -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.5-10) 0.72g.Physical property: m.p.127-129 DEG C.
Embodiment 4-1.
[chemical formula 38]
4- hepta-fluoroiso-propyl -2-aminotoluene the 2.0g recorded in Japanese Unexamined Patent Publication 2001-122836 is dissolved in acetic acid 8ml, sodium nitrite 0.6g is added, carries out diel reaction under stirring at room temperature.After reaction, it is neutralized, is extracted with ethyl acetate with saturated sodium bicarbonate aqueous solution.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 5- hepta-fluoroiso-propyl -1H- indazole 1.1g.Physical property: m.p.129-130 DEG C.
Embodiment 4-2.
[chemical formula 39]
5- hepta-fluoroiso-propyl -1H- indazole 0.86g and 3- methyl -4- nitrobenzyl bromide the 0.76g prepared in embodiment 4-1 is dissolved in acetonitrile 20ml, potassium carbonate 0.82g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 5- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -1H- indazole 0.98g.
1H-NMR(CDCl3, ppm): 2.57 (3H, s), 5.66 (2H, s), 7.15 (1H, d), 7.20 (1H, s), 7.44 (1H, d), 7.58 (1H, d), 7.93 (1H, d), 8.09 (1H, s), 8.18 (1H, s)
Embodiment 4-3.
[chemical formula 40]
5- hepta-fluoroiso-propyl-the 1- prepared in embodiment 4-2 (3- methyl -4- nitrobenzyl) -1H- indazole 0.98g is dissolved in ethyl alcohol 20ml, ammonium chloride 0.53g, iron powder 0.56g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -1H- indazole 0.91g.
1H-NMR(CDCl3, ppm): 2.11 (3H, s), 3.61 (2H, brs), 5.48 (2H, s), 6.61 (1H, d), 6.97 (1H, d), 7.00 (1H, s), 7.47 (1H, d), 7.51 (1H, d), 8.02 (1H, s), 8.11 (1H, s)
The chloro- N of embodiment 4-4. (S) -3-1{ 4- [(5- hepta-fluoroiso-propyl -1H- indazole -1- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.6-1)
[chemical formula 41]
The 1- prepared in embodiment 4-3 (4- amino -3- methylbenzyl) -5- hepta-fluoroiso-propyl -1H- indazole 0.91g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.67g are dissolved in acetonitrile 5ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(5- hepta-fluoroiso-propyl -1H- indazole -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.6-1) 1.28g.Physical property: m.p.100 DEG C.
Embodiment 5-1.
[chemical formula 42]
The chloro- 1H- indoles 0.99g and 3- methyl -4- nitrobenzyl bromide 1.50g of 5- is dissolved in DMF10ml, potassium carbonate 1.08g is added, carries out reacting for 3 hours at 60 DEG C.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- 1- of 5- (3- methyl -4- nitrobenzyl) -1H- indoles 1.5g.
Embodiment 5-2.
[chemical formula 43]
The chloro- 1- of 5- (3- methyl -4- nitrobenzyl) -1H- indoles 1.2g is dissolved in ethyl alcohol 20ml, ammonium chloride 1.07g, iron powder 1.12g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) chloro- 1H- indoles 1.1g of -5-.
Embodiment 5-3.
[chemical formula 44]
1- (4- amino -3- methylbenzyl) -5- chloro- 1H- indoles 1.1g and phthalic anhydride 0.6g is dissolved in acetic acid 10ml, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 2- { 4- [(the chloro- 1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl } isoindoline -1,3- diketone 1.6g.
Embodiment 5-4.
[chemical formula 45]
2- { 4- [(the chloro- 1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl } isoindoline -1,3- diketone 1.6g, seven fluoro- 2- iodopropane 1.4g, sodium carbonate 0.64g and 4-butyl ammonium hydrogen sulfate 0.05g is added sequentially in the mixed liquor of propionitrile 30ml and water 30ml.It is a small amount of successively through 30 minutes addition sodium dithionite 0.84g under stirring at room temperature.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 2- { 4- [(the chloro- 3- hepta-fluoroiso-propyl -1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl } isoindoline -1,3- diketone 1.6g.Physical property: m.p.196-198 DEG C.
Embodiment 5-5.
[chemical formula 46]
2- { 4- [(the chloro- 3- hepta-fluoroiso-propyl -1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl } isoindoline -1,3- diketone 1.25g is dissolved in ethyl alcohol 20ml, hydrazine hydrate 0.33g is added, is reacted within 3 hours being heated to reflux lower progress.After letting cool, it is filtered to remove insoluble matter, solvent is distilled off under reduced pressure.It is dissolved in ether by residue obtained, insoluble matter is removed again, solvent is distilled off, obtains 1- (4- amino -3- methylbenzyl) chloro- 3- hepta-fluoroiso-propyl -1H- indoles 0.96g of -5-.
1H-NMR(CDCl3, ppm): 2.13 (3H, s), 3.62 (2H, brs), 5.18 (2H, s), 6.62 (1H, d), 6.80 (1H, d), 6.83 (1H, s), 7.19 (1H, d), 7.27 (1H, d), 7.34 (1H, s), 7.42 (1H, s)
The chloro- N of embodiment 5-6. (S) -3-1{ 4- [(the chloro- 3- hepta-fluoroiso-propyl -1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.7-10)
[chemical formula 47]
The 1- synthesized according to the preparation method of embodiment 5-5 (4- amino -3- methylbenzyl) the chloro- 3- hepta-fluoroiso-propyl -1H- indoles 0.31g of -5- and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.23g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(the chloro- 3- hepta-fluoroiso-propyl -1H- indoles -1- base of 5-) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.7-10) 0.43g.Physical property: m.p.144-146 DEG C.
Embodiment 6-1.
[chemical formula 48]
2,5- difluoro nitrobenzene 9.55g is dissolved in DMF60ml, cyclopropylamine 3.4g and potassium carbonate 12.4g is added.After being stirred 3 hours at 60 DEG C, ice water is added, is extracted with ethyl acetate.Organic layer is successively washed with saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the fluoro- 2- nitroaniline 11.0g of N- cyclopropyl -4-.
Embodiment 6-2.
[chemical formula 49]
The fluoro- 2- nitroaniline 11.0g of N- cyclopropyl -4- obtained in embodiment 6-1 is dissolved in ethyl alcohol 200ml, ammonium chloride 15.0g, iron powder 15.6g and water 100ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains N1The fluoro- 1,2- phenylenediamine 9.2g of cyclopropyl -4-.
Embodiment 6-3.
[chemical formula 50]
By N obtained in embodiment 6-21The fluoro- 1,2- phenylenediamine 9.2 of cyclopropyl -4-g, seven fluoro- 2- iodopropane 20.0g, sodium carbonate 8.7g and 4-butyl ammonium hydrogen sulfate 0.5g be added sequentially in the mixed liquor of ethyl acetate 100ml and water 100ml.It is a small amount of successively through 30 minutes addition sodium dithionite 11.5g under stirring at room temperature.After addition, it is stirred at room temperature 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains N1The fluoro- 5- hepta-fluoroiso-propyl -1,2- phenylenediamine 12.8g of cyclopropyl -4-.
1H-NMR(CDCl3, ppm): 0.51 (2H, m), 0.77 (2H, m), 2.45 (1H, m), 3.59 (1H, brs), 3.65 (2H, brs), 6.48 (2H, d), 7.13 (1H, d)
Embodiment 6-4.
[chemical formula 51]
By N obtained in embodiment 6-31Fluoro- 5- hepta-fluoroiso-propyl -1, the 2- phenylenediamine 2.6g of cyclopropyl -4- is dissolved in THF10ml, and 1,1'- carbonyl dimidazoles 2.5g is added, and reacts within 2 hours being heated to reflux lower progress.After reaction, ice water is added, is extracted with ethyl acetate.Organic layer is successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 1- cyclopropyl -5- fluoro- 6- (hepta-fluoroiso-propyl) Benzimidazolinone 2.5g.
1H-NMR(CDCl3, ppm): 1.05 (2H, m), 1.20 (2H, m), 2.92 (1H, m), 6.98 (2H, d), 7.34 (1H, d), 10.15 (1H, brs)
Embodiment 6-5.
[chemical formula 52]
1- cyclopropyl -5- fluoro- 6- (hepta-fluoroiso-propyl) Benzimidazolinone 0.72g and 3- methyl -4- nitrobenzyl bromide 0.55g obtained in embodiment 6-4 is dissolved in acetonitrile 10ml, potassium carbonate 0.41g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the fluoro- 5- hepta-fluoroiso-propyl -1- of 3- cyclopropyl -6- (3- methyl -4- nitrobenzyl) -2- oxo -2,3- dihydro -1H- benzimidazole 0.90g.
1H-NMR(CDCl3, ppm): 1.06 (2H, m), 1.19 (2H, m), 2.62 (3H, s), 2.95 (1H, m), 5.08 (2H, s), 6.69 (1H, d), 7.26 (1H, d), 7.29 (1H, s), 7.36 (1H, d), 7.98 (1H, d)
Embodiment 6-6.
[chemical formula 53]
By the fluoro- 5- hepta-fluoroiso-propyl -1- of 3- cyclopropyl -6- obtained in embodiment 6-5 (3- methyl -4- nitrobenzyl) -2- oxo -2,3- dihydro -1H- benzimidazole 0.90g is dissolved in ethyl alcohol 20ml, ammonium chloride 0.53g, iron powder 0.56g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 3- cyclopropyl -1- (4- amino -3- methylbenzyl) fluoro- 5- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole 0.84g of -6-.
1H-NMR(CDCl3, ppm): 1.04 (2H, m), 1.17 (2H, m), 2.16 (3H, s), 2.95 (1H, m), 3.65 (2H, brs), 4.94 (2H, s), 6.61 (1H, d), 6.64 (1H, d), 6.98 (1H, d), 7.02 (1H, s), 7.26 (1H, d)
The chloro- N of embodiment 6-7. (S) -3-1{ 4- [(the fluoro- 5- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- base of 3- cyclopropyl -6-) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.8-136)
[chemical formula 54]
By 3- cyclopropyl -1- obtained in embodiment 6-6 (4- amino -3- methylbenzyl) the fluoro- 5- hepta-fluoroiso-propyl -2- oxo -2 of -6-, 3- dihydro -1H- benzimidazole 0.50g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.34g are dissolved in acetonitrile 5ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(the fluoro- 5- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- base of 3- cyclopropyl -6-) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.8-136) 0.67g.Physical property: m.p.116-118 DEG C.
Embodiment 7-1.
[chemical formula 55]
4- hepta-fluoroiso-propyl -1, the 2- phenylenediamine 20.8g synthesized according to the preparation method of embodiment 1-1 is dissolved in THF150ml, 1,1'- carbonyl dimidazoles 24.5g is added, is reacted within 2 hours being heated to reflux lower progress.After reaction, ice water is added, is extracted with ethyl acetate.Organic layer is successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is recrystallized residue obtained using ethyl acetate, thus obtains 5- (hepta-fluoroiso-propyl) Benzimidazolinone 10.4g.Physical property: m.p.258-259 DEG C.
Embodiment 7-2.
[chemical formula 56]
(hepta-fluoroiso-propyl) Benzimidazolinone of 5- obtained in embodiment 7-1 9.4g is dissolved in DMA80ml, 60% sodium hydride 1.36g is added under stirring at room temperature.After stirring 1 hour, the DMA80ml solution of di-tert-butyl dicarbonate 6.78g is added dropwise.After futher stirring 1 hour, ice water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, it is refined residue obtained with silica gel column chromatography, thus 5- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- t-butyl formate 3.0g and 6- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- t-butyl formate 6.9g is obtained.
1H-NMR(CDCl3, ppm): 1.71 (9H, s), 7.29 (2H, d), 7.46 (1H, d), 8.04 (1H, s), 10.62 (1H, s)
Embodiment 7-3.
[chemical formula 57]
5- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- t-butyl formate 4.1g obtained in embodiment 7-2 is dissolved in DMA50ml, 60% sodium hydride 0.44g is added under stirring at room temperature.After stirring 1 hour, 3- methyl -4- nitrobenzyl bromide 2.34g is added.After futher stirring 1 hour, ice water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is dissolved in acetonitrile 20ml for residue obtained, trifluoroacetic acid 15ml is added, is reacted within 2 hours being heated to reflux lower progress.After reaction, solvent is distilled off under reduced pressure, ice water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- oxo -2,3- dihydro -1H- benzimidazole 2.5g.
1H-NMR(CDCl3, ppm): 2.51 (3H, s), 5.20 (2H, s), 7.19 (1H, s), 7.29-7.36 (3H, m), 7.48 (1H, s), 7.96 (1H, d), 11.36 (1H, s)
Embodiment 7-4.
[chemical formula 58]
By 6- hepta-fluoroiso-propyl -1- obtained in embodiment 7-3 (3- methyl -4- nitrobenzyl) -2- oxo -2,3- dihydro -1H- benzimidazole 0.9g is dissolved in acetonitrile 10ml, dimethylcarbamyl chloride 0.32g and potassium carbonate 0.69g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 1- formyl-dimethylamino -5- hepta-fluoroiso-propyl -3- (3- methyl -4- nitrobenzyl) -2- oxo -2,3- dihydro -1H- benzimidazole 0.94g.
1H-NMR(CDCl3, ppm): 2.60 (3H, s), 5.09 (2H, s), 6.94 (1H, d), 7.29 (1H, d), 7.30 (1H, s), 7.36 (1H, d), 7.64 (1H, s), 7.97 (1H, d)
Embodiment 7-5.
[chemical formula 59]
By 1- formyl-dimethylamino -5- hepta-fluoroiso-propyl -3- obtained in embodiment 7-4 (3- methyl -4- nitrobenzyl) -2- oxo -2; 3- dihydro -1H- benzimidazole 0.90g is dissolved in ethyl alcohol 20ml; ammonium chloride 0.46g, iron powder 0.48g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -3- formyl-dimethylamino -6- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole 0.85g.
1H-NMR(CDCl3, ppm): 2.14 (3H, s), 3.18 (6H, brd), 3.63 (2H, brs), 4.92 (2H, s), 6.62 (1H, d), 7.01-7.05 (3H, m), 7.31 (1H, d), 7.58 (1H, s)
The chloro- N of embodiment 7-6. (S) -3-1{ 4- [(3- formyl-dimethylamino -6- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.8-266)
[chemical formula 60]
By 3- obtained in embodiment 7-5 (4- amino -3- methylbenzyl) -1- formyl-dimethylamino -6- hepta-fluoroiso-propyl -2- oxo -2; 3- dihydro -1H- benzimidazole 0.5g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.32g are dissolved in acetonitrile 3ml; trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(3- formyl-dimethylamino -6- hepta-fluoroiso-propyl -2- oxo -2,3- dihydro -1H- benzimidazole -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.8-266) 0.66g.Physical property: m.p.149-150 DEG C.
Embodiment 8-1.
[chemical formula 61]
Ortho-Aminophenol 6.0g, seven fluoro- 2- iodopropane 19.5g, sodium carbonate 9.2g and 4-butyl ammonium hydrogen sulfate 0.5g are added sequentially in the mixed liquor of ethyl acetate 50ml and water 50ml.It is a small amount of successively through 30 minutes addition sodium dithionite 11.5g under stirring at room temperature.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 5- hepta-fluoroiso-propyl-Ortho-Aminophenol 12.0g.Physical property: m.p.151-152 DEG C.
Embodiment 8-2.
[chemical formula 62]
The hepta-fluoroiso-propyl of 5- obtained in embodiment 8-1-Ortho-Aminophenol 1.66g is dissolved in acetonitrile 20ml, chlorine ethyl carbonate 0.72g and potassium carbonate 0.5g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -2- benzoOxazoline ketone 1.5g.Physical property: m.p.152-153 DEG C.
Embodiment 8-3.
[chemical formula 63]
By 6- hepta-fluoroiso-propyl -2- benzo obtained in embodiment 8-2Oxazoline ketone 0.85g and 2- methyl-3-nitro benzyl chloride 0.57g is dissolved in acetonitrile 20ml, and potassium carbonate 0.58g is added, and reacts within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- (2- methyl-3-nitro benzyl) -2- benzoOxazoline ketone 1.1g.Physical property: m.p.126-128 DEG C.
Embodiment 8-4.
[chemical formula 64]
By 6- hepta-fluoroiso-propyl -3- obtained in embodiment 8-3 (2- methyl-3-nitro benzyl) -2- benzoOxazoline ketone 0.90g is dissolved in ethyl alcohol 20ml, and ammonium chloride 0.56g, iron powder 0.53g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 3- (3- amino-2-methyl benzyl) -6- hepta-fluoroiso-propyl -2- benzoOxazoline ketone 0.84g.Physical property: m.p.162-164 DEG C.
The chloro- N of embodiment 8-5. (S) -3-1{ 3- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzoAzoles -3- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.11-22)
[chemical formula 65]
By 3- obtained in embodiment 8-4 (3- amino-2-methyl benzyl) -6- hepta-fluoroiso-propyl -2- benzoThe oxazoline ketone 0.26g and chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.20g is dissolved in acetonitrile 3ml, and trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 3- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzoAzoles -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.11-22) 0.39g.
m.p.134-138℃。
Embodiment 9-1.
[chemical formula 66]
2- fluoro- 4- (hepta-fluoroiso-propyl) aniline 1.40g, potassium iso-propyl xanthate 1.92g are carried out to react within 3 hours at 100 DEG C in DMF10ml.After reaction, it after acidity is made in solution by addition 1N aqueous hydrochloric acid solution, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 6- hepta-fluoroiso-propyl -2-mercaptobenzothiazole 1.5g.Physical property: m.p.126-128 DEG C.
Embodiment 9-2.
[chemical formula 67]
The hepta-fluoroiso-propyl of 6- obtained in embodiment 9-1-2-mercaptobenzothiazole 0.70g and potassium hydroxide 0.22g are dissolved in water 5ml, 35% aqueous hydrogen peroxide solution 0.70g is added, carries out reacting for 3 hours at 50 DEG C.After reaction, it after acidity is made in solution by addition 1N aqueous hydrochloric acid solution, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains the crude object 0.60g of 6- hepta-fluoroiso-propyl -2-[4-morpholinodithio quinoline ketone.
Embodiment 9-3.
[chemical formula 68]
The hepta-fluoroiso-propyl of 6- obtained in embodiment 9-2-2-[4-morpholinodithio quinoline ketone 0.32g and 3- methyl-4- nitrobenzyl bromide 0.25g is dissolved in acetonitrile 10ml, potassium carbonate 0.21g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- (3- methyl -4- nitrobenzyl) -2-[4-morpholinodithio quinoline ketone 0.41g.
1H-NMR(CDCl3, ppm): 2.60 (3H, s), 5.20 (2H, s), 7.01 (1H, d), 7.26-7.27 (2H, m), 7.49 (1H, d), 7.72 (1H, s), 7.97 (1H, d)
Embodiment 9-4.
[chemical formula 69]
6- hepta-fluoroiso-propyl -3- obtained in embodiment 9-3 (3- methyl -4- nitrobenzyl) -2-[4-morpholinodithio quinoline ketone 0.37g is dissolved in ethyl alcohol 15ml, ammonium chloride 0.21g, iron powder 0.22g and water 8ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 3- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -2-[4-morpholinodithio quinoline ketone 0.34g.
1H-NMR(CDCl3, ppm): 2.14 (3H, s), 3.64 (2H, brs), 5.03 (2H, s), 6.62 (1H, d), 7.02 (1H, d), 7.04 (1H, s), 7.14 (1H, d), 7.45 (1H, d), 7.64 (1H, s)
The chloro- N of embodiment 9-5. (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.12-8) and the chloro- N of (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.12-9)
[chemical formula 70]
(4- amino -3- the methylbenzyl) -6- hepta-fluoroiso-propyl -2-[4-morpholinodithio quinoline ketone 0.26g of 3- obtained in embodiment 9-4 and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.20g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.12-7) 0.36g.
m.p.142-144℃。
1H-NMR(CDCl3, ppm): 1.23 (3H, d), 1.92 (3H, s), 2.30 (3H, s), 2.57 (2H, m), 4.35 (1H, m), 5.12 (2H, s), 6.10 (1H, d), 7.08 (1H, d), 7.15 (1H, s), 7.18 (1H, d), 7.44-7.47 (2H, m), 7.55 (1H, d), 7.67 (1H, s), 7.75 (1H, d), 8.08 (1H, d), 8.35 (1H, s)
[chemical formula 71]
By the chloro- N of (S) -3- obtained in above-described embodiment1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.20g is dissolved in chloroform 3ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.09g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.12-8) the 0.1g and chloro- N of (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -2H- benzothiazole -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.12-9) 0.1g.
M.p.163-165 DEG C of (compound N is o.12-8).1H-NMR(CDCl3, ppm): 1.36 (3H, d), 2.26 (3H, s), 2.27 (3H, s), 2.81 (2H, m), 4.46 (1H, m), 5.12 (2H, s), 7.09 (1H, s), 7.14-7.20 (3H, m), 7.42 (1H, t), 7.47 (1H, d), 7.52 (1H, d), 7.62 (1H, d), 7.69 (1H, s), 7.99 (1H, d), 8.31 (1H, s)
M.p.128-130 DEG C of (compound N is o.12-9).1H-NMR(CDCl3, ppm): 1.47 (3H, d), 2.28 (3H, s), 2.76 (3H, s), 3.24 (2H, m), 4.59 (1H, m), 5.12 (2H, s), 6.64 (1H, d), 7.10 (1H, d), 7.16 (1H, s), 7.17 (1H, d), 7.43 (1H, t), 7.49 (1H, d), 7.53 (1H, d), 7.61 (1H, d), 7.69 (1H, s), 7.93 (1H, d), 8.03 (1H, s)
Embodiment 10-1.
[chemical formula 72]
2- chloromethyl -4- hepta-fluoroiso-propyl phenylcarbamate 1.8g is dissolved in ethyl alcohol 40ml, 2- methoxyethyl amine 0.72g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, solvent is distilled off under reduced pressure, to residue obtained middle addition water, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, makes residue obtained crystallization with ethylacetate-hexane mixed solvent, thus obtains 6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -3,4- dihydro -1H- quinazoline -2- ketone 1.05g.Physical property: m.p.89-90 DEG C.
Embodiment 10-2.
[chemical formula 73]
3- obtained in embodiment 10-1 (2- methoxy ethyl) -6- hepta-fluoroiso-propyl -3,4- dihydro -1H- quinazoline -2- ketone 0.95g is dissolved in monochlorobenzene 3ml, 60% sodium hydride 0.07g, DMA0.26g is added, is stirred at room temperature 30 minutes.3- methyl -4- nitrobenzyl bromide 0.64g is added, is stirred at room temperature 3 hours.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -1- (3- methyl -4- nitrobenzyl) -3,4- dihydro -1H- quinazoline -2- ketone 0.89g.
1H-NMR(CDCl3, ppm): 2.58 (3H, s), 3.39 (3H, s), 3.69 (4H, s), 4.68 (2H, s), 5.14 (2H, s), 6,65 (1H, d), 7.20 (2H, m), 7.29 (1H, s), 7.33 (1H, s), 7.95 (1H, d)
Embodiment 10-3.
[chemical formula 74]
By 6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -1- (3- methyl -4- nitrobenzyl) -3 obtained in embodiment 10-2,4- dihydro -1H- quinazoline -2- ketone 0.81g is dissolved in ethyl alcohol 20ml, ammonium chloride 0.42g, iron powder 0.43g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -3,4- dihydro -1H- quinazoline -2- ketone 0.49g.
1H-NMR(CDCl3, ppm): 2.13 (3H, s), 3.39 (3H, m), 3.56 (2H, brs), 3.68 (4H, s), 4.63 (2H, s), 4.99 (2H, s), 6,61 (1H, d), 6.87 (1H, d), 6.93 (1H, d), 6.97 (1H, s), 7.23 (1H, s), 7.30 (1H, d)
The chloro- N of embodiment 10-4. (S) -3-1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.18-98) and the chloro- N of (S) -3-1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.18-99)
[chemical formula 75]
By 1- obtained in embodiment 10-3 (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -3,4- dihydro -1H- quinazoline -2- ketone 0.39g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.21g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.18-97) 0.31g.Physical property: m.p.90-92 DEG C.
[chemical formula 76]
By the chloro- N of (S) -3- obtained in above-described embodiment1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.23g is dissolved in chloroform 3ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.10g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.18-98) the 0.08g and chloro- N of (S) -3-1(4- { [6- hepta-fluoroiso-propyl -3- (2- methoxy ethyl) -2- oxo -3,4- dihydro -2H- quinazoline -1- base] methyl } -2- aminomethyl phenyl)-N2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.18-99) 0.13g.Physical property: m.p.170-175 DEG C of m.p.118-121 DEG C of (compound N is o.18-98), (compound N is o.18-99).
Embodiment 11-1.
[chemical formula 77]
2- nitrobenzoic acid 1.67g is dissolved in toluene 10ml, DMF0.01g is added, in ice-cold lower dropwise addition thionyl chloride 1.19g.After being heated to reflux 1 hour, solvent is distilled off under reduced pressure.Obtained acyl chlorides is dissolved in THF5ml, is added dropwise in the THF10ml solution of the THF solution 5ml and triethylamine 2.02g of 2M methylamine under ice-cold stirring.After completion of dropwise addition, then after being stirred at room temperature 30 minutes, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains N- methyl -2- nitrobenzamide 1.8g.
1H-NMR(CDCl3, ppm): 3.00 (3H, d), 5.96 (1H, s), 7.50 (1H, d), 7.56 (1H, t), 7.65 (1H, t), 8.03 (1H, d)
Implement 11-2.
[chemical formula 78]
N- methyl -2- nitrobenzamide 1.8g obtained in embodiment 11-1 is dissolved in ethyl alcohol 40ml, ammonium chloride 2.7g, iron powder 2.9g and water 20ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 2- Amino-N-methyl benzamide 1.38g.
1H-NMR(CDCl3, ppm): 2.96 (3H, d), 5.49 (2H, brs), 6.05 (1H, s), 6.64 (1H, t), 6.67 (1H, d), 7.19 (1H, t), 7.28 (1H, d)
Embodiment 11-3.
[chemical formula 79]
2- Amino-N-methyl benzamide 0.69g obtained in embodiment 11-2, seven fluoro- 2- iodopropane 1.64g, sodium carbonate 0.73g and 4-butyl ammonium hydrogen sulfate 0.05g are added sequentially in the mixed liquor of ethyl acetate 5ml and water 5ml.It is a small amount of successively through 30 minutes addition sodium dithionite 1.6g under stirring at room temperature.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 2- amino -5- hepta-fluoroiso-propyl-N-methyl-benzamide 0.89g.
1H-NMR(CDCl3, ppm) and 2.99 (3H, d), 5.83 (2H, s), 6.02 (1H, s), 6.73 (1H, d), 7.36 (1H, d), 7.47 (1H, s)
Embodiment 11-4.
[chemical formula 80]
2- amino -5- hepta-fluoroiso-propyl-N-methyl-benzamide 0.89g obtained in embodiment 11-3 is dissolved in THF6ml, 1,1'- carbonyl dimidazoles 1.4g is added, is reacted within 2 hours being heated to reflux lower progress.After reaction, ice water is added, is extracted with ethyl acetate.Organic layer is successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- methyl-1 H, 3H- quinazoline -2,4- diketone 0.63g.
1H-NMR(CDCl3, ppm): 3.50 (3H, s), 7.23-7.26 (1H, m), 7.82 (1H, d), 8.42 (1H, s), 9.61 (1H, s)
Embodiment 11-5.
[chemical formula 81]
6- hepta-fluoroiso-propyl -3- methyl-1 H, 3H- quinazoline -2,4- diketone 0.63g and 3- methyl -4- nitrobenzyl bromide 0.44g obtained in embodiment 11-4 is dissolved in acetonitrile 15ml, potassium carbonate 0.60g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl-3- methyl-1-(3- methyl-4- nitrobenzyl)-1H, 3H- quinazoline-2,4- diketone 0.74g.
1H-NMR(CDCl3, ppm): 2.60 (3H, s), 3.58 (3H, s), 5.42 (2H, s), 7.14 (1H, d), 7.21-7.26 (2H, m), 7.78 (1H, d), 7.98 (1H, d), 8.54 (1H, s)
Embodiment 11-6.
[chemical formula 82]
By 6- hepta-fluoroiso-propyl-3- methyl-1-obtained in embodiment 11-5 (3- methyl-4- nitrobenzyl)-1H, 3H- quinazoline-2,4- diketone 0.74g is dissolved in ethyl alcohol 5ml, and ammonium chloride 0.41g, iron powder 0.42g and water 3ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 1- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -3- methyl-1 H, 3H- quinazoline -2,4- diketone 0.53g.
1H-NMR(CDCl3, ppm): 2.14 (3H, s), 3.56 (3H, s), 3.62 (2H, brs), 5.26 (2H, s), 6.63 (1H, d), 6.94-6.98 (2H, m), 7.35 (1H, d), 7.74 (1H, d), 8.48 (1H, s)
The chloro- N of embodiment 11-7. (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.18-177) and the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.18-178)
[chemical formula 83]
By (4- amino -3- the methylbenzyl) -3- methyl -6- hepta-fluoroiso-propyl of 1- obtained in embodiment 11-6. -1H, 3H- quinazoline -2,4- diketone 0.27g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.19g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.18-176) 0.36g.Physical property: m.p.123-126 DEG C.
[chemical formula 84]
By the chloro- N of (S) -3- obtained in above-described embodiment1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.22g is dissolved in chloroform 3ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.10g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.18-177) the 0.12g and chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -3- methyl -3,4- dihydro -2H- quinazoline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.18-178) 0.10g.Physical property: m.p.160-166 DEG C of (compound N is o.18-177).M.p.146-147 DEG C of (compound N is o.18-178).
Embodiment 12-1.
[chemical formula 85]
2- aminobenzamide 13.6g, seven fluoro- 2- iodopropane 24.1g, sodium carbonate 15.9g and 4-butyl ammonium hydrogen sulfate 0.8g are added sequentially in the mixed liquor of ethyl acetate 100ml and water 100ml.It is a small amount of successively through 30 minutes addition sodium dithionite 17.4g under stirring at room temperature.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 2- amino -5- sevoflurane isopropyl benzoyl amine 24.1g.
1H-NMR(CDCl3, ppm): 5.70-6.20 (4H, m), 6.74 (1H, d), 7.38 (1H, d), 7.56 (1H, s)
Embodiment 12-2.
[chemical formula 86]
2- amino -5- sevoflurane isopropyl benzoyl amine 5.7g obtained in embodiment 12-1 is dissolved in THF20ml, 1,1'- carbonyl dimidazoles 8.7g is added, is reacted within 2 hours being heated to reflux lower progress.After reaction, ice water is added, is extracted with ethyl acetate.Organic layer is successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -1H, 3H- quinazolinone -2,4- diketone 3.56g.Physical property: m.p.284-286 DEG C.
Embodiment 12-3.
[chemical formula 87]
6- hepta-fluoroiso-propyl -1H, 3H- quinazolinone -2,4- diketone 2.00g obtained in embodiment 12-2 is dissolved in DMA6ml, 60% sodium hydride 0.24g is added, is stirred at room temperature 30 minutes.3- methyl -4- nitrobenzyl bromide 1.39g is added, then is stirred at room temperature 3 hours.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- (3- methyl -4- nitrobenzyl) -1H, 3H- quinazoline -2,4- diketone 0.71g.
1H-NMR(CDCl3, ppm): 2.59 (3H, s), 5.26 (2H, s), 7.19 (1H, d), 7.46 (2H, m), 7.84 (1H, d), 8.43 (1H, s), 8.91 (1H, s)
Embodiment 12-4.
[chemical formula 88]
6- hepta-fluoroiso-propyl -3- obtained in embodiment 12-3 (3- methyl -4- nitrobenzyl) -1H, 3H- quinazoline -2,4- diketone 0.71g are dissolved in DMA4ml, 60% sodium hydride 0.06g is added, is stirred at room temperature 30 minutes.Iodomethane 0.21g is added, then is stirred at room temperature 3 hours.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -1- methyl -3- (3- methyl -4- nitrobenzyl) -1H, 3H- quinazoline -2,4- diketone 0.67g.
1H-NMR(CDCl3, ppm): 2.58 (3H, s), 3.65 (3H, s), 5.29 (2H, s), 7.36 (1H, d), 7.44-7.49 (2H, m), 7.91 (2H, m), 8.51 (1H, s)
Embodiment 12-5.
[chemical formula 89]
By 6- hepta-fluoroiso-propyl -1- methyl -3- obtained in embodiment 12-4 (3- methyl -4- nitrobenzyl) -1H, 3H- quinazoline -2,4- diketone 1.13g is dissolved in ethyl alcohol 4ml, and ammonium chloride 0.37g, iron powder 0.38g and water 2ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 3- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -1- methyl-1 H, 3H- quinazoline -2,4- diketone 0.65g.
1H-NMR(CDCl3, ppm): 2.13 (3H, s), 3.62 (5H, m), 5.15 (2H, s), 6.60 (1H, d), 7.29 (1H, d), 7.47 (1H, m), 7.85 (1H, d), 7.91 (1H, m), 8.50 (1H, s)
Embodiment 12-6.
(S) the chloro- N of -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.19-8) and the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.19-9)
[chemical formula 90]
By (4- amino -3- the methylbenzyl) -6- hepta-fluoroiso-propyl -1- methyl-1 of 3- obtained in embodiment 12-5 H, 3H- quinazoline -2,4- diketone 0.33g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.28g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.19-7) 0.29g.Physical property: m.p.104-107 DEG C.
[chemical formula 91]
By the chloro- N of (S) -3- obtained in above-described embodiment1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.23g is dissolved in chloroform 3ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.09g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2The chloro- N of (1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.19-8) 0.16g and (S) -3-1{ 4- [(2,4- dioxo -6- hepta-fluoroiso-propyl -1- methyl-1,2- dihydro -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.19-9) 0.05g.Physical property: m.p.132-135 DEG C of m.p.134-137 DEG C of (compound N is o.19-8), (compound N is o.19-9).
Embodiment 13-1.
[chemical formula 92]
Ortho-aminobenzoic acid 24.7g, seven fluoro- 2- iodopropane 60g, sodium carbonate 55.3g and 4-butyl ammonium hydrogen sulfate 2g are added sequentially in the mixed liquor of ethyl acetate 200ml and water 200ml.Internal temperature is maintained at 40 DEG C under stiring, and a small amount of successively through 30 minutes addition sodium dithionite 34.8g.After addition, it is stirred for 1 hour.After separating organic layer, successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains 5- hepta-fluoroiso-propyl ortho-aminobenzoic acid 42g.Physical property: m.p.142-144 DEG C.
Embodiment 13-2.
[chemical formula 93]
5- hepta-fluoroiso-propyl ortho-aminobenzoic acid 0.92g obtained in embodiment 13-1 is dissolved in trifluoroacetic anhydride 2ml, is reacted within 1 hour being heated to reflux lower progress.After reaction, it is concentrated under reduced pressure to admittedly, is dissolved in dimethylbenzene 10ml for residue obtained.3- methyl -4- nitro-benzylamine 0.5g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -3- (3- methyl -4- nitrobenzyl) -2- trifluoromethyl -3H- quinazoline-4-one 1.3g.Physical property: m.p.126-127 DEG C.
1H-NMR(CDCl3, ppm): 2.59 (3H, s), 5.45 (2H, s), 7.15 (1H, d), 7.17 (1H, s), 7.96 (1H, d), 8.04 (1H, d), 8.10 (1H, d), 8.62 (1H, s)
Embodiment 13-3.
[chemical formula 94]
(3- methyl -4- the nitrobenzyl) -2- trifluoromethyl -3H- quinazoline-4-one of 6- hepta-fluoroiso-propyl -3- obtained in embodiment 13-2 0.85g is dissolved in ethyl alcohol 10ml, ammonium chloride 0.41g, iron powder 0.42g and water 5ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, obtains the crude object 0.8g of 3- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -2- trifluoromethyl -3H- quinazoline-4-one.
Embodiment 13-4.
(S) the chloro- N of -3-1{ 4- [(6- hepta-fluoroiso-propyl -4- oxo -2- trifluoromethyl -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.23-10)
[chemical formula 95]
3- obtained in embodiment 13-3 (4- amino -3- the methylbenzyl) -6- hepta-fluoroiso-propyl crude object 0.50g of -2- trifluoromethyl -3H- quinazoline-4-one and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.27g are dissolved in acetonitrile 5ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains S) the chloro- N of -3-1{ 4- [(6- hepta-fluoroiso-propyl -4- oxo -2- trifluoromethyl -4H- quinazoline -3- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.23-10) 0.30g.
1H-NMR(CDCl3, ppm): 1.22 (3H, d), 1.98 (3H, s), 2.26 (3H, s), 2.58 (2H, m), 4.34 (1H, m), 5.51 (2H, s), 6.27 (1H, d), 7.20 (1H, s), 7.22 (1H, d), 7.41 (1H, t), 7.54 (1H, d), (7.61 1H, d), 7.73 (1H, d), 7.96 (1H, d), (8.04 1H, d), 8.09 (1H, d), 8.40 (1H, s)
Embodiment 14-1.
[chemical formula 96]
2- aminothiophenol 6.26g and triethylamine 6.07g are dissolved in THF50ml, bromo-acetic acid tert-butyl 9.75g is added under stirring at room temperature.After 1 hour is stirred at room temperature again, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 2- aminophenyl thioacetic acid tert-butyl ester 12.0g.
Embodiment 14-2.
[chemical formula 97]
(2- aminophenyl) the thioacetic acid tert-butyl ester of 2- obtained in embodiment 14-1 11.97g, seven fluoro- 2- iodopropane 17.76g, sodium carbonate 7.95g and 4-butyl ammonium hydrogen sulfate 0.5g are added sequentially in the mixed liquor of ethyl acetate 100ml and water 100ml.Internal temperature is maintained at 40 DEG C under stiring, and a small amount of successively through 30 minutes addition sodium dithionite 10.45g.After addition, it is stirred for 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is washed residue obtained with ether-hexane mixed solvent, thus obtains [2- amino -5- (hepta-fluoroiso-propyl) phenyl] thioacetic acid tert-butyl ester 20g.
1H-NMR(CDCl3, ppm): 1.39 (9H, s), 3.40 (2H, s), 4.75 (2H, brs), 6.76 (1H, d), 7.31 (1H, d), 7.65 (1H, s)
Embodiment 14-3.
[chemical formula 98]
[2- amino -5- (hepta-fluoroiso-propyl) phenyl] thioacetic acid tert-butyl ester 1.43g obtained in embodiment 14-2 is dissolved in 4N hydrogen chloride-ethyl acetate solution 5ml, is reacted within 1 hour being heated to reflux lower progress.After reaction, solvent is distilled off under reduced pressure, is dissolved in THF10ml for residue obtained, the chloro- 1- methylpyridinium iodide 1.8g of triethylamine 1.1g and 2- is added.After being stirred at room temperature 3 hours, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 7- hepta-fluoroiso-propyl -2H- benzo [Isosorbide-5-Nitrae] thiazine -3- ketone 0.9g.Physical property: m.p.123-124 DEG C.
Embodiment 14-4.
[chemical formula 99]
7- hepta-fluoroiso-propyl -2H- benzo [Isosorbide-5-Nitrae] thiazine -3- ketone 0.67g and 3- methyl -4- nitrobenzyl bromide 0.51g obtained in embodiment 14-3 is dissolved in acetonitrile 20ml, potassium carbonate 0.42g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 7- hepta-fluoroiso-propyl -3- (3- methyl -4- nitrobenzyl) -2H- benzo [Isosorbide-5-Nitrae] thiazine -3- ketone 0.85g.Physical property: m.p.147-148 DEG C.
Embodiment 14-5.
[chemical formula 100]
By 7- hepta-fluoroiso-propyl -3- obtained in embodiment 14-4 (3- methyl -4- nitrobenzyl) -2H- benzo [1,4] thiazine -3- ketone 0.82g is dissolved in ethyl alcohol 10ml, ammonium chloride 0.45g, iron powder 0.48g and water 5ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains 3- (4- amino -3- methylbenzyl) -7- hepta-fluoroiso-propyl -2H- benzo [Isosorbide-5-Nitrae] thiazine -3- ketone 0.77g.
1H-NMR(CDCl3, ppm): 2.14 (3H, s), 3.58 (2H, brs), 5.10 (2H, s), 6.62 (1H, d), 6.88 (1H, d), 6.91 (1H, s), 7.19 (1H, d), 7.33 (1H, d), 7.57 (1H, s)
The chloro- N of embodiment 14-6. (S) -3-1{ 4- [(7- hepta-fluoroiso-propyl -3- oxo -2H- benzo [1,4] thiazine -4- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.26-10)
[chemical formula 101]
By 3- obtained in embodiment 14-5 (4- amino -3- methylbenzyl) -7- hepta-fluoroiso-propyl -2H- benzo [1,4] thiazine -3- ketone 0.36g and the chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.27g are dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(7- hepta-fluoroiso-propyl -3- oxo -2H- benzo [1,4] thiazine -4- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.26-10) 0.52g.
Physical property: m.p.130-132 DEG C.
1H-NMR(CDCl3, ppm): 1.23 (3H, d), 1.95 (3H, s), 2.28 (3H, s), 2.58 (2H, m), 3.58 (3H, s), 4.32 (1H, m), 5.18 (2H, s), 6.33 (1H, d), 7.03 (1H, s), 7.05 (1H, d), 7.11 (1H, d), 7.34 (1H, d), 7.41 (1H, t), 7.52 (1H, d), 7.60 (1H, d), 7.71 (1H, d), 7.99 (1H, d), 8.38 (1H, s)
Embodiment 15-1.
[chemical formula 102]
4- hepta-fluoroiso-propyl -1,2- phenylenediamine 1.38g is dissolved in dimethylbenzene 5ml, trifluoroacetone acetoacetic ester 0.85g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, solvent is distilled off under reduced pressure, it is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.8g (physical property: m.p.203-204 DEG C) and 7- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.7g (physical property: m.p.129-130 DEG C).
Embodiment 15-2.
[chemical formula 103]
6- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.38g and 3- methyl -4- nitrobenzyl bromide 0.23g obtained in embodiment 15-1 is dissolved in acetonitrile 20ml, potassium carbonate 0.21g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 6- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.31g.
1H-NMR(CDCl3, ppm): 2.60 (3H, s), 5.55 (2H, s), 7.24 (1H, d), 7.25 (1H, s), 7.38 (1H, d), 7.84 (1H, d), 7.98 (1H, d), 8.33 (1H, s)
[chemical formula 104]
Similarly, 7- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.30g is obtained by 7- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.38g.
1H-NMR(CDCl3, ppm): 2.58 (3H, s), 5.56 (2H, s), 7.27 (1H, d), 7.29 (1H, s), 7.55 (1H, s), 7.66 (1H, d), 7.98 (1H, d), 8.18 (1H, d)
Embodiment 15-3.
[chemical formula 105]
6- hepta-fluoroiso-propyl -1- obtained in embodiment 15-2 (3- methyl -4- nitrobenzyl) -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.27g is dissolved in ethyl alcohol 10ml, ammonium chloride 0.13g, iron powder 0.14g and water 5ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, obtains the crude object 0.25g of 1- (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone.
[chemical formula 106]
Similarly, the crude object 0.25g of 1- (4- amino -3- methylbenzyl) -7- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone is obtained by 7- hepta-fluoroiso-propyl -1- (3- methyl -4- nitrobenzyl) -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone 0.27g.
The chloro- N of embodiment 15-4. (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -3- trifluoromethyl -2H- quinoxaline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.28-13) and the chloro- N of (S) -3-1{ 4- [(7- hepta-fluoroiso-propyl -2- oxo -3- trifluoromethyl -2H- quinoxaline -1- base) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.28-16)
[chemical formula 107]
The chloro- 3- of crude object 0.25g and (S) -4- (1- methyl -2-methylmercaptoethyl the imino group) -3H- isobenzofuran -1- ketone 0.14g of 1- obtained in embodiment 15-3 (4- amino -3- methylbenzyl) -6- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone is dissolved in acetonitrile 3ml, trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [(6- hepta-fluoroiso-propyl -2- oxo -3- trifluoromethyl -2H- quinoxaline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.28-13) 0.23g.
1H-NMR(CDCl3, ppm): 1.22 (3H, d), 1.92 (3H, s), 2.28 (3H, s), 2.56 (2H, m), 4.30 (1H, m), 5.48 (2H, s), 6.35 (1H, d), 7.12 (1H, s), 7.13 (1H, d), 7.41 (1H, t), 7.50 (1H, d), 7.55 (1H, d), 7.67 (1H, d), 7.82 (1H, d), 8.01 (1H, d), 8.30 (1H, s), 8.46 (1H, s)
[chemical formula 108]
Similarly, the chloro- N of (S) -3- is obtained by the crude object 0.25g of 1- (4- amino -3- methylbenzyl) -7- hepta-fluoroiso-propyl -2- oxo -3- Trifluoromethyl-1 H- quinoxaline -2- ketone1{ 4- [(7- hepta-fluoroiso-propyl -2- oxo -3- trifluoromethyl -2H- quinoxaline -1- base) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.28-16) 0.15g.
1H-NMR(CDCl3, ppm): 1.20 (3H, d), 1.96 (3H, s), 2.28 (3H, s), 2.57 (2H, m), 4.31 (1H, m), 5.48 (2H, s), 6.27 (1H, d), 7.17 (1H, s), 7.20 (1H, d), 7.43 (1H, t), 7.53 (1H, d), 7.63 (1H, d), 7.71 (1H, d), 7.74 (1H, s), 8.08 (1H, d), 8.14 (1H, d), 8.39 (1H, s)
Embodiment 16-1.
[chemical formula 109]
By N- methyl-1,2- phenylenediamine dihydrochloride 3.9g, seven fluoro- 2- iodopropane 7.1g, sodium carbonate 6.36g and 4-butyl ammonium hydrogen sulfate 0.2g are added sequentially in the mixed liquor of ethyl acetate 20ml and water 20ml.It is a small amount of successively through 30 minutes addition sodium dithionite 3.56g under stirring at room temperature.After addition, it is warming up to 40 DEG C and stirs 1 hour.After separating organic layer, washed with saturated brine, it is dry with magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains N1Methyl -4- hepta-fluoroiso-propyl -1,2- phenylenediamine and N1The mixture 5.17g of methyl -5- hepta-fluoroiso-propyl -1,2- phenylenediamine.
Embodiment 16-2.
[chemical formula 110]
By N obtained in embodiment 16-11Methyl -4- hepta-fluoroiso-propyl -1,2- phenylenediamine and N1The mixture 2.00g of methyl -5- hepta-fluoroiso-propyl -1,2- phenylenediamine is dissolved in THF10ml, and ethyl isocyanate 0.49g is added, and carries out reacting for 2 hours under stirring at room temperature.After reaction, water is added, is extracted with ethyl acetate.Organic layer is successively washed with 1N aqueous hydrochloric acid solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, it is refined residue obtained with silica gel column chromatography, thus obtains the mixture 2.03g of 1- [2- amino -4- (hepta-fluoroiso-propyl) phenyl] -3- ethyl -1- methylurea and 1- [2- amino -5- (hepta-fluoroiso-propyl) phenyl] -3- ethyl -1- methylurea.
Embodiment 16-3.
[chemical formula 111]
The mixture 2.03g and triethylamine 1.7g of [2- amino -4- (hepta-fluoroiso-propyl) the phenyl] -3- ethyl -1- methylurea of 1- obtained in embodiment 16-2 and 1- [2- amino -5- (hepta-fluoroiso-propyl) phenyl] -3- ethyl -1- methylurea are dissolved in THF10ml, triphosgene 1.66g is added, carries out reacting for 2 hours under stirring at room temperature.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains three azepines -2,4- diketone 1.24g of 3- ethyl -7- hepta-fluoroiso-propyl -1- methyl-1 H, 3H, 5H- benzo [1,3,5].Isomers can not be separated.
1H-NMR(CDCl3, ppm): 1.28 (3H, m), 3.44-3.51 (5H, m), 7.09 (1H, d), 7.49 (1H, d), 8.59 (2H, m)
Embodiment 16-4.
[chemical formula 112]
By 3- ethyl -7- hepta-fluoroiso-propyl -1- methyl-1 H, 3H, 5H- benzo [1 obtained in embodiment 16-3,3,5] three azepines -2,4- diketone 1.24g and 3- methyl -4- nitrobenzyl bromide 0.74g are dissolved in acetonitrile 15ml, potassium carbonate 1.32g is added, is reacted within 3 hours being heated to reflux lower progress.After reaction, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains 3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -5- (3- methyl -4- nitrobenzyl) -1H, 3H, 5H- benzo [1,3,5] three azepines -2,4- diketone 1.07g.
1H-NMR(CDCl3, ppm): 1.11-1.17 (3H, m), 2.52-2.59 (3H, m), 3.37-3.41 (3H, m), 3.60-3.67 (2H, m), 4.80-5.37 (2H, m), 7.09-7.17 (2H, m), 7.20-7.30 (1H, m), 7.32-7.51 (2H, m), 7.86-7.97 (1H, m)
Embodiment 16-5.
[chemical formula 113]
By 3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -5- (3- methyl -4- nitrobenzyl) -1H obtained in embodiment 16-4,3H, 5H- benzo [1,3,5] three azepines -2,4- diketone 1.07g is dissolved in ethyl alcohol 20ml, and ammonium chloride 0.54g, iron powder 0.56g and water 10ml is added, is stirred at room temperature 3 hours.After reaction, after removing insoluble matter using diatomite, water is added, is extracted with ethyl acetate.Organic layer is washed with saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, thus obtains three azepines -2,4- diketone 0.44g of 1- (4- amino -3- methylbenzyl) -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl-1 H, 3H, 5H- benzo [1,3,5].
1H-NMR(CDCl3, ppm): 1.31-1.23 (3H, m), 2.03-2.06 (3H, m), 3.27-3.33 (3H, m), 3.52-3.66 (4H, m), 4.61-5.24 (2H, m), 6.47-6.58 (1H, m), 6.75-6.87 (2H, m), 7.10-7.20 (1H, m), 7.28-7.42 (2H, m)
The chloro- N of embodiment 16-6. (S) -3-1{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.31-8) and the chloro- N of (S) -3-1{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2The synthesis of (1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.31-9)
[chemical formula 114]
By 1- obtained in embodiment 16-5 (4- amino -3- methylbenzyl) -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl-1 H, 3H, 5H- benzo [1,3,5] three azepines -2, the 4- diketone 0.22g and chloro- 3- of (S) -4- (1- methyl -2-methylmercaptoethyl imino group) -3H- isobenzofuran -1- ketone 0.14g is dissolved in acetonitrile 3ml, and trifluoroacetic acid 0.01g is added, is stirred at room temperature 3 hours.After reaction, solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide (compound N is o.31-7) 0.27g.Physical property: m.p.113-115 DEG C
[chemical formula 115]
By the chloro- N of (S) -3- obtained in embodiment 16-51{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2-methylmercaptoethyl) phthalic amide 0.18g is dissolved in chloroform 3ml, in ice-cold lower addition metachloroperbenzoic acid (75%) 0.07g, is stirred at room temperature 1 hour.After reaction, it is successively washed with sodium thiosulfate solution, saturated sodium bicarbonate aqueous solution, saturated brine, it is dry with anhydrous magnesium sulfate.Solvent is distilled off under reduced pressure, is refined residue obtained with silica gel column chromatography, thus obtains the chloro- N of (S) -3-1{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methylsulfinylethyl) phthalic amide (compound N is o.31-8) the 0.06g and chloro- N of (S) -3-1{ 4- [([1,3,5] three azepines -1- base of 2,4- dioxo -3- ethyl -8- hepta-fluoroiso-propyl -5- methyl -2,3,4,5- tetrahydro -1H- benzo) methyl] -2- aminomethyl phenyl }-N2(1- methyl -2- methysulfonylethyl) phthalic amide (compound N is o.31-9) 0.05g.Physical property: m.p.140-150 DEG C of (compound N is o.31-8).M.p.137-144 DEG C of (compound N is o.31-9).
Hereinafter, showing representative preparation example and test example of the invention, but the present invention is not limited to this.
It is explained, in preparation example, the expression with " part " is parts by weight.
Preparation example 1.
10 parts of the compounds of this invention
70 parts of dimethylbenzene
10 parts of N-Methyl pyrrolidone
10 parts of mixture of ethylene nonyl phenyl ether and alkyl benzene calcium sulfonate
The above ingredient is dissolved after evenly mixing, emulsion is made.
Preparation example 2.
3 parts of the compounds of this invention
82 parts of clay powders
15 parts of diatomite powder
The above ingredient is crushed after evenly mixing, pulvis is made.
Preparation example 3.
5 parts of the compounds of this invention
90 parts of mixed-powder of bentonite and clay
5 parts of calcium lignosulfonate
The above ingredient is uniformly mixed, suitable water is added and is kneaded, pelletized, dried, granula is made.
Preparation example 4.
20 parts of the compounds of this invention
75 parts of high dispersive silicic acid of kaolin and synthesis
5 parts of mixture of ethylene nonyl phenyl ether and alkyl benzene calcium sulfonate
The above ingredient is crushed after evenly mixing, wettable powder is made.
Test example 1.
To the insecticidal test of Frankliniella occidentalis (Frankliniella occidentalis)
The female adult pest of Frankliniella occidentalis is seeded on the Phaseolus Leaves being fixed on agar medium, after so that it is laid eggs 1 day, removes female adult pest.Again after 3 days, the larvae number on blade is calculated, the medical fluid of 500ppm will be diluted to using the compound recorded in the 1st table~the 19th table, the 21st table, the 23rd table~the 31st table as the medicament of effective component by then spreading.The larva number of the worm to survive after investigating 4 days calculates dead worm rate by following formula, is judged according to following criterion.Test is divided to two groups of progress.
[mathematical expression 1]
Criterion:
The dead worm rate 100% of A ...
The dead worm rate 99%~90% of B ...
The dead worm rate 89%~80% of C ...
The dead worm rate 79%~50% of D ...
The dead worm rate 49%~0% of E ...
As above-mentioned test result, compound number 1-4,1-5,1-7,1-10,1-13,1-19,1-22,1-25,1-28,1-31,1-34,1-37,1-46,1-49,1-52,1-53,1-54,1-55,1-56,1-57,
1-58、1-59、1-60、1-61、1-62、1-63、1-64、1-65、1-66、1-67、1-68、1-69、
1-73、1-79、1-82、1-85、1-86、1-87、1-91、1-94、1-95、1-96、1-97、1-98、
1-99、1-100、1-101、1-102、1-103、1-104、1-105、1-106、1-107、1-108、
1-112、1-113、1-114、1-117、1-118、1-119、1-124、1-128、1-134、1-137、
1-138、1-139、1-146、1-147、1-148、1-149、1-150、1-151、1-162、1-169、
1-170、1-173、1-180、1-190、1-196、1-199、1-200、1-201、1-202、1-203、
1-204、1-205、1-206、1-207、1-208、1-215、1-216、1-217、1-227、1-228、
1-230、1-231、1-232、1-233、1-236、1-237、1-238、1-239、1-240、1-241、
1-244、1-245、1-246、1-247、1-248、1-249、1-251、1-252、1-253、1-254、
1-255、1-256、1-257、1-276、1-277、1-280、1-281、1-282、1-283、1-284、
1-285、1-286、1-288、1-289、1-290、1-291、1-292、1-293、1-294、1-295、
1-307、1-308、1-309、1-315、1-317、1-318、1-329、1-332、1-335、1-336、
1-337、1-338、1-339、1-340、1-341、1-342、1-343、1-344、1-345、1-346、
1-347、1-348、1-349、1-350、1-351、1-352、1-353、1-354、1-361、1-367
1-370、1-372、1-373、1-375、1-376、1-378、1-379、1-380、1-381、1-383、
1-384、1-385、1-387、1-388、1-389、1-390、1-391、1-392、1-393、1-394、
1-396、1-397、1-398、1-399、1-402、1-403、1-405、1-406、1-407、1-409、
1-410、1-411、1-412、1-413、1-417、1-420、1-423、1-424、1-426、 1-427、
1-428、1-429、1-430、1-431、1-432、1-433、1-434、1-435、1-436、1-437、1-438、
1-439、1-440、1-441、1-442、1-443、1-444、1-445、1-446、1-447、1-450、
1-451、1-452、1-453、1-456、1-457、1-458、1-471、1-472、1-474、
1-495、1-496、1-497、1-498、1-499、1-500、1-501、1-502、
1-503、1-504、1-505、1-506、1-507、1-508、1-509、1-510、1-511、1-512、
1-513、1-514、1-515、1-516、1-517、1-518、1-525、1-526、1-527、1-528、
1-529、1-530、1-531、1-532、1-533、1-534、1-537、1-538、1-540、1-541、
1-543、1-544、1-545、1-549、1-550、1-551、1-552、1-553、1-554、1-558、1-559、1-562、1-565、1-567、1-568、1-569、1-570、1-571、1-572、1-573、1-574、1-575、1-576、1-577、1-578、1-579、1-580、1-581、1-582、1-583、1-584、
1-597、1-598、1-599、1-616、1-617、1-618、1-621、1-622、1-623、1-624、1-625、
1-630、1-631、1-632、1-633、1-634、1-635、1-636、1-638、1-641、1-642、1-644、
1-661、1-663、1-668、1-674、1-696、1-697、1-699、1-700、1-702、1-703、1-704、
1-705、1-706、1-709、1-710、1-713、1-714、1-715、
1-722、1-725、1-726、1-727、1-728、1-729、1-730、1-737、1-738、1-740、1-741、
1-742、1-743、1-744、1-745、1-746、1-747、1-748、1-749、1-750、1-751、1-752、
1-753、1-754、1-755、1-756、1-757、1-758、1-761、1-764、1-765、 1-766、1-767、
1-768、1-769、1-770、1-771、1-772、1-773、1-774、1-775、1-776、1-777、1-778、
1-779、1-780、1-781、1-782、1-783、1-784、1-785、1-786、1-787、1-788、1-789、
1-790、1-791、1-792、1-793、1-794、1-795、1-796、1-797、1-798、1-799、1-800、
1-801、1-802、1-803、1-804、1-805、1-806、1-807、1-808、1-809、1-810、1-811、
1-812、1-813、1-814、1-815、1-816、1-817、1-818、1-819、1-820、1-821、1-822、
1-823、3-4、4-1、4-2、4-4、4-5、4-6、4-10、4-11、4-12、4-13、4-14、5-2、5-5、5-10、5-11、5-14、5-16、5-17、5-19、5-20、5-23、6-1、6-2、6-3、6-4、6-6、
6-7、6-8、6-9、6-19、6-20、6-21、6-22、6-23、6-24、6-29、6-30、
6-32、6-33、6-34、6-35、6-37、6-38、6-39、
7-1、7-2、7-3、7-7、7-8、7-10、7-11、7-23、7-25、7-28、7-29、7-32、7-41、7-46、7-49、7-50、7-52、7-53、7-54、7-56、7-57、8-1、8-2、8-3、8-4、8-5、8-6、8-7、8-8、8-9、8-13、8-14、8-15、8-30、8-31、8-32、8-33、8-34、8-35、8-36、8-37、8-38、8-39、8-42、8-43、8-44、8-59、8-60、8-61、8-62、8-63、8-64、8-65、8-66、8-67、8-68、8-69、8-70、8-71、8-72、8-73、8-74、8-75、8-76、8-77、8-78、8-79、8-80、8-81、8-82、8-83、8-84、8-85、8-86、8-87、8-88、8-89、8-90、8-91、8-92、8-93、8-94、8-95、8-96、8-97、8-98、8-99、8-100、8-101、8-102、8-103、8-104、8-105、8-106、8-107、8-108、8-109、8-110、8-111、8-112、8-113、8-114、8-115、8-116、8-117、8-118、8-119、8-120、8-121、8-122、8-123、8-124、8-125、8-126、8-127、8-128、8-129、8-130、8-131、8-132、8-133、8-134、8-135、8-136、 8-137、8-138、8-139、8-140、8-141、8-142、8-143、8-144、8-145、8-146、
8-147、8-148、8-149、8-150、8-151、8-152、8-153、8-154、8-155、8-156、
8-157、8-158、8-159、8-160、8-161、8-162、8-163、8-164、8-165、8-166、
8-167、8-168、8-169、8-176、8-177、8-178、8-179、8-180、8-181、8-182、
8-183、8-184、8-185、8-186、8-187、8-188、8-189、8-190、8-191、8-192、
8-193、8-194、8-195、8-196、8-197、8-198、8-199、8-200、8-201、8-202、
8-204、8-206、8-207、8-208、8-209、8-210、8-211、8-212、8-213、8-214、
8-215、8-216、8-217、8-218、8-219、8-220、8-221、8-222、8-223、8-224、
8-225、8-226、8-227、8-228、8-229、8-230、8-231、8-232、8-233、8-234、
8-235、8-236、8-237、8-238、8-239、8-240、8-241、8-242、8-243、8-244、
8-245、8-246、8-247、8-248、8-249、8-250、8-251、8-252、8-253、8-254、
8-255、8-256、8-257、8-258、8-259、8-260、8-264、8-265、8-266、8-267、
8-268、8-269、8-270、8-271、8-272、8-273、8-274、8-275、8-276、8-277、
8-278、8-279、8-280、8-281、8-282、8-283、8-284、8-285、8-287、8-291、
8-292、8-293、8-294、8-295、8-296、8-297、8-298、8-312、8-313、 8-314、
8-315、8-316、8-317、8-318、8-319、8-320、8-321、8-322、8-324、8-325、
8-326、8-327、8-328、8-329、8-330、8-331、8-332、8-333、8-334、8-335、
8-336、8-337、8-338、8-339、8-340、8-341、8-354、8-355、8-356、8-357、
8-358、8-359、8-360、8-361、8-362、8-363、8-364、8-365、8-366、8-367、
8-368、8-369、8-370、8-371、8-372、8-373、8-374、8-375、8-376、8-377、
8-378、8-379、8-380、8-381、8-382、8-383、8-390、8-391、8-392、8-393、
8-394、8-395、8-396、8-397、8-398、8-399、8-400、8-401、8-402、8-403、
8-404、8-405、8-406、8-407、8-408、8-409、8-410、8-411、8-412、8-413、
8-414、8-415、8-416、8-417、8-418、8-419、8-420、8-421、8-422、8-426、
8-427、8-428、8-429、8-430、8-431、8-432、8-433、8-434、8-438、8-439、
8-440、8-444、8-445、8-446、8-450、8-451、8-452、8-456、8-457、8-458、
8-462、8-463、8-464、8-465、8-466、8-467、8-468、8-469、8-470、8-471、
8-472、8-473、8-474、8-475、8-476、8-477、8-478、8-479、8-480、8-481、
8-482、8-486、8-487、8-488、8-492、8-493、8-494、8-495、8-496、8-497、
8-498、8-499、8-500、8-501、8-502、8-503、8-504、8-505、8-506、8-507、
8-508、8-509、8-510、8-511、8-512、8-513、8-514、8-515、8-516、8-517、
8-518、8-520、8-521、8-522、8-523、8-524、8-525、8-526、8-527、8-528、
8-529、8-530、8-531、8-532、8-533、8-534、8-535、8-536、8-537、8-538、
8-539、8-540、8-541、8-543、8-544、8-545、8-546、8-547、8-548、8-549、
8-550、8-551、8-558、8-559、8-560、8-561、8-562、8-563、8-564、8-567、
8-568、9-1、9-2、9-3、9-4、9-5、9-6、10-1、10-2、10-3、10-4、10-5、10-6、10-7、10-8、10-9、11-1、11-2、11-3、11-4、11-10、11-13、11-16、11-23、12-7、12-8、12-9、12-10、12-11、12-12、13-3、13-4、16-1、16-2、16-3、16-7、18-1、18-2、18-3、18-4、18-5、18-6、18-7、18-8、18-9、18-10、18-11、18-12、18-19、18-20、18-21、18-23、18-24、18-25、18-26、18-27、18-28、18-29、18-30、18-31、18-32、18-33、18-37、18-38、18-39、18-40、18-41、18-42、18-43、18-44、18-45、18-46、18-47、18-48、18-49、18-52、18-53、18-54、18-55、18-58、18-59、18-60、18-61、18-62、18-63、18-64、18-66、18-67、18-68、18-70、18-71、18-73、18-74、18-76、18-77、18-78、18-79、18-80、18-81、18-82、18-86、18-88、18-89、18-90、18-91、18-92、18-93、18-94、18-95、18-96、18-97、18-98、18-99、18-100、18-101、18-102、18-103、18-104、18-105、18-106、18-113、18-114、18-115、18-116、18-119、18-120、18-122、18-125、18-126、18-127、18-128、18-129、18-130、18-131、18-132、18-133、18-134、18-137、18-138、18-139、18-140、18-144、18-145、18-146、18-148、18-149、18-150、18-151、18-152、18-154、18-155、18-156、18-157、18-158、18-161、 18-162、18-164、18-165、18-166、18-167、18-168、18-169、18-176、18-177、18-178、18-191、18-179、18-180、18-181、18-182、18-183、18-184、18-185、18-186、18-187、18-192、18-194、18-195、18-196、18-197、18-198、18-199、18-200、18-201、18-202、18-203、18-204、18-205、18-206、18-207、18-208、18-209、18-210、18-211、18-212、18-213、18-216、18-217、18-218、18-219、18-220、18-221、18-222、18-223、18-224、18-225、18-226、18-245、18-246、18-247、18-248、18-249、18-250、18-251、18-252、18-253、18-254、18-255、18-256、18-257、18-258、18-259、18-260、18-263、18-264、18-265、18-266、18-267、18-268、18-287、18-288、18-289、18-290、18-291、18-292、18-293、18-294、18-295、18-296、18-297、18-298、18-299、18-300、18-301、18-302、18-303、18-304、18-305、18-306、18-307、18-308、18-309、18-310、18-323、18-324、18-325、18-327、18-329、18-330、18-331、18-332、18-333、18-334、18-350、18-351、18-352、18-353、18-354、18-355、18-356、18-363、18-365、18-366、18-368、18-426、18-427、18-429、18-430、18-431、18-445、18-447、18-462、18-465、18-468、18-469、18-470、18-471、18-474、18-475、18-476、18-477、19-1、19-2、19-3、19-4、19-5、
19-6、19-7、19-8、19-9、19-10、19-11、19-23、19-11、19-12、19-22、19-23、
19-24、19-49、19-50、19-51、19-52、19-67、19-70、19-73、19-74、19-75、
19-76、19-79、19-80、19-81、19-82、19-84、19-91、
21-5、23-10、24-1、24-2、24-3、24-4、24-5、25-1、25-2、25-3、25-4、25-5、25-6、25-9、25-10、25-11、25-12、25-14、25-22、25-25、25-26、25-27、25-28、25-29、25-30、25-31、25-34、25-35、25-40、25-44、25-47、26-4、26-10、26-11、26-12、26-15、26-16、26-17、26-18、27-14、28-13、28-16、29-1、29-2、29-3、29-4、29-5、29-6、30-1、30-2、30-3、30-4、31-7、31-8、31-9、31-10、31-11、31-12、 33-19、33-20、33-31、33-32、33-33、33-34、33-35、33-36、33-56、33-57、33-61、33-62、33-63、33-67、33-68、33-69、33-70、33-71、33-72、
34-1、34-2、34-5、35-1、35-2、35-3、35-7、35-8、35-9、35-10、35-11、35-12、
36-19,36-20,36-21 or 36-22 show the effect of D or more to Frankliniella occidentalis in 500ppm.
In turn, compound number 1-13,1-22,1-25,1-26,1-27,1-28,1-31,1-34,1-37,1-46,1-49,1-52,1-53,1-54,1-55,1-56,1-57,1-58,1-59,1-60,1-61,1-62,1-63,1-64,1-65,1-66,1-67,1-68,1-69,1-85,1-96,1-97,1-98,1-99,1-103,1-104,1-106,1-107,1-108,1-112,1-113,1-117,1-118,1-124,1-128,1-134,
1-137、1-138、1-146、1-147、1-148、1-149、1-150、1-151、1-162、1-169、
1-170、1-180、1-200、1-201、1-202、1-203、1-204、1-205、1-206、1-207、
1-208、1-215、1-230、1-236、1-237、1-241、1-246、1-249、1-252、1-254、
1-255、1-256、1-257、1-276、1-280、1-281、1-284、1-286、1-289、1-291、
1-293、1-295、1-307、1-308、1-318、1-332、1-335、1-336、1-338、1-339、
1-341、1-342、1-343、1-346、1-347、1-348、1-349、1-350、1-351、1-352、
1-353、1-387、1-388、1-391、1-399、1-405、1-409、1-410、1-411、1-412、
1-413、1-420、1-426、1-427、1-428、1-429、1-430、1-431、1-432、1-433、1-434、1-435、1-436、1-437、1-438、1-436、1-437、1-438、1-439、1-440、1-441、1-442、
1-443、1-444、1-445、1-446、1-447、1-450、1-451、1-452、1-453、1-456、
1-457、1-458、1-471、1-472、1-495、1-496、1-497、1-498、1-499、1-500、1-501、1-502、1-503、1-504、1-505、
1-506、1-507、1-508、1-509、1-510、1-511、1-512、1-513、1-514、1-515、1-517、
1-525、1-526、1-528、1-529、1-531、1-532、1-533、1-534、1-537、
1-550、1-551、1-552、1-553、1-554、1-558、1-559、1-565、1-567、1-568、1-569、
1-570、1-571、1-572、1-573、1-574、1-575、1-576、1-577、1-578、1-579、1-580、
1-581、1-582、1-583、1-584、1-598、1-616、1-621、1-622、1-623、1-624、1-630、1-631、1-632、1-634、1-635、1-636、1-642、1-661、1-663、1-674、1-697、1-700、1-702、1-703、1-704、1-715、1-727、1-728、1-729、1-730、1-737、1-738、1-740、1-741、1-742、1-743、1-744、1-745、1-746、1-747、1-748、1-749、1-750、1-751、1-752、1-753、1-754、1-755、1-756、1-757、1-758、1-761、1-764、1-765、1-766、1-767、1-768、1-769、1-770、3-4、4-1、4-4、4-10、4-13、4-14、4-15、5-11、6-1、6-2、6-3、6-7、6-8、6-9、6-19、6-22、6-23、6-29、6-30、6-34、6-35、6-37、6-39、7-2、7-3、7-28、7-50、7-52、7-53、7-54、8-1、8-2、8-3、8-4、8-5、8-6、8-7、8-8、8-9、8-13、8-14、8-15、8-30、8-31、8-32、8-33、8-34、8-35、8-36、8-37、8-38、8-42、8-43、8-44、8-59、8-60、8-61、8-62、8-63、8-64、8-65、8-66、8-67、8-68、8-69、8-70、8-71、8-72、8-73、8-74、8-75、8-76、8-77、8-78、8-79、8-80、8-81、8-82、8-83、8-84、8-85、8-86、8-87、8-88、8-89、8-90、8-92、8-93、8-95、8-96、8-97、8-98、8-99、8-100、8-104、8-105、8-108、8-110、8-113、8-115、8-116、8-117、8-118、8-119、8-120、8-122、8-123、8-124、8-125、8-126、8-128、
8-129、8-130、8-131、8-133、8-134、8-135、8-136、8-137、8-138、 8-139、8-140、
8-141、8-142、8-143、8-144、8-145、8-146、8-147、8-148、8-149、8-150、
8-151、8-152、8-153、8-154、8-155、8-156、8-157、8-158、8-159、8-160、
8-161、8-162、8-163、8-164、8-165、8-166、8-167、8-168、8-169、8-176、
8-177、8-178、8-179、8-180、8-181、8-182、8-183、8-184、8-185、8-186、
8-187、8-188、8-189、8-190、8-191、8-192、8-193、8-194、8-195、8-196、
8-197、8-198、8-199、8-200、8-201、8-202、8-204、8-206、8-207、8-208、
8-209、8-210、8-211、8-212、8-213、8-214、8-216、8-217、8-218、8-219、
8-220、8-221、8-222、8-224、8-225、8-226、8-227、8-228、8-229、8-230、
8-231、8-232、8-233、8-234、8-235、8-236、8-237、8-238、8-239、8-240、
8-241、8-242、8-243、8-244、8-245、8-246、8-247、8-248、8-249、8-250、
8-251、8-252、8-253、8-254、8-255、8-256、8-257、8-258、8-259、8-260、
8-264、8-265、8-266、8-267、8-268、8-269、8-270、8-271、8-272、8-273、
8-274、8-275、8-276、8-277、8-278、8-279、8-280、8-281、8-282、8-283、
8-284、8-285、8-287、8-292、8-293、8-294、8-295、8-297、8-298、8-312、
8-313、8-314、8-315、8-318、8-319、8-320、8-324、8-325、8-326、8-330、
8-331、8-332、8-333、8-334、8-335、8-336、8-337、8-338、8-339、8-340、
8-341、8-354、8-355、8-356、8-357、8-358、8-359、8-360、8-361、8-362、
8-363、8-364、8-365、8-366、8-367、8-368、8-369、8-370、8-371、8-372、
8-373、8-374、8-375、8-376、8-377、8-378、8-379、8-380、8-381、8-382、
8-383、8-390、8-391、8-392、8-393、8-394、8-395、8-396、8-397、8-398、
8-399、8-400、8-401、8-402、8-403、8-404、8-405、8-406、8-407、8-408、
8-409、8-410、8-411、8-412、8-413、8-414、8-415、8-416、8-417、8-418、
8-419、8-420、8-421、8-422、8-426、8-427、8-428、8-429、8-430、8-431、
8-432、8-433、8-434、8-438、8-439、8-440、8-444、8-445、8-446、8-450、
8-451、8-452、8-456、8-457、8-458、8-462、8-463、8-464、8-465、8-466、
8-467、8-468、8-469、8-470、8-471、8-472、8-473、8-474、8-475、8-476、
8-477、8-478、8-479、8-480、8-481、8-482、8-486、8-487、8-488、8-492、
8-493、8-494、8-495、8-496、8-497、8-498、8-499、8-500、8-501、8-502、
8-503、8-504、8-505、8-506、8-507、8-508、8-509、8-510、8-511、 8-513、
8-514、8-515、8-516、8-517、8-518、8-520、8-521、8-522、8-523、8-524、
8-525、8-526、8-527、8-528、8-529、8-530、8-532、8-533、8-534、8-535、
8-536、8-537、8-538、8-539、8-540、8-543、8-544、8-545、8-546、8-547、
8-548、8-549、8-550、8-551、8-558、8-559、8-560、8-561、8-562、8-563、
8-564、8-568、9-2、9-3、10-2、10-3、10-4、10-5、10-7、10-8、10-9、11-1、
11-2、11-3、11-10、11-13、12-7、12-8、12-9、12-11、12-12、16-1、16-2、
18-1、18-2、18-4、18-6、18-7、18-10、18-11、18-12、18-19、18-20、18-23、
18-25、18-26、18-27、18-30、18-31、18-32、18-33、18-37、18-40、18-41、
18-42、18-43、18-44、18-45、18-46、18-47、18-48、18-49、18-52、18-53、
18-54、18-55、18-58、18-59、18-60、18-61、18-62、18-63、18-64、18-66、
18-67、18-68、18-70、18-71、18-74、18-76、18-77、18-78、18-79、18-80、
18-81、18-82、18-86、18-88、18-89、18-90、18-91、18-92、18-93、
18-94、18-95、18-96、18-97、18-98、18-99、18-101、18-103、18-106、18-113、
18-114、18-115、18-116、18-119、18-120、18-122、18-125、18-126、
18-127、18-128、18-129、18-130、18-131、18-132、18-133、18-134、
18-137、18-138、18-139、18-140、18-144、18-148、18-150、18-151、
18-152、18-155、18-158、18-161、18-162、18-164、18-165、18-166、
18-167、18-168、18-169、18-176、18-177、18-178、18-179、18-180、
18-181、18-182、18-183、18-184、18-185、18-186、18-187、18-191、18-192、
18-194、18-195、18-196、18-197、18-198、18-199、18-200、18-201、
18-202、18-203、18-204、18-205、18-206、18-207、18-208、18-209、
18-210、18-211、18-212、18-213、18-216、18-217、
18-218、18-219、18-220、18-221、18-222、18-223、
18-224、18-225、18-226、18-245、18-246、18-247、18-248、18-249、
18-250、18-251、18-252、18-253、18-254、18-255、18-256、
18-257、18-258、18-259、18-260、18-263、18-264、18-265、
18-266、18-267、18-268、18-287、18-288、18-289、18-290、
18-291、18-293、18-294、18-295、18-296、18-297、18-298、
18-299、18-300、18-301、18-302、18-303、18-304、18-305、
18-306、18-307、18-308、18-309、18-310、18-323、18-324、18-330、18-331
18-332、18-333、18-334、18-350、18-351、18-352、18-353、18-354、18-355、
18-356、18-363、18-365、18-366、18-368、18-426、18-427、18-429、18-430、
18-431、18-447、18-462、18-465、18-468、18-469、18-470、18-471、18-474、
18-475、18-476、18-477、19-1、19-2、19-3、19-4、19-6、19-7、19-8、19-9、
19-10、19-11、19-12、19-49、19-50、19-51、19-52、19-67、19-70、19-73、
19-74、19-75、19-76、19-79、19-80、19-81、19-82、19-91、
21-5, 23-10, 24-2, 25-1, 25-2, 25-3, 25-9, 25-11, 25-12, 25-25, 25-27, 25-28, 25-29, 25-30, 25-35, 25-40, 26-4, 26-10, 26-11, 26-12, 26-15, 26-16, 28-16, 29-1, 29-2, 29-3, 29-4, 29-5, 29-6, 30-1, 30-2, 31-7, 31-8, 31-9, 31-10, 31-11, 31-12, 33-19, 33-20, 33-31, 33-32, 33-33, 33-34, 33-36, 33-56, The compound of 33-57,33-61,33-62,33-63,33-67,33-68,33-69,33-70,33-71,33-72,34-2,35-1,35-2,35-3,35-7,35-8,35-9,35-10,35-11,35-12,36-19,36-20,36-21 or 36-22 show the effect of A to Frankliniella occidentalis in 500ppm.
On the other hand, as compound is compared, effect of the compound number 153 recorded in WO/2005/095351 at 500ppm is E.It follows that the compounds of this invention compound compared with is compared, especially excellent insecticidal effect is shown to thrips class pest.
Insecticidal test of the test example 2. to diamondback moth (Plutella xylostella)
The adult that raising diamondback moth is placed in the Chinese cabbage actually grown makes its oviposition, after placing raising 2, it will impregnate about 30 seconds with the Chinese cabbage of ovum given birth to will be diluted in medical fluid made of 50ppm using the compound recorded in the 1st table~the 19th table, the 21st table, the 23rd table~the 31st table as the medicament of effective component, 25 DEG C of thermostatic chamber be statically placed in after air-drying.After medical fluid impregnates 6, investigation hatching borer population calculates dead worm rate by following formula, is determined according to following standards.10 pests are divided into 3 groups to test.
[mathematical expression 2]
Criterion
The dead worm rate 100% of A ...
The dead worm rate 99%~90% of B ...
The dead worm rate 89%~80% of C ...
The dead worm rate 79%~50% of D ...
The dead worm rate 49%~0% of E ...
As above-mentioned test as a result, compound number 1-4,1-5,1-6,1-7,1-10,1-13,1-16,1-19,
1-22、1-34、1-37、1-46、1-49、1-53、1-56、1-58、1-59、1-60、1-61、1-62、
1-63、1-64、1-65、1-66、1-67、1-68、1-69、1-70、1-72、1-73、1-74、1-75、
1-79、1-80、1-81、1-82、1-83、1-84、1-85、1-86、1-87、1-88、1-91、1-94、
1-95、1-96、1-97、1-98、1-99、1-100、1-101、1-102、1-103、1-104、1-105、
1-106、1-107、1-108、1-112、1-113、1-114、1-115、1-116、1-117、1-118、1-119、1-124、1-128、1-134、1-137、1-138、1-139、1-146、1-147、1-148、1-149、1-150、1-151、1-161、1-162、1-163、1-164、1-166、1-167、1-168、1-169、1-170、1-172、1-173、1-174、1-175、1-176、1-177、1-178、1-179、1-180、1-190、1-193、1-195、1-196、1-197、1-198、1-199、1-200、1-201、1-202、1-203、1-204、1-205、1-206、1-207、1-208、1-209、1-210、1-211、1-212、1-214、1-215、1-216、1-217、1-221、1-222、1-223、1-224、1-227、1-228、1-229、1-230、1-231、1-232、1-233、1-236、1-237、1-238、1-239、1-240、1-241、1-242、1-243、1-244、1-245、1-246、1-247、1-248、1-249、1-250、1-251、1-252、1-253、1-254、1-255、1-256、1-257、1-260、1-262、1-263、1-264、1-265、1-266、1-268、1-269、1-270、1-271、1-273、1-274、1-275、1-276、1-277、1-280、1-281、1-282、1-283、1-284、1-285、1-286、1-287、1-288、1-289、1-290、1-291、1-292、1-293、1-294、1-295、1-307、1-308、1-310、1-311、1-313、1-314、1-315、1-316、1-317、1-318、1-319、1-329、1-332、1-335、1-336、1-337、1-338、1-339、1-340、1-341、1-342、1-343、1-344、1-345、1-346、1-347、1-348、1-349、1-350、1-351、1-352、1-353、1-354、1-357、1-358、1-359、1-360、1-361、1-362、1-363、1-364、1-365、1-366、1-367、1-368、1-369、1-370、1-371、1-372、1-373、1-374、1-375、1-376、1-377、1-378、1-379、1-380、1-381、1-382、1-383、 1-384、1-385、1-386、1-387、1-388、1-389、1-390、1-391、1-392、1-393、1-394、1-395、1-396、1-397、1-398、1-399、1-400、1-401、1-402、1-403、1-404、1-405、1-406、1-407、1-408、1-409、1-410、1-411、1-412、1-413、1-414、1-415、1-416、1-417、1-418、1-419、1-420、1-423、1-424、1-425、1-426、1-427、1-428、1-430、1-433、1-436、1-439、1-442、1-445、1-471、1-474、1-495、1-496、1-497、1-498、1-499、1-500、1-501、1-502、1-503、1-504、1-505、1-506、1-507、1-508、1-509、1-510、1-511、1-512、1-513、1-514、1-515、1-516、1-517、1-518、1-528、1-531、1-534、1-537、1-538、1-539、1-540、1-541、1-542、1-543、1-544、
1-545、1-546、1-547、1-548、1-597、1-598、1-599、1-600、1-601、1-604、
1-606、1-609、1-610、1-612、1-613、1-614、1-616、1-617、1-618、1-619、
1-620、1-621、1-622、1-623、1-624、1-625、1-626、1-627、1-630、1-631、
1-632、1-633、1-634、1-635、1-636、1-637、1-640、1-641、1-642、1-643、
1-644、1-645、1-646、1-647、1-648、1-649、1-650、1-651、1-652、1-653、
1-656、1-657、1-659、1-660、1-662、1-663、1-664、1-665、1-666、1-667、
1-668、1-669、1-670、1-671、1-672、1-673、1-674、1-675、1-677、1-678、
1-680、1-681、1-682、1-683、1-684、1-685、1-687、1-688、1-696、1-697、
1-698、1-699、1-700、1-701、1-702、1-703、1-704、1-705、1-706、1-707、
1-708、1-709、1-710、1-711、1-712、1-714、1-715、1-737、2-4、 2-5、2-6、3-4、4-1、4-2、4-3、4-4、4-5、4-6、4-10、4-11、4-12、4-13、4-14、4-15、5-1、5-2、5-4、5-5、5-6、5-7、5-8、5-9、5-10、5-11、5-12、5-13、5-14、5-15、
5-16、5-17、5-18、5-19、5-20、5-21、5-22、5-23、5-24、5-25、5-26、5-27、
6-1、6-2、6-3、6-4、6-6、6-7、6-10、6-11、6-12、6-19、6-22、
6-33、6-34、6-37、
7-1、7-2、7-3、7-7、7-8、7-9、7-10、7-11、7-12、7-13、7-14、7-15、7-19
7-22、7-23、7-24、7-25、7-26、7-27、7-28、7-29、7-30、7-31、7-32、7-34、
7-36、7-37、7-38、7-40、7-41、7-42、7-43、7-44、7-45、7-46、7-47、7-48、
7-56、7-57、
8-1、8-2、8-3、8-4、8-5、8-6、8-13、8-14、8-15、
8-30、8-31、8-32、8-33、8-34、8-35、8-36、8-37、8-38、8-39、8-40、
8-41、8-42、8-43、8-44、8-59、8-60、8-61、8-62、8-63、8-64、8-65、8-66、8-67、8-68、8-69、8-70、8-71、8-72、8-73、8-74、8-75、8-76、8-77、8-78、8-79、8-80、8-81、8-82、8-83、8-84、8-85、8-86、8-87、8-88、8-89、8-90、8-91、8-92、8-93、8-94、8-95、8-96、8-97、8-98、8-99、8-100、
8-101、8-102、8-103、8-104、8-105、8-106、8-107、8-108、8-109、8-110、8-111、8-112、8-113、8-114、8-115、8-116、8-117、8-118、8-119、8-120、8-121、8-122、8-123、8-124、8-125、8-126、8-127、8-128、8-129、8-130、8-131、8-132、8-133、8-134、8-135、8-136、8-137、8-138、8-139、8-140、8-141、8-142、8-143、8-144、8-145、8-146、8-147、8-148、8-149、8-150、8-151、8-152、8-153、8-154、8-155、
8-156、8-157、8-158、8-159、8-160、8-161、8-162、8-163、8-164、8-165
8-166、8-167、8-168、8-169、8-176、8-177、8-178、8-179、8-180、8-181、8-182、8-183、8-184、8-185、8-186、8-187、8-188、8-189、8-190、8-191、
8-192、8-193、8-194、8-195、8-196、8-197、8-198、8-199、8-200、
8-201、8-202、8-203、8-204、8-205、8-206、8-207、8-208、8-209、8-210、8-211、8-212、8-213、8-214、8-215、8-216、8-217、8-218、8-219、8-220、8-221、8-222、8-223、8-224、8-225、8-226、8-227、8-228、8-229、8-230、8-231、8-232、8-233、8-234、8-235、8-236、8-237、8-238、8-239、8-240、8-241、8-243、8-244、
8-245、8-246、8-247、8-248、8-249、8-250、8-251、8-253、
8-255、8-256、8-258、8-264、8-265、8-267、8-268
8-270、8-271、8-274、8-277、8-280、8-283
8-312、8-313、8-314、8-315、8-316、8-317、8-318、8-319、8-320、8-321、8-322、8-323、8-324、8-325、8-326、8-327、8-328、8-329、8-330、8-331、8-332、8-333、8-334、8-335、8-336、8-337、8-338、8-339、8-340、8-341、
8-463、8-466、8-469、8-472、8-475、8-478、8-505、8-507、
8-510、8-513、8-516、8-519、8-522、8-525、8-528、8-531、8-534、8-537、
9-1、9-2、9-3、9-4、9-5、9-6、
10-1、10-2、10-3、10-4、10-5、10-6、10-7、10-8、10-9、
11-1、11-2、11-3、11-4、11-5、11-6、11-7、11-8、11-9、11-10、11-11、11-12、11-13、11-16、11-19、11-20、11-22、11-23、11-24、11-25、11-26、11-27、
12-1、12-4、12-7、12-8、12-9、12-10、12-11、12-12、13-1、13-2、13-3、13-4、13-5、13-6、13-7、13-8、13-9、13-10、13-11、13-12、15-4、16-1、16-2、16-3、16-7、16-8、16-9、16-10、16-11、 16-12、17-3、17-6、
18-1、18-2、18-3、18-4、18-5、18-6、18-7、18-8、18-9、18-10、18-11、18-12、18-19、18-20、18-21、18-22、18-23、18-24、18-25、18-26、18-27、18-28、18-29、18-30、18-31、18-32、18-33、18-37、18-38、18-39、18-40、
18-41、18-42、18-43、18-44、18-45、18-46、18-47、18-48、18-49、
18-52、18-53、18-54、18-55、18-56、18-58、18-59、18-60、18-61、18-62、
18-63、18-64、18-65、18-66、18-67、18-68、18-69、18-70、18-71、18-72、
18-73、18-74、18-75、18-76、18-77、18-78、18-79、18-80、18-81、18-82、
18-86、18-88、18-89、18-90、18-91、18-92、18-93、18-94、18-95、18-96、
18-97、18-98、18-99、18-100、18-101、18-102、18-103、18-104、18-105、18-106、
18-113、18-114、18-115、18-116、18-119、18-120、18-121、18-122、18-125、
18-126、18-127、18-128、18-129、18-130、18-131、18-132、18-133、18-134、18-137、18-138、18-139、18-140、18-144、18-146、18-148、18-149、18-150、18-151、
18-152、18-154、18-155、18-156、18-157、18-158、18-159、18-161、
18-162、18-163、18-164、18-165、18-166、18-167、18-168、18-169、
18-176、18-177、18-178、18-179、18-180、18-181、18-182、18-183、
18-184、18-185、18-186、18-187、18-192、18-194、18-195、18-196、
18-197、18-198、18-199、18-200、18-201、18-202、18-203、18-204、
18-205、18-206、18-207、18-208、18-209、18-210、18-211、18-213、
18-216、18-219、18-221、18-222、18-223、18-224、18-225、18-226、
18-245、18-246、18-247、18-248、18-249、18-250、
18-252、18-255、18-258、18-260、18-264、18-267、
18-288、18-291、18-294、18-297、18-300、18-303、18-305、18-306、18-307、
18-308、18-309、18-310、18-323、18-324、18-325、18-326、18-327、
18-328、18-329、18-330、18-331、18-332、18-333、18-334、
18-351、18-354、18-356、18-364、18-366、18-426、18-427、18-428、18-429、
18-430、18-431、18-445、18-447、18-463、18-465、18-469、18-471、
18-475、18-477、19-1、19-2、19-3、19-4、19-5、19-6、19-8、19-11、19-20、19-23、19-50、19-52、19-67、19-70、19-74、19-76、19-80、19-84、19-91、
21-5、23-2、23-4、23-5、23-7、23-10、23-19、
24-1, 24-2, 24-3, 24-4, 24-5, 24-6, 25-1, 25-2, 25-3, 25-4, 25-5, 25-6, 25-7, 25-8, 25-9, 25-10, 25-11, 25-12, 25-13, 25-14, 25-15, 25-16, 25-17, 25-18, 25-19, 25-22, 25-25, 25-26, 25-27, 25-28, 25-29, 25-30, 25-31, 25-32, 25-33, 25-34, 25-35, 25-36, 25-37, 25-38, 25-39, 25-40, 25-41, 25-42, 25-43, 2 5-44, 25-45, 25-46, 25-47, 25-48, 26-2, 26-3, 26-4, 26-5, 26-6, 26-7, 26-8, 26-9, 26-10, 26-11, 26-12, 26-13, 26-14, 26-15, 26-16, 26-17, 26-18, 26-19, 27-14, 27-15, 27-16, 28-13, 28-16, 29-1, 29-2, 29-3, 29-4, 29-5, 29-6, 30-1, 30-2, 30-3, 30-4, 31-7, 31-8, 31-9, 31-10, 31-11, 31-12, 34-2, 34-5, 36-2 0 and
The compound of 36-22 shows the effect of A to diamondback moth in 50ppm.
Insecticidal test of the test example 3. to Spodoptera litura (Spodoptera litura)
Cabbage leaves (kind: the four seasons are obtained), which are immersed in, to be diluted in medical fluid made of 500ppm about 30 seconds using the compound recorded in the 1st table~the 19th table, the 21st table, the 23rd table~the 31st table as the medicament of effective component, it is put into the vinyl disc of diameter 9cm after air drying, after being inoculated with the larva of the Spodoptera litura of the second age, it closes the lid, is statically placed in 25 DEG C of thermostatic chamber.After inoculation 8 days, the borer population of life and death is investigated, calculates dead worm rate by following formula, criterion is carried out according to test example 1.10 pests are divided into 3 groups to test.
[mathematical expression 3]
As above-mentioned test as a result, compound number 1-4,1-5,1-6,1-7,1-10,1-19,1-34,1-46,1-52,1-54,1-55,1-57,1-58,1-59,1-60,1-61,1-62,1-63,1-64,1-65,1-66,1-67,1-68,1-69,1-70,1-73,1-74,1-75,1-79,1-80,1-81,1-82,1-83,1-84,1-85,1-86,1-87,1-88,1-91,1-94,1-95,1-96,1-97,1-98,1-99,1-100,1-101,1-102,1- 103,1-104,1-105,1-106,1-107,1-108,1-112,1-113,1-114,1-115,1-116,1-117,1-118,1-119,1-124,1-128,1-134,1-137,1-138,1-139,1-146,1-147,1-148,1-149,1-150,1-151,1-161,1-162,1-163,1-164,1-166,1-167,1-168,1-169,1-170,1-171,1-172,1-173,1-174,1-175,1-176,1-177,1-178, 1-179,1-180,1-190,1-193,1-194,1-195,1-196,1-197,1-198,1-199,1-200,
1-201、1-202、1-203、1-204、1-205、1-206、1-207、1-208、1-209、1-210、1-211、1-212、1-214、1-215、1-216、1-217、1-221、1-222、1-223、1-224、1-227、1-228、1-229、1-230、1-231、1-232、1-233、1-236、1-237、1-238、1-239、1-240、1-241、1-242、1-243、1-244、1-245、1-246、1-247、1-248、1-249、1-250、1-251、1-252、1-253、1-254、1-255、1-256、1-257、1-260、1-261、1-262、1-263、1-264、1-265、1-266、1-268、1-269、1-270、1-271、1-272、1-273、1-275、1-276、1-277、1-280、1-281、1-282、1-283、1-284、1-285、1-286、1-287、1-288、1-289、1-290、1-291、1-292、1-293、1-294、1-295、1-307、1-308、1-309、1-310、1-311、1-312、1-313、1-314、1-315、1-317、1-318、1-319、1-329、1-332、1-335、1-336、1-337、1-338、1-339、1-340、1-341、1-342、1-343、1-344、1-345、1-346、1-347、1-348、1-349、1-350、1-351、1-352、1-353、1-354、1-357、1-358、 1-359、1-360、1-361、1-362、1-364、1-366、1-367、1-368、1-369、1-370、1-371、1-372、1-373、1-374、1-375、1-376、1-377、1-378、1-379、1-380、1-381、1-382、1-383、1-384、1-385、1-386、1-387、1-388、1-389、1-390、1-391、1-392、1-393、1-394、1-395、1-396、1-397、1-398、1-399、1-400、1-401、1-402、1-403、1-404、1-405、1-406、1-407、1-408、1-409、1-410、1-411、1-412、1-413、1-414、1-415、1-416、1-417、1-418、1-419、1-420、1-423、1-424、1-425、1-426、1-427、1-428、1-429、1-430、1-431、1-432、1-433、1-434、1-435、1-436、1-437、1-438、1-440、1-441、1-442、1-443、1-444、1-445、1-446、1-452、1-457、1-458、1-471、1-472、1-474、
1-495、1-496、1-497、1-498、1-499、1-500、1-501、1-502、1-503、1-504、1-505、1-506、1-507、1-508、1-509、1-510、1-511、1-512、1-513、1-514、1-515、1-516、1-517、1-518、1-525、1-526、1-527、1-528、1-529、1-530、1-531、1-532、1-533
1-534、1-537、1-538、1-539、1-540、1-541、1-542、1-543、1-544、1-545、1-546、1-547、1-548、1-549、1-550、1-551、1-552、1-553、1-554、1-555、1-556、
1-557、1-559、1-560、1-561、1-562、1-563、1-564、1-565、1-566、1-567、
1-568、1-569、1-570、1-571、1-572、1-573、1-574、1-575、1-576、1-577、
1-578、1-579、1-580、1-581、1-582、1-583、1-584、1-597、1-598、1-599、1-600、1-601、1-604、1-606、1-607、1-609、1-612、1-613、1-615、1-616、1-617、1-618、1-621、1-622、1-623、1-624、1-625、1-626、1-627、1-628、1-629、1-630、
1-631、1-632、1-633、1-634、1-635、1-636、1-637、1-638、1-639、1-640、1-641、1-642、1-643、1-644、1-645、1-646、1-647、1-648、1-649、1-650、
1-651、1-652、1-654、1-657、1-658、1-659、1-661、1-662、1-663、 1-664、1-665、1-666、1-667、1-668、1-669、1-670、1-671、1-672、1-673、1-674、1-675、1-676、1-677、1-678、1-679、1-680、1-681、1-682、1-683、1-684、1-685、1-686、1-687、1-688、1-689、1-696、1-697、1-698、1-699、1-700、1-701、1-702、1-703、1-704、1-706、1-707、1-708、1-709、1-710、1-711、1-712、1-715、1-716、1-717、1-719、1-721、1-722、1-723、1-724、1-725、1-726、1-727、1-728、1-729、1-730、1-737、1-738、1-739、1-740、1-742、1-743、1-744、1-745、1-746、1-747、1-748、1-749、
1-750、1-751、1-753、1-754、1-755、1-756、1-757、1-758、1-761、1-764、
1-765、1-766、1-767、1-768、1-769、1-770、1-771、1-772、1-773、1-774、
1-775、1-776、1-777、1-778、1-779、1-780、1-781、1-782、1-783、1-784、
1-785、1-786、1-787、1-788、1-789、1-790、1-791、1-792、1-793、1-794、
1-795、1-796、1-797、1-798、1-799、1-800、1-801、1-802、1-803、1-804、
1-805、1-806、1-807、1-808、1-809、1-810、1-811、1-812、1-813、1-814、
1-815、1-816、1-817、1-818、1-819、1-820、1-821、1-822、1-823、
2-4、2-5、2-6、3-4、4-1、4-2、4-3、4-4、4-5、4-6、4-10、4-11、4-12、4-13、4-14、4-15、5-1、5-2、5-4、5-5、5-6、5-7、5-8、5-9、5-10、5-11、5-12、5-13、5-14、5-15、5-16、5-19、5-21、5-23、5-24、6-1、6-2、6-3、6-4、6-6、6-10、6-11、6-12、7-7、7-8、7-9、7-10、7-11、7-12、7-13、7-14、7-15、8-1、8-2、8-3、8-4、8-5、8-6、8-13、8-14、8-15、8-34、8-35、8-36、8-37、8-38、8-39、8-40、8-41、8-42、8-43、8-44、8-59、8-60、8-61、8-62、8-63、8-64、8-65、8-66、8-67、8-68、8-69、8-70、8-71、8-72、8-73、8-74、8-75、8-76、8-77、8-78、 8-79、8-80、8-81、8-82、8-83、8-84、8-85、8-86、8-87、8-88、8-89、8-90、8-91、8-92、8-93、8-94、8-96、8-97、8-99、8-100、8-101、8-102、8-103、8-104、8-105、8-106、8-107、8-108、8-109、8-110、8-111、8-112、8-113、8-114、8-115、8-116、8-117、8-118、8-119、8-120、8-121、8-122、8-123、8-124、8-125、8-126、8-127、8-128、8-129、8-130、8-131、8-132、8-133、
8-134、8-135、8-136、8-137、8-138、8-139、8-140、8-141、8-142、8-143、8-144、8-145、8-146、8-147、8-148、8-149、8-150、8-151、8-152、8-153、8-157、8-158、8-159、8-154、8-155、8-156、8-166、8-167、8-168、8-169、8-181、8-182、8-183、8-178、8-179、8-180、8-184、8-185、8-186、8-187、8-188、8-189、8-190、8-191、8-192、8-193、8-194、8-195、8-196、8-197、8-198、8-199、8-200、8-201、8-202、8-203、8-208、8-209、8-210、8-211、8-212、8-213、8-214、8-215、8-216、8-217、8-218、8-219、8-220、8-221、8-222、8-223、8-224、8-225、8-226、8-227、8-228、8-229、8-230、8-231、8-232、8-233、8-234、8-235、8-239、8-246、8-258、8-264、8-273、8-312、8-313、8-308、8-305、8-306、8-307、8-302、8-304、8-317、8-318、8-319、8-314、8-315、8-316、8-323、8-324、8-325、8-320、8-321、8-322、8-328、8-329、8-330、8-326、8-327、8-328、8-329、8-330、8-331、8-332、8-333、8-334、8-335、8-336、8-337、8-338、8-339、8-340、8-341、8-354、8-355、8-356、8-357、8-358、8-359、8-360、8-361、8-362、8-363、8-364、8-365、8-366、8-367、8-368、8-369、8-370、8-371、8-372、8-373、8-374、8-375、8-376、8-377、8-378、8-379、8-380、8-381、8-382、8-383、8-390、8-391、8-392、8-393、8-394、8-395、8-396、8-397、8-398、8-399、8-400、8-401、8-402、8-403、8-404、8-405、8-406、8-407、8-408、8-409、8-410、8-411、8-412、8-413、8-414、8-415、8-416、8-417、8-418、8-419、8-420、8-421、8-422、8-426、8-427、8-428、8-429、8-430、8-431、8-432、8-433、8-434、8-438、8-439、8-440、8-444、8-445、8-446、8-450、 8-451、8-452、8-456、8-457、8-458、8-462、8-463、8-464、8-465、8-466、8-467、8-468、8-469、8-470、8-471、8-472、8-473、8-474、8-475、8-476、8-477、8-478、8-479、8-480、8-481、8-482、8-486、8-487、8-488、8-492、8-493、8-494、8-495、8-496、8-497、8-498、8-499、8-500、8-501、8-502、8-503、8-504、8-506、8-507、8-508、8-509、8-510、8-511、8-512、8-513、8-514、8-515、8-516、8-517、8-518、8-519、8-520、8-521、8-522、8-523、8-524、8-525、8-526、8-527、8-528、8-529、8-530、8-531、8-532、8-533、8-535、8-536、8-540、8-541、8-542、8-543、8-544、8-545、8-546、8-547、8-548、8-549、8-550、8-551、8-558、8-559、8-560、8-561、8-562、8-563、8-564、8-565、8-566、8-567、8-568、8-569、9-1、9-2、9-3、9-4、9-5、9-6、10-1、10-2、10-3、10-4、10-5、10-6、10-7、10-8、10-9、11-1、11-2、11-3、11-4、11-5、11-6、11-7、11-8、11-9、11-10、11-11、11-12、11-13、11-16、11-25、11-26、11-27、12-1、12-4、12-7、12-8、12-9、12-10、12-11、12-12、13-7、13-8、13-9、13-10、13-11、13-12、14-1、16-1、16-3、16-7、16-8、16-9、16-10、16-11、16-12、17-3、18-1、18-2、18-3、18-4、18-5、18-6、18-7、18-8、18-9、
18-10、18-11、18-12、18-19、18-20、18-21、18-22、18-23、18-24、18-25、18-26、
18-27、18-28、18-29、18-30、18-31、18-32、18-38、18-39、18-40、18-41、
18-42、18-43、18-33、18-37、18-44、18-45、18-46、18-47、
18-48、18-49、18-52、18-53、18-54、18-55、18-56、18-58、18-59、18-60、
18-61、18-62、18-63、18-64、18-65、18-66、18-67、18-68、18-69、18-70、
18-71、18-72、18-73、18-74、18-75、18-76、18-77、18-78、
18-79、18-80、18-81、18-82、18-88、18-89、18-90、18-91、
18-92、18-93、18-94、18-95、18-96、18-97、18-98、18-99、
18-100、18-101、18-102、18-103、18-104、18-105、18-106、18-113、
18-114、18-115、18-116、18-119、18-120、18-121、18-122、18-125、
18-126、18-127、18-128、18-129、18-130、18-131、18-133、18-134、
18-137、18-138、18-139、18-140、18-144、18-145、18-146、18-148、
18-149、18-150、18-151、18-152、18-154、18-156、18-157、18-158、
18-159、18-161、18-162、18-163、18-164、18-165、18-166、18-167、
18-168、18-169、18-176、18-177、18-178、18-179、18-180、18-181、
18-182、18-183、18-184、18-185、18-186、18-187、18-192、18-194、
18-195、18-196、18-197、18-198、18-199、18-200、18-201、18-202、
18-203、18-204、18-205、18-206、18-207、18-208、18-209、18-210、
18-211、18-213、18-216、18-219、18-221、18-222、18-223、18-224、
18-225、18-226、18-245、18-246、18-247、18-248、18-249、18-250、
18-291、18-294、18-297、18-305、18-306、18-307、18-308、18-309、
18-310、18-323、18-324、18-325、18-326、18-327、18-328、18-329、
18-331、18-332、18-333、18-334、18-350、18-352、18-353、18-354、18-355、18-356、18-363、18-365、18-366、18-368、18-444、18-445、18-446、18-447、18-462、18-464、18-468、18-470、18-474、18-476、18-477、19-1、19-2、19-3、19-4、19-5、19-6、19-8、19-11、19-12、19-19、19-22、19-24、19-49、19-50、19-51、19-52、19-67、19-70、19-73、9-74、19-75、19-76、19-79、19-80、19-81、19-82、19-84、19-91、23-7、23-8、23-9、23-10、23-19、23-20、23-21、23-22、23-8、23-9、23-10、23-19、23-20、23-21、23-22、23-23、23-24、23-25、23-26、23-27、23-28、23-37、23-38、23-39、24-1、24-2、24-3、24-4、24-5、24-6、25-1、25-2、25-3、25-4、25-5、25-6、25-7、25-8、25-9、25-10、25-11、25-12、25-13、25-14、25-15、25-16、25-17、25-18、25-19、25-22、25-25、25-26、25-27、25-28、25-29、25-30、25-31、25-32、25-33、25-34、25-35、25-36、25-37、25-38、25-39、25-40、25-41、25-42、25-43、25-44、25-45、25-46、25-47、25-48、26-2、 26-4、26-5、26-6、26-7、26-8、26-9、26-10、26-11、26-12、26-13、26-14、26-15、26-16、26-17、26-18、26-19、28-1、28-3、28-4、28-5、28-6、28-7、28-8、28-9、28-10、28-11、28-12、28-13、28-16、28-17、28-18、28-19、28-20、28-21、28-22、28-23、28-31、28-32、28-33、28-34、28-36、28-37、28-38、28-39、28-40、28-41、28-42、29-1、29-2、29-3、29-4、29-5、29-6、30-1、30-2、30-3、30-4、31-7、31-8、31-9、31-10、31-11、31-12、33-19、33-20、33-31、33-32、33-33、33-34、33-35、33-36、33-55、33-56、33-57、33-61、33-62、33-63、33-67、33-68、33-69、33-70、33-71、33-72、34-1、34-2、34-3、34-4、35-1、35-2、35-3、35-7、35-8、
The compound of 35-9,35-10,35-11,35-12,36-19,36-20,36-21 and 36-22 show the effect of A to Spodoptera litura at 500ppm.
Insecticidal test of the test example 4. to tea olethreutid (Adoxophyes sp.)
Tealeaves, which is immersed in, to be diluted in medical fluid made of 500ppm about 30 seconds using the compound recorded in the 1st table~the 19th table, the 21st table, the 23rd table~the 31st table as the medicament of effective component, it is put into the vinyl disc of diameter 9cm after air drying, after being inoculated with tea olethreutid larva, it is statically placed in the thermostatic chamber of 25 DEG C, humidity 70%.After inoculation 8 days, life and death borer population is investigated, is carried out similarly judgement with test example 3.10 pests are divided into 3 groups to test.
As above-mentioned test as a result, compound number 1-1,1-4,1-5,1-6,1-10,1-19,1-31,1-34,1-37,1-46,1-49,1-52,1-54,1-55,1-56,1-57,1-58,1-59,1-60,1-61,1-62,1-63,1-64,1-65,1-66,1-67,1-68,1-69,1-70,1-72,1-73,1-74,1-75,1-79,1-80,1-81,1-82,1-83,1-84,1-85,1-86,1-87,1-88,1-91,1-94,1-95,1-96,1-97,1-98, 1-99,1-100,
1-101、1-102、1-103、1-104、1-105、1-106、1-107、1-108、1-112、1-113、1-114、1-115、1-116、1-117、1-118、1-119、1-124、1-128、1-134、1-137、1-138、1-139、1-146、1-147、1-148、1-149、1-150、1-151、1-161、1-162、1-163、1-164、1-166、1-167、1-168、1-169、 1-170、1-171、1-172、1-173、1-174、1-175、1-176、1-177、1-178、1-179、1-180、1-190、1-193、1-194、1-195、1-196、1-197、1-198、1-199、1-200、1-201、1-202、1-203、1-204、1-205、1-206、1-207、1-208、
1-209、1-210、1-211、1-212、1-213、1-214、1-215、1-216、1-217、1-221、1-222、1-223、1-224、1-227、1-228、1-229、1-230、1-231、1-232、1-233、1-236、1-237、1-238、1-239、1-240、1-241、1-242、1-243、1-244、1-245、1-246、1-247、1-248、1-249、1-250、1-251、1-252、1-253、1-254、1-255、1-256、1-257、1-260、1-261、1-262、1-263、1-264、1-265、1-266、1-268、1-269、1-270、1-271、1-272、1-273、1-274、1-275、1-276、1-277、1-280、1-281、1-282、1-283、1-284、1-285、1-286、1-287、1-288、1-289、1-290、1-291、1-292、1-293、1-294、1-295、
1-307、1-308、1-309、1-310、1-311、1-312、1-313、1-314、1-315、1-317、1-318、1-319、1-329、1-332、1-335、1-336、1-337、1-338、1-339、1-340、1-341、1-342、1-343、1-344、1-345、1-346、1-347、1-348、1-349、1-350、
1-351、1-352、1-353、1-354、1-357、1-358、1-359、1-360、1-361、1-362、1-363、
1-364、1-365、1-366、1-367、1-368、1-369、1-370、1-371、1-372、1-373、1-374、1-375、1-376、1-377、1-378、1-379、1-380、1-381、1-382、1-383、
1-384、1-385、1-386、1-387、1-388、1-389、1-390、1-391、1-392、1-393、1-394、1-395、1-396、1-397、1-398、1-399、1-400、1-401、1-402、1-403、1-404、1-405、1-406、1-407、1-408、1-409、1-410、1-411、1-412、1-413、1-414、1-415、1-416、1-417、1-418、1-419、1-420、1-423、1-424、1-425、1-426、1-427、1-428、
1-429、1-430、1-431、1-432、1-433、1-434、1-435、1-436、1-437、1-438、
1-439、1-440、1-441、1-442、1-443、1-444、1-445、1-446、1-451、1-452、1-457、1-458、1-471、1-472、1-474、1-495、1-496、1-497、1-498、1-499、1-500、1-501、1-502、1-503、1-504、1-505、1-506、1-507、1-508、1-509、1-510、1-511、1-512、1-513、1-514、1-515、1-516、1-517、1-518、
1-525、1-526、1-527、1-528、1-529、1-530、1-531、1-532、1-533
1-534、1-537、1-538、1-539、1-540、1-541、1-542、1-543、1-544、1-545、1-546、1-547、1-548、1-549、1-550、1-551、1-552、1-553、1-554、1-555、1-556、
1-557、1-559、1-560、1-561、1-562、1-563、1-564、1-565、1-566、1-567、
1-568、1-569、1-570、1-571、1-572、1-573、1-574、1-575、1-576、1-577、
1-578、1-579、1-580、1-581、1-582、1-583、1-584、
1-597、1-598、1-599、1-600、1-601、1-604、1-606、1-607、1-609、1-612、1-613、1-614、
1-615、1-616、1-617、1-618、1-619、1-620、1-621、1-622、1-623、1-624、1-625、1-626、1-627、1-628、1-629、1-630、1-631、1-632、1-633、1-634、1-635、1-636、1-637、1-638、1-639、1-640、1-641、1-642、1-643、1-644、1-645、1-646、1-647、1-648、1-649、1-650、1-651、1-652、1-654、1-657、1-658、1-659、1-660、1-6611-662、1-663、1-664、1-665、1-666、1-667、1-668、1-669、1-670、1-671、1-672、1-673、1-674、1-675、1-676、1-677、1-678、1-679、1-680、1-681、1-682、1-683、1-684、1-685、1-686、1-687、1-688、1-689、1-696、1-697、1-698、1-699、1-700、1-701、1-702、1-703、1-704、1-706、1-707、1-708、1-709、1-710、1-711、1-712、1-715、1-716、1-717、1-719、1-721、1-722、
1-723、1-724、1-725、1-726、1-727、1-728、1-729、1-730、1-737、1-738、
1-739、1-740、1-742、1-743、1-744、1-745、1-746、1-747、1-748、1-749、
1-750、1-751、1-753、1-754、1-755、1-756、1-757、1-758、1-761、1-764、
1-765、1-766、1-767、1-768、1-769、1-770、1-771、1-772、1-773、1-774、
1-775、1-776、1-777、1-778、1-779、1-780、1-781、1-782、1-783、1-784、
1-785、1-786、1-787、1-788、1-789、1-790、1-791、1-792、1-793、1-794、
1-795、1-796、1-797、1-798、1-799、1-800、1-801、1-802、1-803、1-804、
1-805、1-806、1-807、1-808、1-809、1-810、1-811、1-812、1-813、1-814、
1-815、1-816、1-817、1-818、1-819、1-820、1-821、1-822、1-823、
2-4、2-5、2-6、3-4、4-1、4-2、4-3、4-4、4-5、4-6、4-10、4-11、4-12、4-13、4-14、4-15、5-5、5-6、5-7、5-8、5-9、5-10、5-11、5-12、5-13、5-14、5-15、5-16、5-17、5-18、5-19、5-20、5-21、5-22、5-23、5-24、5-25、5-26、
6-1、6-2、6-3、6-4、6-6、6-7、6-8、6-9、6-10、6-11、6-12、6-19、6-20、6-21、6-22、6-23、6-24、6-29、6-30、6-32、6-33、6-34、6-35、6-36、6-37、6-38、6-39、7-1、7-2、7-3、7-7、7-8、7-9、7-10、7-11、7-12、7-13、7-14、7-15、
7-16、7-18、7-19、7-22、7-23、7-24、7-25、7-26、7-27、7-28、
7-29、7-30、7-31、7-34、7-36、7-37、7-40、7-41、7-42、7-43、
7-44、7-45、7-46、7-47、7-48、7-49、7-50、7-51、7-52、7-53、
7-54、7-55、7-56、7-57、8-1、8-2、8-3、8-4、8-5、8-6、8-7、8-8、8-9、
8-13、8-14、8-15、8-30、8-31、8-32、8-33、8-34、8-35、8-36、 8-37、8-38、8-39、8-40、8-41、8-42、8-43、8-44、8-59、8-60、8-61、8-62、8-63、8-64、8-65、8-66、8-67、8-68、8-69、8-70、8-71、8-72、8-73、8-74、8-75、8-76、8-77、8-78、8-79、8-80、8-81、8-82、8-83、8-84、8-85、8-86、8-87、8-88、8-89、8-90、8-91、8-92、8-93、8-94、8-95、8-96、8-97、8-98、8-99、8-100、8-101、8-102、8-103、8-104、8-105、8-106、8-107、8-108、8-109、8-110、8-111、8-112、8-113、8-114、8-115、8-116、8-117、8-118、8-119、8-120、8-121、8-122、8-123、8-124、8-125、8-126、8-127、8-128、8-129、8-130、8-131、8-132、8-133、8-134、8-135、8-136、8-137、8-138、8-139、8-140、8-141、8-142、8-143、8-144、8-145、8-146、8-147、8-148、8-149、8-150、8-151、8-152、8-153、8-154、8-155、8-156、8-157、8-158、
8-159、8-160、8-162、8-163、8-164、8-165、8-166、8-167、8-168、8-169、8-176、8-177、8-178、8-179、8-180、8-181、
8-182、8-183、8-184、8-185、8-186、8-187、8-188、8-189、8-190、8-191、8-192、8-193、8-194、8-195、8-196、8-197、8-198、8-199、8-200、8-201、8-202、8-203、8-204、8-205、8-206、8-207、8-208、8-209、8-210、8-211、8-212、8-213、8-214、8-215、8-216、8-217、8-218、8-219、8-220、8-221、8-222、8-223、8-224、8-225、8-226、8-227、8-228、8-229、8-230、8-231、8-232、8-233、8-234、8-235、8-236、8-237、8-238、8-239、8-240、8-241、8-242、8-243、8-244、8-245、8-246、8-247、8-248、8-249、8-250、8-253、8-254、8-255、8-256、8-257、8-258、8-259、8-260、8-264、8-265、8-266、
8-267、8-268、8-269、8-270、8-271、8-272、8-273、8-274、8-275、8-276、
8-277、8-278、8-279、8-280、8-281、8-282、8-283、8-284、8-285
8-286、8-287、8-291、8-292、8-293、8-294、8-295、8-296、8-297、
8-298、8-299、8-302、8-303、8-304、8-305、8-306、8-307、8-308、8-309、8-310、8-312、8-313、8-314、8-315、8-316、8-317、8-318、8-319、8-320、8-321、8-322、8-323、8-324、8-325、8-326、8-327、 8-328、8-329、8-330、8-331、
8-332、8-333、8-334、8-335、8-336、8-337、8-338、8-339、8-340、8-341、
8-354、8-355、8-356、8-357、8-358、8-359、8-360、8-361、8-362、8-363、
8-364、8-365、8-366、8-367、8-368、8-369、8-370、8-371、8-372、8-373、
8-374、8-375、8-376、8-377、8-378、8-379、8-380、8-381、8-382、8-383、
8-390、8-391、8-392、8-393、8-394、8-395、8-396、8-397、8-398
8-399、8-400、8-401、8-402、8-403、8-404、8-405、8-406、8-407、
8-408、8-409、8-410、8-411、8-412、8-413、8-414、8-415、8-416、8-417、
8-418、8-419、8-420、8-421、8-422、8-426、8-427、8-428、8-429、
8-430、8-431、8-432、8-433、8-434、8-438、8-439、8-440、8-444、
8-445、8-446、8-450、8-451、8-452、8-456、8-457、8-458、8-462、
8-463、8-464、8-465、8-466、8-467、8-468、8-469、8-470、8-471、
8-472、8-473、8-474、8-475、8-476、8-477、8-478、8-479、
8-480、8-481、8-482、8-486、8-487、8-488、8-492、8-493、8-494、
8-495、8-496、8-497、8-498、8-499、8-500、8-501、8-502、8-503、8-504、
8-505、8-506、8-507、8-508、8-509、8-510、8-511、8-512、8-513、
8-514、8-515、8-516、8-517、8-518、8-519、8-520、8-521、8-522、
8-523、8-524、8-525、8-526、8-527、8-528、8-529、8-530、8-531、
8-532、8-533、8-534、8-535、8-536、8-537、8-538、8-539、8-540、
8-541、8-542、8-543、8-544、8-545、8-546、8-547、8-548、8-549、8-550、8-551、
8-558、8-559、8-560、8-561、8-562、8-563、8-564、8-565、8-566、8-567、8-568、
8-569、9-1、9-2、9-3、9-4、9-5、9-6、10-1、10-2、10-3、10-4、10-5、10-6、10-7、10-8、10-9、11-1、11-2、11-3、11-4、11-5、11-6、11-7、11-8、11-9、11-10、11-11、11-12、11-13、11-16、11-20、11-22、11-23、11-24、11-25、11-26、11-27、12-1、12-4、12-7、12-8、12-9、12-10、12-11、12-12、12-13、13-1、13-2、13-3、13-4、13-5、13-6、13-7、13-8、13-9、13-10、13-11、13-12、14-1、15-4、
16-1、16-2、16-3、16-7、16-8、16-9、16-10、16-11、16-12、17-1、17-2、17-3、17-6、18-1、18-2、18-3、18-4、18-5、18-6、18-7、18-8、18-9、18-10、18-11、18-12、18-19、18-20、18-21、18-22、18-23、18-24、18-25、18-26、18-27、18-28、18-29、18-30、18-31、18-32、18-33、18-37、18-38、18-39、18-40、18-41、18-42、18-43、18-44、18-45、18-46、18-47、18-48、18-49、18-52、18-53、18-54、18-55、18-56、18-58、18-59、18-60、18-61、18-62、18-63、18-64、18-65、18-66、18-67、18-68、18-69、18-70、18-71、18-72、18-73、18-74、18-75、18-76、18-77、18-78、18-79、18-80、18-81、18-82、18-86、18-88、18-89、18-90、18-91、18-92、18-93、18-94、18-95、18-96、18-97、18-98、18-99、18-100、18-101、18-102、18-103、18-104、18-105、18-106、18-113、18-114、18-115、18-116、18-119、18-120、18-121、18-122、18-125、18-126、18-127、18-128、18-129、18-130、18-131、18-132、18-133、
18-134、18-137、18-138、18-139、18-140、18-144、18-145、18-146、18-148、18-149、18-150、18-151、18-152、18-154、18-155、18-156、18-157、18-158、18-159、18-160、18-161、18-162、18-163、18-164、18-165、18-166、18-167、18-168、18-169、18-176、18-177、18-178、18-179、18-180、18-181、18-182、18-183、18-184、18-185、18-186、18-187、18-191、18-192、18-193、
18-194、18-195、18-196、18-197、18-198、18-199、18-200、
18-201、18-202、18-203、18-204、18-205、18-206、
18-207、18-208、18-209、18-210、18-211、18-212、18-213、18-214、 18-216、18-217、18-218、18-220、18-221、18-222、18-223、18-224、18-225、18-226、18-245、18-246、18-247、18-248、18-249、18-250、18-251、18-252、18-253、18-254、18-255、18-256、18-257、18-258、18-259、18-260、18-263、18-264、
18-265、18-266、18-267、18-268、18-287、18-288、18-289、18-290、18-291、18-292、18-293、18-294、18-295、18-296、18-297、18-298、18-299、18-301、18-302、
18-303、18-304、18-305、18-306、18-307、18-308、18-309、18-310、18-323、18-324、18-325、18-326、18-327、18-328、18-329、18-334、18-350、18-352、
18-353、18-354、18-355、18-356、18-363、18-364、18-365、18-366、18-368、
18-426、18-427、18-428、18-429、18-430、18-431、18-444、18-445、18-446、18-462、18-464、18-468、18-470、18-474、18-476、18-477、
19-1、19-2、19-3、19-4、19-5、19-6、19-7、19-8、19-9、19-10、19-11、19-12、19-19、19-22、19-24、19-49、19-50、19-51、19-52、19-67、19-70、19-73、9-74、19-75、19-76、19-79、19-80、19-81、19-82、19-84、19-91、19-19、19-20、19-22、19-23、19-24、19-49、19-50、19-51、19-52、19-67、
19-70、19-73、19-74、19-75、19-76、19-79、19-80、19-81、19-82、19-84、
19-91、21-5、23-2、23-3、23-5、23-6、23-7、23-10、23-13、23-14
23-19、23-20、23-21、23-22、23-23、23-24、23-25、23-26、23-27、
23-28、23-37、23-38、23-39、24-1、24-2、24-3、24-4、24-5、24-6、25-1、25-2、25-3、25-4、25-5、25-6、25-7、25-8、25-9、25-10、25-11、25-12、25-13、25-14、25-15、25-16、25-17、25-18、25-19、25-22、25-25、25-26、25-27、25-28、25-29、25-30、25-31、25-32、25-33、25-34、25-35、25-36、25-37、25-38、25-39、25-40、25-41、 25-42、25-43、25-44、25-45、25-46、25-47、25-48、26-1、26-2、26-3、26-4、26-5、26-6、26-7、26-8、26-9、26-10、26-11、26-12、26-13、26-14、26-15、26-16、26-17、26-18、26-19、27-13、27-14、27-16、27-20、27-22、27-23、27-24、27-25、28-1、28-3、28-4、28-5、28-6、28-7、28-8、28-9、28-10、28-11、28-12、
28-13、28-16、28-17、28-18、28-19、28-20、28-21、28-22、28-23、28-24、28-31、28-32、28-33、28-34、28-36、28-37、28-38、28-39、28-40、28-41、28-42、
29-1、29-2、29-3、29-4、29-5、29-6、30-1、30-2、30-3、30-4、
31-7、31-8、31-9、31-10、31-11、31-12、33-19、33-20、33-31、33-32、33-33、33-34、33-35、33-36、33-56、33-57、33-61、33-62、33-63、33-67、33-68、33-69、33-70、33-71、33-72、34-1、34-2、34-3、34-4、34-5、35-1、35-2、
The compound of 35-3,35-7,35-8,35-9,35-10,35-11,35-12,36-19,36-20,36-21 and 36-22 show the effect of A to tea olethreutid at 500ppm.
Test example 5.
To the preventing iron test of black peach aphid (Myzus persicae)
Diameter 8cm, high 8cm plastic tub in plant Chinese cabbage and be inoculated with 10 black peach aphid larvas.2nd day, it will be interspersed among on the cauline leaf of potting Chinese cabbage using the compound recorded in the 1st table~the 19th table, the 21st table, the 23rd table~the 31st table as the medicament (500ppm) of effective component, after air-drying, basin is stored in greenhouse, investigate the 6th day number of parasites for parasitizing the black peach aphid on each Chinese cabbage after medicament is spread, value is prevented and kill off by the calculating of following formula, is determined according to following standards.
[mathematical expression 4]
Prevent and kill off value=100- { (T × Ca)/(Ta × C) } × 100
Ta: number of parasites before the distribution for the treatment of region
T: number of parasites after the distribution for the treatment of region
Ca: number of parasites before the distribution of no treatment area
C: number of parasites after the distribution of no treatment area
Criterion
A ... prevents and kill off value 100%
B ... prevents and kill off value 99%~90%
C ... prevents and kill off value 89%~80%
D ... prevents and kill off value 79%~50%
E ... prevents and kill off value 0%~49%
Compound number 1-5, 1-6, 1-19, 1-25, 1-26, 1-27, 1-28, 1-31, 1-34, 1-37, 1-46, 1-49, 1-53, 1-58, 1-59, 1-60, 1-61, 1-62, 1-65, 1-66, 1-67, 1-68, 1-69, 1-85, 1-86, 1-87, 1-94, 1-95, 1-97, 1-98, 1-99, 1-100, 1-101, 1-112, 1-113, 1-114, 1-117, 1-118, 1-124, 1-137, 1-138, 1-149, 1-150, 1-161, 1-163, 1-164, 1-167, 1- 170,1-180,1-201,1-203,1-204,1-205,1-206,1-207,1-208,1-230,1-231,1-239,1-241,1-242,1-243,1-244,1-248,1-257,1-260,1-273,1-274,1-275,1-283,1-284,1-287,1-288,1-307,1-317,1-318,1-338,1-348,1-349,1-350,1-370,1-373,1-378,1-381,1-382,1-384,1-385,1-386,1-390,1-391, 1-392,1-394,1-396,1-397,1-399,1-403,1-404,1-412,1-430,1-433,1-439,1-442,1-445,1-474,1-495,1-496,1-497,1-498,1-499,1-502,1-503,1-504,1-505,1-507,1-508,1-509,1-510,1-511,1-512,1-513,1-514,1-515,1-518,1-531,1-534,1-537,1-548,1-597,1-612,1-616,1-617,1-618,1-62 0, 1-621, 1-622, 1-635, 1-658, 1-673, 1-680, 1-681, 1-683, 1-697, 1-700, 1-703, 1-706, 1-710, 1-711, 1-714, 4-10, 4-13, 4-15, 5-1, 5-4, 5-5, 5-6, 5-7, 5-8, 5-11, 5-12, 5-13, 5-15, 5-20, 6-7, 6-19, 6-22, 6-31, 7-1, 7-3, 7-8, 7-12, 7-19, 7-30, 7-34, 7-38, 7-41, 7-42, 7-46, 7-48, 8-2, 8-3, 8-5, 8-6, 8-13, 8-1 4, 8-15, 8-30, 8-31, 8-33, 8-34, 8-35, 8-36, 8-37, 8-38, 8-39, 8-40, 8-41, 8-42, 8-43, 8-45, 8-46, 8-47, 8-50, 8-51, 8-52, 8-53, 8-54, 8-55, 8-56, 8-57, 8-58, 8-59, 8-60, 8-61, 8-62, 8-63, 8-64, 8-65, 8-66, 8-67, 8-68, 8-69, 8-70, 8-71, 8-72, 8-73, 8-74, 8-75, 8-76, 8-77, 8-78, 8-79, 8-80, 8-81, 8-82, 8-83, 8-84, 8-85, 8-87, 8-89, 8-90, 8-91, 8-92, 8-93, 8-94, 8-95, 8-96, 8-98, 8-99, 8-100, 8-101, 8-102, 8-103, 8-104, 8-105, 8-106, 8-107, 8-108, 8-109, 8-110, 8-111, 8-112, 8-113, 8-115, 8-116, 8-117, 8-118, 8-119, 8-120, 8-121, 8-122, 8-123, 8-124, 8-125, 8-126, 8-127, 8-128, 8-129, 8-130, 8-131, 8-132,8-133,8-134,8-135,8-136,8-137,8-138,8-139,8-140,8-141,8-142,8-143,8-144,8-145,8-146,8-147,8-148,8-149,8-150,8-151,8-152,8-156,8-155,8-157,8-158,8-159,8-160,8-161,8-162,8-163,8-164,8-166,8-167,8-168,8-169,8-170,8-176,8-177,8-178,8-179,8-180,8-181,8-18 2,8-183,8-184,8-185,8-186,8-187,8-188,8-189,8-190,8-191,8-192,8-193,8-194,8-195,8-196,8-197,8-198,8-199,8-201,8-202,8-203,8-204,8-205,8-206,8-207,8-208,8-209,8-210,8-211,8-212,8-213,8-214,8-215,8-216,8-217,8-218,8-219,8-220,8-221,8-222,8-223,8-224,8-225,8- 226,8-227,8-228,8-229,8-230,8-231,8-232,8-233,8-234,8-235,8-238,8-240,8-241,8-242,8-243,8-244,8-246,8-249,8-250,8-251,8-253,8-255,8-256,8-258,8-259,8-261,8-264,8-265,8-267,8-268,8-270,8-271,8-274,8-277,8-280,8-294,8-307,8-311,8-312,8-313,8-314,8-315,8-316, 8-317, 8-318, 8-320, 8-324, 8-325, 8-326, 8-327, 8-328, 8-329, 8-330, 8-331, 8-336, 8-337, 8-338, 8-339, 8-340, 8-341, 8-463, 8-466, 8-469, 8-472, 8-478, 8-507, 8-513, 8-531, 8-534, 9-1, 9-2, 9-3, 9-5, 9-6, 10-1, 10-2, 10-3, 10-6, 10-8, 10-9, 11-1, 11-3, 11-4, 11-5, 11-6, 11-7, 11-8, 11-9, 11-13, 11-1 6,11-23,11-26,12-9,12-10,12-11,13-3,13-8,16-2,16-3,
18-2、18-3、18-4、18-5、18-9、18-11、18-12、18-28、18-38、18-40、18-41、18-43、18-45、18-46、18-47、18-49、18-52、18-59、18-70、18-74、18-80、18-81、18-92、18-94、18-95、18-96、18-103、 18-106、18-114、18-115、18-125、18-126、18-128、18-129、18-138、18-139、18-140、18-145、18-154、18-176、18-177、18-178、18-179、18-180、18-181、18-182、18-183、18-185、18-186、18-187、18-192、18-194、18-195、18-196、18-197、18-198、18-200、18-201、18-203、18-204、18-206、18-209、18-211、18-213、18-216、18-221、18-222、18-224、18-225、18-245、18-246、18-247、18-248、18-249、18-250、18-252、18-264、18-267、
18-297,18-305,18-306,18-307,18-308,18-309,18-310,18-323,18-324,18-331,18-332,18-333,18-354,18-356,18-364,18-366,18-428,18-429,18-430,18-431,18-445,18-447,18-469,19-3,19-8,19-11,19-23,19-50,19-67,19-70,19-74,19-76,19-91,21-5,23-10,23-19,25-1,25-4,25-5,25-7, The compound of 25-11,25-15,25-18,25-22,25-25,25-26,25-27,25-29,25-31,25-41,25-42,26-4,26-9,26-18,27-16,29-3,31-8 and 33-55 show the effect of D or more to black peach aphid in 500ppm.

Claims (9)

1. phthaloyl amide derivatives or its esters that logical formula (I) indicates,
In formula, X1It indicates
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；
(a12)(C1-C8) halogenated alkyl sulfonyl；
(a13) carbamoyl；
(a14) amino；
(a15)(C1-C8) alkyl amino；
(a16)(C3-C8) cycloalkyl amino；
(a17)(C3-C8) naphthenic base (C1-C8) alkyl amino；
(a18)(C1-C8) alkoxy (C1-C8) alkyl amino；
(a19) bis- (C1-C8) alkyl amino, wherein alkyl may be the same or different；
(a20) Formylamino；
(a21)(C1-C8) alkyl-carbonyl-amino；
(a22)(C1-C8) alkoxycarbonyl amino；
(a23) phenyl；
(a24) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenyl；
(a25) phenoxy group；Or
(a26) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenoxy group,
X2It may be the same or different, indicate
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；
(b6)(C1-C8) halogenated alkoxy；
(b7) carbamoyl；
(b8) amino；
(b9)(C1~C8) alkyl amino；
(b10)(C3~C8) cycloalkyl amino；
(b11)(C3~C8) naphthenic base (C1~C8) alkyl amino；
(b12)(C1~C8) alkoxy (C1~C8) alkyl amino；
(b13) bis- (C1~C8) alkyl amino, wherein alkyl may be the same or different；
(b14) Formylamino；
(b15)(C1~C8) alkyl-carbonyl-amino；
(b16)(C1~C8) alkoxycarbonyl amino；
(b17) phenyl；
(b18) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenyl；
(b19) phenoxy group；Or
(b20) (a) halogen atom, (b) cyano, (c) nitro, (d) (C are selected from identical or different on ring1-C8) alkyl, (e) halogenated (C1-C8) alkyl, (f) (C1-C8) alkoxy, (g) halogenated (C1-C8) alkoxy, (h) (C2-C8) alkenyloxy group, (i) halogenated (C2-C8) alkenyloxy group, (j) (C2-C8) alkynyloxy group, (k) halogenated (C2-C8) alkynyloxy group, (l) (C3-C8) cycloalkyloxy, (m) halogenated (C3-C8) cycloalkyloxy, (n) (C3-C8) naphthenic base (C1-C8) alkoxy, (o) halogenated (C3-C8) naphthenic base (C1-C8) alkoxy, (p) (C1-C8) alkylthio group, (q) halogenated (C1-C8) alkylthio group, (r) (C1-C8) Alkylsulfinyl, (s) halogenated (C1-C8) Alkylsulfinyl, (t) (C1-C8) alkyl sulphonyl and (u) halogenated (C1-C8) 1~5 substituent group in alkyl sulphonyl phenoxy group,
M indicates 0,1,2 or 3,
Y1It indicates
(c1) hydrogen atom；
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c5)(C1-C8) halogenated alkyl；
(c6)(C1-C8) alkoxy；
(c7)(C1-C8) halogenated alkoxy；
(c8)(C1-C8) alkylthio group；
(c9)(C1-C8) halogenated alkylthio；
(c10)(C1-C8) Alkylsulfinyl；
(c11)(C1-C8) haloalkylsulfinyl；
(c12)(C1-C8) alkyl sulphonyl；Or
(c13)(C1-C8) halogenated alkyl sulfonyl,
Y2It may be the same or different, indicate
(d2) halogen atom；
(d3)(C1-C8) alkyl；
(d4)(C1-C8) halogenated alkyl；
(d5)(C1-C8) alkoxy；
(d6)(C1-C8) halogenated alkoxy；
(d7)(C1-C8) alkylthio group；
(d8)(C1-C8) halogenated alkylthio；
(d9)(C1-C8) Alkylsulfinyl；
(d10)(C1-C8) haloalkylsulfinyl；
(d11)(C1-C8) alkyl sulphonyl；Or
(d12)(C1-C8) halogenated alkyl sulfonyl,
N indicates 0,1 or 2,
Z1、Z2And Z3It may be the same or different, indicate nitrogen-atoms, CH, C-Y2Or C-A-Q, wherein in logical formula (I), C-A-Q can also only with Z1、Z2And Z3Any of bonding,
(the C of A expression linear chain or branched chain1-C8) alkylidene,
Q indicates annelated heterocycles base selected from the following,
In formula, it is bonded with the part that symbol " " marks with A,
W1It may be the same or different, indicate
(e1) hydrogen atom；
(e2) halogen atom；
(e3) cyano；
(e4) formoxyl；
(e5) cyano (C1-C8) alkyl；
(e6)(C1-C8) alkyl；
(e7)(C2-C8) alkenyl；
(e8)(C2-C8) alkynyl；
(e9)(C2-C8) halogenated alkenyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e16)(C3-C8) halogenated cycloalkyl；
(e17)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e20)(C1-C8) alkyl sulphonyl；
(e21)(C1-C8) alkylthio group (C1-C8) alkyl；
(e22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(e23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(e24)(C1-C8) halogenated alkylthio；
(e25)(C1-C8) haloalkylsulfinyl；
(e26)(C1-C8) halogenated alkyl sulfonyl；
(e27)(C1-C8) alkoxy carbonyl；
(e28)(C2-C8) allyloxycarbonyl；
(e29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(e30)(C1-C8) alkyl-carbonyl；
(e31)(C3-C8) naphthene base carbonyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, heterocycle, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl, in formula, R4And R5It is as defined above；
(e34)R4(R5) NCO- base, in formula, R4And R5It is as defined above；
(e35)R4(R5) NCOO- base, in formula, R4And R5It is as defined above；
(e36)R4(R5)NSO2Base, in formula, R4And R5It is as defined above；
(e37)R4(R5)NCON(R5)-base, in formula, R4And R5It is as defined above, R5It is same or different to each other；
(e38) aryl；
(e39) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(e40) aryloxycarbonyl epoxide；
(e41) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryloxycarbonyl epoxide of 1~5 substituent group in phenoxy group；
(e42) aryl (C1-C8) alkyl；
(e43) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e44) heterocycle；
(e45) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group；
(e46) heterocycle (C1-C8) alkyl；Or
(e47) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl,
W2、W2a、W2bAnd W2cIt may be the same or different, indicate
(f1) hydrogen atom；
(f2)(C1-C8) alkyl；
(f3) work as W2And W2aOr W2bAnd W2cWhen being bonded on same carbon atom, > C=O base；
(f4) work as W2And W2aOr W2bAnd W2cWhen being bonded on same carbon atom, > C=N-R6Base, wherein R6Indicate cyano, (C1-C8) alkyl or (C1-C8) alkoxy；
(f5) in Q18 or Q27, W2And W3It can also be bonded and form 5~8 yuan of saturation nitrogen-containing heterocycles containing 1 nitrogen-atoms；
(f6) halogen atom；
(f7)(C1-C8) alkoxy；Or
(f8)W2bAnd W2cCarbon atom that is bonding and being bonded with them is formed together unsubstituted 5~8 yuan of saturated or unsaturated aliphatic rings, which contains 0~2 oxygen atom,
W3And W3aIt may be the same or different, indicate
(m1) hydrogen atom；
(m2) cyano；
(m3) formoxyl；
(m4) cyano (C1-C8) alkyl；
(m5)(C1-C8) alkyl；
(m6)(C2-C8) alkenyl；
(m7)(C2-C8) alkynyl；
(m8)(C2-C8) halogenated alkenyl；
(m9)(C3-C8) naphthenic base；
(m10)(C1-C8) alkoxy (C1-C8) alkyl；
(m11)(C1-C8) halogenated alkyl；
(m12)(C3-C8) halogenated cycloalkyl；
(m13)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(m14)(C1-C8) alkylthio group (C1-C8) alkyl；
(m15)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(m16)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(m17)(C1-C8) alkoxy carbonyl；
(m18)(C2-C8) allyloxycarbonyl；
(m19)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(m20)(C1-C8) alkyl-carbonyl；
(m21)(C3-C8) naphthene base carbonyl；
(m22)R4(R5)N(C1-C8) alkyl, in formula, R4And R5It is as defined above；
(m23)R4(R5) NCO- base, in formula, R4And R5It is as defined above；
(m24)R4(R5) NCOO- base, in formula, R4And R5It is as defined above；
(m25)R4(R5)NSO2Base, in formula, R4And R5It is as defined above；
(m26)R4(R5)NCON(R5)-base, in formula, R4And R5It is as defined above；
(m27) aryl；
(m28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(m29) aryl (C1-C8) alkyl；
(m30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(m31) heterocycle；
(m32) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group；
(m33) heterocycle (C1-C8) alkyl；Or
(m34) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g3) cyano；
(g4) formoxyl；
(g5) cyano (C1-C8) alkyl；
(g6)(C1-C8) alkyl；
(g7)(C2-C8) alkenyl；
(g8)(C2-C8) alkynyl；
(g9)(C2-C8) halogenated alkenyl；
(g10)(C3-C8) naphthenic base；
(g11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(g12)(C1-C8) alkoxy；
(g13)(C1-C8) alkoxy (C1-C8) alkyl；
(g14)(C1-C8) halogenated alkyl；
(g15)(C1-C8) halogenated alkoxy；
(g16)(C3-C8) halogenated cycloalkyl；
(g17)(C3-C8) halogenated cycloalkyl (C1-C8) alkyl；
(g18)(C1-C8) alkylthio group；
(g19)(C1-C8) Alkylsulfinyl；
(g20)(C1-C8) alkyl sulphonyl；
(g21)(C1-C8) alkylthio group (C1-C8) alkyl；
(g22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(g23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(g24)(C1-C8) halogenated alkylthio；
(g25)(C1-C8) haloalkylsulfinyl；
(g26)(C1-C8) halogenated alkyl sulfonyl；
(g27)(C1-C8) alkoxy carbonyl；
(g28)(C2-C8) allyloxycarbonyl；
(g29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(g30)(C1-C8) alkyl-carbonyl；Or
(g31)(C3-C8) naphthene base carbonyl,
P indicates 0,1 or 2,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h4)(C3-C8) naphthenic base；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h6) hydroxyl (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h11) aryl；
(h12) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h13) arylthio (C1-C8) alkyl；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h15) aryl (C1-C8) alkylthio group (C1-C8) alkyl；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h17) aryl (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h19) aryloxy group (C1-C8) alkyl；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h21) aryl (C1-C8) alkoxy (C1-C8) alkyl；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h23) aryl (C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h25) aryl carbonyl epoxide (C1-C8) alkyl；
(h26) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl carbonyl epoxide (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h27) aryl methylene imino group oxygroup (C1-C8) alkyl；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h29) aryl (C1-C8) Alkoximino (C1-C8) alkyl；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h31)R4(R5) N carbonyl oxygroup (C1-C8) alkyl, in formula, R4And R5It is as defined above；
(h32)R4(R5) N carbonyl (C1-C8) alkyl, in formula, R4And R5It is as defined above；
(h33)R4(R5) N carbonyl (R4)N(C1-C8) alkyl, in formula, R4And R5It is as defined above, R4It is same or different to each other；
(h34) heterocycle (C1-C8) alkyl；Or
(h35) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) (C2-C8) 1~5 substituent group in alkynyl heterocycle (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；Or
Indicate substituent group below, wherein the part marked with symbol " " and nitrogen atom bonding,
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j2)(C1-C8) alkyl；
(j3) cyano；
(j4)(C1-C8) alkyl-carbonyl；
(j5)(C1-C8) halogenated alkyl carbonyl；
(j6)(C1-C8) alkoxy carbonyl；
(j7) aryl；
(j8) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(j9) aryl sulfonyl；Or
(j10) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl sulfonyl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；
(k2)(C1-C8) alkyl；
(k3)(C3-C8) naphthenic base；Or
(k4)(C3-C8) naphthenic base (C1-C8) alkyl；Or
(k5)R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3It indicates
(l1) hydrogen atom；
(l2)(C1-C8) alkyl；
(l3)(C3-C8) naphthenic base；Or
(l4)(C3-C8) naphthenic base (C1-C8) alkyl.
2. phthaloyl amide derivatives described in claim 1 or its esters, wherein X1For
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；Or
(a12)(C1-C8) halogenated alkyl sulfonyl,
X1Substituent group in addition is as defined in claim 1.
3. phthaloyl amide derivatives described in claim 1 or its esters, wherein X2For
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；Or
(b6)(C1-C8) halogenated alkoxy,
X2Substituent group in addition is as defined in claim 1.
4. phthaloyl amide derivatives described in claim 1 or its esters, wherein X1For
(a1) hydrogen atom；
(a2) halogen atom；
(a3)(C1-C8) alkyl；
(a4)(C1-C8) halogenated alkyl；
(a5)(C1-C8) alkoxy；
(a6)(C1-C8) halogenated alkoxy；
(a7)(C1-C8) alkylthio group；
(a8)(C1-C8) halogenated alkylthio；
(a9)(C1-C8) Alkylsulfinyl；
(a10)(C1-C8) haloalkylsulfinyl；
(a11)(C1-C8) alkyl sulphonyl；Or
(a12)(C1-C8) halogenated alkyl sulfonyl,
X2For
(b2) halogen atom；
(b3)(C1-C8) alkyl；
(b4)(C1-C8) halogenated alkyl；
(b5)(C1-C8) alkoxy；Or
(b6)(C1-C8) halogenated alkoxy,
X1And X2Substituent group in addition is as defined in claim 1.
5. phthaloyl amide derivatives described in claim 1 or its esters, wherein X1It indicates
(a1) hydrogen atom；
(a2) halogen atom；
(a7)(C1-C8) alkylthio group；
(a9)(C1-C8) Alkylsulfinyl；Or
(a11)(C1-C8) alkyl sulphonyl,
X2It indicates
(b2) halogen atom,
M indicates 0 or 1,
Y1It indicates
(c1) hydrogen atom；
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
Y2It indicates
(d2) halogen atom；
(d3)(C1-C8) alkyl；
(d4)(C1-C8) halogenated alkyl；
(d5)(C1-C8) alkoxy；Or
(d6)(C1-C8) halogenated alkoxy,
N indicates 0 or 1,
Q indicates Q1, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q16, Q18, Q19, Q21, Q23, Q24, Q25, Q26, Q27, Q28, Q29, Q30 or Q31, wherein W1It may be the same or different, indicate
(e1) hydrogen atom；
(e2) halogen atom；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e21)(C1-C8) alkylthio group (C1-C8) alkyl；
(e22)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(e23)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(e27)(C1-C8) alkoxy carbonyl；
(e29)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；Heterocycle with identical or different is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl, in formula, R4And R5It is as defined above；
(e34)R4(R5) NCO- base, in formula, R4And R5It is as defined above；
(e35)R4(R5) NCOO- base, in formula, R4And R5It is as defined above；
(e36)R4(R5)NSO2Base, in formula, R4And R5It is as defined above；
(e37)R4(R5)NCON(R5)-base, in formula, R4And R5It is as defined above, R5It is same or different to each other；
(e38) aryl；
(e39) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(e44) heterocycle；Or
(e46) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；
(g14)(C1-C8) halogenated alkyl；Or
(g27)(C1-C8) alkoxy carbonyl；
P indicates 0,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h12) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h17) aryl (C1-C8) alkyl；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h26) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl carbonyl epoxide (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h31)R4(R5) N carbonyl oxygroup (C1-C8) alkyl, in formula, R4And R5It is as defined above；
(h32)R4(R5) N carbonyl (C1-C8) alkyl, in formula, R4And R5It is as defined above；
(h33)R4(R5) N carbonyl (R4)N(C1-C8) alkyl, in formula, R4And R5It is as defined above, R4It is same or different to each other；Or
(h34) heterocycle (C1-C8) alkyl；
Alternatively, indicating
Substituent group below, wherein the part marked with symbol " " and nitrogen atom bonding,
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j2)(C1-C8) alkyl；
(j3) cyano；
(j4)(C1-C8) alkyl-carbonyl；
(j5)(C1-C8) halogenated alkyl carbonyl；
(j6)(C1-C8) alkoxy carbonyl；
(j8) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above；
Or
(j10) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl sulfonyl of 1~5 substituent group in phenoxy group, in R4(R5) in N carbonyl, R4And R5It is as defined above,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl；Or
(k5)R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3For
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl,
Substituent group other than above-mentioned each substituent group is as defined in claim 1.
6. phthaloyl amide derivatives described in claim 1 or its esters, wherein X1It indicates
(a2) halogen atom,
M indicates 0,
Y1It is identical or different, it indicates
(c2) halogen atom；
(c3) cyano；
(c4)(C1-C8) alkyl；
(c6)(C1-C8) alkoxy；
(c8)(C1-C8) alkylthio group；Or
(c10)(C1-C8) Alkylsulfinyl,
N indicates 0,
Z2Indicate C-A-Q,
Q indicates Q1, Q8 or Q18, wherein
W1It indicates
(e1) hydrogen atom；
(e4) formoxyl；
(e6)(C1-C8) alkyl；
(e10)(C3-C8) naphthenic base；
(e11)(C3-C8) naphthenic base (C1-C8) alkoxy；
(e12)(C1-C8) alkoxy；
(e13)(C1-C8) alkoxy (C1-C8) alkyl；
(e14)(C1-C8) halogenated alkyl；
(e15)(C1-C8) halogenated alkoxy；
(e18)(C1-C8) alkylthio group；
(e19)(C1-C8) Alkylsulfinyl；
(e27)(C1-C8) alkoxy carbonyl；
(e32)R4(R5) N base, in formula, R4And R5It may be the same or different, indicate hydrogen atom, (C1-C8) alkyl, (C3-C8) naphthenic base, (C2-C8) alkenyl, (C2-C8) alkynyl, (C3-C8) naphthenic base (C1-C8) alkyl, (C1-C8) halogenated alkyl, (C3-C8) halogenated cycloalkyl, (C1-C8) alkyl-carbonyl, (C1-C8) alkoxy carbonyl, aryl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group, aryl carbonyl, on ring with identical or different be selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl carbonyl of 1~5 substituent group in phenoxy group, aryl (C1-C8) alkyl, on ring with identical or different it is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl；Heterocycle with identical or different is selected from (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle of 1~5 substituent group in phenoxy group, heterocycle (C1-C8) alkyl or (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) heterocycle (C of 1~5 substituent group in phenoxy group1-C8) alkyl；
(e33)R4(R5)N(C1-C8) alkyl, in formula, R4And R5It is as defined above；
(e34)R4(R5) NCO- base, in formula, R4And R5It is as defined above；
(e35)R4(R5) NCOO- base, in formula, R4And R5It is as defined above；
(e36)R4(R5)NSO2Base, in formula, R4And R5It is as defined above；
(e37)R4(R5)NCON(R5)-base, in formula, R4And R5It is as defined above, R5It is same or different to each other；
(e38) aryl；Or
(e44) heterocycle,
W2And W2aIt may be the same or different, indicate
(f1) hydrogen atom；
(f2)(C1-C8) alkyl；Or
(f3) work as W2And W2aWhen being bonded on same carbon atom, > C=O base,
W3It indicates
(m1) hydrogen atom；
(m2) cyano；
(m4) cyano (C1-C8) alkyl；
(m5)(C1-C8) alkyl；
(m6)(C2-C8) alkenyl；
(m7)(C2-C8) alkynyl；
(m8)(C2-C8) halogenated alkenyl；
(m9)(C3-C8) naphthenic base；
(m10)(C1-C8) alkoxy (C1-C8) alkyl；
(m11)(C1-C8) halogenated alkyl；
(m14)(C1-C8) alkylthio group (C1-C8) alkyl；
(m15)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(m16)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(m17)(C1-C8) alkoxy carbonyl；
(m18)(C2-C8) allyloxycarbonyl；
(m19)(C1-C8) alkoxy carbonyl (C1-C8) alkyl；
(m20)(C1-C8) alkyl-carbonyl；
(m21)(C3-C8) naphthene base carbonyl；
(m23)R4(R5) NCO- base, in formula, R4And R5It is as defined above；
(m24)R4(R5) NCOO- base, in formula, R4And R5It is as defined above；
(m25)R4(R5)NSO2Base, in formula, R4And R5It is as defined above；
(m26)R4(R5)NCON(R5)-base, in formula, R4And R5It is as defined above；
(m27) aryl；
(m28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl and (s) aryl of 1~5 substituent group in phenoxy group；
(m29) aryl (C1-C8) alkyl；
(m31) heterocycle；Or
(m33) heterocycle (C1-C8) alkyl,
W4、W5、W6And W7It may be the same or different, indicate
(g1) hydrogen atom；
(g2) halogen atom；
(g6)(C1-C8) alkyl；
(g12)(C1-C8) alkoxy；Or
(g14)(C1-C8) halogenated alkyl,
P indicates 0,
R1It indicates
(h1)(C1-C8) alkyl；
(h2)(C2-C8) alkenyl；
(h3)(C2-C8) alkynyl；
(h5)(C3-C8) naphthenic base (C1-C8) alkyl；
(h7)(C1-C8) alkoxy (C1-C8) alkyl；
(h8)(C1-C8) alkylthio group (C1-C8) alkyl；
(h9)(C1-C8) Alkylsulfinyl (C1-C8) alkyl；
(h10)(C1-C8) alkyl sulphonyl (C1-C8) alkyl；
(h14) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) arylthio (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h16) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkylthio group (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h18) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h20) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryloxy group (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h22) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h24) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C3-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) alkoxy carbonyl (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h28) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) the aryl methylene imino group oxygroup (C of 1~5 substituent group in phenoxy group1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；
(h30) (a) halogen atom, (b) cyano, (c) nitro, (d) formoxyl, (e) (C are selected from identical or different on ring1-C8) alkyl, (f) (C1-C8) halogenated alkyl, (g) (C1-C8) alkoxy, (h) (C1-C8) halogenated alkoxy, (i) (C5-C8) naphthenic base (C1-C8) alkoxy, (j) (C1-C8) alkylthio group, (k) (C1-C8) halogenated alkylthio, (l) (C1-C8) Alkylsulfinyl, (m) (C1-C8) haloalkylsulfinyl, (n) (C1-C8) alkyl sulphonyl, (o) (C1-C8) halogenated alkyl sulfonyl, (p) (C1-C8) alkyl-carbonyl, (q) carboxyl, (r) (C1-C8) alkoxy carbonyl, (s) R4(R5) N carbonyl and (t) aryl (C of 1~5 substituent group in phenoxy group1-C8) Alkoximino (C1-C8) alkyl, in R4(R5) in N carbonyl, R4And R5It is as defined above；Or
(h34) heterocycle (C1-C8) alkyl；
Alternatively, indicating
Substituent group below, wherein the part marked with symbol " " and nitrogen atom bonding,
In formula, B indicates the (C of linear chain or branched chain1-C8) alkylidene,
R7It indicates
(i1)(C1-C8) alkyl,
R8It indicates
(j1) hydrogen atom；
(j3) cyano；Or
(j5)(C1-C8) halogenated alkyl carbonyl,
T indicates 0 or 1,
R2It indicates
(k1) hydrogen atom；Or
(k2)(C1-C8) alkyl, or
(k5)R1And R2It is bonding and formed containing 1 nitrogen-atoms and also containing 1~2 identical or different heteroatomic 5~8 yuan of saturations nitrogen-containing heterocycle selected from oxygen atom, nitrogen-atoms and sulphur atom,
R3For
(l1) hydrogen atom；Or
(l2)(C1-C8) alkyl,
Substituent group other than above-mentioned each substituent group is as defined in claim 1.
7. agricultural and horticultural pesticide, which is characterized in that contain the described in any item phthaloyl amide derivatives of claim 1~6 or its esters as effective component.
8. the application method of agricultural and horticultural pesticide as claimed in claim 7, which is characterized in that use a effective amount of agricultural and horticultural pesticide processing plant or soil.
9. animal parasite agent for preventing and eliminating, which is characterized in that contain the described in any item phthaloyl amide derivatives of claim 1~6 or its esters as effective component.
CN201280053503.4A 2011-11-02 2012-10-31 Phthalamide derivative, pesticide for agricultural and horticultural applications which comprises said derivative, and method of utilizing said pesticide Pending CN104024222A (en)

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CN104402785A (en) * 2014-09-26 2015-03-11 南开大学 Novel bisamides derivative and preparation method and application thereof
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US8940742B2 (en) 2012-04-10 2015-01-27 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
JP2016145155A (en) * 2013-04-30 2016-08-12 日本農薬株式会社 Phthalamide derivative, agricultural and horticultural insecticide containing the same, and application method thereof
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US9708348B2 (en) 2014-10-03 2017-07-18 Infinity Pharmaceuticals, Inc. Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
US10160761B2 (en) 2015-09-14 2018-12-25 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
WO2017161116A1 (en) 2016-03-17 2017-09-21 Infinity Pharmaceuticals, Inc. Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors
US10919914B2 (en) 2016-06-08 2021-02-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
CN115536597A (en) * 2022-09-29 2022-12-30 山东新华制药股份有限公司 Preparation method of high-purity alogliptin benzoate intermediate

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1360573A (en) * 1999-07-05 2002-07-24 日本农药株式会社 Phthalamide derivs., intermediates in production thereof, and agricultural/horticultural insecticides and method of using same
CN1328246C (en) * 1998-11-30 2007-07-25 日本农药株式会社 Butyl benzene orthobenzol diacid amide derivative or its salt, garderning pesticide and its application method
CN100358863C (en) * 1999-09-24 2008-01-02 日本农药株式会社 Aromatic diamide derivatives or salts thereof, agricultural/norticultural chemicals and method of using the same
CN101103014A (en) * 2004-11-18 2008-01-09 拜尔农作物科学股份公司 N-heterocyclyl phthalic acid diamides as insecticides
CN102171190A (en) * 2008-07-31 2011-08-31 拜尔农作物科学股份公司 Insecticidal benzenedicarboxamide derivative

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3358024B2 (en) * 1998-11-30 2002-12-16 日本農薬株式会社 Phthalamide derivatives or salts thereof, agricultural and horticultural insecticides, and methods of using the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1328246C (en) * 1998-11-30 2007-07-25 日本农药株式会社 Butyl benzene orthobenzol diacid amide derivative or its salt, garderning pesticide and its application method
CN1360573A (en) * 1999-07-05 2002-07-24 日本农药株式会社 Phthalamide derivs., intermediates in production thereof, and agricultural/horticultural insecticides and method of using same
CN100358863C (en) * 1999-09-24 2008-01-02 日本农药株式会社 Aromatic diamide derivatives or salts thereof, agricultural/norticultural chemicals and method of using the same
CN101103014A (en) * 2004-11-18 2008-01-09 拜尔农作物科学股份公司 N-heterocyclyl phthalic acid diamides as insecticides
CN102171190A (en) * 2008-07-31 2011-08-31 拜尔农作物科学股份公司 Insecticidal benzenedicarboxamide derivative

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402785A (en) * 2014-09-26 2015-03-11 南开大学 Novel bisamides derivative and preparation method and application thereof
CN111971283A (en) * 2018-03-26 2020-11-20 肿瘤研究所基金会 Novel compounds with enhanced antitumor effect
CN111971283B (en) * 2018-03-26 2023-04-14 肿瘤研究所基金会 Novel compounds with enhanced antitumor effect
CN110294719A (en) * 2019-07-15 2019-10-01 五邑大学 A kind of synthetic method of thiazolidinone compound
CN110294719B (en) * 2019-07-15 2023-02-28 五邑大学 Synthesis method of thiazolidone compound
CN115583922A (en) * 2022-10-17 2023-01-10 黄山学院 Fluorine-containing N- (3- (benzoxazole-2-yl) phenyl) amide compound and preparation method and application thereof
CN115583922B (en) * 2022-10-17 2023-09-19 黄山学院 Fluorine-containing N- (3- (benzoxazol-2-yl) phenyl) amide compound and preparation method and application thereof

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