CN1871218A - Isopentyl carboxanilides for combating undesired micro-organisms - Google Patents

Isopentyl carboxanilides for combating undesired micro-organisms Download PDF

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CN1871218A
CN1871218A CNA2004800311768A CN200480031176A CN1871218A CN 1871218 A CN1871218 A CN 1871218A CN A2004800311768 A CNA2004800311768 A CN A2004800311768A CN 200480031176 A CN200480031176 A CN 200480031176A CN 1871218 A CN1871218 A CN 1871218A
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alkyl
chlorine
fluorine
haloalkyl
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CN100522948C (en
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R·邓克尔
H-L·埃尔比
J·N·格罗尔
B·哈特曼
U·瓦赫诺夫-诺伊曼
P·丹门
K-H·库克
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Bayer Pharma AG
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    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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Abstract

The invention relates to novel isopentyl carboxanilides of formula (I), wherein L, R1, R3 and A have the meaning cited in the description, to several methods for the production of said substances and to the use thereof in order to combat undesired micro-organisms, in addition to intermediate products and to the production thereof.

Description

Be used to prevent and treat the isopentyl carbonyl aniline of unwanted microorganisms
The present invention relates to new isopentyl carbonyl aniline (isopentyl carboxanilide), its multiple preparation method and be used to prevent and treat the purposes of unwanted microorganisms.
Known numerous carbonyl aniline has fungicidal properties (reference, for example WO 02/059086, WO 00/09482, EP-A 0 824 099, EP-A 0 755 927, EP-A 0 589 301, EP-A 0 545 099, JP 11-335364, JP 10-310577 and JP 10-251240).Known for example 1-methyl-N-[2-(3-methyl butyl) phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (EP-A 0 824 099) and 2,5-dimethyl-N-[3-(3-methyl butyl) phenyl]-3-furoamide (EP-A 0 755 927).The activity of above-claimed cpd is good; But it is unsatisfactory when hanging down rate of application sometimes.
The present invention now provides the isopentyl carbonyl aniline of new formula (I)
Figure A20048003117600191
Wherein
The L representative
Figure A20048003117600192
Wherein the key with the * mark links to each other with acid amides, and the key that marks with # links to each other with alkyl group side chain,
R 1Represent hydrogen, C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4,-CONR 5R 6Or-CH 2NR 7R 8,
R 2Represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R 3Represent hydrogen, halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
R 4Represent hydrogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 6Halogenated alkoxy, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl,
R 5And R 6Represent hydrogen, C independently of one another separately 1-C 8Alkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 8Haloalkyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl,
R 5And R 6Also can form saturated heterocyclic, optional halogen and the C of being selected from of described heterocycle with the nitrogen-atoms that they connect with 5 to 8 annular atomses 1-C 4The identical or different substituting group list of alkyl replaces or is polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 7And R 8Represent hydrogen, C independently of one another 1-C 8Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 8Haloalkyl, C 3-C 8Halogenated cycloalkyl,
R 7And R 8Also can form saturated heterocyclic, optional halogen and the C of being selected from of described heterocycle with the nitrogen-atoms that they connect with 5 to 8 annular atomses 1-C 4The identical or different substituting group list of alkyl replaces or is polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 9Represent hydrogen or C 1-C 6Alkyl,
A represents formula (A1) group
Figure A20048003117600201
Wherein
R 10Represent hydrogen, hydroxyl, formyl radical, cyano group, halogen, nitro, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio, C 3-C 6Cycloalkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy or C 1-C 4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C 1-C 4Alkyl,
R 11Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkylthio, and
R 12Represent hydrogen, C 1-C 4Alkyl, hydroxyl-C 1-C 4Alkyl, C 2-C 6Alkenyl, C 3-C 6Cycloalkyl, C 1-C 4Alkylthio-C 1-C 4Alkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio-C 1-C 4Alkyl, C 1-C 4Halogenated alkoxy-C 1-C 4Alkyl is perhaps represented phenyl,
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and
Prerequisite is if R 3And R 11Represent hydrogen, and R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl,
Perhaps
A represents (A2) group
Figure A20048003117600211
Wherein
R 13And R 14Represent hydrogen, halogen, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 15Represent halogen, cyano group or C 1-C 4Alkyl, or have the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkoxy,
Perhaps
A represents formula (A3) group
Figure A20048003117600212
Wherein
R 16And R 17Represent hydrogen, halogen, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 18Represent hydrogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A4) group
Figure A20048003117600213
Wherein
R 19Represent hydrogen, halogen, hydroxyl, cyano group, C 1-C 6Alkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy or C 1-C 4Halogenated alkylthio,
Perhaps
A represents formula (A5) group
Figure A20048003117600221
Wherein
R 20Represent halogen, hydroxyl, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio or C 1-C 4Halogenated alkoxy, and
R 21Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy, C 1-C 4Alkyl sulphinyl or C 1-C 4Alkyl sulphonyl,
Perhaps
A represents formula (A6) group
Figure A20048003117600222
Perhaps
A represents formula (A7) group
Figure A20048003117600223
Wherein
R 22Represent C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A8) group
Wherein
R 23Represent C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A9) group
Figure A20048003117600225
Wherein
R 24And R 25Represent hydrogen, halogen, amino, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 26Represent hydrogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Prerequisite is if R 25Represent hydrogen, then R 24And R 26Different times table methyl,
Perhaps
A represents formula (A10) group
Wherein
R 27And R 28Represent hydrogen, halogen, amino, nitro, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 29Represent halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A11) group
Wherein
R 30Represent hydrogen, halogen, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 31Represent halogen, hydroxyl, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 3-C 6Cycloalkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkoxy,
Prerequisite is if R 3Represent hydrogen, and R 30Represent methylidene, then R 31Do not represent trifluoromethyl, difluoromethyl or methyl,
Perhaps
A represents formula (A12) group
Figure A20048003117600233
Wherein
R 32Represent hydrogen, halogen, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 33Represent halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A13) group
Figure A20048003117600241
Wherein
R 34Represent hydrogen or C 1-C 4Alkyl, and
R 35Represent halogen or C 1-C 4Alkyl,
Perhaps
A represents formula (A14) group
Wherein
R 36Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A15) group
Wherein
R 37Represent halogen, hydroxyl, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio or C 1-C 4Halogenated alkoxy,
Perhaps
A represents formula (A16) group
Wherein
R 38Represent hydrogen, cyano group, C 1-C 4Alkyl, has the C of 1 to 5 halogen atom 1-C 4Haloalkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, hydroxyl-C 1-C 4Alkyl, C 1-C 4Alkyl sulphonyl, two (C 1-C 4Alkyl) amino-sulfonyl, C 1-C 6Alkyl-carbonyl or optional separately benzenesulfonyl or the benzoyl that replaces,
R 39Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
R 40Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
R 41Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Prerequisite is R 40Do not represent trifluoromethyl,
Perhaps
A represents formula (A17) group
Wherein
R 42Represent C 1-C 4Alkyl.
If suitable, if the mixture existence, particularly steric isomer, for example E type and Z type, threo form and erythro of the possible isomeric forms that compound of the present invention can be different, and optically active isomer are and suitable tautomer in addition.Claimed existing E type and Z type isomer also have any mixture of threo form and erythro and optically active isomer, above-mentioned isomer and possible tautomeric forms.
And, have been found that the isopentyl carbonyl aniline of formula (I) makes by following reaction:
If a) be suitably under the existence of catalyzer, if be suitably under the existence of condensing agent, if if being suitably in the existence of acid binding agent descends and is suitably under the existence of thinner, the anils reaction of the carboxylic acid derivative of formula (II) and formula (III),
Figure A20048003117600252
Wherein
A defines as above, and
X 1Represent halogen or hydroxyl,
Figure A20048003117600253
Wherein L, R 1And R 3Define as above,
Perhaps
B) in the presence of alkali and in the presence of thinner, the halide reaction of the isopentyl carbonyl aniline of formula (I-a) and formula (IV)
Figure A20048003117600261
Wherein
L, A and R 3Definition as above
R 1-A-X 2 (IV)
Wherein
X 2Represent chlorine, bromine or iodine,
R 1-ARepresent C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl, (C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8,
R wherein 4, R 5, R 6, R 7And R 8Define as above,
Perhaps
C) in the presence of alkali, and if be suitably under the existence of thinner, the isoamyl ketone derivatives of formula V and hydrazine (or hydrazine hydrate) reaction,
Figure A20048003117600262
Wherein
R 1, R 2, R 3Define as above with A,
Perhaps
D) if be suitably under the existence of thinner, and if be suitably under the existence of catalyzer, the isopentene derivative hydrogenation of formula (VI),
Figure A20048003117600271
R wherein 1, R 2, R 3Define as above with A,
Perhaps
E) if be suitably under the existence of thinner, and if be suitably under the existence of catalyzer, the isopropyl-acetylene derivative hydrogenation of formula (VII),
R wherein 1, R 2, R 3Define as above with A.
At last, have been found that the isopentyl carbonyl aniline of new formula (I) has extraordinary microbicidel characteristic, can in Crop protection and material protection, be used to prevent and treat unwanted microorganisms.
Formula (I) provides the General Definition of isopentyl carbonyl aniline of the present invention.Below provided the preferred group definition of above and structural formula shown below.Described definition both had been applicable to formula (I) final product, was applicable to all intermediates too.
L PreferablyRepresent following L-1, wherein R 2Can have general, preferred, particularly preferred, extremely particularly preferred or especially preferred implication separately.
L also PreferablyRepresent L-2.
L also PreferablyRepresent L-3.
L also PreferablyRepresent L-4.
L Preferred especiallyRepresent following L-1, wherein R 2Can have general, preferred, particularly preferred, extremely particularly preferred or especially preferred implication separately.
L also Preferred especiallyRepresent L-2.
L Preferred extremely especiallyRepresent following L-1, wherein R 2Have general, preferred, particularly preferred, extremely particularly preferred or especially preferred implication separately.
R 1 PreferablyRepresent hydrogen, C 1-C 6Alkyl, C 1-C 4Alkyl sulphinyl, C 1-C 4Alkyl sulphonyl, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 6Alkyl) carbonyl, (C 1-C 4Alkoxyl group) carbonyl, (C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl) carbonyl, (C 1-C 4Halogenated alkoxy) carbonyl, (halo-C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4,-CONR 5R 6Or-CH 2NR 7R 8
R 1 Preferred especiallyRepresent hydrogen; methyl; ethyl; n-propyl or sec.-propyl; normal-butyl; isobutyl-; the sec-butyl or the tertiary butyl; amyl group or hexyl; methylsulfinyl; the ethyl sulfinyl; n-propyl sulfinyl or sec.-propyl sulfinyl; the normal-butyl sulfinyl; the isobutyl-sulfinyl; sec-butyl sulfinyl or tertiary butyl sulfinyl; methyl sulphonyl; ethylsulfonyl; n-propyl alkylsulfonyl or sec.-propyl alkylsulfonyl; the normal-butyl alkylsulfonyl; the isobutyl-alkylsulfonyl; sec-butyl alkylsulfonyl or tertiary butyl alkylsulfonyl; methoxymethyl; methoxy ethyl; ethoxyl methyl; ethoxyethyl group; cyclopropyl; cyclopentyl; cyclohexyl; trifluoromethyl; trichloromethyl; trifluoroethyl; the difluoro methylthio group; difluoro chloro methylthio group; trifluoromethylthio; the trifluoromethyl sulphinyl base; trifluoromethyl sulfonyl; the trifluoromethoxy methyl, formyl radical;-CH 2-CHO ,-(CH 2) 2-CHO ,-CH 2-CO-CH 3,-CH 2-CO-CH 2CH 3,-CH 2-CO-CH (CH 3) 2,-(CH 2) 2-CO-CH 3,-(CH 2) 2-CO-CH 2CH 3,-(CH 2) 2-CO-CH (CH 3) 2,-CH 2-CO 2CH 3,-CH 2-CO 2CH 2CH 3,-CH 2-CO 2CH (CH 3) 2,-(CH 2) 2-CO 2CH 3,-(CH 2) 2-CO 2CH 2CH 3,-(CH 2) 2-CO 2CH (CH 3) 2,-CH 2-CO-CF 3,-CH 2-CO-CCl 3,-CH 2-CO-CH 2CF 3,-CH 2-CO-CH 2CCl 3,-(CH 2) 2-CO-CH 2CF 3,-(CH 2) 2-CO-CH 2CCl 3,-CH 2-CO 2CH 2CF 3,-CH 2-CO 2CF 2CF 3,-CH 2-CO 2CH 2CCl 3,-CH 2-CO 2CCl 2CCl 3,-(CH 2) 2-CO 2CH 2CF 3,-(CH 2) 2-CO 2CF 2CF 3,-(CH 2) 2-CO 2CH 2CCl 3,-(CH 2) 2-CO 2CCl 2CCl 3,
Methyl carbonyl, ethyl carbonyl, n-propyl carbonyl, sec.-propyl carbonyl, tertiary butyl carbonyl, methoxycarbonyl, ethoxy carbonyl, tert-butoxycarbonyl, cyclopropyl carbonyl, trifluoromethyl carbonyl, trifluoromethoxy carbonyl or-C (=O) C (=O) R 5,-CONR 6R 7Or-CH 2NR 8R 9
R 1 Preferred extremely especiallyRepresent hydrogen, methyl, methoxymethyl, formyl radical ,-CH 2-CHO ,-(CH 2) 2-CHO ,-CH 2-CO-CH 3,-CH 2-CO-CH 2CH 3,-CH 2-CO-CH (CH 3) 2,-C (=O) CHO ,-C (=O) C (=O) CH 3,-C (=O) C (=O) CH 2OCH 3,-C (=O) CO 2CH 3,-C (=O) CO 2CH 2CH 3
R 2 PreferablyRepresent hydrogen.
R 2Also PreferablyRepresent fluorine, wherein fluorine Preferred especiallyBe positioned at 4-, 5-or the 6-position of anilide group, Preferred extremely especially4-or 6-position, especially preferred 4-position [with reference to following formula (I)].
R 2Also PreferablyRepresent chlorine, wherein chlorine Preferred especiallyBe positioned at the 5-position [with reference to following formula (I)] of anilide group.Chlorine also Preferred especiallyBe positioned at the 4-position of anilide group.
R 2Also PreferablyRepresent methylidene, wherein methyl Preferred especiallyBe positioned at the 3-position [with reference to following formula (I)] of anilide group.
R 2Also PreferablyRepresent trifluoromethyl, wherein trifluoromethyl Preferred especiallyBe positioned at 4-or 5-position [with reference to following formula (I)] of anilide group.
R 3 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, iodine, C 1-C 6Alkyl, has the C of 1 to 13 fluorine, chlorine and/or bromine atoms 1-C 6Haloalkyl.
R 3 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl or have the C of 1 to 9 fluorine, chlorine and/or bromine atoms 1-C 4Haloalkyl.
R 3 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine or methyl, ethyl or trifluoromethyl.
R 4 PreferablyRepresent hydrogen, C 1-C 6Alkyl, C 1-C 4Alkoxyl group, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Halogenated cycloalkyl.
R 4 Preferred especiallyRepresent hydrogen, methyl, ethyl, n-propyl or sec.-propyl, the tertiary butyl, methoxyl group, oxyethyl group, positive propoxy or isopropoxy, tert.-butoxy, cyclopropyl, trifluoromethyl, trifluoromethoxy.
R 5And R 6Independently of one another PreferablyRepresent hydrogen, C 1-C 6Alkyl, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Halogenated cycloalkyl.
R 5And R 6Also can be with the nitrogen-atoms of their connections PreferablyRepresentative has the saturated heterocyclic of 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces to four replacements, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss.
R 5And R 6Independently of one another Preferred especiallyRepresent hydrogen, methyl, ethyl, n-propyl or sec.-propyl, normal-butyl, isobutyl-, sec-butyl or the tertiary butyl, methoxymethyl, methoxy ethyl, ethoxyl methyl, ethoxyethyl group, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxy methyl.
R 5And R 6Also can be with the nitrogen-atoms of their connections Preferred especiallyRepresentative is selected from the saturated heterocyclic of morpholine, thiomorpholine and piperazine, and the optional identical or different substituting group list that is selected from fluorine, chlorine, bromine and methyl of described heterocycle replaces to four replacements, and wherein piperazine can be by R on second nitrogen-atoms 9Replace.
R 7And R 8Independently of one another PreferablyRepresent hydrogen, C 1-C 6Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 3-C 6Halogenated cycloalkyl.
R 7And R 8Also can be with the nitrogen-atoms of their connections PreferablyRepresentative has the saturated heterocyclic of 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces to polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss.
R 7And R 8Independently of one another Preferred especiallyRepresent hydrogen, methyl, ethyl, n-propyl or sec.-propyl, normal-butyl, isobutyl-, sec-butyl or the tertiary butyl, methoxymethyl, methoxy ethyl, ethoxyl methyl, ethoxyethyl group, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxy methyl.
R 7And R 8Also can be with the nitrogen-atoms of their connections Preferred especiallyRepresentative is selected from the saturated heterocyclic of morpholine, thiomorpholine and piperazine, and the optional identical or different substituting group list that is selected from fluorine, chlorine, bromine and methyl of described heterocycle replaces to four replacements, and wherein piperazine can be by R on second nitrogen-atoms 9Replace.
R 9 PreferablyRepresent hydrogen or C 1-C 4Alkyl.
R 9 Preferred especiallyRepresent hydrogen, methyl, ethyl, n-propyl or sec.-propyl, normal-butyl, isobutyl-, sec-butyl or the tertiary butyl.
A PreferablyOne of the A1 that provides more than the representative, A2, A3, A4, A5, A6, A9, A10, A11, A12, A13, A14, A15 or A16 group.
A Preferred especiallyOne of the A1 that provides more than the representative, A2, A4, A5, A6, A9, A11, A12, A13, A14, A15 or A16 group.
A Preferred extremely especiallyRepresent the A1 group.
A also Preferred extremely especiallyRepresent the A2 group.
A also Preferred extremely especiallyRepresent the A4 group.
A also Preferred extremely especiallyRepresent the A5 group.
A also Preferred extremely especiallyRepresent the A6 group.
A also Preferred extremely especiallyRepresent the A9 group.
A also Preferred extremely especiallyRepresent the A11 group.
A also Preferred extremely especiallyRepresent the A12 group.
A also Preferred extremely especiallyRepresent the A13 group.
A also Preferred extremely especiallyRepresent the A14 group.
A also Preferred extremely especiallyRepresent the A16 group.
R 10 PreferablyRepresent hydrogen, hydroxyl, formyl radical, cyano group, fluorine, chlorine, bromine, iodine, methyl, ethyl, sec.-propyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, cyclopropyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl, C 1-C 2Halogenated alkoxy, trifluoromethylthio, difluoro methylthio group, aminocarboxyl, amino carbonyl methyl or aminocarboxyl ethyl,
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and prerequisite is if R 3And R 11Represent hydrogen, R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl.
R 10 Preferred especiallyRepresent hydrogen, hydroxyl, formyl radical, fluorine, chlorine, bromine, iodine, methyl, ethyl, sec.-propyl, methoxyl group, oxyethyl group, a methyl fluoride, a fluoro ethyl, difluoromethyl, trifluoromethyl, difluoro chloro methyl, trichloromethyl, dichloromethyl, pentafluoroethyl group, cyclopropyl, methoxyl group, oxyethyl group, trifluoromethoxy, difluoro-methoxy, trichlorine methoxyl group, methylthio group, ethylmercapto group, trifluoromethylthio or difluoro methylthio group
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and prerequisite is if R 3And R 11Represent hydrogen, R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl.
R 10 Preferred extremely especiallyRepresent hydrogen, hydroxyl, formyl radical, fluorine, chlorine, bromine, iodine, methyl, ethyl, sec.-propyl, methoxyl group, cyclopropyl, a methyl fluoride, a fluoro ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, difluoro chloro methyl, trichloromethyl ,-CHFCH 3Or difluoro-methoxy,
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and prerequisite is if R 3And R 11Represent hydrogen, R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl.
R 10Especially preferably represent hydrogen, hydroxyl, formyl radical, chlorine, methyl, ethyl, methoxyl group, cyclopropyl, a methyl fluoride, difluoromethyl, dichloromethyl, trifluoromethyl ,-CHFCH 3Or difluoro-methoxy,
Prerequisite is if R 3And R 11Represent hydrogen, R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl.
R 11 PreferablyRepresent hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
R 11 Preferred especiallyRepresent hydrogen, chlorine, bromine, iodine, methyl or-CHFCH 3
R 11 Preferred extremely especiallyRepresent hydrogen, chlorine, methyl or-CHFCH 3
R 12 PreferablyRepresent hydrogen, methyl, ethyl, n-propyl, sec.-propyl, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, methylol, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl.
R 12 Preferred especiallyRepresent hydrogen, methyl, ethyl, sec.-propyl, trifluoromethyl, difluoromethyl, methylol, hydroxyethyl or phenyl.
R 12 Preferred extremely especiallyRepresent hydrogen, methyl, trifluoromethyl or phenyl.
R 12Especially preferred represent methylidene.
R 13And R 14Independently of one another PreferablyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 13And R 14Independently of one another Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluoro chloro methyl or trichloromethyl.
R 13And R 14Independently of one another Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R 13And R 14Especially preferably represent hydrogen.
R 15 PreferablyRepresent fluorine, chlorine, bromine, iodine, cyano group, methyl, ethyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy.
R 15 Preferred especiallyRepresent fluorine, chlorine, bromine, iodine, cyano group, methyl, trifluoromethyl, trifluoromethoxy, difluoro-methoxy, difluoro chloro methoxyl group or trichlorine methoxyl group.
R 15 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.
R 15Especially preferably represent chlorine or methyl.
R 16And R 17Independently of one another PreferablyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 16And R 17Independently of one another Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluoro chloro methyl or trichloromethyl.
R 16And R 17Independently of one another Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine or methyl.
R 16And R 17Especially preferably represent hydrogen separately.
R 18 PreferablyRepresent hydrogen, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 18 Preferred especiallyRepresent hydrogen, methyl or trifluoromethyl.
R 18 Preferred extremely especiallyRepresent methylidene.
R 19 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, C 1-C 4Alkyl has the C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl, C 1-C 2Halogenated alkoxy or C 1-C 2Halogenated alkylthio.
R 19 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, difluoromethyl, trifluoromethyl, difluoro chloro methyl, trichloromethyl, trifluoromethoxy, difluoro-methoxy, difluoro chloro methoxyl group, trichlorine methoxyl group, trifluoromethylthio, difluoro methylthio group, difluoro chloro methylthio group or trichloro-methylthio.
R 19 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R 19Especially preferably represent iodine, methyl, difluoromethyl or trifluoromethyl.
R 20 PreferablyRepresent fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, difluoro methylthio group, trifluoromethylthio, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy.
R 20 Preferred especiallyRepresent fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl, trichloromethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, difluoro methylthio group, trifluoromethylthio, trifluoromethoxy, difluoro-methoxy, difluoro chloro methoxyl group or trichlorine methoxyl group.
R 20 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 21 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, iodine, cyano group, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy, C 1-C 2Alkyl sulphinyl or C 1-C 2Alkyl sulphonyl.
R 21 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, cyano group, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl, trichloromethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, trifluoromethoxy, difluoro-methoxy, difluoro chloro methoxyl group, trichlorine methoxyl group, methylsulfinyl or methyl sulphonyl.
R 21 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methyl sulphonyl.
R 21Especially preferably represent hydrogen.
R 22 PreferablyRepresent methylidene, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 22 Preferred especiallyRepresent methylidene, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 22 Preferred extremely especiallyRepresent methylidene, trifluoromethyl, difluoromethyl or trichloromethyl.
R 23 PreferablyRepresent methylidene, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 23 Preferred especiallyRepresent methylidene, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 23 Preferred extremely especiallyRepresent methylidene, trifluoromethyl, difluoromethyl or trichloromethyl.
R 24And R 25Independently of one another PreferablyRepresent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 24And R 25Independently of one another Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 24And R 25Independently of one another Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine or methyl.
R 24And R 25Especially preferably represent hydrogen separately.
R 26 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 26 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 26 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R 26Especially preferred represent methylidene or trifluoromethyl.
R 27And R 28Independently of one another PreferablyRepresent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 27And R 28Independently of one another Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 27And R 28Independently of one another Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 27And R 28Especially preferably represent hydrogen separately.
R 29 PreferablyRepresent fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 29 Preferred especiallyRepresent fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 29 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 29Especially preferred represent methylidene.
R 30 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 30 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, amino, methylamino-, dimethylamino, cyano group, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 30 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, amino, methylamino-, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 30Especially preferably represent amino, methylamino-, dimethylamino, methyl or trifluoromethyl.
R 31 PreferablyRepresent fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxyl group, oxyethyl group, cyclopropyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy.
R 31 Preferred especiallyRepresent fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxyl group, oxyethyl group, cyclopropyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 31 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, hydroxyl, methyl, methoxyl group, cyclopropyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 32 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 32 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, amino, methylamino-, dimethylamino, cyano group, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 32 Preferred extremely especiallyRepresent hydrogen, fluorine, chlorine, bromine, amino, methylamino-, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 32Especially preferably represent amino, methylamino-, dimethylamino, methyl or trifluoromethyl.
R 33 PreferablyRepresent fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 33 Preferred especiallyRepresent fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 33 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 33Especially preferred represent methylidene, trifluoromethyl or difluoromethyl.
R 34 PreferablyRepresent hydrogen, methyl or ethyl.
R 34 Preferred especiallyRepresent methylidene.
R 35 PreferablyRepresent fluorine, chlorine, bromine, methyl or ethyl.
R 35 Preferred especiallyRepresent fluorine, chlorine or methyl.
R 36 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 36 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R 37 PreferablyRepresent fluorine, chlorine, bromine, iodine, hydroxyl, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, difluoro methylthio group, trifluoromethylthio, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy.
R 37 Preferred especiallyRepresent fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, the tertiary butyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl, trichloromethyl.
R 37 Preferred extremely especiallyRepresent fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 38 PreferablyRepresent hydrogen, methyl, ethyl, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, C 1-C 2Alkoxy-C 1-C 2Alkyl, methylol, hydroxyethyl, methyl sulphonyl or dimethylamino alkylsulfonyl.
R 38 Preferred especiallyRepresent hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxyl methyl, methylol or hydroxyethyl.
R 38 Preferred extremely especiallyRepresent methylidene or methoxymethyl.
R 39 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 39 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R 39 Preferred extremely especiallyRepresent hydrogen or methyl.
R 40 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, cyano group, methyl, ethyl, sec.-propyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 40 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, cyano group, methyl, ethyl, sec.-propyl, trifluoromethyl, difluoromethyl, difluoro chloro methyl or trichloromethyl.
R 40 Preferred extremely especiallyRepresent hydrogen, fluorine, methyl or trifluoromethyl.
R 41 PreferablyRepresent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl.
R 41 Preferred especiallyRepresent hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
R 41 Preferred extremely especiallyRepresent hydrogen or trifluoromethyl.
R 42 PreferablyRepresent methylidene, ethyl, n-propyl or sec.-propyl.
R 42 Preferred especiallyRepresent methylidene or ethyl.
Emphasize that wherein L represents L-1, wherein R with following formula (I) compound 2Has above-mentioned general implication.
Emphasize that wherein L represents L-1, wherein R with following formula (I) compound 2Has above-mentioned preferred implication.
Emphasize that wherein L represents L-1, wherein R with following formula (I) compound 2Has above-mentioned particularly preferred implication.
Emphasize that wherein L represents L-1, wherein R with following formula (I) compound 2Has above-mentioned extremely particularly preferred implication.
Emphasize that wherein L represents L-1, wherein R with following formula (I) compound 2Has above-mentioned especially preferred implication.
Emphasize that wherein L represents L-2 with following formula (I) compound.
Emphasize with following formula (I) compound, wherein R 1Represent hydrogen.
Emphasize with following formula (I) compound, wherein R 1Represent formyl radical.
Also emphasize with following formula (I) compound, wherein R 1Representative-C (=O) C (=O) R 4, R wherein 4Definition as above.
Emphasize that wherein A represents A1 with following formula (I) compound.
Emphasize with following formula (I) compound, wherein R 3Represent hydrogen.
Emphasize with following formula (I) compound, wherein R 3Represent halogen, preferred fluorine, chlorine, bromine or iodine, preferred especially fluorine, chlorine or bromine, preferred extremely especially fluorine or chlorine.
Emphasize with following formula (I) compound, wherein R 3Represent C 1-C 8Alkyl, preferred C 1-C 6Alkyl, special preferable methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl or the tertiary butyl, extremely special preferable methyl or ethyl.
Emphasize with following formula (I) compound, wherein R 3Represent C 1-C 8Haloalkyl preferably has the C of 1 to 13 fluorine, chlorine and/or bromine atoms 1-C 6Haloalkyl especially preferably has the C of 1 to 9 fluorine, chlorine and/or bromine atoms 1-C 4Haloalkyl, preferred extremely especially trifluoromethyl.
Saturated or unsaturated alkyl, for example alkyl or alkenyl, or even with heteroatomic combination, alkoxyl group for example all can be respectively a straight chain or have side chain.
Optional substituted group can be single replacement or polysubstituted, and wherein under polysubstituted situation, substituting group can be identical or different.
The halo group, for example haloalkyl is single halo or how halogenated.Under how halogenated situation, halogen atom can be identical or different.Among the application, halogen is represented fluorine, chlorine, bromine and iodine, particularly fluorine, chlorine and bromine.
Yet above-mentioned general or preferred group definition or explanation be combination with one another as required, promptly comprises the combination between the scope and preferable range separately.Described definition both had been applicable to final product, and therefore also was applicable to precursor and intermediate.
Above-mentioned definition is combination with one another as required.And the discrete definition can be inapplicable.
Preferably, the particularly preferred or utmost point particularly preferably is with following formula (I) compound, it has above-mentioned respectively as preferred, particularly preferred and extremely particularly preferred substituting group.
Preparation formula of the present invention (I) isopentyl carbonyl aniline and intermediate method
Method (a)
With 5-fluoro-1,3-dimethyl-1H-pyrazoles-4-carbonyl chloride and [2-(3-methyl butyl) phenyl] amine are raw material, and method of the present invention (a) can be expressed as following reaction scheme figure:
Formula (II) provides the General Definition as the carboxylic acid derivative of the inventive method (a) raw material.In formula (II), A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred A.X 1Preferred chlorine, bromine or the hydroxyl represented.
The carboxylic acid derivative of formula (II) is known and/or can be prepared (with reference to WO93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313) by currently known methods.
Formula (III) provides the General Definition as the anils of the inventive method (a) raw material.In formula (III), L, R 1And R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
Some wherein L to represent formula (III) anils of L-1 be new compound.On behalf of formula (III) anils of L-1, L can prepare by the following method:
F) in the first step, if be suitably under the existence of thinner, make the cyano-aniline of formula (VIII) and the Grignard reagent reaction of formula (IX), in second step, at alkali (for example alkali metal hydroxide or alkaline earth metal hydroxides, for example sodium hydroxide or potassium hydroxide) existence under, and if be suitably under the existence of thinner, make the alkane ketone aniline and hydrazine (or hydrazine hydrate) reaction of the formula (X) that obtains
Figure A20048003117600401
R wherein 1And R 2Definition as above
Wherein
R 3Define as above,
X 3Represent chlorine, bromine or iodine
Figure A20048003117600403
R wherein 1, R 2And R 3Definition as above.
Formula (VIII) provides the General Definition as the cyano-aniline of the inventive method (f) raw material.In formula (VIII), R 1And R 2Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The cyano-aniline of formula (VIII) is known and/or can be prepared by currently known methods.R 1Do not represent the cyano-aniline of the formula (VIII) of hydrogen to prepare by the following method:
In the presence of alkali and in the presence of thinner, [reaction conditions of method (b) is corresponding to be suitable for to make the cyano-aniline of formula (V-a) and the halide reaction of formula (IV).]
Figure A20048003117600411
R wherein 2Definition as above
R 1-A-X 2 (IV)
R wherein 1-ADefinition as above.
Formula (IX) provides the General Definition as the Grignard reagent of the inventive method (f) raw material.In formula (IX), R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.X 3The preferred bromine of representing.
The Grignard reagent of formula (IX) is known or can be prepared by currently known methods.
The alkane ketone aniline of the intermediate formula (X) of the inventive method (f) is new compound, also constitutes the part of theme of the present invention.In formula (X), radicals R 1, R 2And R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
Hydrazine (or hydrazine hydrate) as the inventive method (f) reagent is to be used for the synthetic known compound.
Method of the present invention (f) can be different the variation scheme implementation.Therefore, can make the cyano-aniline of formula (V-a) be converted into the alkane ketone aniline of corresponding formula (VII-a) earlier, if it is suitable then, with the halide reaction of formula (IV), [reaction conditions of method (b) is corresponding to be suitable for to make corresponding formula (X) alkane ketone aniline in the presence of alkali and in the presence of thinner.]
Figure A20048003117600421
R wherein 2And R 3Definition as above
R 1-A-X 2 (IV)
R wherein 1-ADefinition as above.
Yet, also can make formula (VII-a) alkane ketone aniline be converted into the anils of corresponding formula (III-a) according to method of the present invention (f), if suitable then, the halide reaction with formula (IV) in the presence of alkali and in the presence of thinner obtains corresponding formula (III) anils
Figure A20048003117600422
R wherein 2And R 3Definition as above
R 1-A-X 2 (IV)
R wherein 1-ADefinition as above.[reaction conditions of method (b) is corresponding to be suitable for.]
The anils of formula (III-b) is a new compound, also constitutes the part of the application's theme
Wherein
A) R 1-BRepresent C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl, (C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8, and
R 3-BRepresent hydrogen, halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
Perhaps
B) R 1-BRepresent hydrogen, C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl, (C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8, and
R 3-BRepresent halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
And, R 2, R 4, R 5, R 6, R 7And R 8Definition as above.
R 1And R 3Preferably, the corresponding R that is applicable to of preferred especially and extremely particularly preferred implication 1-BAnd R 3-B, R under situation a) wherein 1-BDo not represent hydrogen respectively, and at b) situation under R 3-BDo not represent hydrogen.R 2, R 4, R 5, R 6, R 7And R 8Preferably, preferred especially and extremely particularly preferred implication is equally applicable to new formula (III-b) compound.
Emphasize with following formula (III-b) compound, wherein R 1And R 2Represent hydrogen and R separately 3Represent fluorine, chlorine, methyl, ethyl, trifluoromethyl and pentafluoroethyl group.
On behalf of the anils of the formula (III) of L-1, L also can prepare by the following method:
G) in the first step, in the presence of catalyzer, if descend and be suitably under the existence of thinner if be suitably in the existence of alkali, make the aniline halogenide and the reaction of formula (XII) alkynes of formula (XI), in second step, if descend and be suitably under the existence of catalyzer if be suitably in the existence of thinner, make the alkynes aniline hydrogenation of the formula (XIII) that obtains
Figure A20048003117600441
Wherein
R 1-AAnd R 2Define as above, and
X 4Represent halogen
Figure A20048003117600442
R wherein 3Definition as above
Figure A20048003117600443
R wherein 1-A, R 2And R 3Definition as above.
Formula (XI) provides the halid General Definition of aniline as the inventive method (g) raw material.In formula (XI), R 2Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.R 1-APreferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (IV) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The aniline halogenide of formula (XI) is known and/or can be prepared by currently known methods, for example by substituted corresponding derivative and formula (IV) halide reaction and preparing on nitrogen not.
Formula (XII) provides the General Definition as the alkynes of the inventive method (g) raw material.In formula (XII), R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The alkynes of formula (XII) is known.
The General Definition of the alkynes aniline of gained intermediate when formula (XIII) provides as enforcement the inventive method (g).In formula (XIII), R 2And R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.R 1-APreferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (IV) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The alkynes aniline of some formulas (XIII) is known.Above-mentioned alkynes aniline is prepared by method of the present invention (g).
If R wherein 1Represent formula (III) anils of hydrogen to wait to make, then will be to R 1-AThereby select to make it to become after the inventive method (g) protecting group that can remove by ordinary method.
L represents formula (III) anils of L-2, L-3 or L-4 known and/or can be prepared (reference, for example EP-A 1 036 793 and EP-A 0 737 682) by currently known methods.
L represents L-2, L-3 or L-4 and R 1Do not represent formula (III) anils of hydrogen to prepare by the following method:
In the presence of alkali, and in the presence of thinner, make the aniline of formula (III-c) and the halide reaction of formula (IV) [reaction conditions of method (b) is corresponding to be suitable for]
Figure A20048003117600451
Wherein
L 1Represent L-2, L-3 or L-4, and
L-2, L-3, L-4 and R 3Definition as above
R 1-A-X 2 (IV)
R wherein 1-AAnd X 2Definition as above.
Method (b)
With 5-fluoro-1,3-dimethyl-N-[2-(3-methyl butyl) phenyl]-1H-pyrazole-4-carboxamide and chloro (oxo) ethyl acetate are raw material, the process of the inventive method (b) can be expressed as following reaction scheme figure:
Formula (I-a) provides the General Definition as the isopentyl carbonyl aniline of the inventive method (b) raw material.In formula (I-a), R 2, R 3With A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The isopentyl carbonyl aniline of formula (I-a) also is a compound of the present invention, also constitutes the part of the application's theme.Described isopentyl carbonyl aniline can be by method of the present invention (a), (c), (d) or (e) (R wherein 1=hydrogen) preparation.
Formula (IV) provides the halid General Definition as the inventive method (b) raw material.
R 1-A PreferablyRepresent C 1-C 6Alkyl, C 1-C 4Alkyl sulphinyl, C 1-C 4Alkyl sulphonyl, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 6Alkyl) carbonyl, (C 1-C 4Alkoxyl group) carbonyl, (C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl) carbonyl, (C 1-C 4Halogenated alkoxy) carbonyl, (halo-C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8
R 1-A Preferred especiallyRepresent methylidene; ethyl; n-propyl or sec.-propyl; normal-butyl; isobutyl-; the sec-butyl or the tertiary butyl; amyl group or hexyl; methylsulfinyl; the ethyl sulfinyl; n-propyl sulfinyl or sec.-propyl sulfinyl; the normal-butyl sulfinyl; the isobutyl-sulfinyl; sec-butyl sulfinyl or tertiary butyl sulfinyl; methyl sulphonyl; ethylsulfonyl; n-propyl alkylsulfonyl or sec.-propyl alkylsulfonyl; the normal-butyl alkylsulfonyl; the isobutyl-alkylsulfonyl; sec-butyl alkylsulfonyl or tertiary butyl alkylsulfonyl; methoxymethyl; methoxy ethyl; ethoxyl methyl; ethoxyethyl group; cyclopropyl; cyclopentyl; cyclohexyl; trifluoromethyl; trichloromethyl; trifluoroethyl; the difluoro methylthio group; difluoro chloro methylthio group; trifluoromethylthio; the trifluoromethyl sulphinyl base; trifluoromethyl sulfonyl; the trifluoromethoxy methyl, formyl radical;-CH 2-CHO ,-(CH 2) 2-CHO ,-CH 2-CO-CH 3,-CH 2-CO-CH 2CH 3,-CH 2-CO-CH (CH 3) 2,-(CH 2) 2-CO-CH 3,-(CH 2) 2-CO-CH 2CH 3,-(CH 2) 2-CO-CH (CH 3) 2,-CH 2-CO 2CH 3,-CH 2-CO 2CH 2CH 3,-CH 2-CO 2CH (CH 3) 2,-(CH 2) 2-CO 2CH 3,-(CH 2) 2-CO 2CH 2CH 3,-(CH 2) 2-CO 2CH (CH 3) 2,-CH 2-CO-CF 3,-CH 2-CO-CCl 3,-CH 2-CO-CH 2CF 3,-CH 2-CO-CH 2CCl 3,-(CH 2) 2-CO-CH 2CF 3,-(CH 2) 2-CO-CH 2CCl 3,-CH 2-CO 2CH 2CF 3,-CH 2-CO 2CF 2CF 3,-CH 2-CO 2CH 2CCl 3,-CH 2-CO 2CCl 2CCl 3,-(CH 2) 2-CO 2CH 2CF 3,-(CH 2) 2-CO 2CF 2CF 3,-(CH 2) 2-CO 2CH 2CCl 3,-(CH 2) 2-CO 2CCl 2CCl 3,
Methyl carbonyl, ethyl carbonyl, n-propyl carbonyl, sec.-propyl carbonyl, tertiary butyl carbonyl, methoxycarbonyl, ethoxy carbonyl, tert-butoxycarbonyl, cyclopropyl carbonyl, trifluoromethyl carbonyl, trifluoromethoxy carbonyl or-C (=O) C (=O) R 5,-CONR 6R 7Or-CH 2NR 8R 9
R 1-A Preferred extremely especiallyRepresent methylidene, methoxymethyl, formyl radical ,-CH 2-CHO ,-(CH 2) 2-CHO ,-CH 2-CO-CH 3,-CH 2-CO-CH 2CH 3,-CH 2-CO-CH (CH 3) 2,-C (=O) CHO ,-C (=O) C (=O) CH 3,-C (=O) C (=O) CH 2OCH 3,-C (=O) CO 2CH 3,-C (=O) CO 2CH 2CH 3
X 2 PreferablyRepresent chlorine or bromine.
The halogenide of formula (IV) is known.
Method (c)
With 2-iodo-N-[2-(3-methylbutyryl base) phenyl] benzamide is raw material, with hydrazine and alkali, the process of the inventive method (c) can be expressed as following reaction scheme figure:
Formula V provides the General Definition as the isoamyl ketone derivatives of the inventive method (c) raw material.In formula V, R 1, R 2, R 3With A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The isoamyl ketone derivatives of formula V is a new compound.Described isoamyl ketone derivatives prepares by the following method:
H) if be suitably under the existence of catalyzer, if be suitably under the existence of condensing agent, if, make the carboxylic acid derivative and formula (X) the alkane ketone aniline reaction of formula (II) if being suitably in the existence of acid binding agent descends and be suitably under the existence of thinner
Figure A20048003117600472
Wherein
The A definition as above
X 1Table halogen or hydroxyl
Figure A20048003117600481
R wherein 1, R 2And R 3Definition as above.
Formula (II) carboxylic acid derivative narration in about method of the present invention (a) as the inventive method (h) raw material.
Formula (X) alkane ketone aniline narration in about method of the present invention (f) as the inventive method (h) raw material.
Method (d)
With N-{2-[3,3-dimethyl but-1-ene-1-yl] phenyl }-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide is a raw material, uses hydrogen, the process of the inventive method (d) can be expressed as following reaction scheme figure:
Figure A20048003117600482
Formula (VI) provides the General Definition as the isopentene derivative of the inventive method (d) raw material.In formula (VI), R 1, R 2, R 3With A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The isopentene derivative of formula (VI) is a new compound.Described isopentene derivative prepares by the following method:
J) in the presence of catalyzer, if, make the reaction of formula (XIV) acid amides and formula (XV) alkene if being suitably in the existence of alkali descends and be suitably under the existence of thinner
Figure A20048003117600491
Wherein
R 1, R 2Define as above with A, and
X 5Represent chlorine, bromine, iodine or-OSO 2CF 3
R wherein 3Definition as above.
Formula (XIV) provides the General Definition as the acid amides of the inventive method (j) raw material.In formula (XIV), R 1, R 2With A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.X 5Preferred represent bromine or-OSO 2CF 3
Formula (XIV) acid amides is a known compound, and perhaps available currently known methods makes (with reference to WO02/08195 and WO 02/08197).
Formula (XV) provides the General Definition as the alkene of the inventive method (j) raw material.In formula (XV), R 3Preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
The alkene of formula (XV) is known.
Method (e)
With N-[2-(3,3-dimethyl butyrate-1-alkynes-1-yl) phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide is a raw material, uses hydrogen, the process of the inventive method (e) can be expressed as following reaction scheme figure:
Figure A20048003117600493
Formula (VII) provides the General Definition as the isopropyl-acetylene derivative of the inventive method (e) raw material.In formula (VII), R 1, R 2, R 3With A preferably, especially preferably and extremely especially preferably have provided in the narration about formula of the present invention (I) compound respectively as preferably, the implication of preferred especially and extremely particularly preferred described group.
Wherein not represent formula (VII) the isopropyl-acetylene derivative of A1 be new compound to A.The isopropyl-acetylene derivative of formula (VII) prepares by the following method:
K) in the presence of catalyzer, if, make the reaction of formula (XIV) acid amides and formula (XII) alkynes if being suitably in the existence of alkali descends and be suitably under the existence of thinner
Figure A20048003117600501
Wherein
R 1, R 2Define as above with A, and
X 5Represent chlorine, bromine, iodine or-OSO 2CF 3
Figure A20048003117600502
R wherein 3Definition as above.
Formula (XIV) acid amides narration in about method of the present invention (j) as the inventive method (k) raw material.
Formula (XII) alkynes narration in about method of the present invention (g) as the inventive method (k) raw material.
Reaction conditions
Being suitable for the inventive method (a) and thinner (h) is all inert organic solvents.It preferably includes aliphatic hydrocrbon, alicyclic hydrocarbon or aromatic hydrocarbon, for example sherwood oil, hexane, heptane, hexanaphthene, methylcyclohexane, benzene,toluene,xylene or naphthane; Halohydrocarbon, for example chlorobenzene, dichlorobenzene, methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride or trichloroethane; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether, 1,2-diethoxyethane or methyl-phenoxide; Or acid amides, N for example, dinethylformamide, N,N-dimethylacetamide, N-methyl formyl aniline, N-Methyl pyrrolidone or HMPA.
If suitable, method of the present invention (a) and (h) in the presence of the acid acceptor that is fit to, implement.The acid acceptor that is fit to is all conventional mineral alkali or organic basess.It preferably includes alkaline-earth metal or alkali-metal hydride, oxyhydroxide, amides, alkoxide, acetate, carbonate or supercarbonate, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert.-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, lime acetate, ammonium acetate, yellow soda ash, salt of wormwood, saleratus, sodium bicarbonate or volatile salt; And tertiary amine, for example Trimethylamine 99, triethylamine, Tributylamine, N, accelerine, N, N-dimethyl benzylamine, pyridine, N-methyl piperidine, N-methylmorpholine, N, N-dimethyl aminopyridine, diazabicyclo octane (DABCO), diazabicyclo-nonene (DBN) or diazabicyclo undecane (DBU).
If suitable, method of the present invention (a) and (h) in the presence of the condensing agent that is fit to, implement.The condensing agent that is fit to is usually used in the condensing agent of this type of amidate action for all.The carboxylic acid halides that has that can propose by way of example forms agent, for example carbonyl chloride, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphoryl chloride or thionyl chloride; Acid anhydrides forms agent, for example Vinyl chloroformate, methyl-chloroformate, isopropyl chlorocarbonate, isobutyl chlorocarbonate or Methanesulfonyl chloride; Carbodiimide, N for example, N '-dicyclohexyl carbodiimide (DCC); Or other conventional condensing agents, for example Vanadium Pentoxide in FLAKES, Tripyrophosphoric acid, N, N '-carbonyl dimidazoles, 2-oxyethyl group-N-ethoxy carbonyl-1,2-dihydroquinoline (EEDQ), triphenyl phosphine/tetracol phenixin or phosphofluoric acid bromo tripyrrole Wan phosphonium salt (bromotripyrrolidinophosphonium hexafluorophosphate).
If suitable, method of the present invention (a) and (h) in the presence of the catalyzer that is fit to, implement.The example that can propose has 4-dimethylaminopyridine, I-hydroxybenzotriazole or dimethyl formamide.
Implement method of the present invention (a) and (h) time, temperature of reaction can change in wide relatively scope.Generally speaking, the temperature of enforcement aforesaid method is 0 ℃ to 150 ℃, preferred 0 ℃ to 80 ℃.
For implementing method of the present invention (a) with preparation formula (I) compound, general every mole formula (II) carboxylic acid derivative use 0.2 to 5mol, preferred 0.5 to 2mol formula (III) anils.
For implementing method of the present invention (h) with preparation formula V compound, general every mole formula (II) carboxylic acid derivative use 0.2 to 5mol, preferred 0.5 to 2mol formula (X) alkane ketone aniline.
The thinner that is suitable for the inventive method (b) is all inert organic solvents.It preferably includes aliphatic hydrocrbon, alicyclic hydrocarbon or aromatic hydrocarbon, for example sherwood oil, hexane, heptane, hexanaphthene, methylcyclohexane, benzene,toluene,xylene or naphthane; Halohydrocarbon, for example chlorobenzene, dichlorobenzene, methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride or trichloroethane; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether, 1,2-diethoxyethane or methyl-phenoxide; Or acid amides, N for example, dinethylformamide, N,N-dimethylacetamide, N-methyl formyl aniline, N-Methyl pyrrolidone or HMPA.
Method of the present invention (b) is implemented in the presence of alkali.The alkali that is fit to is all conventional mineral alkali or organic basess.It preferably includes alkaline-earth metal or alkali-metal hydride, oxyhydroxide, amides, alkoxide, acetate, carbonate or supercarbonate, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert.-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, lime acetate, ammonium acetate, yellow soda ash, salt of wormwood, saleratus, sodium bicarbonate or cesium carbonate; And tertiary amine, for example Trimethylamine 99, triethylamine, Tributylamine, N, accelerine, N, N-dimethyl benzylamine, pyridine, N-methyl piperidine, N-methylmorpholine, N, N-dimethyl aminopyridine, diazabicyclo octane (DABCO), diazabicyclo-nonene (DBN) or diazabicyclo undecane (DBU).
When implementing method of the present invention (b), temperature of reaction can change in wide relatively scope.Generally speaking, the temperature of enforcement aforesaid method is 0 ℃ to 150 ℃, preferred 20 ℃ to 110 ℃.
For implementing method of the present invention (b) with preparation formula (I) compound, general every mole formula (I-a) isopentyl carbonyl aniline use 0.2 to 5mol, preferred 0.5 to 2mol formula (IV) halogenide.
The thinner that is suitable for second step of the inventive method (c) and method (f) is all inert organic solvents.It preferably includes aliphatic hydrocrbon, alicyclic hydrocarbon or aromatic hydrocarbon, for example sherwood oil, hexane, heptane, hexanaphthene, methylcyclohexane, benzene,toluene,xylene or naphthane; Halohydrocarbon, for example chlorobenzene, dichlorobenzene, methylene dichloride, chloroform, tetracol phenixin, ethylene dichloride or trichloroethane; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether, 1,2-diethoxyethane or methyl-phenoxide; Ketone, for example acetone, butanone, methyl tertbutyl ketone or pimelinketone; Nitrile, for example acetonitrile, propionitrile, n-Butyronitrile or isopropyl cyanide or benzonitrile; Acid amides, N for example, dinethylformamide, N,N-dimethylacetamide, N-methyl formyl aniline, N-Methyl pyrrolidone or HMPA; Sulfoxide, for example dimethyl sulfoxide (DMSO); Sulfone, for example tetramethylene sulfone; Alcohol, for example methyl alcohol, ethanol, n-propyl alcohol or Virahol, propyl carbinol, isopropylcarbinol, sec-butyl alcohol or the trimethyl carbinol, ethylene glycol, the third-1, the mixture of 2-glycol, ethoxy ethanol, methyl cellosolve, diethylene glycol monomethyl ether, ethyl carbitol, triglycol, above-claimed cpd and water or pure water.
Second step of method of the present invention (c) and method (f) implements in the presence of alkali.Preferred alkali has alkaline-earth metal or alkali metal hydroxide, for example sodium hydroxide, potassium hydroxide, ammonium hydroxide.
When implementing second step of method of the present invention (c) and method (f), temperature of reaction can change in wide relatively scope.Generally speaking, temperature of reaction is 100 ℃ to 300 ℃, preferred 150 ℃ to 250 ℃.
When implementing method of the present invention (c) with preparation formula (I) compound, general every mole formula V isoamyl ketone derivatives use 0.2 to 5mol, preferred 0.5 to 3mol hydrazine (or hydrazine hydrate).
Go on foot with preparation formula (III) anils general every mole formula (X) alkane ketone aniline use 0.2 to 5mol, preferred 0.5 to 3mol hydrazine (or hydrazine hydrate) for implementing second of the inventive method (f).
Be suitable for the inventive method (d) and (e) and the thinner in method (g) second step be all inert organic solvents.It preferably includes aliphatic hydrocrbon or alicyclic hydrocarbon, for example sherwood oil, hexane, heptane, hexanaphthene, methylcyclohexane or naphthane; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether or 1,2-diethoxyethane; Alcohol, for example methyl alcohol, ethanol, n-propyl alcohol or Virahol, propyl carbinol, isopropylcarbinol, sec-butyl alcohol or the trimethyl carbinol, ethylene glycol, the third-1, the mixture of 2-glycol, ethoxy ethanol, methyl cellosolve, diethylene glycol monomethyl ether, ethyl carbitol, above-claimed cpd and water or pure water.
Method of the present invention (d) and (e) and method (g) second step in the presence of catalyzer, implement.The catalyzer that is fit to is usually used in the hydrogenant catalyzer for all.What mode that can example proposed has: if be suitably on the carrier, for example Raney nickel on activated carbon, palladium or platinum.
In the presence of combining with catalyzer at hydrogen, method of the present invention (d) and (e) and the hydrogenation in method (g) second step also can in the presence of triethyl silicane, implement.
Implement method of the present invention (d) and (e) and method (g) the second during step, temperature of reaction can change in wide relatively scope.Generally speaking, temperature of reaction is 0 ℃ to 150 ℃, preferred 20 ℃ to 100 ℃.
Method of the present invention (d) and (e) and the hydrogen-pressure in method (g) second step be 0.5 to 200bar, preferred 2 to 50bar, preferred especially 3 to 10bar.
The thinner that is suitable for the inventive method (f) the first step is all inert organic solvents.It preferably includes aliphatic hydrocrbon or alicyclic hydrocarbon, for example sherwood oil, hexane, heptane, hexanaphthene, methylcyclohexane or naphthane; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether or 1,2-diethoxyethane.
When implementing the inventive method (f) the first step, temperature of reaction can change in wide relatively scope.Generally speaking, temperature of reaction is 0 ℃ to 200 ℃, preferred 20 ℃ to 150 ℃.
For the first step of implementing the inventive method (f) with preparation formula (X) alkane ketone aniline, general every mole formula (VIII) cyano-aniline uses 0.2 to 5mol, preferred 0.5 to 3mol formula (IX) Grignard reagent.
Being suitable for the inventive method (g) the first step and method (j) and thinner (k) is all inert organic solvents.It preferably includes nitrile, for example acetonitrile, propionitrile, n-Butyronitrile or isopropyl cyanide or benzonitrile; Or acid amides, N for example, dinethylformamide, N,N-dimethylacetamide, N-methyl formyl aniline, N-Methyl pyrrolidone or HMPA; Ether, for example ether, isopropyl ether, methyl tertiary butyl ether, tert amyl methyl ether(TAME), diox, tetrahydrofuran (THF), 1,2-glycol dimethyl ether or 1,2-diethoxyethane.
If suitable, method of the present invention (g) the first step and method (j) and (k) in the presence of the acid acceptor that is fit to, implement.The acid acceptor that is fit to is all conventional mineral alkali or organic basess.It preferably includes alkaline-earth metal or alkali-metal hydride, oxyhydroxide, amides, alkoxide, acetate, carbonate or supercarbonate, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert.-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, lime acetate, ammonium acetate, yellow soda ash, salt of wormwood, saleratus, sodium bicarbonate or volatile salt; And tertiary amine, for example Trimethylamine 99, triethylamine, Tributylamine, N, accelerine, N, N-dimethyl benzylamine, pyridine, N-methyl piperidine, N-methylmorpholine, N, N-dimethyl aminopyridine, diazabicyclo octane (DABCO), diazabicyclo-nonene (DBN) or diazabicyclo undecane (DBU).
Method of the present invention (g) the first step and method (j) and (k) in the presence of one or more catalyzer, implement.
The catalyzer that is fit to has, particularly palladium salt or title complex.Being suitable for this purpose has, and is preferably Palladous chloride, acid chloride, four (triphenylphosphine) closes palladium or dichloro two (triphenylphosphine) closes palladium.Also can in reaction, add palladium salt and part respectively with the palladium complex in the formation reaction mixture.
The part that is fit to has, and is preferably organo phosphorous compounds.What can propose by way of example has: triphenylphosphine, tri-o-tolyl phosphine, 2,2 '-two (diphenylphosphine)-1,1 '-dinaphthyl, dicyclohexylphosphontetrafluoroborate phenylbenzene, 1,4-two (diphenylphosphine) butane, two diphenylphosphine ferrocene, two (tertiary butyl phosphine) phenylbenzene, two (cyclohexyl phosphine) phenylbenzene, 2-dicyclohexylphosphontetrafluoroborate-2 '-N, N-dimethylamino phenylbenzene, tricyclohexyl phosphine, tri-butyl phosphine.Yet, also can be without part.
If suitable, method of the present invention (g) the first step and method (j) and (k) also can in the presence of another kind of metal-salt, for example mantoquita, for example cupric iodide (I), implement.
Implement the inventive method (g) the first step and method (j) and (k) time, temperature of reaction can change in wide relatively scope.Generally speaking, temperature of reaction is 20 ℃ to 180 ℃, preferred 50 ℃ to 150 ℃.
For the first step of implementation method (g) with preparation formula (III) anils, general every mole formula (XI) aniline halogenide uses 1 to 5mol, preferred 1 to 3mol formula (XII) alkynes.
For implementing method of the present invention (j) with preparation formula (VI) isopentene derivative, general every mole formula (XIV) acid amides use 1 to 5mol, preferred 1 to 3mol formula (XV) alkene.
For implementing method of the present invention (k) with preparation formula (VII) isopropyl-acetylene derivative, general every mole formula (XIV) acid amides use 1 to 5mol, preferred 1 to 3mol formula (XII) alkynes.
Unless stated otherwise, generally all enforcement under atmospheric pressure of all methods of the present invention.Yet, also can under the pressure that raises or reduce, operate---be generally 0.1bar to 10bar.
Material of the present invention has strong microbiocidal activity, can be used to prevent and treat unwanted microorganisms, for example fungi and bacterium in Crop protection and material protection.
Mycocide can be used to prevent and treat plasmodiophora brassicae (Plasmodiophoromycetes), oomycetes (Oomycetes), chytrid (Chytridiomycetes), zygomycetes (Zygomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes) and imperfect fungi (Deuteromycetes) in Crop protection.
Bactericide can be used to prevent and treat pseudomonas (Pseudomonadaceae), root nodule bacterium (Rhizobiaceae), enterobacteria (Enterobacteriaceae), coryneform bacteria (Corynebacteriaceae) and streptomycete (Streptomycetaceae) in Crop protection.
Some pathogenic agent that cause fungi and bacterial disease that are included into above-mentioned general name can be used as the limiting examples proposition:
Yellow unit cell (Xanthomonas) bacterial classification, for example pathogenic mutation (Xanthomonas campestris pv.oryzae) of xanthomonas campestris paddy rice;
False unit cell (Pseudomonas) bacterial classification, for example pathogenic mutation (Pseudomonas syringae pv.lachrymans) of pseudomonas syringae cucumber;
Ou Wenshi (Erwinia) bacterial classification is for example separated starch Erwinia (Erwiniaamylovora);
Rotten mould (Pythium) bacterial classification, for example ultimate corruption mould (Pythium ultimum);
Epidemic disease mould (Phytophthora) bacterial classification, for example phytophthora infestans (Phytophthorainfestans);
False downy mildew (Pseudoperonospora) bacterial classification, the false downy mildew (Pseudoperonosporacubensis) of for example careless false downy mildew (Pseudoperonospora humuli) or Cuba;
Axle downy mildew (Plasmopara) bacterial classification, for example grape is given birth to axle downy mildew (Plasmoparaviticola);
Dish downy mildew (Bremia) bacterial classification, for example lettuce dish downy mildew (Bremia lactucae);
Downy mildew (Peronospora) bacterial classification, for example pea downy mildew (Peronospora pisi) or Cruciferae downy mildew (P.brassicae);
Powdery mildew (Erysiphe) bacterial classification, for example cereal powdery mildew (Erysiphe graminis);
Single softgel shell belongs to (Sphaerotheca) bacterial classification, for example Flower of Garden Balsam list softgel shell (Sphaerothecafuliginea);
Podosphaera (Podosphaera) bacterial classification, for example white cross hair list softgel shell (Podosphaera leucotricha);
Venturia (Venturia) bacterial classification, for example apple black star bacteria (Venturiainaequalis);
Nuclear cavity Pseudomonas (Pyrenophora) bacterial classification, and for example round nuclear cavity bacteria (Pyrenophora teres) or wheat class nuclear cavity bacteria (P.graminea) (conidial form: Drechslera, syn:Helminthosporium);
Cochliobolus belongs to (Cochliobolus) bacterial classification, for example standing grain cochliobolus (Cochliobolussativus) (conidial form: Drechslera, syn:Helminthosporium);
Uromyces (Uromyces) bacterial classification, for example wart top uromyce (Uromycesappendiculatus);
Handle rest fungus (Puccinia) bacterial classification, for example Puccinia recondita (Puccinia recondita);
Sclerotinia (Sclerotinia) bacterial classification, for example sclerotinite (Sclerotiniasclerotiorum);
Tilletia (Tilletia) bacterial classification, for example wheat net fungus tilletia (Tilletiacaries);
Ustilago (Ustilago) bacterial classification, for example naked smut (Ustilago nuda) or oat ustilago (Ustilago avenae);
The film lead fungi belongs to (Pellicularia) bacterial classification, for example assistant assistant wooden film lead fungi (Pellicularia sasakii);
Pears spore (Pyricularia) bacterial classification, for example Magnaporthe grisea (Pyricularia oryzae);
Fusarium (Fusarium) bacterial classification, for example yellow sickle spore (Fusarium culmorum);
Staphlosporonites (Botrytis) bacterial classification, for example Botrytis cinerea (Botrytis cinerea);
Septoria (Septoria) bacterial classification, for example clever withered septoria musiva (Septoria nodorum);
Leptosphaeria (Leptosphaeria) bacterial classification, for example Leptosphaeria nodorum;
Cercospora (Cercospora) bacterial classification for example turns grey tail spore (Cercosporacanescens);
Alternaria (Alternaria) bacterial classification, for example rape chain lattice spore (Alternariabrassicae); And
False Cercosporalla (Pseudocercosporella) bacterial classification, the rotten germ (Pseudocercosporella herpotrichoides) of wheat-based for example,
Rhizoctonia (Rhizoctonia) bacterial classification, for example dry thread Pyrenomycetes (Rhizoctoniasolani).
Active compound of the present invention also has extraordinary strengthening effect (invigorating action) in plant.Therefore above-mentioned active compound is applicable to and transfers the inside defence capability that microbiological attack is not wanted in the plant antagonism.
Among the application, the implication of plant reinforcement (induction of resistance) compound is interpreted as exciting the material of plant defense system, and this material makes treated plant when inoculating unwanted microorganisms subsequently, can show the strong resistance to described microorganism.
In this case, the implication of unwanted microorganisms is interpreted as phytopathogenic fungi, bacterium and virus.Therefore, compound of the present invention can be used for protective plant is avoided above-mentioned pathogenic agent in the certain period after processing invasion and attack.Behind active compound processing plant, the protection period that provides can extend to 1 to 10 day usually, preferred 1 to 7 day.
The good plant tolerance that active compound has under control plant disease desired concn makes and can handle position, ground, in-vitro propagate strain (propagation stock) and seed and the soil of plant.
Herein, active compound of the present invention can good especially effect be used to prevent and treat the cereal disease, for example resist handle rest fungus bacterial classification, and the disease in control viticulture and the fruits and vegetables cultivation, Staphlosporonites bacterial classification, Venturia bacterial classification or Alternaria bacterial classification for example resisted.
Active compound of the present invention also is applicable to the raising crop yield.In addition, above-mentioned active compound also shows the toxicity of reduction and good plant tolerance.
If suitable, compound of the present invention also can be used as weedicide under finite concentration or rate of application, is used for coordinate plant growth and control animal pest.If suitable, above-claimed cpd also can be used as the intermediate or the precursor of synthetic other active compounds.
Can handle all plants and plant parts according to the present invention.The implication of plant is interpreted as all plants and plant population herein, for example need with unwanted wild plant or crop plants (comprising the crop plants that nature exists).Crop plants can be by conventional breeding and optimum seeking method or the plant that obtains by biotechnology and genetic engineering method or the combination by described method, comprises transgenic plant, also comprises the plant cultivars that is subjected to the protection of plant seedling power or is not subjected to its protection.The implication of plant parts is interpreted as all grounds of plant and underground position and organ, for example bud, leaf, Hua Hegen, the example that can propose have leaf, needle, stem, do, flower, sporophore (fruit-body), fruit and seed and root, stem tuber and rhizome.Plant parts also comprises harvested material and asexual and sexual propagation thing, for example rice shoot, stem tuber, rhizome, cutting and seed.
The processing that use active compound of the present invention carries out plant and plant parts, directly carry out or make compound effects according to conventional treatment method in environment, habitat or storage space, described conventional treatment method for example soaks, sprays, evaporates, atomizes (atomizing), broadcasts sowing, smears (painting-on), particularly under the situation of seed, also can be coated with one or more layers at the breeding thing.
Aspect material protection, compound of the present invention can be used for the safeguard industries material and avoids infecting of unwanted microorganisms and destroy.
Among the application, the implication of Industrial materials is interpreted as making non-living body (non-living) material of preparing to be used for industry.For example, intend by active compound protection of the present invention to avoid microorganism and change or the destructive Industrial materials can be tackiness agent, sizing material, paper and sheet material, fabric, leather, timber, lacquer and plastics, cooling lubricant (cooling lubricant) and other can be subjected to microbial infection or destructive material.Production plant's parts that can be damaged by microbial reproduction, for example the chilled(cooling) water return (CWR) also can propose in the scope of material to be protected.The Industrial materials that can propose within the scope of the present invention are preferably tackiness agent, sizing material, paper and sheet material, leather, timber, lacquer, cooling lubricant and heat transfer liquids, preferred especially timber.
Can propose Industrial materials are degenerated (degrading) or the microorganism that changes has, for example bacterium, fungi, yeast, algae and mucus biology.Active compound of the present invention preferably acts on fungi, particularly mould, timber fade fungi and wood-rotting fungi (basidiomycetes) and mucus biology and algae.
As an example following microorganism belonging to genus can be proposed:
Alternaria (Alternaria), chain lattice spore (Alternaria tenuis) for example,
Aspergillus (Aspergillus), aspergillus niger (Aspergillus nigar) for example,
Chaetomium (Chaetomium), chaetomium globosum (Chaetomium globosum) for example, Coniophora, Coniophora puetana for example,
Lentinus (Lentinus), Lentinus tigrinus bacterium (Lentinus tigrinus) for example,
Penicillium (Penicilium), Penicillum glaucum (Penicillium glaucum) for example,
Polyporus (Polyporus), for example variegated pore fungus (Polyporus versicolor),
Aureobasidium genus (Aureobasidium), Aureobasidium pullulans (Aureobasidiumpullulans) for example,
Nuclear stem point genus (Sclerophoma), Sclerophoma pityophila for example,
Trichoderma (Trichoderma), viride (Trichoderma viride) for example,
Escherichia (Escherichia), colon bacillus (Escherichiacoli) for example,
Rhodopseudomonas (Pseudomonas), Pseudomonas aeruginosa (Pseudomonasaeruginosa) for example, and
Staphylococcus (Staphylococcus), for example streptococcus aureus (Staphylococcus aureus).
According to its specific physics and/or chemical property, active compound can be converted into conventional formulation, for example microcapsule in solution, emulsion, suspension agent, pulvis, foam, paste, granule, aerosol and polymkeric substance and seed pelleting (coating) composition and ULV cooling and the atomizing preparation of heating (fogging formulation).
Above-mentioned preparation prepares in a known way, for example active compound is mixed with weighting agent, promptly mixes with liquid solvent, pressurized liquefied gas and/or solid carrier, alternative simultaneously tensio-active agent, i.e. emulsifying agent and/or dispersion agent and/or the whipping agent of using.If the weighting agent that uses is water, for example then also can use organic solvent as solubility promoter.The liquid solvent that is fit to mainly contains: aromatics, for example dimethylbenzene, toluene or alkylnaphthalene, chlorination aromatics or chlorination aliphatic hydrocrbon, for example chlorobenzene, vinylchlorid or methylene dichloride, aliphatic hydrocrbon, for example hexanaphthene or paraffin, as petroleum fractions, alcohol, for example butanols or ethylene glycol and ether thereof and ester, ketone, for example acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or pimelinketone, intensive polar solvent, for example dimethyl formamide or dimethyl sulfoxide (DMSO), perhaps water.The implication of liquefied gas weighting agent or carrier is interpreted as standard temperature and normal atmosphere and is gasiform liquid down, aerosol propellants for example, for example halohydrocarbon, or butane, propane, nitrogen and carbonic acid gas.The solid carrier that is fit to has: the natural mineral of Fen Suiing for example, for example kaolin, clay, talcum powder, chalk, quartz, attapulgite, montmorillonite or diatomite, and the synthetic mineral of pulverizing for example silicon-dioxide, aluminum oxide and the silicate of porphyrize.The solid carrier that is suitable for granule has: for example pulverize and the fractionated natural rock, for example calcite, marble, float stone, sepiolite and rhombspar, or the inorganic and organic powder particles of synthetic, and organic materials particle, for example wood sawdust, coconut husk, corn cob and tobacco stem.The emulsifying agent and/or the whipping agent that are fit to have: for example nonionic and anionic emulsifier, for example polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example alkylaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate or protein hydrolyzate.The dispersion agent that is fit to has: for example lignin sulfite waste lye and methylcellulose gum.
Can use tackifier in the preparation, carboxymethyl cellulose for example, powder, particle or the natural and synthetic polymer of glue lactous, for example Sudan Gum-arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipid, for example kephalin and Yelkin TTS, and synthetic phospholipid.Other additives can be mineral oil and vegetables oil.
Can use tinting material, for example mineral dye, for example ferric oxide, titanium oxide and Prussian blue, and organic dye, for example alizarine dyestuff, azoic dyestuff and metal phthalocyanine dyestuff, and micro-nutrients, for example molysite, manganese salt, boron salt, mantoquita, cobalt salt, molybdenum salt and zinc salt.
Preparation generally comprises the active compound of 0.1 to 95 weight %, preferred 0.5 to 90 weight %.
Active compound of the present invention also can itself or its preparation form mix use with known mycocide, bactericide, acarus-killing, nematocides or insecticide, for example to widen action spectrum or to prevent to produce resistance.Obtain synergistic effect as a rule, promptly the activity of mixture is greater than the activity of independent component.
The blending ingredients that is fit to has for example following compound:
Mycocide:
2 - phenylphenol; 8 - hydroxyquinoline quinoline sulfate; acibenzolar-S-methyl; aldimorph; amidoflumet; aminopropyl phosphonate (ampropylfos); aminopropyl potassium phosphonate; andoprim; enemy benomyl (anilazine); E propiconazole (azaconazole); azoxystrobin (azoxystrobin); Benalaxyl (benalaxyl); wheat rust Ling (benodanil); benomyl (benomyl); isopropyl-benthiavalicarb; benzyl acid (benzamacril); butyl benzyl acid; dual alanyl phosphine (bilahafos); Binapacryl (binapacryl); biphenyl; bitertanol (bitertanol); blasticidin (blasticidin-S); bromuconazole (bromuconazole); methyl ethyl benomyl (bupirimate); powder and fixed (buthiobate); butylamine; lime sulfur (calcium polysulphide); Kaba Xi neomycin (capsimycin); captafol (captafol); Captan (captan); carbendazim (carbendazim) ; Vitavax (carboxin); chlorine cyclopropyl amide (carpropamid); carvone (carvone); Chinomethionate (chinomethionat); blast off azole (chlobenthiazone); benzene imidazole bacteria (chlorfenazole); Tei Mou bulk (chloroneb) ; chlorothalonil (chlorothalonil); B strains Lee (chlozolinate); clozylacon; Cyazofamid (cyazofamid); cyflufenamid (cyflufenamid); clear iprodione (cymoxanil); Cyproconazole (cyproconazole); Cyprodinil (cyprodinil); cyprofuram (cyprofuram); Dagger G; pair ethoxycarbonyl imidazole Granville (debacarb); bacteriostatic Ling (dichlofluanid); dichloro-naphthoquinone (dichlone); diclofenac (dichlorophen); diclocymet; clatter clear bacteria (diclomezine); Dicloran (dicloran); Diethofencarb (diethofencarb); Difenoconazole (difenoconazole); fluorine MEPANIPYRIM (diflumetorim); A bacterium fixed (dimethirimol); Dimethomorph (dimethomorph); dimoxystrobin; Diniconazole (diniconazole); diniconazole-M (diniconazole-M); dinocap (dinocap); diphenylamine; pair pyrithione (dipyrithione); sterile phosphate (ditalimfos); Dithianon (dithianon) ; dodine; enemy cycloheximide (drazoxolon); edifenphos (edifenphos); oxygen azole bacteria (epoxiconazole); Hanle Ning (ethaboxam); ethirimol (ethirimol); chlorazol Ling (etridiazole); oxazolone bacteria (famoxadone) ; imidazole cycloheximide (fenamidone); bacteria take Ling (fenapanil); different azoxystrobin alcohol (fenarimol); fenbuconazole (fenbuconazole); A furosemide discretion aniline (fenfuram); ring amine acid bacteria (fenhexamid); seed coat ester ( fenitropan); rice blast amide (fenoxanil); fenpiclonil (fenpiclonil); Fenpropidine (fenpropidin); fenpropimorph (fenpropimorph); ferbam (ferbam); Fluazinam (fluazinam); flubenzimine; fluorine bad bacteria (fludioxonil); Fluorobiphenyl bacteria (flumetover); flumorph (flumorph); CFC sclerotia Lee (fluoromide); fluoxastrobin (fluoxastrobin); quinazolinone cycloheximide (fluquinconazole); furosemide ethyl alcohol (flurprimidol) ; Flusilazole (flusilazole); flusulfamide (flusulfamide); fluorine amide (flutolanil); Flutriafol (flutriafol); folpet (folpet); phycomycetes phosphorus (fosetyl-Al); phycomycetes sodium phosphate (fosetyl -sodium); fuberidazole (fuberidazole); furosemide metalaxyl (furalaxyl); furosemide pyrazole Ling (furametpyr); sterilization amine (furcarbanil); dressing amine (furmecyclox); guazatine (guazatine); hexachlorobenzene ; Hexaconazole (hexaconazole); hymexazol (hymexazole); ene benomyl (imazalil); amide azole (imibenconazole); Iminoctadine acetate (iminoctadinetriacetate); Iminoctadine acetate (iminoctadine tris (albesil)); iodocarb; cyclopentyl tebuconazole (ipconazole); iprobenfos (iprobenfos); isopropyl set (iprodione); Valerian Diethofencarb (iprovalicarb); human ADM (irumamycin); Isoprothiolane (isoprothiolane); chlorobenzene microphone bacteria ketone (isovaledione); kasugamycin (kasugamycin); imine bacteria (kresoxim-methyl); mancozeb (mancozeb); maneb (maneb); meferimzone; MEPANIPYRIM (mepanipyrim); propoxyphene mepronil (mepronil); metalaxyl (metalaxyl); metalaxyl-M (metalaxyl-M); cyclopentyl azole bacteria (metconazole); sulfur bacteria Granville (methasulfocarb); A furosemide bacteria amine (methfuroxam); METIRAM (metiram) ; fork aminobenzamide (metominostrobin); thiabendazole amine (metsulphovax); mildiomycin (mildiomycin); myclobutanil (myclobutanil); A bacterium Lee (myclozolin); Thomas neomycin (natamycin); nicobifen; isopropyl elimination (nitrothal-isopropyl); noviflumuron; nuarimol (nuarimol); ofurace (ofurace); orysastrobin; oxadixyl (oxadixyl); oxolinic acid (oxolinic acid); oxpoconazole; oxidation Vitavax (oxycarboxin) ; oxyfenthiin; MET (paclobutrazole); pefurazoate (pefurazoate); penconazole (penconazole); Pencycuron (pencycuron); pair chlorobenzene phosphorus (phosdiphen); tetrachlorophthalide (phthalide); Picoxystrobin ( picoxystrobin); powdery mildew Ling (piperalin); polymyxin (polyoxins); polyoxorim; thiabendazole (probenazole); prochloraz (prochloraz); sterilization Lee (procymidone); POWAVE Ling (propamocarb); propanosine-sodium ; propiconazole (propiconazole); Propineb (propineb); proquinazid; prothioconazole; pyrazole Kresoxim (pyraclostrobin); gnotobiotic phosphorus (pyrazophos); pyridine spot oxime (pyrifenox); dimethyl MEPANIPYRIM (pyrimethanil) ; pyroquilon (pyroquilon); chlorine topiramate furosemide ether (pyroxyfur); pyrrolenitrine; azole oxolinic acid (quinconazole); quinoxyfen (quinoxyfen); PCNB (quintozene); simeconazole (simeconazole); snails dioxolen amine (spiroxamine); sulfur; tebuconazole (tebuconazole); leaf blight phthalocyanine (tecloftalam); tecnazene (tecnazene); tetcyclacis; isoflurane azole (tetraconazole); thiabendazole (thiabendazole); thiabendazole nitrile (thicyofen); thifluzamide (thifluzamide); thiophanate (thiophanate-methyl); Thiram (thiram); tioxymid; tolclofos (tolclofos-methyl); pair A bacteriostatic Ling (tolylfluanid) ; triadimefon (triadimefon); azole bacteria alcohol (triadimenol); Ding triazole (triazbutil); azole bacteria triazine (triazoxide); tricyclamide; Tricyclazole (tricyclazole); g morpholine bacteria (tridemorph); trifloxystrobin (trifloxystrobin ); triflumizole (triflumizole); triforine (triforine); amyl fork azole bacteria (triticonazole); Uniconazole (uniconazole); validamycin A (validamycin A); ene cycloheximide (vinclozolin); Zineb (zineb); ziram (ziram); zoxamide (zoxamide); (2S)-N-[2 - [4 - [[3 - (4 - chlorophenyl) -2 - propynyl] oxy] -3 - methoxyphenyl] ethyl] -3 - methyl-2 - [(methylsulfonyl) amino] butanamide; 1 - (1 - naphthyl)-1H-pyrrole-2; 5 - two one; 2; 3; 5; 6 - tetrachloro-4 - (methylsulfonyl) pyridine; 2 - amino -4 - methyl-N-phenyl-5 - thiazolecarboxamide China; - chloro-N-( 2; 3 - dihydro-1;; 1 3 - trimethyl-1H-inden-4 - yl) -3 - pyridinecarboxamide; 3; 4; 5 - trichloro-2; 6 - pyridinedicarboxylic nitrile; actinovate ; cis -1 - (4 - chlorophenyl) -2 - (1H-1; 2; 4 - triazol-1 - yl) cycloheptyl alcohol; 1 - (2; 3 - dihydro-2; 2 - 2- methyl-1H-inden-1 - yl)-1H-imidazole-5 - carboxylate; potassium; N-(6 - methoxy-3 - pyridyl)-cyclopropane carboxamide; N-butyl -8 - (1,1 - dimethylethyl) -1 - oxa-spiro [4.5] decane-3 - amine; sodium tetrathiocarbonate;. And mantoquita and preparation thereof, for example Bordeaux mixture, copper hydroxide, copper naphthenate, COPPER OXYCHLORIDE 37,5 (copper oxychloride), copper sulfate, cufraneb (cufraneb), Red copper oxide, mancopper (mancopper), oxinecopper (oxine-copper) ....
Bactericide:
Bronopol (bronopol), dichlorophen, nitrapyrin (nitrapyrin), nickel dimethyldithiocarbamate (nickel-dimethyldithiocarbamate), kasugamycin, different thiophene bacterium ketone (octhilinone), carboxylic acid furans (furancarboxylic acid), terramycin (oxytetracyclin), thiabendazole, Streptomycin sulphate (streptomycin), tecloftalam, copper sulfate and other copper agents.
Insecticide/miticide/nematocides:
Oleanolic avermectin (abamectin), ABG-9008, acephate (acephate), mites quinone (Acequinocyl), imidacloprid Qing (acetamiprid), acetyl Fipronil (acetoprole), Fluoroester permethrin (acrinathrin), AKD-1022, AKD-3059, AKD-3088, boll Granville (Alanycarb), aldicarb (aldicarb), sulfone off Granville (aldoxycarb), propylene addition Tetramethrin (allethrin), allethrin isomers 1R, methyl-cypermethrin (Alpha-cypermethrin, alphamethrin), amidoflumet, aminocarb (Aminocarb), insects and mites amidine (amitraz), avermectin (avermectin), AZ-60541, Ai Zhading (azadirachtin), azole pyridine phosphorus (azamethiphos), azinphos-methyl (Azinphos-methyl), ethyl azinphos-methyl (azinphos-ethyl), azole ring tin (Azocyclotin), Pauline Bacillus (Bacillus popilliae), spherical Bacillus Bacteria (Bacillus sphaericus), Ke enemy g bacteria (Bacillus subtilis), Bacillus Gold bacillus (Bacillus thuringiensis), Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis Coli strain GC-91, Bacillus thuringiensis strain NCTC-11821, baculovirus (baculoviruses), Ba Xian bassiana (Beauveria bassiana), slim bassiana (Beauveria tenella), benclothiaz, BENDIOCARB (bendiocarb), Benfuracarb (Benfuracarb), bensultap (bensultap), benzene propargite (benzoximate), β- Cyfluthrin (beta-cyfluthrin), B-cypermethrin (beta-cypermethrin), Bifenazate (bifenazate), bifenthrin (bifenthrin), Binapacryl, in addition to anti-propylene Tetramethrin (bioallethrin), trans allethrin-S-cyclopentyl isomer, bioethanomethrin, biological permethrin (biopermethrin), D-trans permethrin pest (Bioresmethrin), Bis (trifluoromethyl) insects urea (bistrifluron), BPMC, brofenprox, Parathion ethyl bromide (bromophos-ethyl), bromopropylate (bromopropylate), bromobenzene alkenyl Phosphorus (- methyl) (bromfenvinfos (-methyl)), BTG-504, BTG-505, together kill Wei (Bufencarb), buprofezin (buprofezin), especially ethyl parathion (butathiofos), Ding Fork Wei (butocarboxim), oxygen Ding Wei fork (butoxycarboxim), butyl Pyridaben (Butylpyridaben), Cadusafos (cadusafos), Toxaphene (camphechlor), Carbaryl (carbaryl), carbofuran (carbofuran), three parathion (carbophenothion), Carbosulfan (carbosulphan), Bataan (cartap), CGA-50439, Chinomethionate (Chinomethionat), chlordane (chlordane), chlordimeform (chlordimeform), chloethocarb, soil insects phosphorus chloride (chlorethoxyfos), chlorfenapyr (Chlorfenapyr), chlorfenvinphos (chlorfenvinphos), Chlorfluazuron (Chlorfluazuron), chloroformate, phosphorus (chlormephos), chlorobenzilate (Chlorobenzilate), chloropicrin (chloropicrin), chlorproxyfen, A Base chlorpyrifos (chlorpyrifos-methyl), chlorpyrifos (- ethyl), chlovaporthrin, Ring tebufenozide (chromafenozide), cis - cypermethrin, cis - resmethrin (Cis-resmethrin), cis - permethrin (cis-permethrin), cyhalothrin (Clocythrin), in addition to line Granville (cloethocarb), clofentezine (clofentezine), Clothianidin (clothianidin), clothiazoben, dodecyl-ol (codlemone), Coumaphos (coumaphos), benzonitrile phosphorus (cyanofenphos), Cyanophos (cyanophos), cycloprene, Cycloprothrin (cycloprothrin), Cydia pomonella, cyanuric fluoride Permethrin (cyfluthrin), (RS) cyhalothrin (cyhalothrin), cyhexatin (Cyhexatin), cypermethrin (cypefmethrin), benzene, ether, permethrin (1R-trans-isomer Body) (cyphenothrin (1R-trans isomer)), cyromazine (cyromazine), DDT, Deltamethrin (deltamethrin), methyl Zero Five Nine (demeton-S-methyl), sulfur Phosphorus uptake (demeton-S-methylsulfone), acaricidal sulfur Long (diafenthiuron), chlorine Phosphorous (dialifos), diazinon (diazinon), except fenamiphos (dichlofenthion), DDVP (dichlorvos), dicofol (dicofol), dicrotophos (dicrotophos), Dicyclanil (dicyclanil), Diflubenzuron (diflubenzuron), dimefluthrin, Dimethoate (dimethoate), methyl chlorfenvinphos (dimethylvinphos), dinobuton (Dinobuton), dinocap (dinocap), Dinotefuran (dinotefuran), evil Mao ether (Diofenolan), disulfoton (disulphoton), succinic acid octyl iodide (docusat-sodium), Phenoxy alkyne mites (dofenapyn), DOWCO-439, eflusilanate, emamectin (Emamectin), emamectin benzoate (emamectin-benzoate), empenthrin (1R isomer) (empenthrin (1R isomer)), endosulfan (endosulphan), Entomophthora Species (Entomopthora spp.), EPN, esfenvalerate (esfenvalerate), benzene Insects Wei (ethiofencarb), B worms clear (ethiprole), ethion (ethion), off G P (ethoprophos), permethrin (etofenprox), special benzoxazole (etoxazole), Alloxan phosphorus (etrimfos), ammonia, sulfur phosphorus (famphur), fenamiphos (fenamiphos), quinoline Mites ether (fenazaquin), fenbutatin oxide (fenbutatin oxide), pentafluorophenyl permethrin (Fenfluthrin), fenitrothion (fenitrothion), BPMC (fenobucarb), Fenothiocarb (fenothiocarb), fenoxacrim, fenoxycarb (fenoxycarb), a cyanide Permethrin (fenpropathrin), must mites gram (fenpyrad), topiramate cypermethrin (Fenpyrithrin), Fenpyroximate (fenpyroximate), fensulfothion (fensulfothion), Fenthion (fenthion), flunitrazepam diphenylamine (fentrifanil), killing permethrin (Fenvalerate), fipronil (fipronil), flonicamid (flonicamid), fluacrypyrim, fluorine ticks urea (fluazuron), thiazole mites (flubenzimine), bromine Fluorine permethrin (flubrocythrinate), fluorine mites urea (flucycloxuron), flucythrinate (Flucythrinate), flufenerim, flufenoxuron (flufenoxuron), fluoro-benzyl ether C (Flufenprox), Flumethrin (flumethrin), fluazifop parathion (flupyrazofos), Fluticasone A triazine (flutenzin) (fluorine clofentezine (flufenzine)), fluvalinate (Fluvalinate), FONOFOS (fonofos), formetanate (formetanate), formothion (Formothion), styrene-butadiene parathion (fosmethilan), phosphorus thiazolone (fosthiazate), fubfenprox (benzyl ether mites (fluproxyfen)), Furathiocarb (furathiocarb), gamma-cyhalothrin, lindane (gamma-HCH), attracting insects sixteen ester (gossyplure), Booby ene mixtures (grandlure), granulosis virus (granuloviruses), halogen Ethofenprox (Halfenprox), tert-phenyl hydrazide (halofenozide), HCH, HCN-801, G insects Phosphorus (heptenophos), hexaflumuron (hexaflumuron), hexythiazox (hexythiazox), Mirex hydrazone (hydramethylnone), Mongolia five hundred twelve (hydroprene), IKA-2002, topiramate Insects phosphorus (imidacloprid), Imiprothrin (imiprothrin), oxadiazole insects (Indoxacarb), iodofenphos (iodofenphos), iprobenfos (iprobenfos), Fluorine triazophos (isazofos), propylamine phosphorus (isofenphos), isoprocarb (isoprocarb), Isoxazoline (isoxathion), ivermectin (ivermectin), japonilure, thiophene Ah permethrin (kadethrin), nuclear polyhedrosis virus (nuclear polyhedrosis virus), Mongolia seven hundred seventy-seven (kinoprene), cyhalothrin (lamda-cyhalothrin), lindane (Lindane), fluorine propoxyphene urea (lufenuron), Marathon (malathion), aphid phosphorus (Mecarbam), sulfoxide phosphorus (mesulfenfos), metaldehyde (metaldehyde), Granville Mu (metam-sodium), insects and mites fear (methacrifos), methamidophos (methamidophos), Metarhizium anisopliae (Metharhizium anisopliae), yellow and green anisopliae (Metharhizium flavoviride), methidathion (methidathion), methiocarb (methiocarb), off Buggy (methomyl), methoprene (methoprene), methoxychlor (methoxychlor), Methicillin hydrazide (methoxyfenozide), metofluthrin, metolcarb (metolcarb), Evil insects ketone (metoxadiazone), mevinphos (mevinphos), Mir avermectin (Milbemectin), milbemycin (milbemycin), MKI-245, MON-45700, Monocrotophos (monocrotophos), moxidectin (moxidyectin), MTI-800, dibromo Phosphorus (naled), NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide (Niclosamide), nicotine (nicotine), Nitramine ene pyridine (nitenpyram), nitrate insects Thiazine (nithiazine), NNI-0001, NNI-0101, NNI-0250, NNI-9768, double Benzene fluorouracil (novaluron), multi-fluorouracil (noviflumuron), OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate (omethoate), A Ammonia fork Wei (oxamyl), oxydemeton (oxydemeton-methyl), Paecilomyces fumosoroseus (Paecilomyces fumosoroseus), methyl Six Zero Five(parathion methyl), One thousand six hundred and five (- ethyl), permethrin (cis -, trans -), oil, PH-6045, phenothrin (1R Trans isomer) (phenothrin (1R-trans isomer), phenthoate (phenthoate), Three thousand nine hundred and eleven (phorate), Phosalone (phosalone), phosmet (phosmet), phosphorus Amine (phosphamidon), ethylene-propylene phosphorus Wei (phosphocarb), nitrile oxime phosphorus (phoxim), Piperonyl butoxide (piperonyl butoxide), pirimicarb (pirimicarb), pirimiphos (Pirimiphos-methyl), pirimiphos-ethyl (pirimiphos-ethyl), potassium oleate, Prallethrin (prallethrin), Profenofos (profenofos), profluthrin, Meng Kill Wei (promecarb), propaphos (propaphos), propargite (propargite), en- Insects phosphorus (propetamphos), propoxur (propoxur), C parathion (prothiofos), Fat fruit (prothoate), protrifenbute, refused triazone (pymetrozine), pyrazole sulfur Phosphorus (pyraclofos), anti-resmethrin (pyresmethrin), pyrethrins (pyrethrum), Pyridaben (pyridaben), acetamiprid propyl ether (pyridalyl), imputed phosphorus (Pyridaphenthion), pyridathion, ethyl amine ether (pyrimidifen), mosquitoes Ether (pyriproxyfen), quinalphos (quinalphos), resmethrin, RH-5849, ribavirin Ribavirin (ribavirin), RU-12457, RU-15525, S-421, S-1833, to kill anti-loose (Salithion), Cadusafos (sebufos), SI-0009, silafluofen (silafluofen), Ike enemy 105 (spinosad), Spirodiclofen (spirodiclofen), spiromesifen (Spiromesifen), sulfluramid (sulfluramid), sulfur Trapp (sulfotep), B C parathion (sulprofos), SZI-121, fluvalinate (tau-fluvalinate), dual Phenyl hydrazide (tebufenozide), tebufenpyrad (tebufenpyrad), ethyl propyl phosphate (Tebupirimfos), V insect phosphorus (teflubenzuron), tefluthrin (tefluthrin), Temephos (temephos), pest control fear (temivinphos), tert-Weigel (terbam), tert- Phosphorus (terbufos), tetrachlorvinphos (tetrachlorvinphos), Tetradifon (Tetradifon), tetramethrin (tetramethrin), tetramethrin (1R isomer), acaricidal Good (tetrasul), Xin-cypermethrin (theta-cypermethrin), thiacloprid (Thiacloprid), thiamethoxam (thiamethoxam), moth flies nitrile (thiapronil), thiatriphos, sulfur ring to kill (thiocyclam hydrogenoxalate), sulfur double methomyl (Thiodicarb), especially ammonia fork Wei (thiofanox), methyl disulfoton (thiometon), Bisultap (thiosultap-sodium), the enemy Bet (thuringiensin), tolfenpyrad, Fluorine deltamethrin (tralocythrin), tetrabromobisphenol permethrin (tralomethrin), PTFE permethrin (Transfluthrin), benzene race mites (triarathene), azole pirimicarb (triazamate), Triazophos (triazophos), triazuron, trichlophenidine, trichlorfon (Trichlorfon), Trichoderma atroviride, insecticidal Long (triflumuron), Mixed kill Wei (trimethacarb), vamidothion (vamidothion), fluorine-pyrazole insects (Vaniliprole), verbutin, Verticillium lecanii fungus (Verticillium lecanii), WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, culling K (Xylylcarb), ZA-3274, has cypermethrin (zeta-cypermethrin), zolaprofos, ZXI-8901, compound 3 - methyl phenyl carbamate (Z metolcarb (Tsumacide Z)), the compound 3 - (5 - chloro-3 - pyridyl) -8 - (2,2,2 - trifluoroethyl) -8 - Azabicyclo [3.2.1] octane-3 - carbonitrile (CAS Registry Number 185982-80-3) and the corresponding 3 - Endo-isomer (CAS Registry Number 185984-60-5) (see WO-96/37494, WO-98/25923), and including the insecticidally active plant extracts, nematodes, fungi or viruses Preparation. ...
Also can with other the known activity compound for example weedicide mix, or mix with fertilizer and growth regulator, safener and/or semiochemicals.
In addition, formula of the present invention (I) compound also has extraordinary anti-mycotic activity.Above-claimed cpd has the antifungic action spectrum of non-constant width, particularly resist dermatophytosis (dermatophyte) and yeast, mould and two-phase fungi (diphasic fungi) (are for example resisted Candida (Candida) bacterial classification, for example Candida albicans (Candida albicans), Candida glabrata (Candida glabrata)) and cotton-shaped surperficial tinea bacterium (Epidermophytonfloccosum), aspergillus (Aspergillus) bacterial classification is aspergillus niger (Aspergillus niger) and Aspergillus fumigatus (Aspergillus fumigatus) for example, trichophyton (Trichophyton) bacterial classification is alpha fungus (Trichophyton mentagrophytes) for example, Microsporon (Microsporon) bacterial classification is microsporum canis (Microsporon canis) and Microsporon audouinii for example.Described fungi only for the purpose of illustration, and the unrestricted fungi spectrum that contains.
Active compound can itself, its dosage form or type of service prepared therefrom use, for example i.e. solution of usefulness, suspension agent, wettable powder, paste, soluble powder, powder agent and granule.Use in a usual manner and carry out, for example water, spray, atomize, broadcast sowing, dust, foam, shed etc.Also can use active compound, or active agent preparations or active compound itself are injected in the soil by ultra-low volume method (ultra-low-volume method).Also can handle plant seed.
When active compound of the present invention was used as mycocide, rate of application can change in wide relatively scope according to using type.For the processing of plant parts, the active compound rate of application is generally 0.1 to 10,000g/ha, and preferred 10 to 1000g/ha.For seed dressing, the active compound rate of application is generally 0.001 to 50g every kilogram of seed, preferred 0.01 to 10g every kilogram of seed.For soil treatment, the active compound rate of application is generally 0.1 to 10, and 000g/ha is preferred 1 to 5,000g/ha.
As mentioned above, can handle all plants and position thereof according to the present invention.In preferred embodiments, handled wild plant kind and plant cultivars, or by the biological breeding method of routine, for example by plant species and the plant cultivars and the position thereof of hybridizing or the protoplastis fusion obtains.In a further preferred embodiment, if handled transgenic plant and plant cultivars and the position thereof that obtains by suitable also can the combining of genetic engineering with ordinary method (biology of genetic modification (genetically modified organism)).Term " position " or " position of plant " or " plant parts " are explained as above.
Particularly preferably, according to the present invention the plant commercially available or plant cultivars used is separately handled.The implication of plant cultivars is interpreted as the plant with new features (" feature ") that is obtained by conventional breeding, mutagenesis or recombinant DNA technology.Above-mentioned plant can be cultivar, mutation, biotype (biotype) or genotype.
According to plant species or plant cultivars, its plantation place and growing environment (soil, weather, vegetation period, nutrition (nutrition)), processing of the present invention also can produce superadditivity (superadditive) (" collaborative ") effect.Thus, for example can reduce rate of application and/or widen action spectrum and/or improve the material that can use by the present invention and the activity of composition, improve plant-growth, improve high temperature or cold tolerance, raising arid or water or soil salt content tolerance, improve the quality of blooming, simplify and gather, accelerates maturing, raising output, improve and gather quality product and/or improve its nutritive value, improve storage character and/or its processing characteristics of the product of gathering, these can surpass the effect of actual desired.
Preferably be included in all plants of accepting genetic material in the genetic modification according to the present invention pending transgenic plant or plant cultivars (promptly obtaining by genetic engineering), described genetic material is given described plant with particularly advantageous useful property (" feature ").The example of described characteristic has the tolerance improving plant-growth, improve high temperature or cold tolerance, raising arid or water or soil salt content, improve the quality of blooming, simplify and gather, accelerates maturing, raising output, improve the quality of the product of gathering and/or improve its nutritive value, improve storage character and/or its processing characteristics of the product of gathering.The example of other special described characteristics that propose has and improves the defence capability of plant to animal and microorganism insect, for example to insect, acarid, phytopathogenic fungi, bacterium and/or virus, and improves the tolerance of plant to some weeding active compound.The example of the transgenic plant that can propose is important crop plants, such as grain (wheat, rice), corn, soybean, potato, cotton, tobacco, rape (oilseed rape) and fruit tree (fruit is apple, pears, citrus fruits and grape), lay special stress on corn, soybean, potato, cotton, tobacco and rape.The feature of emphasizing is the toxin by forming in the plant materials particularly, particularly, improve the defence capability of plant in plant materials to insect, arachnid, nematode and snail (slugs and snails) by genetic material (for example gene C ry I A (a), Cry I A (b), Cry I A (c), Cry II A, CryIII A, Cry III B2, Cry9c, Cry2Ab, Cry3Bb and Cry I F and the combination thereof) toxin that (hereinafter to be referred as " Bt plant ") forms of Bacillus thuringiensis.Ben feature also has by systemic acquired resistance (SAR), systemin, phytoalexin, releaser and resistant gene and corresponding marking protein and toxin and improves plant to fungi, bacterium and viral defence capability.Ben feature improves the tolerance of plant to some weeding active compound in addition, for example imidazolone type, sulfonylurea, glyphosate (glyphosate) or phosphinotricin (for example " PAT " gene).The gene of giving the feature of described needs also can be bonded to each other in the transgenic plant body.It is corn mutation, cotton mutation, soybean mutation and the potato mutation of YIELD GARD_ (for example corn, cotton, soybean), KnockOut_ (for example corn), StarLink_ (for example corn), Bollgard_ (cotton), Nucotn_ (cotton) and NewLeaf_ (potato) that the example of " the Bt plant " that can propose has commercially available trade(brand)name.It is that Roundup Ready_ (has the glyphosate tolerance that the example of the plant with herbicide tolerant that can propose has commercially available trade(brand)name, for example corn, cotton, soybean), Liberty Link_ (has the phosphinotricin tolerance, rape for example), corn mutation, cotton mutation and the soybean mutation of IMI_ (having imidazolinone-tolerant) and STS_ (having the sulfonylurea tolerance, for example corn).The plant with Herbicid resistant that can propose (with the plant of conventional herbicide tolerant mode breeding) also comprises the commercially available mutation (for example corn) of Clearfield_.Certainly, more than narration is applicable to also that the plant that has described hereditary feature or wait to develop hereditary feature is carried and cultivates, and described plant cultivars will be developed and/or goes on the market in future.
Described plant can be handled with general formula of the present invention (I) compound or active compound combinations in particularly advantageous mode according to the present invention.The preferable range of above-mentioned active compound and mixture also is applicable to the processing of described plant.Lay special stress on is handled plant with the compound or the mixture that clearly propose among the application.
The preparation and the purposes of active compound of the present invention illustrate by following examples.
Preparation embodiment
Embodiment 1
Figure A20048003117600711
326.5mg (2.0mmol) [2-(3-methyl butyl) phenyl] amine (III-1) added to comprise 388.5mg (2.2mmol) 5-fluoro-1, in tetrahydrofuran (THF) (20ml) solution of 3-dimethyl-1H-pyrazoles-4-carbonyl chlorine and 0.45ml (3.2mmol) triethylamine.Stirred 90 minutes during 60 ℃ of reaction solns, filtered through silica gel also concentrates.Column chromatography (cyclohexane/ethyl acetate gradient) obtains the 5-fluoro-1 of 592mg (theoretical value 98%) logP (pH 2.3)=3.12,3-dimethyl-N-[2-(3-methyl butyl) phenyl]-the 1H-pyrazole-4-carboxamide.
To be similar to the method for embodiment 1,, obtain formula (I) compound shown in the following table 1 according to the explanation of method summation:
Table 1
Figure A20048003117600712
Figure A20048003117600713
Figure A20048003117600721
The preparation of formula (III) raw material
Embodiment (III-1)
Heating is 6 hours in the time of will comprising 210 ℃ of triglycol (90ml) solution of 8.0g (0.045mol) 1-(2-aminophenyl)-3-methyl fourth-1-ketone (X-1), 6.8g (0.135mol) hydrazine hydrate and 7.6g (0.135mol) potassium hydroxide.For carrying out aftertreatment, add entry and ethyl acetate under the room temperature.Organic phase washes with water again, dried over mgso, decompression concentrate down.Column chromatography (cyclohexane/ethyl acetate 3: 1) purifying obtains 5.3g (theoretical value 71.5%) [2-(3-methyl butyl) phenyl] amine.
Embodiment (III-2)
Earlier with 3.23g (15mmol) N-[2-(3,3-dimethyl butyrate-1-alkynyl) phenyl] ethanamide (XIII-1) adds in the 40ml methyl alcohol, add 0.5g carbon and carry palladium (palladium-on-carbon) (5%), then with mixture hydrogenation 20 hours under the 4bar hydrogen-pressure in autoclave.Remove N-[2-(3, the 3-dimethylbutyl) phenyl that catalyzer and solvent obtain 3.1g (theoretical value 94%) logP (pH 2.3)=2.69] ethanamide.
Embodiment (III-3)
0.5g (2.3mmol) N-[2-(3, the 3-dimethylbutyl) phenyl] ethanamide (III-2) stirred 5 hours 100 ℃ the time in 20ml 2N hydrochloric acid.After the cooling, use ethyl acetate extraction mixture 3 times, each 20ml.Tell organic phase, dried over sodium sulfate concentrates.Obtain 2-(3, the 3-dimethylbutyl) the aniline salt acidulants of 390mg (theoretical value 79%) logP (pH 2.3)=2.20.
The preparation of formula V raw material
Embodiment (V-1)
During room temperature, 355.0mg (2.0mmol) 1-(2-aminophenyl)-3-methyl fourth-1-ketone added to comprise 388.5mg (2.2mmol) 5-fluoro-1, in tetrahydrofuran (THF) (20ml) solution of 3-dimethyl-1H-pyrazoles-4-carbonyl chlorine and 0.45ml (3.2mmol) triethylamine.Stirred 1.5 hours during 60 ℃ of reaction mixtures, filtered through silica gel also concentrates.Column chromatography (cyclohexane/ethyl acetate: 3/1) obtain N-[2-(the 3-methylbutyryl base) phenyl of 577.7mg (1.8mmol, theoretical value 88%) logP (pH2.3)=3.42]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide.
To be similar to the method for embodiment (V-1),, obtain formula V compound shown in the following table 2 according to the explanation of method summation:
Table 2
The preparation of formula (VII) raw material
Embodiment (VII-1)
190mg (1.0mmol) 2-trifluoromethylbenzoic acid, 178mg (0.83mmol) 2-(3,3-dimethyl butyrate-1 alkynyl) aniline, 215mg (1.67mmol) N, N-diisopropylethylamine and 583mg (1.25mmol) PyBrOP stirring at room 4 days in the 8ml acetonitrile.10ml ethyl acetate/water is added in the mixture at 1: 1, and organic phase is separated, and with the washing of 10ml saturated ammonium chloride solution, uses the 10ml water washing again.Organic phase is separated, is concentrated and be dry, obtains the thick product of 950mg.Silica gel 60 (10: 1 → ethyl acetate of petrol ether/ethyl acetate) upper prop chromatography purification obtains 110mg N-[2-(3,3-dimethyl butyrate-1-alkynyl) phenyl]-2-trifluoromethyl benzamide [logP (pH 2.3)=4.55].
To be similar to the method for embodiment (VII-1),, obtain formula (VII) compound shown in the following table 3 according to the explanation of method summation:
Table 3
Figure A20048003117600763
The preparation of formula (X) raw material
Embodiment (X-1)
Figure A20048003117600772
Under the reflux conditions, tetrahydrofuran (THF) (150ml) solution of 29.5g (0.25mol) anthranilo nitrile is splashed in the suspension that comprises 18.2g (0.75mmol) magnesium, 375ml 2M isobutyl-bromination magnesium tetrahydrofuran solution and 15ml ether.Behind the reflux 5 hours, in reaction mixture, add 100ml water in the time of 0 ℃, transfer pH to 6 with hydrochloric acid.Organic phase washing, dried over mgso.Decompression concentrates down, silica gel (moving phase: sherwood oil/acetonitrile 95: 5) go up purifying, obtain 1-(2-aminophenyl)-3-espeleton of 11.0g (theoretical value 25%) logP (pH 2.3)=2.89.
The preparation of formula (XIII) raw material
Embodiment (XIII-1)
Figure A20048003117600781
Under the argon gas condition, earlier with the adjacent bromo Acetanilide of 25.7g (120mmol), 5.05g (7.2mmol) dichloro two (triphenylphosphines) close palladium (II) and 1.37g (7.2mmol) cupric iodide (I) adds in the 450ml triethylamine.Under the room temperature, splash into 17.8g (180mmol) 3 again, 3-dimethyl-ethyl acetylene, stirred 5 hours during 50 ℃ in mixture at 10 minutes dropping time.Reaction mixture is poured in the 2l water, used extracted with diethyl ether 3 times, each 250ml, extraction liquid also concentrates with dried over sodium sulfate.At silica gel 60 upper prop chromatogram purifications, obtain N-[2-(3, the 3-dimethyl butyrate-1-alkynyl) phenyl of 25.9g logP (pH 2.3)=3.03 with methylene dichloride] ethanamide.
The mensuration of the logP value that preparation embodiment provides in reaching and upward showing is undertaken by reversed-phase column (C18) HPLC (high performance liquid chromatography) method according to EEC the 79/831st trumpeter's volume appendix V.A8 (EEC-Directive 79/831 Annex V.A8).Temperature: 43 ℃.
Phosphate aqueous solution and acetonitrile with 0.1% are made moving phase, measure in the acid range of pH 2.3; Linear gradient is from 10% acetonitrile to 90% acetonitrile.
With unbranched alkane-2-ketone (3 to 16 carbon atoms) calibration, the logP value of described compound known (push away by in linear between two successive alkane ketone, determine the logP value) based on retention time.
UV spectrum with 200nm to 400nm is measured the λ maximum value at chromatographic signal distorted peak place.
Purposes embodiment
Embodiment A
Cross hair list softgel shell test (apple)/protectiveness
Solvent: 24.5 weight part acetone
24.5 weight part N,N-DIMETHYLACETAMIDE
Emulsifying agent: 1 weight part alkylaryl polyglycol ether
For preparing suitable active agent preparations, mix the active compound of 1 weight part and the solvent and the emulsifying agent of described amount, dope is diluted with water to desired concn.
Active for the test protection, the plant of childhood is sprayed with described rate of application with active agent preparations.After spraying the coating drying, described plant inoculates with the aqueous spore suspension of the white cross hair list of apple mildew (apple mildew) pathogenic agent softgel shell.Then plant is put into about 23 ℃, the relative greenhouse of atmospheric moisture about 70%.
Cultivate and evaluate and test after 10 days.0% expression drug effect with to equating in the same old way, 100% drug effect is represented not observe and is infected.
Table A
Cross hair list softgel shell test (apple)/protectiveness
Figure A20048003117600801
Cross hair list softgel shell test (apple)/protectiveness
Embodiment B
Black star bacterium test (apple)/protectiveness
Solvent: 24.5 weight part acetone
24.5 weight part N,N-DIMETHYLACETAMIDE
Emulsifying agent: 1 weight part alkylaryl polyglycol ether
For preparing suitable active agent preparations, mix the active compound of 1 weight part and the solvent and the emulsifying agent of described amount, dope is diluted with water to desired concn.
Active for the test protection, the plant of childhood is sprayed with described rate of application with active agent preparations.After spraying the coating drying, described plant is with the conidium aqeous suspension inoculation of scab of apple (apple scab) pathogenic agent apple black star bacteria, placement 1 day in about 20 ℃, the culturing room of 100% relative atmospheric moisture then.
Then plant is put into about 21 ℃, the relative greenhouse of atmospheric moisture about 90%.
Table B
Black star bacterium test (apple)/protectiveness
Figure A20048003117600821
Black star bacterium test (apple)/protectiveness
Figure A20048003117600831
Embodiment C
Grape spore test (Kidney bean)/protectiveness
Solvent: 24.5 weight part acetone
24.5 weight part N,N-DIMETHYLACETAMIDE
Emulsifying agent: 1 weight part alkylaryl polyglycol ether
For preparing suitable active agent preparations, mix the active compound of 1 weight part and the solvent and the emulsifying agent of described amount, dope is diluted with water to desired concn.
Active for the test protection, the plant of childhood is sprayed with described rate of application with active agent preparations.After spraying the coating drying, the agar of 2 small pieces being grown ash charge grape spore is placed on the every leaf.Postvaccinal plant is put into about 20 ℃, the darkroom of 100% relative atmospheric moisture.
Inoculate the size that is infected area after 2 days on the evaluation and test leaf.0% expression drug effect with to equating in the same old way, 100% drug effect is represented not observe and is infected.
Table C
Grape spore test (Kidney bean)/protectiveness
Figure A20048003117600841
Grape spore test (Kidney bean)/protectiveness
Figure A20048003117600851
Embodiment D
Handle rest fungus test (wheat)/therapeutic
Solvent: 50 weight part N,N-dimethylacetamide
Emulsifying agent: 1 weight part alkylaryl polyglycol ether
For preparing suitable active agent preparations, mix the active compound of 1 weight part and the solvent and the emulsifying agent of described amount, dope is diluted with water to desired concn.
Be the test therapeutic activity, use the conidial suspension of Puccinia recondita to spray the plant of childhood.Described plant was placed in 20 ℃, the culturing room of 100% relative atmospheric moisture 48 hours.Then plant is sprayed with described rate of application with active agent preparations.
Then plant is put into about 20 ℃, the greenhouse of 80% relative atmospheric moisture, to promote rust spore (rust pustule) growth.
Inoculate and evaluate and test after 8 days.0% expression drug effect with to equating in the same old way, 100% drug effect is represented not observe and is infected.
Table D
Handle rest fungus test (wheat)/therapeutic
Figure A20048003117600861
Handle rest fungus test (wheat)/therapeutic
Embodiment E
Single softgel shell test (cucumber)/protectiveness
Solvent: the N of 49 weight parts, dinethylformamide
Emulsifying agent: the alkylaryl polyglycol ether of 1 weight part
For preparing suitable active agent preparations, mix the active compound of 1 weight part and the solvent and the emulsifying agent of described amount, dope is diluted with water to desired concn.
Active for the test protection, the cucumber plant of childhood is sprayed with described rate of application with active agent preparations.Handle after 1 day, described plant inoculates with the spore suspension of Flower of Garden Balsam list softgel shell.Then plant is put into the greenhouse of 23 ℃ of relative atmospheric moistures 70%, temperature.
Cultivate and evaluate and test after 7 days.0% expression drug effect with to equating in the same old way, 100% drug effect is represented not observe and is infected.
Table E
Single softgel shell test (cucumber)/protectiveness
Figure A20048003117600881

Claims (18)

1. the isopentyl carbonyl aniline of formula (I)
Wherein
The L representative
Figure A2004800311760002C2
Wherein the key with the * mark links to each other with acid amides, and the key that marks with # links to each other with alkyl group side chain,
R 1Represent hydrogen, C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4,-CONR 5R 6Or-CH 2NR 7R 8,
R 2Represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R 3Represent hydrogen, halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
R 4Represent hydrogen, C 1-C 8Alkyl, C 1-C 8Alkoxyl group, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 6Halogenated alkoxy, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl,
R 5And R 6Represent hydrogen, C independently of one another separately 1-C 8Alkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 8Haloalkyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl,
R 5And R 6Also the nitrogen-atoms that connects with them forms the saturated heterocyclic with 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces or is polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 7And R 8Represent hydrogen, C independently of one another 1-C 8Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 8Haloalkyl, C 3-C 8Halogenated cycloalkyl,
R 7And R 8Also the nitrogen-atoms that connects with them forms the saturated heterocyclic with 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces or is polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 9Represent hydrogen or C 1-C 6Alkyl,
A represents formula (A1) group
Wherein
R 10Represent hydrogen, hydroxyl, formyl radical, cyano group, halogen, nitro, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio, C 3-C 6Cycloalkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy or C 1-C 4Halogenated alkylthio, aminocarboxyl or aminocarboxyl-C 1-C 4Alkyl,
R 11Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkylthio, and
R 12Represent hydrogen, C 1-C 4Alkyl, hydroxyl-C 1-C 4Alkyl, C 2-C 6Alkenyl, C 3-C 6Cycloalkyl, C 1-C 4Alkylthio-C 1-C 4Alkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio-C 1-C 4Alkyl, C 1-C 4Halogenated alkoxy-C 1-C 4Alkyl is perhaps represented phenyl,
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and
Prerequisite is if R 3And R 11Represent hydrogen, and R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl,
Perhaps
A represents (A2) group
Wherein
R 13And R 14Represent hydrogen, halogen, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 15Represent halogen, cyano group or C 1-C 4Alkyl, or have the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkoxy,
Perhaps
A represents formula (A3) group
Wherein
R 16And R 17Represent hydrogen, halogen, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 18Represent hydrogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A4) group
Wherein
R 19Represent hydrogen, halogen, hydroxyl, cyano group, C 1-C 6Alkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy or C 1-C 4Halogenated alkylthio,
Perhaps
A represents formula (A5) group
Wherein
R 20Represent halogen, hydroxyl, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio or C 1-C 4Halogenated alkoxy, and
R 21Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy, C 1-C 4Alkyl sulphinyl or C 1-C 4Alkyl sulphonyl,
Perhaps
A represents formula (A6) group
Figure A2004800311760005C1
Perhaps
A represents formula (A7) group
Figure A2004800311760005C2
Wherein
R 22Represent C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A8) group
Figure A2004800311760005C3
Wherein
R 23Represent C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A9) group
Figure A2004800311760005C4
Wherein
R 24And R 25Represent hydrogen, halogen, amino, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 26Represent hydrogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Prerequisite is if R 25Represent hydrogen, then R 24And R 26Different times table methyl,
Perhaps
A represents formula (A10) group
Wherein
R 27And R 28Represent hydrogen, halogen, amino, nitro, C independently of one another 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 29Represent halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A11) group
Figure A2004800311760006C1
Wherein
R 30Represent hydrogen, halogen, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 31Represent halogen, hydroxyl, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 3-C 6Cycloalkyl has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl or C 1-C 4Halogenated alkoxy,
Prerequisite is if R 3Represent hydrogen, and R 30Represent methylidene, then R 31Do not represent trifluoromethyl, difluoromethyl or methyl,
Perhaps
A represents formula (A12) group
Wherein
R 32Represent hydrogen, halogen, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl, and
R 33Represent halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A13) group
Wherein
R 34Represent hydrogen or C 1-C 4Alkyl, and
R 35Represent halogen or C 1-C 4Alkyl,
Perhaps
A represents formula (A14) group
Figure A2004800311760006C4
Wherein
R 36Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Perhaps
A represents formula (A15) group
Wherein
R 37Represent halogen, hydroxyl, C 1-C 4Alkyl, C 1-C 4Alkoxyl group, C 1-C 4Alkylthio has the C of 1 to 5 halogen atom separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio or C 1-C 4Halogenated alkoxy,
Perhaps
A represents formula (A16) group
Figure A2004800311760007C2
Wherein
R 38Represent hydrogen, cyano group, C 1-C 4Alkyl, has the C of 1 to 5 halogen atom 1-C 4Haloalkyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, hydroxyl-C 1-C 4Alkyl, C 1-C 4Alkyl sulphonyl, two (C 1-C 4Alkyl) amino-sulfonyl, C 1-C 6Alkyl-carbonyl or optional separately benzenesulfonyl or the benzoyl that replaces,
R 39Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
R 40Represent hydrogen, halogen, cyano group, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
R 41Represent hydrogen, halogen, C 1-C 4Alkyl or have the C of 1 to 5 halogen atom 1-C 4Haloalkyl,
Prerequisite is R 40Do not represent trifluoromethyl,
Perhaps
A represents formula (A17) group
Wherein
R 42Represent C 1-C 4Alkyl.
2. the isopentyl carbonyl aniline of the formula of claim 1 (I), wherein
The L representative
Figure A2004800311760008C1
Wherein the key with the * mark links to each other with acid amides, and the key that marks with # links to each other with alkyl group side chain,
R 1Represent hydrogen, C 1-C 6Alkyl, C 1-C 4Alkyl sulphinyl, C 1-C 4Alkyl sulphonyl, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 6Alkyl) carbonyl, (C 1-C 4Alkoxyl group) carbonyl, (C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl) carbonyl, (C 1-C 4Halogenated alkoxy) carbonyl, (halo-C 1-C 3Alkoxy-C 1-C 3Alkyl) carbonyl, (C 3-C 6Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4,-CONR 5R 6Or-CH 2NR 7R 8,
R 2Represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R 3Represent hydrogen, fluorine, chlorine, bromine, iodine, C 1-C 6Alkyl, has the C of 1 to 13 fluorine, chlorine and/or bromine atoms 1-C 6Haloalkyl,
R 4Represent hydrogen, C 1-C 6Alkyl, C 1-C 4Alkoxyl group, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 1-C 4Halogenated alkoxy, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Halogenated cycloalkyl,
R 5And R 6Represent hydrogen, C independently of one another 1-C 6Alkyl, C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, halo-C 1-C 3Alkoxy-C 1-C 3Alkyl, C 3-C 6Halogenated cycloalkyl,
R 5And R 6Also the nitrogen-atoms that connects with them forms the saturated heterocyclic with 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces to four replacements, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 7And R 8Represent hydrogen, C independently of one another 1-C 6Alkyl, C 3-C 6Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 4Haloalkyl, C 3-C 6Halogenated cycloalkyl,
R 7And R 8Also the nitrogen-atoms that connects with them forms the saturated heterocyclic with 5 to 8 annular atomses, optional halogen and the C of being selected from of described heterocycle 1-C 4The identical or different substituting group list of alkyl replaces to polysubstituted, and wherein heterocycle also can comprise 1 or 2 non-conterminous oxygen, sulphur and NR of being selected from 9Other heteroatomss,
R 9Represent hydrogen or C 1-C 4Alkyl,
A represents formula (A1) group
Wherein
R 10Represent hydrogen, hydroxyl, formyl radical, cyano group, fluorine, chlorine, bromine, iodine, methyl, ethyl, sec.-propyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, cyclopropyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl, C 1-C 2Halogenated alkoxy, trifluoromethylthio, difluoro methylthio group, aminocarboxyl, amino carbonyl methyl or aminocarboxyl ethyl,
R 11Represent hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
R 12Represent hydrogen, methyl, ethyl, n-propyl, sec.-propyl, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, methylol, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl,
Prerequisite is if R 11Represent hydrogen, then R 10Do not represent iodine, and
Prerequisite is if R 3And R 11Represent hydrogen, and R 12Represent methylidene, then R 10Do not represent trifluoromethyl or difluoromethyl,
Perhaps
A represents (A2) group
Wherein
R 13And R 14Represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl independently of one another or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
R 15Represent fluorine, chlorine, bromine, iodine, cyano group, methyl, ethyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy,
Perhaps
A represents formula (A3) group
Figure A2004800311760010C1
Wherein
R 16And R 17Represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl independently of one another or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, and
R 18Represent hydrogen, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A4) group
Wherein
R 19Represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, C 1-C 4Alkyl has the C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl, C 1-C 2Halogenated alkoxy or C 1-C 2Halogenated alkylthio,
Perhaps
A represents formula (A5) group
Figure A2004800311760010C3
Wherein
R 20Represent fluorine, chlorine, bromine, iodine, hydroxyl, cyano group, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, difluoro methylthio group, trifluoromethylthio, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy, and
R 21Represent hydrogen, fluorine, chlorine, bromine, iodine, cyano group, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy, C 1-C 2Alkyl sulphinyl or C 1-C 2Alkyl sulphonyl,
Perhaps
A represents formula (A6) group
Figure A2004800311760010C4
Perhaps
A represents formula (A7) group
Wherein
R 22Represent methylidene, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A8) group
Figure A2004800311760011C2
Wherein
R 23Represent methylidene, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A9) group
Figure A2004800311760011C3
Wherein
R 24And R 25Represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl independently of one another or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, and
R 26Represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Prerequisite is if R 25Represent hydrogen, then R 24And R 26Different times table methyl,
Perhaps
A represents formula (A10) group
Figure A2004800311760011C4
Wherein
R 27And R 28Represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl independently of one another or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, and
R 29Represent fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A11) group
Figure A2004800311760012C1
Wherein
R 30Represent hydrogen, fluorine, chlorine, bromine, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, and
R 31Represent fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxyl group, oxyethyl group, cyclopropyl, have a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy,
Prerequisite is if R 3Represent hydrogen, and R 30Represent methylidene, then R 31Do not represent trifluoromethyl, difluoromethyl or methyl,
Perhaps
A represents formula (A12) group
Wherein
R 32Represent hydrogen, fluorine, chlorine, bromine, amino, C 1-C 4Alkylamino, two (C 1-C 4Alkyl) amino, cyano group, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, and
R 33Represent fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A13) group
Figure A2004800311760012C3
Wherein
R 34Represent hydrogen, methyl or ethyl, and
R 35Represent fluorine, chlorine, bromine, methyl or ethyl,
Perhaps
A represents formula (A14) group
Wherein
R 36Represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Perhaps
A represents formula (A15) group
Figure A2004800311760013C2
Wherein
R 37Represent fluorine, chlorine, bromine, iodine, hydroxyl, C 1-C 4Alkyl, methoxyl group, oxyethyl group, methylthio group, ethylmercapto group, difluoro methylthio group, trifluoromethylthio, has a C of 1 to 5 fluorine, chlorine and/or bromine atoms separately 1-C 2Haloalkyl or C 1-C 2Halogenated alkoxy,
Perhaps
A represents formula (A16) group
Wherein
R 38Represent hydrogen, methyl, ethyl, have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl, C 1-C 2Alkoxy-C 1-C 2Alkyl, methylol, hydroxyethyl, methyl sulphonyl or dimethylamino alkylsulfonyl,
R 39Represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
R 40Represent hydrogen, fluorine, chlorine, bromine, cyano group, methyl, ethyl, sec.-propyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
R 41Represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or have the C of 1 to 5 fluorine, chlorine and/or bromine atoms 1-C 2Haloalkyl,
Prerequisite is R 40Do not represent trifluoromethyl,
Perhaps
A represents formula (A17) group
Wherein
R 42Represent methylidene, ethyl, n-propyl or sec.-propyl.
3. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein L represents L-1.
4. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein L represents L-2.
5. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein R 1Represent hydrogen, formyl radical or-C (=O) C (=O) R 4, R wherein 4As claim 1 or 2 definition.
6. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein A represents A1.
7. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein R 3Represent hydrogen.
8. the isopentyl carbonyl aniline of claim 1 or 2 formula (I), wherein R 3Represent halogen, C 1-C 8Alkyl or C 1-C 8Haloalkyl.
9. the method for formula (I) compound of preparation claim 1 is characterized in that
If a) be suitably under the existence of catalyzer, if be suitably under the existence of condensing agent, if if being suitably in the existence of acid binding agent descends and is suitably under the existence of thinner, the anils reaction of the carboxylic acid derivative of formula (II) and formula (III),
Figure A2004800311760014C2
Wherein
A such as claim 1 definition, and
X 1Represent halogen or hydroxyl,
Wherein L, R 1And R 3Define as above,
Perhaps
B) in the presence of alkali and in the presence of thinner, the halide reaction of the isopentyl carbonyl aniline of formula (I-a) and formula (IV)
Figure A2004800311760014C4
Wherein
L, A and R 3As claim 1 definition,
R 1-A-X 2 (IV)
Wherein
X 2Represent chlorine, bromine or iodine,
R 1-ARepresent C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8,
R wherein 4, R 5, R 6, R 7And R 8As claim 1 definition,
Perhaps
C) in the presence of alkali, and if be suitably under the existence of thinner, the isoamyl ketone derivatives of formula V and hydrazine (or hydrazine hydrate) reaction,
Wherein
R 1, R 2, R 3With A such as claim 1 definition,
Perhaps
D) if be suitably under the existence of thinner, and if be suitably under the existence of catalyzer, the isopentene derivative hydrogenation of formula (VI),
R wherein 1, R 2, R 3With A such as claim 1 definition,
Perhaps
E) if be suitably under the existence of thinner, and if be suitably under the existence of catalyzer, the isopropyl-acetylene derivative hydrogenation of formula (VII),
R wherein 1, R 2, R 3With A such as claim 1 definition.
10. be used to prevent and treat the composition of unwanted microorganisms, it is characterized in that described composition comprises formula (I) the isopentyl carbonyl aniline of at least a claim 1, adds weighting agent and/or tensio-active agent.
11. the formula of claim 1 (I) isopentyl carbonyl aniline is used to prevent and treat the purposes of unwanted microorganisms.
12. prevent and treat the method for unwanted microorganisms, it is characterized in that formula (I) the isopentyl carbonyl aniline of claim 1 is applied to described microorganism and/or its habitat.
13. preparation is used to prevent and treat the method for compositions of not wanting microorganism, it is characterized in that making formula (I) the isopentyl carbonyl aniline of claim 1 to mix with weighting agent and/or tensio-active agent.
14. the anils of formula (III-b)
Wherein
A) R 1-BRepresent C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8, and
R 3-BRepresent hydrogen, halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
Perhaps
B) R 1-BRepresent hydrogen, C 1-C 8Alkyl, C 1-C 6Alkyl sulphinyl, C 1-C 6Alkyl sulphonyl, C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Cycloalkyl has the C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl, C 1-C 4Halogenated alkylthio, C 1-C 4Haloalkyl sulfinyl, C 1-C 4Halogenated alkyl sulfonyl, halo-C 1-C 4Alkoxy-C 1-C 4Alkyl, C 3-C 8Halogenated cycloalkyl, formyl radical, formyl radical-C 1-C 3Alkyl, (C 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, (C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl has the halo-(C of 1 to 13 fluorine, chlorine and/or bromine atoms separately 1-C 3Alkyl) carbonyl-C 1-C 3Alkyl, halo-(C 1-C 3Alkoxyl group) carbonyl-C 1-C 3Alkyl,
(C 1-C 8Alkyl) carbonyl, (C 1-C 8Alkoxyl group) carbonyl, (C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Cycloalkyl) carbonyl has the (C of 1 to 9 fluorine, chlorine and/or bromine atoms separately 1-C 6Haloalkyl) carbonyl, (C 1-C 6Halogenated alkoxy) carbonyl, (halo-C 1-C 4Alkoxy-C 1-C 4Alkyl) carbonyl, (C 3-C 8Halogenated cycloalkyl) carbonyl, or-C (=O) C (=O) R 4, CONR 5R 6Or-CH 2NR 7R 8, and
R 3-BRepresent halogen, C 1-C 8Alkyl, C 1-C 8Haloalkyl,
And R 2, R 4, R 5, R 6, R 7And R 8Define as claim 1.
15. the isoamyl ketone derivatives of formula V
Figure A2004800311760017C1
R wherein 1, R 2, R 3With A such as claim 1 definition.
16. the isopentene derivative of formula (VI)
Figure A2004800311760018C1
R wherein 1, R 2, R 3With A such as claim 1 definition.
17. the isopropyl-acetylene derivative of formula (VII)
R wherein 1, R 2And R 3As claim 1 definition,
A such as claim 1 definition, but be not A1.
18. the alkane ketone aniline of formula (X)
Figure A2004800311760018C3
R wherein 1, R 2And R 3Define as claim 1.
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