CN1306523A - Substituted 6-aryl-3-thioxo-5-(thi) oxo-2,3,4,5-tetrahydro-1,2,4-triazines - Google Patents

Substituted 6-aryl-3-thioxo-5-(thi) oxo-2,3,4,5-tetrahydro-1,2,4-triazines Download PDF

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CN1306523A
CN1306523A CN99807687A CN99807687A CN1306523A CN 1306523 A CN1306523 A CN 1306523A CN 99807687 A CN99807687 A CN 99807687A CN 99807687 A CN99807687 A CN 99807687A CN 1306523 A CN1306523 A CN 1306523A
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base
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P·沙弗
M·拉克
R·高兹
G·汉普莱彻特
O·曼克
M·曼戈斯
R·莱恩哈德
C·扎噶
M·奥顿
K-O·威斯特法兰
H·沃尔特
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BASF SE
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    • C07C59/40—Unsaturated compounds
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    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
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    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
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    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
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    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract

The invention relates to substituted 6-aryl-3-thioxo-5-(thi)oxo-2,3,4,5-tetrahydro-1,2,4-triazines of formula (I) and to their salts. In said formula, R<1> is C1-C6-alkyl, C1-C6-halogen alkyl, and possibly substituted phenyl; R<2> is NH2, C1-C6-alkyl, C1-C6-halogen alkyl, C2-C6-alkenyl, C3-C6-alkinyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C3-C6-cycloalkyl; Ar is a group corresponding to formula Ar<1>, Ar<2>, Ar<3> or Ar<4>; Y is O, S; Z is O, S, NH, N(C1-C6-alkyl) and R<4>, R<5>, R<6>, R<7> and R<8> have the meaning given in the description. Said compounds are used as herbicides and for the desiccation/defoliation of plants.

Description

6-aryl-3-sulfo--5-(sulfo-) oxo-2,3,4 that replaces, 5-tetrahydrochysene-1,2,4-triazine
The present invention relates to 6-aryl-3-sulfo--5-(sulfo-) oxo-2,3,4 of the replacement of new formula I, 5-tetrahydrochysene-1,2, applicable salt on the agricultural of 4-triazine and chemical compounds I;
Figure A9980768700071
Wherein:
X is oxygen or sulphur;
R 1Be C 1-C 6-alkyl, C 1-C 6-haloalkyl or as need to have one to three substituent phenyl, each substituting group is selected from following group: nitro, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl and C 1-C 6-alkoxyl group;
R 2Be amino, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 2-C 6-alkenyl, C 3-C 6-alkynyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, C 1-C 6-alkylthio-C 1-C 6-alkyl or C 3-C 6-cycloalkyl;
Ar is general formula Ar 1-Ar 4The aryl of replacement:
Figure A9980768700072
R 3It is hydrogen or halogen;
R 4Be cyano group, halogen ,-CS-N-H 2, hydroxyl, C 1-C 6-alkoxyl group, C 1-C 6-halogenated alkoxy, C 2-C 4-alkenyloxy, C 2-C 4-alkynyloxy group, (C 1-C 4-alkoxyl group) carbonyl-C 1-C 4-alkoxyl group or do not replace or phenyl ring on have one to three substituent benzyloxy, each substituting group is selected from following group: halogen, C 1-C 6-alkyl, C 2-C 6-alkoxyl group and C 1-C 6-halogenated alkoxy;
R 5Be hydrogen, nitro, cyano group, amino, hydroxylamino, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, formyl radical ,-CH=N-OR 9,-CH (OR 10) 2,
Figure A9980768700081
R 11, R 12,-CO-Cl ,-CO-OR 13,-CO-OR 14-CO-OR 13,-CO-N (R 15)-R 16,-CO-OR 14-CO-N (R 15)-R 16,-CH2-CH (R 17)-CO-OR 13,-CH=C (R 17)-CO-OR 13,-OCH (CH 3)-COOH ,-OCH (CH 3)-COOCH 3,-N (R 20)-R 19,-SO 2-Cl ,-SO 2-N (R 15)-R 16,-CO-NH-OR 15,
Figure A9980768700082
-CO-N (R 22)-OR 15
Or and R 4Represent chain O-CH together 2-CH 2-O wherein can have cyano group, halogen, C 1-C 6-alkyl, oxo, hydroxycarbonyl group or (C 1-C 6-alkoxyl group) carbonyl substituted base;
R 6Be hydrogen, hydroxyl, C 1-C 6-alkyl, C 1-C 6-alkoxyl group, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkoxyl group-(C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group)-carbonyl-C 1-C 6-alkoxyl group, C 3-C 6-alkenyl, C 3-C 6-alkynyl, C 3-C 6-alkenyloxy or C 3-C 6-alkynyloxy group;
R 7Be hydrogen, C 1-C 6-alkyl or (C 1-C 6-alkoxyl group) carbonyl;
R 8Be hydrogen, hydroxyl, sulfydryl, halogen, C 1-C 6-alkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, hydroxycarbonyl group, hydroxycarbonyl group-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl, C 1-C 6-alkoxyl group, C 1-C 6-alkoxy-C 1-C 6-alkoxyl group, C 3-C 6-alkenyloxy, C 3-C 6-alkynyloxy group, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkoxyl group, C 1-C 6-alkylthio, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkylthio, C 3-C 6-alkenyl thio, C 3-C 6-alkynes sulfenyl ,-N (R 23)-R 24,-CH 2-CH (R 17)-CO-OR 13Or-CH=C (R 17)-CO-OR 13
N is 0 or 1;
Y is oxygen or sulphur;
Z is an oxygen, sulphur or-N (R 23)-;
R 9Be hydrogen, C 1-C 6-alkyl or (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl;
R 10Be C 1-C 6-alkyl;
R 11, R 12On 4 or 5 of dioxolane, be hydrogen independently of one another, C 1-C 6-alkyl, hydroxycarbonyl group or (C 1-C 6-alkoxyl group) carbonyl;
R 13Be hydrogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, cyano group-C 1-C 6-alkyl, C 3-C 7-cycloalkyl, 3-oxetanyl, C 3-C 6-alkenyl, C 3-C 6-halogenated alkenyl or C 3-C 6-alkynyl;
R 14Be C 1-C 6-alkylidene group;
R 15Be hydrogen or C 1-C 6-alkyl;
R 16Be hydrogen, C 1-C 6-alkyl, C 3-C 7-cycloalkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkyl sulphonyl or and R 15Representative can be interrupted by oxo bridge and/or by (C together 1-C 6-alkoxyl group) tetramethylene of carbonyl substituted or five methene chain;
R 17Be hydrogen, halogen or C 1-C 6-alkyl;
R 19Be C 1-C 6-alkyl sulphonyl;
R 20Be hydrogen, C 1-C 6-alkyl or C 1-C 6-alkyl sulphonyl;
R 21, R 22Be C independently of one another 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 3-C 6-alkenyl, C 3-C 6-alkynyl or benzyl;
R 23Be hydrogen or C 1-C 6-alkyl;
R 24Be hydrogen, C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 3-C 6-alkenyl, C 3-C 6-alkynyl or benzyl.
In addition, the present invention relates to
-these chemical compounds Is are as the purposes of weedicide or plant dehydration agent/defoliating agent,
-contain herbicidal composition and the plant dehydration agent/defoliating agent composition of chemical compounds I as activeconstituents,
-use chemical compounds I control not need plant and the method that is used for plant dehydration/disleave,
The herbicidal composition and the plant dehydration agent/defoliating agent preparation of compositions method of-use chemical compounds I, and
Structural formula Va ' the intermediate of-Xin.
Following publication discloses 2 6-phenyl-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, and the 4-triaizine compounds, but the content of any weeding characteristic is not disclosed: Daunis et al.; BSCFAS; Bull.Soc.Chim.Fr.; 1972; 1511,1513,1514,1517; Prystas; Gut; CCCCAK; Collect.Czech.Chem.Commun.27 (1962), 1898,1903; Mansour; Ibrahim; JPCEAO; J.Prakt.Chem.315 (1973), 221,223; Ibrahim; IJSBDB; Indian J.Chem.Sect.B, 14 (1976), 273;
Figure A9980768700102
Prystas; Gut; CCCCAK; Collect.Czech.Chem.Commun.27 (1962), 1898,1903; Daunis et al.; BSCFAS; Bull.Soc.Chim.Fr.; 1972; 1975,1980-1982.WO 94/03454 discloses the triazone with weeding activity, especially structural formula II Compound C 1-C 4-alkyl C 1-C 4-haloalkyl
Figure A9980768700111
R wherein aBe C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 3-C 4-alkenyl or C 3-C 4-alkynyl and Q are the adjacent halogenophenyls that has 1 or 2 other substituting group or condense specific heterocyclic radical on it.
EP-A 044 696 discloses the triazone with weeding activity, especially structural formula III compound:
C 1-C 4-alkoxyl group
C 1-C 4-alkylthio two (C 1-C 4-alkyl) amino
Figure A9980768700112
{ halogen/C 1-C 4-alkyl/C 1-C 4-alkoxyl group/NO 2/ C (halogen) 3} 0-2H 2N/C 1-C 4-alkyl
Other weeding activity triazineon compounds is disclosed in U.S.3, and 671,523, U.S.3,966,715, U.S.3,544,570 and W.Oettmeier etc., Pestic.Sci.33 (1991) is among the 399-409.
At last, JP-A 10/,053 508 discloses 1,2 of structural formula X, 4-triaizine compounds
Figure A9980768700113
R wherein bBe C 1-C 4-alkyl, C 2-C 4-alkenyl, C 2-C 4-alkynyl or C 1-C 4-haloalkyl, R cBe hydrogen or R bAnd R dEspecially H, C 1-C 6-alkyl or-CH (C 1-C 4-alkyl)-COO (H/C 1-C 6-alkyl), and equally disclose these compounds and had weeding activity.
Yet known weedicide always can not be entirely satisfactory to the weeding activity of noxious plant.
The purpose of this invention is to provide new weeding active compound, it is compared with known compound and can optionally control undesired plant growth better.Another purpose provides the new compound with dehydration/disleave effect.
We find, above-mentioned purpose can be by 6-aryl-3-sulfo--5-(sulfo-) oxo-2,3,4 in the replacement of the structural formula I of the present invention that begins to describe, 5-tetrahydrochysene-1,2,4 triaizine compounds and the herbicide effect that has thereof and realize.
And we also find the herbicidal composition that contains chemical compounds I and good herbicide effect is arranged.And, the method that we have also found to prepare these method for compositions and have controlled undesired plant growth with chemical compounds I.
And we find that also chemical compounds I also can be used for the dehydration and/or the disleave of plant each several part, and suitable plant can be crop such as cotton, potato, rape, Sunflower Receptacle, soybean or broad bean, particularly cotton.Therefore, we find plant dehydration and/or defoliating agent composition, these preparation of compositions methods and the method for using chemical compounds I to carry out plant dehydration and/or disleave.
According to the replacement mode, formula I compound can contain one or more chiral centres, and therefore they can be used as enantiomorph or non-enantiomer mixture existence.Have at least at chemical compounds I under the situation of a thiazolinyl, also can contain the E/Z isomer.The present invention relates to pure enantiomorph or diastereomer and composition thereof.
6-aryl-3-sulfo--5-(sulfo-) oxo-2,3,4 that replaces, 5-tetrahydrochysene-1,2, the 4-triazine can their agriculturals go up the salt form existence of using, and the type of salt is unimportant usually.Generally, do not have negative impact as long as compare the salt pair herbicide effect of formation with the free cpds I, then the salt and the acid salt of the formation of chemical compounds I and those alkali are fit to.
Particularly suitable subsalt is those an alkali metal salts, preferred sodium and sylvite, and alkaline earth salt, preferred calcium and magnesium salts, transition metal salt, preferred zinc and molysite, and ammonium salt are wherein as needing ammonium ion can have one to four C 1-C 4-alkyl, hydroxyl-C 1-C 4-alkyl substituent and/or phenyl or benzyl substituting group, preferred di-isopropyl ammonium, tetramethyl-ammonium, TBuA, tri methyl benzyl ammonium and trimethylammonium-(2-hydroxyethyl) ammonium salt, Hai You phosphonium salt in addition, sulfonium salt is as preferred three-(C 1-C 4-alkyl) sulfonium salt and oxidation sulfonium salt such as preferred three-(C 1-C 4-alkyl) oxidation sulfonium salt.
Available acid salt negatively charged ion at first is a muriate, bromide, fluorochemical, hydrosulfate, vitriol, dihydrogen phosphate, hydrophosphate, phosphoric acid salt, nitrate, supercarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and C 1-C 4-paraffinic acid negatively charged ion, preferable formic acid salt, acetate, propionic salt and butyrates.
In substituent R 1, R 2And R 4-R 24Definition described in organic moiety represent single group member's general name.All carbochains; promptly all alkyl, haloalkyl, alkoxyl group, halogenated alkoxy, alkylthio, alkyl sulphonyl, cyano group alkyl, hydroxycarbonyl group alkyl, alkoxy carbonyl; alkenyl, alkynyl, alkenyloxy, alkynyloxy group, alkenyl thio and alkynes sulfenyl part can be straight or brancheds.Halogenated substituting group preferably has one to five identical or different halogen atom.
Halogen is represented fluorine, chlorine, bromine or iodine under every kind of situation, preferred fluorine or chlorine.
The example of other definition is:
-C 1-C 6-alkyl: CH 3, C 2H 5, n-propyl, CH (CH 3) 2, normal-butyl, CH (CH 3)-C 2H 5, CH 2-CH (CH 3) 2, C (CH 3) 3N-pentyl, the 1-methyl butyl, the 2-methyl butyl, the 3-methyl butyl, 2, the 2-dimethyl propyl, the 1-ethyl propyl, n-hexyl, 1, the 1-dimethyl propyl, 1, the 2-dimethyl propyl, the 1-methyl amyl, the 2-methyl amyl, the 3-methyl amyl, the 4-methyl amyl, 1, the 1-dimethylbutyl, 1, the 2-dimethylbutyl, 1, the 3-dimethylbutyl, 2, the 2-dimethylbutyl, 2, the 3-dimethylbutyl, 3, the 3-dimethylbutyl, the 1-ethyl-butyl, the 2-ethyl-butyl, 1,1,2-trimethylammonium propyl group, 1,2,2-trimethylammonium propyl group, 1-ethyl-1-methyl-propyl or 1-ethyl-2-methyl-propyl, preferred CH 3, C 2H 5, n-propyl, CH (CH 3) 2, normal-butyl, C (CH 3) 3, n-pentyl or n-hexyl;
-C 1-C 6-haloalkyl: above-mentioned C 1-C 6-alkyl is partly or entirely replaced by fluorine, chlorine, bromine and/or iodine, i.e. CH for example 2F, CHF 2, CF 3, CH 2Cl, CH (Cl) 2, C (Cl) 3, CHFCl, CF (Cl) 2, CF 2Cl, CF 2Br, 1-fluoro ethyl, 2-fluoro ethyl, 2-chloroethyl, 2-bromotrifluoromethane, 2-iodine ethyl, 2,2-two fluoro ethyls, 2,2,2-trifluoroethyl, 2-chloro-2-fluoro ethyl, 2-chloro-2,2-two fluoro ethyls, 2,2-two chloro-2-fluoro ethyls, 1,2-Dichloroethyl, 2,2,2-three chloroethyls, C 2F 5, 2-fluoropropyl, 3-fluoropropyl, 2,2-two fluoropropyls, 2,3-two fluoropropyls, 2-chloropropyl, 3-chloropropyl, 2,3-two chloropropyls, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoro propyl, 3,3,3-three chloropropyls, CH 2-C 2F 5, CF 2-C 2F 5, 1-(methyl fluoride)-2-fluoro ethyl, 1-(chloromethyl)-2-chloroethyl, 1-(brooethyl)-2-bromotrifluoromethane, 4-fluorine butyl, 4-chlorobutyl, 4-brombutyl, n-C 4F 9, 5-fluorine amyl group, 5-chlorine amyl group, 5-bromine amyl group, 5-iodine amyl group, 5,5,5-trichlorine amyl group, 11 fluorine amyl groups, 6-fluorine hexyl, 6-chlorine hexyl, 6-bromine hexyl, 6-iodine hexyl, 6,6,6-trichlorine hexyl or ten difluoro hexyls, preferred C 1-C 2-haloalkyl such as CH 2F, CHF 2, CF 3, CH 2Cl, 2-fluoro ethyl, 2-chloroethyl, 1,2-Dichloroethyl, 2,2,2-trifluoroethyl or C 2F 5
-C 3-C 7-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or suberyl, particularly cyclopentyl or cyclohexyl;
-hydroxycarbonyl group-C 1-C 6-alkyl: CH for example 2COOH, 2-hydroxycarbonyl group second-1-base, 2-hydroxycarbonyl group third-1-base, 3-hydroxycarbonyl group third-1-base, 1-hydroxycarbonyl group third-2-base, 2-hydroxycarbonyl group fourth-1-base, 3-hydroxycarbonyl group fourth-1-base, 4-hydroxycarbonyl group fourth-1-base, 1-hydroxycarbonyl group fourth-2-base, 1-hydroxycarbonyl group fourth-3-base, 2-hydroxycarbonyl group fourth-3-base, 1-hydroxycarbonyl group-2-methyl-prop-3-base, 2-hydroxycarbonyl group-2-methyl-third-3-base or 2-(hydroxycarbonyl group methyl) third-2-base, particularly 2-hydroxycarbonyl group ethyl;
-cyano group-C 1-C 6-alkyl: CH for example 2CN, 1-cyano group second-1-base, 2-cyano group second-1-base, 1-cyano group third-1-base, 2-cyano group the third-1 base, 3-cyano group third-1-base, 1-cyano group third-2-base, 2-cyano group third-2-base, 1-cyano group fourth-1-base, 2-cyano group fourth-1-base, 3-cyano group fourth-1-base, 4-cyano group fourth-1-base, 1-cyano group fourth-2-base, 2-cyano group fourth-2-base, 1-cyano group fourth-3-base, 2-cyano group fourth-3-base, 1-cyano group-2-methyl-prop-3-base, 2-cyano group-2-methyl-prop-3-base, 3-cyano group-2-methyl-prop-3-base or 2-cyano methyl-third-2-base, particularly CH 2CN or 2-cyano ethyl;
-C 1-C 6Alkoxyl group: above-mentioned C 1-C 4Alkoxyl group, and, n-pentyloxy for example, 1-methyl butoxy, 2-methyl butoxy, 3-methyl butoxy, 1,1-dimethyl propoxy-, 1,2-dimethyl propoxy-, 2,2-dimethyl propoxy-, 1-ethyl propoxy-, positive hexyloxy, 1-methyl-pentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy, 4-methyl pentyloxy, 1,1-dimethyl butoxy, 1,2-dimethyl butoxy, 1,3-dimethyl butoxy, 2,2-dimethyl butoxy, 2,3-dimethyl butoxy, 3,3-dimethyl butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1,1,2-trimethylammonium propoxy-, 1,2,2-trimethylammonium propoxy-, 1-ethyl-1-methyl propoxy-and 1-ethyl-2-methyl propoxy-, particularly OCH 3, OC 2H 5Or OCH (CH 3) 2
-C 1-C 6-halogenated alkoxy: above-mentioned C 1-C 6Alkoxyl group is partly or entirely replaced by fluorine, chlorine, bromine and/or iodine, i.e. OCH for example 2F, OCHF 2, OCF 3, OCH 2Cl, OCH (Cl) 2, OC (Cl) 3, OCHFCl, OCF 2Cl, OCF (Cl) 2, 2-fluorine oxyethyl group, 2-chloroethoxy, 2-bromine oxethyl, 2-iodine oxyethyl group, 2,2-difluoroethoxy, 2,2,2-trifluoro ethoxy, 2-chloro-2-fluorine oxyethyl group, 2-chloro-2,2-difluoroethoxy, 2,2-two chloro-2-fluorine oxyethyl groups, 2,2,2-three chloroethoxies, OC 2F 5, 2-fluorine propoxy-, 3-fluorine propoxy-, 2,2-difluoro propoxy-, 2,3-difluoro propoxy-, 2-chlorine propoxy-, 3-chlorine propoxy-, 2,3-dichloro propoxy-, 2-bromine propoxy-, 3-bromine propoxy-, 3,3,3-trifluoro propoxy-, 3,3,3-trichlorine propoxy-, OCH 2-C 2F 5, OCF 2-C 2F 5, 1-(methyl fluoride)-2-fluorine oxyethyl group, 1-(chloromethyl)-2-chloroethoxy, 1-(brooethyl)-2-bromine oxethyl, 4-fluorine butoxy, 4-chlorine butoxy, 4-bromine butoxy or n-C 4F 95-fluoro-1-pentyloxy, 5-chloro-1-pentyloxy, 5-bromo-1-pentyloxy, 5-iodo-1-pentyloxy, 5,5,5-three chloro-1-pentyloxys, 11 fluorine pentyloxys, 6-fluoro-1-hexyloxy, 6-chloro-1-hexyloxy, 6-bromo-1-hexyloxy, 6-iodo-1-hexyloxy, 6,6,6-three chloro-1-hexyloxy or ten difluoro hexyloxy, particularly C 1-C 2-halogenated alkoxy such as OCH 2F, OCHF 2, OCF 3, OCH 2Cl, 2-fluorine oxyethyl group, 2-chloroethoxy, 1,2-two chloroethoxies, 2,2,2-trifluoro ethoxy or OC 2F 5
-(C 1-C 6-alkoxyl group) carbonyl: CO-OCH for example 3, CO-OC 2H 5, CO-OCH 2-C 2H 5, CO-OCH (CH 3) 2, n-butoxy carbonyl, CO-OCH (CH 3)-C 2H 5, CO-OCH 2-CH (CH 3) 2, CO-OC (CH 3) 3The n-pentyloxy carbonyl, 1-methyl butoxy carbonyl, 2-methyl butoxy carbonyl, 3-methyl butoxy carbonyl, 2,2-dimethyl propoxycarbonyl, 1-ethyl propoxycarbonyl, positive hexyloxy carbonyl, 1,1-dimethyl propoxycarbonyl, 1,2-dimethyl propoxycarbonyl, 1-methyl pentyloxy carbonyl, 2-methyl pentyloxy carbonyl, 3-methyl pentyloxy carbonyl, 4-methyl pentyloxy carbonyl, 1,1-dimethyl butoxy carbonyl, 1,2-dimethyl butoxy carbonyl, 1,3-dimethyl butoxy carbonyl, 2,2-dimethyl butoxy carbonyl, 2,3-dimethyl butoxy carbonyl, 3,3-dimethyl butoxy carbonyl, 1-ethyl butoxy carbonyl, 2-ethyl butoxy carbonyl, 1,1,2-trimethylammonium propoxycarbonyl, 1,2,2-trimethylammonium propoxycarbonyl, 1-ethyl-1-methyl propoxycarbonyl or 1-ethyl-2-methyl propoxycarbonyl, particularly CO-OCH 3, CO-OC 2H 5, CO-OCH (CH 3) 2Or CO-OCH 2-CH (CH 3) 2-(C 1-C 6-alkoxyl group) carbonyl oxygen base: O-CO-OCH 3, O-CO-OC 2H 5Positive propoxy carbonyl oxygen base, 1-methyl ethoxy carbonyl oxygen base, n-butoxy carbonyl oxygen base, 1-methyl propoxy-carbonyl oxygen base, 2-methyl propoxy-carbonyl oxygen base, 1,1-dimethyl oxyethyl group carbonyl oxygen base, n-pentyloxy carbonyl oxygen base, 1-methyl butoxy carbonyl oxy, 2-methyl butoxy carbonyl oxy, 3-methyl butoxy carbonyl oxy, 2,2-dimethyl propoxy-carbonyl oxygen base, 1-ethyl propoxy-carbonyl oxygen base, positive hexyloxy carbonyl oxygen base, 1,1-dimethyl propoxy-carbonyl oxygen base, 1,2-dimethyl propoxy-carbonyl oxygen base, 1-methyl pentyloxy carbonyl oxygen base, 2-methyl pentyloxy carbonyl oxygen base, 3-methyl pentyloxy carbonyl oxygen base, 4-methyl pentyloxy carbonyl oxygen base, 1,1-dimethyl butoxy carbonyl oxygen base, 1,2-dimethyl butoxy carbonyl oxygen base, 1,3-dimethyl butoxy carbonyl oxygen base, 2,2-dimethyl butoxy carbonyl oxygen base, 2,3-dimethyl butoxy carbonyl oxygen base, 3,3-dimethyl butoxy carbonyl oxygen base, 1-ethyl butoxy carbonyl oxy, 2-ethyl butoxy carbonyl oxy, 1,1,2-trimethylammonium propoxy-carbonyl oxygen base, 1,2,2-trimethylammonium propoxy-carbonyl oxygen base, 1-ethyl-1-methyl propoxy-carbonyl oxygen base or 1-ethyl-2-methyl propoxy-carbonyl oxygen base, particularly methoxyl group carbonyl oxygen base, oxyethyl group carbonyl oxygen base or 1-methyl ethoxy carbonyl oxygen base;
-(C1-C6-alkoxyl group) carbonyl sulfenyl: methoxyl group carbonyl sulfenyl, oxyethyl group carbonyl sulfenyl, positive propoxy carbonyl sulfenyl, 1-methyl ethoxy carbonyl sulfenyl, n-butoxy carbonyl sulfenyl, 1-methyl propoxy-carbonyl sulfenyl, 2-methyl propoxy-carbonyl sulfenyl, 1,1-dimethyl oxyethyl group carbonyl sulfenyl, n-pentyloxy carbonyl sulfenyl, 1-methyl butoxy carbonyl sulfenyl, 2-methyl butoxy carbonyl sulfenyl, 3-methyl butoxy carbonyl sulfenyl, 2,2-dimethyl propoxy-carbonyl sulfenyl, 1-ethyl propoxy-carbonyl sulfenyl, positive hexyloxy carbonyl sulfenyl, 1,1-dimethyl propoxy-carbonyl sulfenyl, 1,2-dimethyl propoxy-carbonyl sulfenyl, 1-methyl pentyloxy carbonyl sulfenyl, 2-methyl pentyloxy carbonyl sulfenyl, 3-methyl pentyloxy carbonyl sulfenyl, 4-methyl pentyloxy carbonyl sulfenyl, 1,1-dimethyl butoxy carbonyl sulfenyl, 1,2-dimethyl butoxy carbonyl sulfenyl, 1,3-dimethyl butoxy carbonyl sulfenyl, 2,2-dimethyl butoxy carbonyl sulfenyl, 2,3-dimethyl butoxy carbonyl sulfenyl, 3,3-dimethyl butoxy carbonyl sulfenyl, 1-ethyl butoxy carbonyl sulfenyl, 2-ethyl butoxy carbonyl sulfenyl, 1,1,2-trimethylammonium propoxy-carbonyl sulfenyl, 1,2,2-trimethylammonium propoxy-carbonyl sulfenyl, 1-ethyl-1-methyl-propoxy-carbonyl sulfenyl or 1-ethyl-2-methyl propoxy-carbonyl sulfenyl, methoxyl group carbonyl sulfenyl particularly, oxyethyl group carbonyl sulfenyl or 1-methyl ethoxy carbonyl sulfenyl;
-C 1-C 6-alkylthio: SCH 3, SC 2H 5, SCH 2-C 2H 5, SCH (CH 3) 2, positive butylthio, SCH (CH 3)-C 2H 5, SCH 2-CH (CH 3) 21,1-dimethyl ethylmercapto group, positive penta sulfenyl, 1-methyl butylthio, 2-methyl butylthio, 3-methyl butylthio, 2,2-dimethyl propylene sulfenyl, 1-ethyl rosickyite base, just own sulfenyl, 1,1-dimethyl propylene sulfenyl, 1,2-dimethyl propylene sulfenyl, 1-methylpent sulfenyl, 2-methylpent sulfenyl, 3-methylpent sulfenyl, 1,3-dimethyl butyrate sulfenyl, 2,2-dimethyl butyrate sulfenyl, 2,3-dimethyl butyrate sulfenyl, 3,3-dimethyl butyrate sulfenyl, 1-ethyl butylthio, 2-ethyl butylthio, 1,1,2-trimethylammonium rosickyite base, 1,2,2-trimethylammonium rosickyite base, 1-ethyl-1-methyl-prop sulfenyl or 1-ethyl-2-methyl-prop sulfenyl, preferred SCH 3Or SC 2H 5-C 1-C 6-alkoxy-C 1-C 6-alkyl: by above-mentioned C 1-C 6The C that-alkoxyl group replaces 1-C 6-alkyl, i.e. methoxymethyl for example, ethoxyl methyl, n-propoxymethyl, (1-methyl ethoxy) methyl, the n-butoxy methyl, (1-methyl propoxy-) methyl, (2-methyl propoxy-) methyl, (1,1-dimethyl oxyethyl group) methyl, 2-(methoxyl group) ethyl, 2-(oxyethyl group) ethyl, 2-(positive propoxy) ethyl, 2-(1-methyl ethoxy) ethyl, 2-(n-butoxy) ethyl, 2-(1-methyl propoxy-) ethyl, 2-(2-methyl propoxy-) ethyl, 2-(1,1-dimethyl oxyethyl group) ethyl, 2-(methoxyl group) propyl group, 2-(oxyethyl group) propyl group, 2-(positive propoxy) propyl group, 2-(1-methyl ethoxy) propyl group, 2-(n-butoxy) propyl group, 2-(1-methyl propoxy-) propyl group, 2-(2-methyl propoxy-) propyl group, 2-(1,1-dimethyl oxyethyl group) propyl group, 3-(methoxyl group) propyl group, 3-(oxyethyl group)-propyl group, 3-(positive propoxy) propyl group, 3-(1-methyl ethoxy) propyl group, 3-(n-butoxy) propyl group, 3-(1-methyl propoxy-) propyl group, 3-(2-methyl propoxy-) propyl group, 3-(1,1-dimethyl oxyethyl group) propyl group, 2-(methoxyl group) butyl, 2-(oxyethyl group) butyl, 2-(positive propoxy) butyl, 2-(1-methyl ethoxy) butyl, 2-(n-butoxy) butyl, 2-(1-methyl propoxy-) butyl, 2-(2-methyl propoxy-) butyl, 2-(1,1-dimethyl oxyethyl group) butyl, 3-(methoxyl group) butyl, 3-(oxyethyl group) butyl, 3-(positive propoxy) butyl, 3-(1-methyl ethoxy) butyl, 3-(n-butoxy) butyl, 3-(1-methyl propoxy-) butyl, 3-(2-methyl propoxy-) butyl, 3-(1,1-dimethyl oxyethyl group) butyl, 4-(methoxyl group) butyl, 4-(oxyethyl group) butyl, 4-(positive propoxy) butyl, 4-(1-methyl ethoxy) butyl, 4-(n-butoxy) butyl, 4-(1-methyl propoxy-) butyl, 4-(2-methyl propoxy-) butyl or 4-(1,1-dimethyl oxyethyl group) butyl, preferred methoxymethyl or 2-methoxy ethyl;
-C 1-C 6-alkoxy-C 1-C 6-alkoxyl group: by above-mentioned C 1-C 6The C that-alkoxyl group replaces 1-C 6-alkoxyl group, i.e. methoxymethoxy for example, oxyethyl group methoxy base, the positive propoxy methoxyl group, (1-methyl ethoxy) methoxyl group, the n-butoxy methoxyl group, (1-methyl propoxy-) methoxyl group, (2-methyl propoxy-) methoxyl group, (1,1-dimethyl oxyethyl group) methoxyl group, 2-(methoxyl group) oxyethyl group, 2-(oxyethyl group) oxyethyl group, 2-(positive propoxy) oxyethyl group, 2-(1-methyl ethoxy) oxyethyl group, 2-(n-butoxy) oxyethyl group, 2-(1-methyl propoxy-) oxyethyl group, 2-(2-methyl propoxy-) oxyethyl group, 2-(1,1-dimethyl oxyethyl group) oxyethyl group, 2-(methoxyl group) propoxy-, 2-(oxyethyl group) propoxy-, 2-(positive propoxy) propoxy-, 2-(1-methyl ethoxy) propoxy-, 2-(n-butoxy) propoxy-, 2-(1-methyl propoxy-) propoxy-, 2-(2-methyl propoxy-) propoxy-, 2-(1,1-dimethyl oxyethyl group) propoxy-, 3-(methoxyl group) propoxy-, 3-(oxyethyl group)-propoxy-, 3-(positive propoxy) propoxy-, 3-(1-methyl ethoxy) propoxy-, 3-(n-butoxy) propoxy-, 3-(1-methyl propoxy-) propoxy-, 3-(2-methyl propoxy-) propoxy-, 3-(1,1-dimethyl oxyethyl group) propoxy-, 2-(methoxyl group) butoxy, 2-(oxyethyl group) butoxy, 2-(positive propoxy) butoxy, 2-(1-methyl ethoxy) butoxy, 2-(n-butoxy) butoxy, 2-(1-methyl propoxy-) butoxy, 2-(2-methyl propoxy-) butoxy, 2-(1,1-dimethyl oxyethyl group) butoxy, 3-(methoxyl group) butoxy, 3-(oxyethyl group) butoxy, 3-(positive propoxy) butoxy, 3-(1-methyl ethoxy) butoxy, 3-(n-butoxy) butoxy, 3-(1-methyl propoxy-) butoxy, 3-(2-methyl propoxy-) butoxy, 3-(1,1-dimethyl oxyethyl group) butoxy, 4-(methoxyl group) butoxy, 4-(oxyethyl group) butoxy, 4-(positive propoxy) butoxy, 4-(1-methyl ethoxy) butoxy, 4-(n-butoxy) butoxy, 4-(1-methyl propoxy-) butoxy, 4-(2-methyl propoxy-) butoxy or 4-(1,1-dimethyl oxyethyl group) butoxy, 5-(methoxyl group) pentyloxy, 5-(oxyethyl group) pentyloxy, 5-(positive propoxy) pentyloxy, 5-(1-methyl ethoxy)-pentyloxy, 5-(n-butoxy) pentyloxy, 5-(1-methyl propoxy-) pentyloxy, 5-(2-methyl propoxy-) pentyloxy, 5-(1,1-dimethyl oxyethyl group) pentyloxy, 6-(methoxyl group) hexyloxy, 6-(oxyethyl group) hexyloxy, 6-(positive propoxy) hexyloxy, 6-(1-methyl ethoxy) hexyloxy, 6-(n-butoxy) hexyloxy, 6-(1-methyl propoxy-) hexyloxy, 6-(2-methyl propoxy-) hexyloxy or 6-(1,1-dimethyl oxyethyl group) hexyloxy, preferred methoxymethoxy or oxyethyl group methoxy base;
-(C 1-C 4-alkoxyl group) carbonyl-C 1-C 4-alkoxyl group: have group CO-OCH 3, CO-OC 2H 5, CO-OCH 2-C 2H 5, CO-OCH (CH 3) 2, CO-O (CH 2) 2-C 2H 5, CO-OCH (CH 3)-C 2H 5, CO-OCH 2-CH (CH 3) 2Or CO-OC (CH 3) 3C 1-C 4-alkoxyl group is as OCH 3, OC 2H 5, OCH 2-C 2H 5, OCH (CH 3) 2, OCH (CH 3)-C 2H 5, OCH 2-CH (CH 3) 2Or OC (CH 3) 3I.e. OCH for example 2-CO-OCH 3, OCH (CH 3)-CO-OCH 3, OCH 2-CO-OC 2H 5Or OCH (CH 3)-CO-OC 2H 5
-(C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkoxyl group: by above-mentioned (C 1-C 6-alkoxyl group) C of carbonyl substituted 1-C 6-alkoxyl group, i.e. OCH for example 2-CO-OCH 3, OCH 2-CO-OC 2H 5, OCH 2-CO-OCH 2-C 2H 5, OCH 2-CO-OCH (CH 3) 2N-butoxy carbonyl methoxyl group, 1-(methoxycarbonyl) oxyethyl group, 2-(methoxycarbonyl) oxyethyl group, 2-(ethoxy carbonyl) oxyethyl group, 2-(positive propoxy carbonyl) oxyethyl group, 2-(n-butoxy carbonyl) oxyethyl group, 3-(methoxycarbonyl) propoxy-, 3-(ethoxy carbonyl) propoxy-, 3-(positive propoxy carbonyl) propoxy-, 3-(n-butoxy carbonyl) propoxy-, 4-(methoxycarbonyl) butoxy, 4-(ethoxy carbonyl) butoxy, 4-(positive propoxy carbonyl) butoxy, 4-(n-butoxy carbonyl) butoxy, 5-(methoxycarbonyl) pentyloxy, 5-(ethoxy carbonyl) pentyloxy, 5-(positive propoxy carbonyl) pentyloxy, 5-(n-butoxy carbonyl) butoxy, 6-(methoxycarbonyl) hexyloxy, 6-(ethoxy carbonyl) hexyloxy, 6-(positive propoxy carbonyl) hexyloxy or 6-(n-butoxy carbonyl) hexyloxy, particularly OCH 2-CO-OCH 3Or 1-(methoxycarbonyl) oxyethyl group;
-(C 1-C 9-alkoxyl group) carbonyl-C 1-C 6-alkyl: by above-mentioned (C 1-C 6-alkoxyl group) C of carbonyl substituted 1-C 6-alkyl, i.e. for example methoxycarbonyl methyl, ethoxy carbonyl methyl, 1-(methoxycarbonyl) ethyl, 2-(methoxycarbonyl) ethyl, 2-(ethoxy carbonyl) ethyl, 3-(methoxycarbonyl) propyl group, 4-(methoxycarbonyl) butyl, 5-(methoxycarbonyl) amyl group or 6-(methoxycarbonyl) hexyl;
-C 1-C 6-alkylthio-C 1-C 6-alkyl: by above-mentioned C 1-C 6The C that-alkylthio replaces 1-C 6-alkyl, for example CH 2-SCH 3, CH 2-SC 2H 5, positive rosickyite ylmethyl, CH 2-SCH (CH 3) 2, positive butylthio methyl, (1-methyl-prop sulfenyl) methyl, CH 2-SCH 2-CH (CH 3) 2, CH 2-SC (CH 3) 32-methylmercaptoethyl, 2-ethylmercapto group ethyl, 2-(positive rosickyite base) ethyl, 2-(1-methyl ethylmercapto group) ethyl, 2-(positive butylthio) ethyl, 2-(1-methyl-prop sulfenyl) ethyl, 2-(2-methyl-prop sulfenyl) ethyl, 2-(1,1-dimethyl ethylmercapto group) ethyl, 2-(methylthio group) propyl group, 3-(methylthio group) propyl group, 2-(ethylmercapto group) propyl group, 3-(ethylmercapto group) propyl group, 3-(rosickyite base) propyl group, 3-(butylthio) propyl group, 4-(methylthio group) butyl, 4-(ethylmercapto group) butyl, 4-(positive rosickyite base) butyl or 4-(positive butylthio) butyl, preferred 2-(methylthio group) ethyl;
-C 1-C 6-alkoxyl group-(C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl: by above-mentioned C 1-C 6(the C that-alkoxyl group replaces 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, i.e. CH for example 2-COOCH 2-OCH 3, CH 2-COOCH 2-OC 2H 5, CH 2-COOCH 2-OCH (CH 3) 2Or CH 2-COOCH 2-OC (CH 3) 3
-C 3-C 6-alkenyl: third-1-alkene-1-base, third-2-alkene-1-base, the 1-methyl ethylene, n-butene-1-base, n-butene-2-base, n-butene-3-base, 1-methyl-third-1-alkene-1-base, 2-methyl-prop-1-alkene-1-base, 1-methyl-prop-2-alkene-1-base, 2-methyl-prop-2-alkene-1-base, positive amylene-1-base, positive 2-pentenyl, positive amylene-3-base, positive amylene-4-base, 1-methyl but-1-ene-1-base, 2-methyl but-1-ene-1-base, 3-methyl but-1-ene-1-base, 1-methyl but-2-ene-1-base, 2-methyl but-2-ene-1-base, 3-methyl but-2-ene-1-base, 1-methyl fourth-3-alkene-1-base, 2-methyl fourth-3-alkene-1-base, 3-methyl fourth-3-alkene-1-base, 1,1-dimethyl propylene-2-alkene-1-base, 1,2-dimethyl propylene-1-alkene-1-base, 1,2-dimethyl propylene-2-alkene-1-base, 1-ethyl third-1-alkene-2-base, 1-ethyl third-2-alkene-1-base, just oneself-1-alkene-1-base, just oneself-2-alkene-1-base, just oneself-3-alkene-1-base, just oneself-4-alkene-1-base, just oneself-5-alkene-1-base, 1-methylpent-1-alkene-1-base, 2-methylpent-1-alkene-1-base, 3-methylpent-1-alkene-1-base, 4-methylpent-1-alkene-1-base, 1-methylpent-2-alkene-1-base, 2-methylpent-2-alkene-1-base, 3-methylpent-2-alkene-1-base, 4-methylpent-2-alkene-1-base, 1-methylpent-3-alkene-1-base, 2-methylpent-3-alkene-1-base, 3-methylpent-3-alkene-1-base, 4-methylpent-3-alkene-1-base, 1-methylpent-4-alkene-1-base, 2-methylpent-4-alkene-1-base, 3-methylpent-4-alkene-1-base, 4-methylpent-4-alkene-1-base, 1,1-dimethyl but-2-ene-1-base, 1,1-dimethyl butyrate-3-alkene-1-base, 1,2-dimethyl but-1-ene-1-base, 1,2-dimethyl but-2-ene-1-base, 1,2-dimethyl butyrate-3-alkene-1-base, 1,3-dimethyl but-1-ene-1-base, 1,3-dimethyl but-2-ene-1-base, 1,3-dimethyl butyrate-3-alkene-1-base, 2,2-dimethyl butyrate-3-alkene-1-base, 2,3-dimethyl but-1-ene-1-base, 2,3-dimethyl but-2-ene-1-base, 2,3-dimethyl butyrate-3-alkene-1-base, 3,3-dimethyl but-1-ene-1-base, 3,3-dimethyl but-2-ene-1-base, 1-ethyl but-1-ene-1-base, 1-ethyl but-2-ene-1-base, 1-ethyl fourth-3-alkene-1-base, 2-ethyl but-1-ene-1-base, 2-ethyl but-2-ene-1-base, 2-ethyl fourth-3-alkene-1-base, 1,1,2-trimethylammonium third-2-alkene-1-base, 1-ethyl-1-methyl-prop-2-alkene-1-base, 1-ethyl-2-methyl-prop-1-alkene-1-base or 1-ethyl-2-methyl-prop-2-alkene-1-base, particularly allyl group or 2-butylene-1-base;
-C 2-C 6-alkenyl: vinyl or C 3-C 6Arbitrary group, particularly vinyl described in the-alkenyl or third-2-alkene-1-base;
-C 3-C 6-halogenated alkenyl: above-mentioned C 3-C 6-alkenyl is partly or entirely replaced by fluorine, chlorine, bromine and/or iodine, i.e. for example 2-chlorallyl, 3-chlorallyl, 2,3-two chlorallyls, 3,3-two chlorallyls, 2,3,3-three chlorallyls, 2,3-dichloro but-2-ene base, 2-bromine allyl group, 3-bromine allyl group, 2,3-dibromo allyl group, 3,3-dibromo allyl group, 2,3,3-tribromo allyl group or 2,3-dibromo but-2-ene base, particularly 2-chlorallyl, 3-chlorallyl or 3,3-two chlorallyls;
-C 3-C 6-alkenyloxy: third-1-alkene-1-base oxygen base for example, third-2-alkene-1-base oxygen base, 1-ethylene methacrylic oxygen base, n-butene-1-base oxygen base, n-butene-2-base oxygen base, n-butene-3-base oxygen base, 1-methyl-third-1-alkene-1-base oxygen base, 2-methyl-prop-1-alkene-1-base oxygen base, 1-methyl-prop-2-alkene-1-base oxygen base, 2-methyl-prop-2-alkene-1-base oxygen base, positive amylene-1-base oxygen base, positive 2-pentenyl oxygen base, positive amylene-3-base oxygen base, positive amylene-4-base oxygen base, 1-methyl but-1-ene-1-base oxygen base, 2-methyl but-1-ene-1-base oxygen base, 3-methyl but-1-ene-1-base oxygen base, 1-methyl but-2-ene-1-base oxygen base, 2-methyl but-2-ene-1-base oxygen base, 3-methyl but-2-ene-1-base oxygen base, 1-methyl fourth-3-alkene-1-base oxygen base, 2-methyl fourth-3-alkene-1-base oxygen base, 3-methyl fourth-3-alkene-1-base oxygen base, 1,1-dimethyl propylene-2-alkene-1-base oxygen base, 1,2-dimethyl propylene-1-alkene-1-base oxygen base, 1,2-dimethyl propylene-2-alkene-1-base oxygen base, 1-ethyl third-1-alkene-2-base oxygen base, 1-ethyl third-2-alkene-1-base oxygen base, just oneself-1-alkene-1-base oxygen base, just oneself-2-alkene-1-base oxygen base, just oneself-3-alkene-1-base oxygen base, just oneself-4-alkene-1-base oxygen base, just oneself-5-alkene-1-base oxygen base, 1-methylpent-1-alkene-1-base oxygen base, 2-methylpent-1-alkene-1-base oxygen base, 3-methylpent-1-alkene-1-base oxygen base, 4-methylpent-1-alkene-1-base oxygen base, 1-methylpent-2-alkene-1-base oxygen base, 2-methylpent-2-alkene-1-base oxygen base, 3-methylpent-2-alkene-1-base oxygen base, 4-methylpent-2-alkene-1-base oxygen base, 1-methylpent-3-alkene-1-base oxygen base, 2-methylpent-3-alkene-1-base oxygen base, 3-methylpent-3-alkene-1-base oxygen base, 4-methylpent-3-alkene-1-base oxygen base, 1-methylpent-4-alkene-1-base oxygen base, 2-methylpent-4-alkene-1-base oxygen base, 3-methylpent-4-alkene-1-base oxygen base, 4-methylpent-4-alkene-1-base oxygen base, 1,1-dimethyl but-2-ene-1-base oxygen base, 1,1-dimethyl butyrate-3-alkene-1-base oxygen base, 1,2-dimethyl but-1-ene-1-base oxygen base, 1,2-dimethyl but-2-ene-1-base oxygen base, 1,2-dimethyl butyrate-3-alkene-1-base oxygen base, 1,3-dimethyl but-1-ene-1-base oxygen base, 1,3-dimethyl but-2-ene-1-base oxygen base, 1,3-dimethyl butyrate-3-alkene-1-base oxygen base, 2,2-dimethyl butyrate-3-alkene-1-base oxygen base, 2,3-dimethyl but-1-ene-1-base oxygen base, 2,3-dimethyl but-2-ene-1-base oxygen base, 2,3-dimethyl butyrate-3-alkene-1-base oxygen base, 3,3-dimethyl but-1-ene-1-base oxygen base, 3,3-dimethyl but-2-ene-1-base oxygen base, 1-ethyl but-1-ene-1-base oxygen base, 1-ethyl but-2-ene-1-base oxygen base, 1-ethyl fourth-3-alkene-1-base oxygen base, 2-ethyl but-1-ene-1-base oxygen base, 2-ethyl but-2-ene-1-base oxygen base, 2-ethyl fourth-3-alkene-1-base oxygen base, 1,1,2-trimethylammonium third-2-alkene-1-base oxygen base, 1-ethyl-1-methyl-prop-2-alkene-1-base oxygen base, 1-ethyl-2-methyl-prop-1-alkene-1-base oxygen base or 1-ethyl-2-methyl-prop-2-alkene-1-base oxygen base, particularly third-2-alkene-1-base oxygen base;
-C 2-C 4-alkenyloxy: vinyloxy group, third-1-alkene-1-base oxygen base, third-2-alkene-1-base oxygen base, 1-ethylene methacrylic oxygen base, n-butene-1-base oxygen base, n-butene-2-base oxygen base, n-butene-3-base oxygen base, 1-methyl-prop-1-alkene-1-base oxygen base, 2-methyl-prop-1-alkene-1-base oxygen base, 1-methyl-prop-2-alkene-1-base oxygen base or 2-methyl-prop-2-alkene-1-base oxygen base, particularly third-2-alkene-1-base oxygen base;
-C 3-C 6-alkenyl thio: third-1-alkene-1-base sulfenyl for example, third-2-alkene-1-base sulfenyl, 1-ethylene methacrylic sulfenyl, n-butene-1-base sulfenyl, n-butene-2-base sulfenyl, n-butene-3-base sulfenyl, 1-methyl-third-1-alkene-1-base sulfenyl, 2-methyl-prop-1-alkene-1-base sulfenyl, 1-methyl-prop-2-alkene-1-base sulfenyl, 2-methyl-prop-2-alkene-1-base sulfenyl, positive amylene-1-base sulfenyl, positive 2-pentenyl sulfenyl, positive amylene-3-base sulfenyl, positive amylene-4-base sulfenyl, 1-methyl but-1-ene-1-base sulfenyl, 2-methyl but-1-ene-1-base sulfenyl, 3-methyl but-1-ene-1-base sulfenyl, 1-methyl but-2-ene-1-base sulfenyl, 2-methyl but-2-ene-1-base sulfenyl, 3-methyl but-2-ene-1-base sulfenyl, 1-methyl fourth-3-alkene-1-base sulfenyl, 2-methyl fourth-3-alkene-1-base sulfenyl, 3-methyl fourth-3-alkene-1-base sulfenyl, 1,1-dimethyl propylene-2-alkene-1-base sulfenyl, 1,2-dimethyl propylene-1-alkene-1-base sulfenyl, 1,2-dimethyl propylene-2-alkene-1-base sulfenyl, 1-ethyl third-1-alkene-2-base sulfenyl, 1-ethyl third-2-alkene-1-base sulfenyl, just oneself-1-alkene-1-base sulfenyl, just oneself-2-alkene-1-base sulfenyl, just oneself-3-alkene-1-base sulfenyl, just oneself-4-alkene-1-base sulfenyl, just oneself-5-alkene-1-base sulfenyl, 1-methylpent-1-alkene-1-base sulfenyl, 2-methylpent-1-alkene-1-base sulfenyl, 3-methylpent-1-alkene-1-base sulfenyl, 4-methylpent-1-alkene-1-base sulfenyl, 1-methylpent-2-alkene-1-base sulfenyl, 2-methylpent-2-alkene-1-base sulfenyl, 3-methylpent-2-alkene-1-base sulfenyl, 4-methylpent-2-alkene-1-base sulfenyl, 1-methylpent-3-alkene-1-base sulfenyl, 2-methylpent-3-alkene-1-base sulfenyl, 3-methylpent-3-alkene-1-base sulfenyl, 4-methylpent-3-alkene-1-base sulfenyl, 1-methylpent-4-alkene-1-base sulfenyl, 2-methylpent-4-alkene-1-base sulfenyl, 3-methylpent-4-alkene-1-base sulfenyl, 4-methylpent-4-alkene-1-base sulfenyl, 1,1-dimethyl but-2-ene-1-base sulfenyl, 1,1-dimethyl butyrate-3-alkene-1-base sulfenyl, 1,2-dimethyl but-1-ene-1-base sulfenyl, 1,2-dimethyl but-2-ene-1-base sulfenyl, 1,2-dimethyl butyrate-3-alkene-1-base sulfenyl, 1,3-two-methyl but-1-ene-1-base sulfenyl, 1,3-dimethyl but-2-ene-1-base sulfenyl, 1,3-dimethyl butyrate-3-alkene-1-base sulfenyl, 2,2-dimethyl butyrate-3-alkene-1-base sulfenyl, 2,3-dimethyl but-1-ene-1-base sulfenyl, 2,3-dimethyl but-2-ene-1-base sulfenyl, 2,3-dimethyl butyrate-3-alkene-1-base sulfenyl, 3,3-dimethyl but-1-ene-1-base sulfenyl, 3,3-dimethyl but-2-ene-1-base sulfenyl, 1-ethyl but-1-ene-1-base sulfenyl, 1-ethyl but-2-ene-1-base sulfenyl, 1-ethyl fourth-3-alkene-1-base sulfenyl, 2-ethyl but-1-ene-1-base sulfenyl, 2-ethyl but-2-ene-1-base sulfenyl, 2-ethyl fourth-3-alkene-1-base sulfenyl, 1,1,2-trimethylammonium third-2-alkene-1-base sulfenyl, 1-ethyl-1-methyl-prop-2-alkene-1-base sulfenyl, 1-ethyl-2-methyl-prop-1-alkene-1-base sulfenyl or 1-ethyl-2-methyl-prop-2-alkene-1-base sulfenyl, particularly third-2-alkene-1-base sulfenyl;
-C 3-C 6-alkynyl group: third-1-alkynes-1-base for example, propargyl, positive fourth-1-alkynes-1-base, positive fourth-1-alkynes-3-base, positive fourth-1-alkynes-4-base, positive fourth-2-alkynes-1-base, positive penta-1-alkynes-1-base, positive penta-1-alkynes-3-base, positive penta-1-alkynes-4-base, positive penta-1-alkynes-5-base, positive penta-2-alkynes-1-base, positive penta-2-alkynes-4-base, positive penta-2-alkynes-5-base, 3-methyl fourth-1-alkynes-3-base, 3-methyl fourth-1-alkynes-4-base, just oneself-1-alkynes-1-base, just oneself-1-alkynes-3-base, just oneself-1-alkynes-4-base, just oneself-1-alkynes-5-base, just oneself-1-alkynes-6-base, just oneself-2-alkynes-1-base, just oneself-2-alkynes-4-base, just oneself-2-alkynes-5-base, just oneself-2-alkynes-6-base, just oneself-3-alkynes-1-base, just oneself-3-alkynes-2-base, 3-methylpent-1-alkynes-1-base, 3-methylpent-1-alkynes-3-base, 3-methylpent-1-alkynes-4-base, 3-methylpent-1-alkynes-5-base, 4-methylpent-1-alkynes-1-base, 4-methylpent-2-alkynes-4-base or 4-methylpent-2-alkynes-5-base, preferred propargyl;
-C 3-C 6-alkynyloxy group: third-1-alkynes-1-base oxygen base for example, third-2-alkynes-1-base oxygen base, positive fourth-1-alkynes-1-base oxygen base, positive fourth-1-alkynes-3-base oxygen base, positive fourth-1-alkynes-4-base oxygen base, positive fourth-2-alkynes-1-base oxygen base, positive penta-1-alkynes-1-base oxygen base, positive penta-1-alkynes-3-base oxygen base, positive penta-1-alkynes-4-base oxygen base, positive penta-1-alkynes-5-base oxygen base, positive penta-2-alkynes-1-base oxygen base, positive penta-2-alkynes-4-base oxygen base, positive penta-2-alkynes-5-base oxygen base, 3-methyl fourth-1-alkynes-3-base oxygen base, 3-methyl fourth-1-alkynes-4-base oxygen base, just oneself-1-alkynes-1-base oxygen base, just oneself-1-alkynes-3-base oxygen base, just oneself-1-alkynes-4-base oxygen base, just oneself-1-alkynes-5-base oxygen base, just oneself-1-alkynes-6-base oxygen base, just oneself-2-alkynes-1-base oxygen base, just oneself-2-alkynes-4-base oxygen base, just oneself-2-alkynes-5-base oxygen base, just oneself-2-alkynes-6-base oxygen base, just oneself-3-alkynes-1-base oxygen base, just oneself-3-alkynes-2-base oxygen base, 3-methylpent-1-alkynes-1-base oxygen base, 3-methylpent-1-alkynes-3-base oxygen base, 3-methylpent-1-alkynes-4-base oxygen base, 3-methylpent-1-alkynes-5-base oxygen base, 4-methylpent-1-alkynes-1-base oxygen base, 4-methylpent-2-alkynes-4-base oxygen base or 4-methylpent-2-alkynes-5-base oxygen base, preferred third-2-alkynes-1-base oxygen base;
-C 2-C 4-alkynyloxy group: second alkynyloxy group, third-1-alkynes-1-base oxygen base or third-2-alkynes-1-base oxygen base, particularly third-2-alkynes-1-base oxygen base;
-C 3-C 6-alkynes sulfenyl: third-1-alkynes-1-base sulfenyl, third-2-alkynes-1-base sulfenyl, positive fourth-1-alkynes-1-base sulfenyl, positive fourth-1-alkynes-3-base sulfenyl, positive fourth-1-alkynes-4-base sulfenyl, positive fourth-2-alkynes-1-base sulfenyl, positive penta-1-alkynes-1-base sulfenyl, positive penta-1-alkynes-3-base sulfenyl, positive penta-1-alkynes-4-base sulfenyl, positive penta-1-alkynes-5-base sulfenyl, positive penta-2-alkynes-1-base sulfenyl, positive penta-2-alkynes-4-base sulfenyl, positive penta-2-alkynes-5-base sulfenyl, 3-methyl fourth-1-alkynes-3-base sulfenyl, 3-methyl fourth-1-alkynes-4-base sulfenyl, just oneself-1-alkynes-1-base sulfenyl, just oneself-1-alkynes-3-base sulfenyl, just oneself-1-alkynes-4-base sulfenyl, just oneself-1-alkynes-5-base sulfenyl, just oneself-1-alkynes-6-base sulfenyl, just oneself-2-alkynes-1-base sulfenyl, just oneself-2-alkynes-4-base sulfenyl, just oneself-2-alkynes-5-base sulfenyl, just oneself-2-alkynes-6-base sulfenyl, just oneself-3-alkynes-1-base sulfenyl, just oneself-3-alkynes-2-base sulfenyl, 3-methylpent-1-alkynes-1-base sulfenyl, 3-methylpent-1-alkynes-3-base sulfenyl, 3-methylpent-1-alkynes-4-base sulfenyl, 3-methylpent-1-alkynes-5-base sulfenyl, 4-methylpent-1-alkynes-1-base sulfenyl, 4-methylpent-2-alkynes-4-base sulfenyl or 4-methylpent-2-alkynes-5-base sulfenyl, preferred third-2-alkynes-1-base sulfenyl;
-C 1-C 6-alkylidene group: methylene radical, 1 for example, 1-ethylidene, ethylene, trimethylene, 2,2-propylidene, tetramethylene, pentamethylene or hexamethylene, particularly methylene radical, 1,1-ethylidene or 2,2-propylidene.
According to 6-aryl-3-sulfo--5-(sulfo-) oxo-2,3 that replaces, 4,5-tetrahydrochysene-1,2,4-triazine I is as weedicide and/or have the purposes of the compound of dehydration/disleave effect, variable group preferably has following implication, under every kind of situation or represent their itself or their combination:
X is an oxygen;
R 1Be C 1-C 6-alkyl, particularly methyl;
R 2Be amino or C 1-C 6-alkyl, particularly amino or methyl;
Ar is Ar 1, Ar 2Or Ar 3
R 3Be halogen, fluorine or chlorine particularly;
R 4Be halogen, chlorine particularly;
R 5Be hydrogen, nitro, amino, C on the one hand 1-C 6-alkyl, C 1-C 6-haloalkyl, formyl radical ,-CH=N-OR 9,-CH (OR 10) 2,
Figure A9980768700241
R 11, R 12,-CO-Cl ,-CO-OR 13,-CO-OR 14-CO-OR 13,-CO-N (R 15)-R 16Or-N (R 20)-R 19,
Be on the other hand hydrogen ,-CO-OR 13,-OCH (CH 3)-COOH ,-OCH (CH 3)-COOCH 3Or-N (R 20)-R 19
R 6Be hydrogen, hydroxyl, C 1-C 6-alkyl, C 1-C 6-alkoxyl group, C 3-C 6-alkenyl or C 3-C 6-alkynyl, particularly C 3-C 6-alkynyl;
R 7Be hydrogen;
R 8Be hydrogen, C 1-C 6-alkyl or (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl;
N is 1;
Y is an oxygen;
Z is oxygen or sulphur, particularly oxygen;
R 9Be C 1-C 6-alkyl;
R 10, R 11, R 12, R 13, R 15, R 16Represent hydrogen or C independently of one another 1-C 6-alkyl;
R 14Be methylene radical or 1, the 1-ethylidene;
R 20Be hydrogen.
Particularly preferably be the 6-aryl-3-sulfo--5-oxo-2,3,4 of the replacement of the structural formula I a that is given, 5-tetrahydrochysene-1,2, {=I is X=oxygen wherein for the 4-triazine; R 1, R 2=methyl; Ar=Ar 1R 3=fluorine and R 4=chlorine }, listed I I compound a.248 a.1-in the table 1 particularly:
Figure A9980768700261
Table 1
?No. -R 5 m.p./ 1H NMR data
Ⅰa.1 -H ?6.48(s,1H), 7.20-7.35(m,2H), 8.02(t,1H)
Ⅰa.2 -CH 3
Ⅰa.3 -CH 2-Cl
Ⅰa.4 -CH(Cl) 2
Ⅰa.5 -C(Cl) 3
Ⅰa.6 -CH 2-Br
Ⅰa.7 -CH(Br) 2
Ⅰa.8 -CHO
Ⅰa.9 -CH=N-OH
Ⅰa.10 -CH=N-OCH 3
Ⅰa.11 -CH=N-OC 2H 5
Ⅰa.12 -CH=N-OCH 2-C 2H 5
Ⅰa.13 -CH=N-OCH(CH 3) 2
Ⅰa.14 -CH=N-OCH 2-CO-OCH 3
Ⅰa.15 -CH=N-OCH 2-CO-OC 2H 5
Ⅰa.16 -CH=N-OCH(CH 3)-CO-OCH 3
Ⅰa.17 -CH=N-OCH(CH 3)-CO-OC 2H 5
Ⅰa.18 -CH(OCH 3) 2
Ⅰa.19 -CH(OC 2H 5) 2
Ⅰa.20 -CH(OCH 2-C 2H 5) 2
Ⅰa.21 1,3-dioxolane-2-base
Ⅰa.22 ?4-(CH 3)-1,3-dioxolane-2-base
Ⅰa.23 ?4,5-(CH 3) 2-1,3-dioxolane-2-base
Ⅰa.24 ?4-(COOCH 3)-1,3-dioxolane-2-base
Ⅰa.25 ?4-(COOC 2H 5)-1,3-dioxolane-2-base
Ⅰa.26 ?4,5-(COOCH 3) 2-1,3-dioxolane-2-base
Ⅰa.27 ?4,5-(COOC 2H 5) 2-1,3-dioxolane-2-base
Ⅰa.28 -CN
No. -R 5 ?m.p./ 1H NMR data
Ⅰa.29 -CO-Cl
Ⅰa.30 -COOH
Ⅰa.31 -CO-OCH 3
Ⅰa.32 -CO-OC 2H 5
Ⅰa.33 -CO-OCH 2-C 2H 5
Ⅰa.34 -CO-OCH(CH 3) 2
Ⅰa.35 -CO-OCH 2-CH 2-C 2H 5
Ⅰa.36 -CO-OCH(CH 3)-C 2H 5
Ⅰa.37 -CO-OCH 2-CH(CH 3) 2
Ⅰa.38 -CO-OC(CH 3) 3
Ⅰa.39 -CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰa.40 -CO-O (cyclopropyl)
Ⅰa.41 -CO-O (cyclobutyl)
Ⅰa.42 -CO-O (cyclopentyl)
Ⅰa.43 -CO-O (cyclohexyl)
Ⅰa.44 -CO-O (oxyethane-3-yl)
Ⅰa.45 -CO-OCH 2-CH 2-OCH 3
Ⅰa.46 -CO-OCH 2-CH 2-OC 2H 5
Ⅰa.47 -CO-OCH 2-CH 2-OCH 2-C 2H 5
Ⅰa.48 -CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰa.49 -CO-OCH 2-CH=CH 2
Ⅰa.50 -CO-OCH 2-CH 2-CH=CH 2
Ⅰa.51 -CO-OCH(CH 3)-CH=CH 2
Ⅰa.52 -CO-OCH 2-C(CH 3)=CH 2
Ⅰa.53 -CO-OCH 2-CH=CH-CH 3
Ⅰa.54 -CO-OCH 2-C≡CH
Ⅰa.55 -CO-OCH(CH 3)-C≡CH
Ⅰa.56 -CO-OCH 2-C≡C-CH 3
Ⅰa.57 -CO-OCH 2-COOH
Ⅰa.58 -CO-OCH(CH 3)-COOH
Ⅰa.59 -CO-OC(CH 3) 2-COOH
Ⅰa.60 -CO-OCH 2-CO-OCH 3
Ⅰa.61 -CO-OCH(CH 3)-CO-OCH 3
Ⅰa.62 -CO-OC(CH 3) 2-CO-OCH 3
Ⅰa.63 -CO-OCH 2-CO-OC 2H 5
Ⅰa.64 -CO-OCH(CH 3)-CO-OC 2H 5
Ⅰa.65 -CO-OC(CH 3) 2-CO-O C2H 5
Ⅰa.66 -CO-OCH 2-CO-OCH 2-C 2H 5
Ⅰa.67 -CO-OCH(CH 3)-CO-OCH 2-C 2H 5
No. -R 5 m.p./ 1H NMR data
Ⅰa.68 -CO-OC(CH 3) 2-CO-OCH 2-C 2H 5
Ⅰa.69 -CO-OCH 2-CO-OCH(CH 3) 2
Ⅰa.70 -CO-OCH(CH 3)-CO-OCH(CH 3) 2
Ⅰa.71 -CO-OC(CH 3) 2-CO-OCH(CH 3) 2
Ⅰa.72 -CO-OCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰa.73 -CO-OCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰa.74 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-C 2H 5
Ⅰa.75 -CO-OCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰa.76 -CO-OCH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰa.77 -CO-OC(CH 3) 2-CO-OCH(CH 3)-C 2H 5
Ⅰa.78 -CO-OCH 2-CO-OCH 2-CH(CH 3) 2
Ⅰa.79 -CO-OCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰa.80 -CO-OC(CH 3) 2-CO-OCH 2-CH(CH 3) 2
Ⅰa.81 -CO-OCH 2-CO-OC(CH 3) 3
Ⅰa.82 -CO-OCH(CH 3)-CO-OC(CH 3) 3
Ⅰa.83 -CO-OC(CH 3) 2-CO-OC(CH 3) 3
Ⅰa.84 -CO-OCH 2-CO-O (cyclopropyl)
Ⅰa.85 -CO-OCH(CH 3)-CO-O (cyclopropyl)
Ⅰa.86 -CO-OC(CH 3) 2-CO-O (cyclopropyl)
Ⅰa.87 -CO-OCH 2-CO-O (cyclobutyl)
Ⅰa.88 -CO-OCH(CH 3)-CO-O (cyclobutyl)
Ⅰa.89 -CO-OC(CH 3) 2-CO-O (cyclobutyl)
Ⅰa.90 -CO-OCH 2-CO-O (cyclopentyl)
Ⅰa.91 -CO-OCH(CH 3)-CO-O (cyclopentyl)
Ⅰa.92 -CO-OC(CH 3) 2-CO-O (cyclopentyl)
Ⅰa.93 -CO-OCH 2-CO-O (cyclohexyl)
Ⅰa.94 -CO-OCH(CH 3)-CO-O (cyclohexyl)
Ⅰa.95 -CO-OC(CH 3) 2-CO-O (cyclohexyl)
Ⅰa.96 -CO-OCH 2-CO-O (trimethylene oxide-3-yl)
Ⅰa.97 -CO-OCH(CH 3)-CO-O (trimethylene oxide-3-yl)
Ⅰa.98 -CO-OC(CH 3) 2-CO-O (trimethylene oxide-3-yl)
Ⅰa.99 -CO-OCH 2-CO-OCH 2-CH 2-OCH 3
Ⅰa.100 -CO-OCH(CH 3)-CO-OCH 2-CH 2-OCH 3
Ⅰa.101 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-OCH 3
Ⅰa.102 -CO-OCH 2-CO-OCH 2-CH 2-OC 2H 5
Ⅰa.103 -CO-OCH(CH 3)-CO-OCH 2-CH 2-OC 2H 5
Ⅰa.104 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-OC 2H 5
Ⅰa.105 -CO-OCH 2-CO-OCH 2-CH 2-OCH 2-C 2H 5
Ⅰa.106 -CO-OCH(CH 3)-CO-OCH 2-CH 2-OCH 2-C 2H 5
?No. -R 5 ?m.p./ 1H NMR data
Ⅰa.107 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-OCH 2-C 2H 5
Ⅰa.108 -CO-OCH 2-CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰa.109 -CO-OCH(CH 3)-CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰa.110 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰa.111 -CO-OCH 2-CO-OCH 2-CH=CH 2
Ⅰa.112 -CO-OCH(CH 3)-CO-OCH 2-CH=CH 2
Ⅰa.113 -CO-OC(CH 3) 2-CO-OCH 2-CH=CH 2
Ⅰa.114 -CO-OCH 2-CO-OCH 2-CH 2-CH=CH 2
Ⅰa.115 -CO-OCH(CH 3)-CO-OCH 2-CH 2-CH=CH 2
Ⅰa.116 -CO-OC(CH 3) 2-CO-OCH 2-CH 2-CH=CH 2
Ⅰa.117 -CO-OCH 2-CO-OCH 2-C(CH 3)=CH 2
Ⅰa.118 -CO-OCH(CH 3)-CO-OCH 2-C(CH 3)=CH 2
Ⅰa.119 -CO-OC(CH 3) 2-CO-OCH 2-C(CH 3)=CH 2
Ⅰa.120 -CO-OCH 2-CO-OCH 2-CH=CH-CH 3
Ⅰa.121 -CO-OCH(CH 3)-CO-OCH 2-CH=CH-CH 3
Ⅰa.122 -CO-OC(CH 3) 2-CO-OCH 2-CH=CH-CH 3
Ⅰa.123 -CO-OCH 2-CO-OCH 2-C≡CH
Ⅰa.124 -CO-OCH(CH 3)-CO-OCH 2-C≡CH
Ⅰa.125 -CO-OC(CH 3) 2-CO-OCH 2-C≡CH
Ⅰa.126 -CO-OCH 2-CO-OCH 2-C≡C-CH 3
Ⅰa.127 -CO-OCH(CH 3)-CO-OCH 2-C≡C-CH 3
Ⅰa.128 -CO-OC(CH 3) 2-CO-OCH 2-C≡C-CH 3
Ⅰa.129 -CO-OCH 2-CO-OCH(CH 3)-C≡CH
Ⅰa.130 -CO-OCH(CH 3)-CO-OCH(CH 3)-C≡CH
Ⅰa.131 -CO-OC(CH 3) 2-CO-OCH(CH 3)-C≡CH
Ⅰa.132 -CO-OCH 2-COOH
Ⅰa.133 -CO-OCH(CH 3)-COOH
Ⅰa.134 -CO-OC(CH 3) 2-COOH
Ⅰa.135 -CO-NH 2
Ⅰa.136 -CO-NH-CH 3
Ⅰa.137 -CO-N(CH 3) 2
Ⅰa.138 -CO-NH-CH 2-CO-OCH 3
Ⅰa.139 -CO-N(CH 3)-CH 2-CO-OCH 3
Ⅰa.140 -CO-NH-CH 2-CO-OC 2H 5
Ⅰa.141 -CO-N(CH 3)-CH 2-CO-OC 2H 5
Ⅰa.142 -CO-NH-CH(CH 3)-CO-OCH 3
Ⅰa.143 -CO-N(CH 3)-CH(CH 3)-CO-OCH 3
Ⅰa.144 -CO-NH-CH(CH 3)-CO-OC 2H 5
Ⅰa.145 -CO-N(CH 3)-CH(CH 3)-CO-OC 2H 5
?No. -R 5 ?m.p./ 1H NMR data
Ⅰa.146 -CO-(tetramethyleneimine-1-yl)
Ⅰa.147 -CO-(piperidines-1-yl)
Ⅰa.148 -CO-(morpholine-4-yl)
Ⅰa.149 -CO-[4-(COOCH 3) (tetramethyleneimine-1-yl)
Ⅰa.150 -CO-[4-(COOC 2H 5) tetramethyleneimine-1-yl]
Ⅰa.151 -CH 2-CH(CH 3)-COOH
Ⅰa.152 -CH 2-CH(Cl)-COOH
Ⅰa.153 -CH 2-CH(CH 3)-CO-OCH 3
Ⅰa.154 -CH 2-CH(Cl)-CO-OCH 3
Ⅰa.155 -CH 2-CH(CH 3)-CO-OC 2H 5
Ⅰa.156 -CH 2-CH(Cl)-CO-OC 2H 5
Ⅰa.157 -CH=CH 2-COOH
Ⅰa.158 -CH=C(Cl)-COOH
Ⅰa.159 -CH=C(CH 3)-COOH
Ⅰa.160 -CH=CH 2-CO-OCH 3
Ⅰa.161 -CH=C(Cl)-CO-OCH 3
Ⅰa.162 -CH=C(CH 3)-CO-OCH 3
Ⅰa.163 -CH=CH-CO-OC 2H 5
Ⅰa.164 -CH=C(Cl)-CO-OC 2H 5
Ⅰa.165 -CH=C(CH 3)-CO-OC 2H 5
Ⅰa.166 -OCH(CH 3)-COOH 141-143℃
Ⅰa.167 -OCH(CH 3)-CO-OCH 3 124℃
Ⅰa.168 -NO 2
Ⅰa.169 -NH-OH
Ⅰa.170 -NH 2
Ⅰa.171 -NH-SO 2-CH 3
Ⅰa.172 -N(CH 3)-SO 2-CH 3
Ⅰa.173 -NH-SO 2-C 2H 5
Ⅰa.174 -N(CH 3)-SO 2-C 2H 5
Ⅰa.175 -NH-SO 2-CH 2-C 2H 5
Ⅰa.176 -N(CH 3)-SO 2-CH 2-C 2H 5
Ⅰa.177 -NH-SO 2-CH(CH 3) 2
Ⅰa.178 -N(CH 3)-SO 2-CH(CH 3) 2
Ⅰa.179 -N(SO 2-CH 3) 2
Ⅰa.180 -N(SO 2-C 2H 5) 2
Ⅰa.181 -N(SO 2-CH 2-C 2H 5) 2
Ⅰa.182 -N[SO 2-CH(CH 3) 2] 2
Ⅰa.183 -SO 2-Cl
Ⅰa.184 -SO 2-NH 2
?No. -R 5 ?m.p./ 1H NMR data
Ⅰa.185 -SO 2-NH-CH 3
Ⅰa.186 -SO 2-N(CH 3) 2
Ⅰa.187 -SO 2-NH-C 2H 5
Ⅰa.188 -SO 2-N(C 2H 5) 2
Ⅰa.189 -SO 2-(tetramethyleneimine-1-yl]
Ⅰa.190 -SO 2-(piperidines-1-yl)
Ⅰa.191 -SO 2-(morpholine-4-yl)
Ⅰa.192 -SO 2-NH-CH 2-CO-OCH 3
Ⅰa.193 -SO 2-N(CH 3)-CH 2-CO-OCH 3
Ⅰa.194 -SO 2-NH-CH 2-CO-OC 2H 5
Ⅰa.195 -SO 2-N(CH 3)-CH 2-CO-OC 2H 5
Ⅰa.196 -SO 2-NH-CH(CH 3)-CO-OCH 3
Ⅰa.197 -SO 2-N(CH 3)-CH(CH 3)-CO-OCH 3
Ⅰa.198 -SO 2-NH-CH(CH 3)-CO-OC 2H 5
Ⅰa.199 -SO 2-N(CH 3)-CH(CH 3)-CO-OC 2H 5
Ⅰa.200 -SO 2-[2-(COOCH 3) tetramethyleneimine-1-yl]
Ⅰa.201 -SO 2-[2-(COOC 2H 5) tetramethyleneimine-1-yl]
Ⅰa.202 -CO-NH-OH
Ⅰa.203 -CO-NH-OCH 3
Ⅰa.204 -CO-NH-OC 2H 5
Ⅰa.205 -C(=N-OCH 3)-OCH 3
Ⅰa.206 -C(=N-OC 2H 5)-OCH 3
Ⅰa.207 -C(=N-OCH 3)-OC 2H 5
Ⅰa.208 -C(=N-OC 2H 5)-OC 2H 5
Ⅰa.209 -C(=N-OCH 3)-OCH 2-C 2H 5
Ⅰa.210 -C(=N-OC 2H 5)-OCH 2-C 2H 5
Ⅰa.211 -C(=N-OCH 3)-OCH(CH 3) 2
Ⅰa.212 -C(=N-OC 2H 5)-OCH(CH 3) 2
Ⅰa.213 -C(=N-OCH 3)-OCH 2-CH=CH 2
Ⅰa.214 -C(=N-OC 2H 5)-OCH 2-CH=CH 2
Ⅰa.215 -C(=N-OCH 3)-OCH 2-C≡CH
Ⅰa.216 -C(=N-OC 2H 5)-OCH 2-C≡CH
Ⅰa.217 -C(=N-OCH 3)-OCH 2-C 6H 5
Ⅰa.218 -C(=N-OC 2H 5)-OCH 2-C 6H 5
Ⅰa.219 -C(=N-OCH 3)-OCH 2-CO-OCH 3
Ⅰa.220 -C(=N-OC 2H 5)-OCH 2-OCH 3
Ⅰa.221 -C(=N-OCH 3)-OCH 2-CO-OC 2H 5
Ⅰa.222 -C(=N-OC 2H 5)-OCH 2-CO-OC 2H 5
Ⅰa.223 -C(=N-OCH 3)-OCH(CH 3)-CO-OCH 3
?No. -R 5 M.p./1H NMR data
Ⅰa.224 -C(=N-OC 2H 5)-OCH(CH 3)-CO-OCH 3
Ⅰa.225 -C(=N-OCH 3)-OCH(CH 3)-CO-OC 2H 5
Ⅰa.226 -C(=N-OC 2H 5)-OCH(CH 3)-CO-OC 2H 5
Ⅰa.227 -CO-N(OCH 3)-CH 3
Ⅰa.228 -CO-N(OC 2H 5)-CH 3
Ⅰa.229 -CO-N(OCH 3)-C 2H 5
Ⅰa.2?30 -CO-N(OC 2H 5)-C 2H 5
Ⅰa.231 -CO-N(OCH 3)-CH 2-C 2H 5
Ⅰa.232 -CO-N(OC 2H 5)-CH 2-C 2H 5
Ⅰa.233 -CO-N(OCH 3)-CH(CH 3) 2
Ⅰa.234 -CO-N(OC 2H 5)-CH(CH 3) 2
Ⅰa.235 -CO-N(OCH 3)-CH 2-CH=CH 2
Ⅰa.236 -CO-N(OC 2H 5)-CH 2-CH=CH 2
Ⅰa.237 -CO-N(OCH 3)-CH 2-C≡CH
Ⅰa.238 -CO-N(OC 2H 5)-CH 2-C≡CH
Ⅰa.239 -CO-N(OCH 3)-CH 2-C 6H 5
Ⅰa.240 -CO-N(OC 2H 5)-CH 2-C 6H 5
Ⅰa.241 -CO-N(OCH 3)-CH 2-CO-OCH 3
Ⅰa.242 -CO-N(OC 2H 5)-CH 2-CO-OCH 3
Ⅰa.243 -CO-N(OCH 3)-CH 2-CO-OC 2H 5
Ⅰa.244 -CO-N(OC 2H 5)-CH 2-CO-OC 2H 5
Ⅰa.245 -CO-N(OCH 3)-CH(CH 3)-CO-OCH 3
Ⅰa.246 -CO-N(OC 2H 5)-CH(CH 3)-CO-OCH 3
Ⅰa.247 -CO-N(OCH 3)-CH(CH 3)-CO-OC 2H 5
Ia.248 -CO-N(OC 2H 5)-CH(CH 3)-CO-OC 2H 5
In addition, the 6-aryl-3-sulfo--5-oxo-2,3,4 of the replacement shown in the special preferred structure formula I b-I m, 5-tetrahydrochysene-1,2, the 4-triazine, particularly
-compounds .1-I b.248, itself and corresponding compounds I a.1-I difference a.248 only are R 3Be chlorine:
Figure A9980768700321
-chemical compounds I c.1-I c.248, itself and corresponding compounds I a.1-I difference a.248 only are R 3Be hydrogen:
Figure A9980768700331
-chemical compounds I d.1-I d.248, itself and corresponding compounds I a.1-I difference a.248 only are R 4Be cyano group:
-chemical compounds I e.1-I e.248, itself and corresponding compounds I a.1-I difference a.248 only are R 6Be chlorine and R 4Be cyano group:
Figure A9980768700333
-chemical compounds I f.1-I f.248, itself and corresponding compounds I a.1-I difference a.248 only are R 3Be hydrogen and R 4Be cyano group:
-chemical compounds I g.1-I g.248, itself and corresponding compounds I a.1-I difference a.248 only are R 2Be amino:
-chemical compounds I h.1-I h.248, itself and corresponding compounds I a.1-I difference a.248 only are R 2Be amino and R 3Be chlorine:
Figure A9980768700343
-chemical compounds I i.1-I i.248, itself and corresponding compounds I a.1-I difference a.248 only are R 2Amino and be R 3Be hydrogen:
Figure A9980768700351
-chemical compounds I k.1-I k.248, itself and corresponding compounds I a.1-I difference a.248 only are R 2Be amino and R 4Be cyano group:
Figure A9980768700352
-chemical compounds I m.1-I m.248, itself and corresponding compounds I a.1-I difference a.248 only are R 2Be amino, R 3Be hydrogen and R 4Be cyano group:
Particularly preferably be chemical compounds I a.166, I a.167, I b.166, I b.167, I c.166, I c.167, I d.166, I d.167, I e.166, I e.167, I f.166, I f.167, I g.166, I g.167, I h.166, I h.167, I k.166, I k.167, I m.166, I m.167.
And, the 6-aryl of the replacement of the structural formula I n shown in particularly preferably being-3-sulfo--5-oxo-2,3,4,5-tetrahydrochysene-1,2, {=I is Ar=Ar wherein for the 4-triazine 2N=1; X, Y=oxygen; R 1, R 2=methyl; R 3=fluorine; R 7=hydrogen }, listed I I compound n.80 n.1-in the table 2 particularly: table 2
Figure A9980768700361
?NO. -R 6
Ⅰn.1 -H
Ⅰn.2 -CH 3
Ⅰn.3 -C 2H 5
Ⅰn.4 -CH 2-C 2H 5
Ⅰn.5 -CH(CH 3) 2
Ⅰn.6 -CH 2-CH 2-C 2H 5
Ⅰn.7 -CH 2-CH(CH 3) 2
Ⅰn.8 -CH(CH 3)-C 2H 5
Ⅰn.9 -CH 2-CH 2-CH 2-C 2H 5
Ⅰn.10 -CH 2-CH=CH 2
Ⅰn.11 -CH(CH 3)-CH=CH 2
Ⅰn.12 -CH 2-C(CH 3)=CH 2
Ⅰn.13 -CH 2-CH=CH-CH 3
Ⅰn.14 -CH 2-CH=C(CH 3) 2
Ⅰn.15 -CH 2-CH 2-CH=CH-CH 3
Ⅰn.16 -CH 2-CH 2-C(CH 3)=CH 2
Ⅰn.17 -CH 2-C≡CH
Ⅰn.18 -CH(CH 3)-C≡CH
Ⅰn.19 -CH 2-C≡C-CH 3
Ⅰn.20 -OH
Ⅰn.21 -OCH 3
Ⅰn.22 -OC 2H 5
Ⅰn.23 -OCH 2-C 2H 5
Ⅰn.24 -OCH(CH 3) 2
Ⅰn.25 -OCH 2-CH 2-C 2H 5
Ⅰn.26 -OCH(CH 3)-C 2H 5
Ⅰn.27 -OCH 2-CH(CH 3) 2
Ⅰn.28 -OC(CH 3) 3
?NO. -R 6
Ⅰn.29 -OCH 2-CH 2-CH 2-C 2H 5
Ⅰn.30 -OCH 2-CH=CH 2
Ⅰn.31 -OCH(CH 3)-CH=CH 2
Ⅰn.32 -OCH 2-C(CH 3)=CH 2
Ⅰn.33 -OCH 2-CH=CH-CH 3
Ⅰn.34 -OCH 2-CH=C(CH 3) 2
Ⅰn.35 -OCH 2-CH 2-CH=CH-CH 3
Ⅰn.36 -OCH 2-CH 2-CH 2-CH=CH 2
Ⅰn.37 -OCH 2-C≡CH
Ⅰn.38 -OCH(CH 3)-C≡CH
Ⅰn.39 -OCH 2-C≡C-CH 3
Ⅰn.40 -CH 2-CO-OCH 3
Ⅰn.41 -CH 2-CO-OC 2H 5
Ⅰn.42 -CH 2-CO-OCH 2-C 2H 5
Ⅰn.43 -CH 2-CO-OCH(CH 3) 2
Ⅰn.44 -CH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰn.45 -CH 2-CO-OCH(CH 3)-C 2H 5
Ⅰn.46 -CH 2-CO-OCH 2-CH(CH 3) 2
Ⅰn.47 -CH 2-CO-OC(CH 3) 3
Ⅰn.48 -CH(CH 3)-CO-OCH 3
Ⅰn.49 -CH(CH 3)-CO-OC 2H 5
Ⅰn.50 -CH(CH 3)-CO-OCH(CH 3) 2
Ⅰn.51 -CH(CH 3)-CO-OCH 2-C 2H 5
Ⅰn.52 -CH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰn.53 -CH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰn.54 -CH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰn.55 -CH(CH 3)-CO-OC(CH 3) 3
Ⅰn.56 -OCH 2-CO-OCH 3
Ⅰn.57 -OCH 2-CO-OC 2H 5
Ⅰn.58 -OCH 2-CO-OCH 2-C 2H 5
Ⅰn.59 -OCH 2-CO-OCH(CH 3) 2
Ⅰn.60 -OCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰn.61 -OCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰn.62 -OCH 2-CO-OCH 2-CH(CH 3) 2
Ⅰn.63 -OCH 2-CO-OC(CH 3) 3
Ⅰn.64 -OCH(CH 3)-CO-OCH 3
Ⅰn.65 -OCH(CH 3)-CO-OC 2H 5
Ⅰn.66 -OCH(CH 3)-CO-OCH 2-C 2H 5
Ⅰn.67 -OCH(CH 3)-CO-OCH(CH 3) 2
?NO. -R 6
Ⅰn.68 -OCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰn.69 -OCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰn.70 -OCH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰn.71 -OCH(CH 3)-CO-OC(CH 3) 3
Ⅰn.72?? -CH 2-CO-OCH 2-CH 2-OCH 3
Ⅰn.73?? -CH 2-CO-OCH 2-CH 2-OC 2H 5
Ⅰn.74?? -CH 2-CO-OCH 2-CH 2-OCH 2-C 2H 5
Ⅰn.75?? -CH 2-CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰn.76?? -CH(CH 3)-CO-OCH 2-CH 2-OCH 3
Ⅰn.77?? -CH(CH 3)-CO-OCH 2-CH 2-OC 2H 5
Ⅰn.78?? -CH(CH 3)-CO-OCH 2-CH 2-OCH 2-C 2H 5
Ⅰn.79?? -CH(CH 3)-CO-OCH 2-CH 2-OCH(CH 3) 2
Ⅰn.80 -CH(CH 3)-CO-OCH 2-CH 2-OCH 2-CH 2-C 2H 5
In addition, the 6-aryl-3-sulfo--5-oxo-2,3,4 of the replacement shown in the special preferred structure formula I o-I s, 5-tetrahydrochysene-1,2, the 4-triazine, particularly
-chemical compounds I 0.1-I 0.80, itself and corresponding compounds I n.1-I difference n.80 only are R 3Be chlorine:
Figure A9980768700381
-chemical compounds I p.1-I p.80, itself and corresponding compounds I n.1-I difference n.80 only are R 3Be hydrogen:
Figure A9980768700391
-chemical compounds I q.1-I q.80, itself and corresponding compounds I n.1-I difference n.80 only are that n is 0:
Figure A9980768700392
-chemical compounds I r.1-I r.80, itself and corresponding compounds I n.1-I difference n.80 only are that n is 0 and R 3Be chlorine:
Figure A9980768700393
-chemical compounds I s.1-I s.80, itself and corresponding compounds I n.1-I difference n.80 only are that n is 0 and R 3Be hydrogen:
Figure A9980768700394
And, the 6-aryl of the replacement of the structural formula I t shown in particularly preferably being-3-sulfo--5-oxo-2,3,4,5-tetrahydrochysene-1,2, {=I is X=oxygen wherein for the 4-triazine; R 1, R 2=methyl; Ar=Ar 3R 3=fluorine and R 4=chlorine }, listed I I compound t.310 t.1-in the table 3 particularly: table 3
Figure A9980768700401
No. Z -R 8
Ⅰt.1 ?O -H
Ⅰt.2 ?S -H
Ⅰt.3 ?O -CH 3
Ⅰt.4 ?S -CH 3
Ⅰt.5 ?O -C 2H 5
Ⅰt.6 ?S -C 2H 5
Ⅰt.7 ?O -CH 2-C 2H 5
Ⅰt.8 ?S -CH 2-C 2H 5
Ⅰt.9 ?O -CH(CH 3) 2
Ⅰt.10 ?S -CH(CH 3) 2
Ⅰt.11 ?O -CH 2-CH 2-C 2H 5
Ⅰt.12 ?S -CH 2-CH 2-C 2H 5
Ⅰt.13 ?O -CH(CH 3)-C 2H 5
Ⅰt.14 ?S -CH(CH 3)-C 2H 5
Ⅰt.15 ?O -CH 2-CH(CH 3) 2
Ⅰt.16 ?S -CH 2-CH(CH 3) 2
Ⅰt.17 ?O -C(CH 3) 3
Ⅰt.18 ?S -C(CH 3) 3
Ⅰt.19?? ?O -CH 2-CH 2-CH 2-C 2H 5
Ⅰt.20 ?S -CH 2-CH 2-CH 2-C 2H 5
Ⅰt.21 ?O -CH 2-OCH 3
Ⅰt.22 ?S -CH 2-OCH 3
Ⅰt.23 ?O -CH 2-OC 2H 5
Ⅰt.24 ?S -CH 2-OC 2H 5
Ⅰt.25 ?O -CH 2-OCH 2-C 2H 5
Ⅰt.26 ?S -CH 2-OCH 2-C 2H 5
Ⅰt.27 ?O -CH 2-OCH(CH 3) 2
Ⅰt.28 ?S -CH 2-OCH(CH 3) 2
No. Z -R 8
Ⅰt.29 ?O -CH 2-OCH 2-CH 2-C 2H 5
Ⅰt.30 ?S -CH 2-OCH 2-CH 2-C 2H 5
Ⅰt.31 ?O -CH 2-OCH(CH 3)-C 2H 5
Ⅰt.32 ?S -CH 2-OCH(CH 3)-C 2H 5
Ⅰt.33 ?O -CH 2-OCH 2-CH(CH 3) 2
Ⅰt.34 ?S -CH 2-OCH 2-CH(CH 3) 2
Ⅰt.35 ?O -CH 2-OC(CH 3) 3
Ⅰt.36 ?S -CH 2-OC(CH 3) 3
Ⅰt.37 ?O -CH 2-COOH
Ⅰt.38 ?S -CH 2-COOH
Ⅰt.39 ?O -CH 2-CH 2-COOH
Ⅰt.40 ?S -CH 2-CH 2-COOH
?Ⅰt.41 ?O -CH 2-CH 2-CH 2-COOH
Ⅰt.42 ?S -CH 2-CH 2-CH 2-COOH
Ⅰt.43 ?O -CH 2-CH 2-CH 2-CH 2-COOH
Ⅰt.44 ?S -CH 2-CH 2-CH 2-CH 2-COOH
Ⅰt.45 ?O -CH 2-CO-OCH 3
Ⅰt.46 ?S -CH 2-CO-OCH 3
Ⅰt.47 ?O -CH 2-CO-OC 2H 5
Ⅰt.48 ?S -CH 2-CO-OC 2H 5
Ⅰt.49 ?O -CH 2-CO-OCH 2-C 2H 5
Ⅰt.50 ?S -CH 2-CO-OCH 2-C 2H 5
Ⅰt.51 ?O -CH 2-CO-OCH(CH 3) 2
Ⅰt.52 ?S -CH 2-CO-OCH(CH 3) 2
Ⅰt.53 ?O -CH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.54 ?S -CH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.55 ?O -CH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.56 ?S -CH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.57 ?O -CH 2-CO-OCH 2-CH(CH 3) 2
Ⅰt.58 ?S -CH 2-CO-OCH 2-CH(CH 3) 2
Ⅰt.59 ?O -CH 2-CO-OC(CH 3) 3
Ⅰt.60 ?S -CH 2-CO-OC(CH 3) 3
Ⅰt.61 ?O -CH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.62 ?S -CH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.63 ?O -CH 2-CH 2-CO-OCH 3
Ⅰt.64 ?S -CH 2-CH 2-CO-OCH 3
Ⅰt.65 ?O -CH 2-CH 2-CO-OCH 2-C 2H 5
Ⅰt.66 ?S -CH 2-CH 2-CO-OCH 2-C 2H 5
Ⅰt.67 ?O -CH 2-CH 2-CO-OCH(CH 3) 2
No. Z -R 8
Ⅰt.68 ?S -CH 2-CH 2-CO-OCH(CH 3) 2
Ⅰt.69 ?O -CH 2-CH 2-CH 2-CO-OCH 3
Ⅰt.70 ?S -CH 2-CH 2-CH 2-CO-OCH 3
Ⅰt.71 ?O -CH 2-CH 2-CH 2-CO-OC 2H 5
Ⅰt.72 ?S -CH 2-CH 2-CH 2-CO-OC 2H 5
Ⅰt.73 ?O -CH 2-CH 2-CH 2-CH 2-CO-OCH 3
Ⅰt.74 ?S -CH 2-CH 2-CH 2-CH 2-CO-OCH 3
Ⅰt.75 ?O -CH 2-CH 2-CH 2-CH 2-CO-OC 2H 5
Ⅰt.76 ?S -CH 2-CH 2-CH 2-CH 2-CO-OC 2H 5
Ⅰt.77 ?O -COOH
Ⅰt.78 ?S -COOH
Ⅰt.79 ?O -CO-OCH 3
Ⅰt.80 ?S -CO-OCH 3
Ⅰt.81 ?O -CO-OC 2H 5
Ⅰt.82 ?S -CO-OC 2H 5
Ⅰt.83 ?O -CO-OCH 2-C 2H 5
Ⅰt.84 ?S -CO-OCH 2-C 2H 5
Ⅰt.85 ?O -CO-OCH(CH 3) 2
Ⅰt.86 ?S -CO-OCH(CH 3) 2
Ⅰt.87 ?O -CO-OCH 2-CH 2-C 2H 5
Ⅰt.88 ?S -CO-OCH 2-CH 2-C 2H 5
Ⅰt.89 ?O -CO-OCH(CH 3)-C 2H 5
Ⅰt.90 ?S -CO-OCH(CH 3)-C 2H 5
Ⅰt.91 ?O -CO-OCH 2-CH(CH 3) 2
Ⅰt.92 ?S -CO-OCH 2-CH(CH 3) 2
Ⅰt.93 ?O -CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.94 ?S -CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.95 ?O -OH
Ⅰt.96 ?S -OH
Ⅰt.97 ?O -OCH 3
Ⅰt.98 ?S -OCH 3
Ⅰt.99 ?O -OC 2H 5
Ⅰt.100 ?S -OC 2H 5
Ⅰt.101 ?O -OCH(CH 3) 2
Ⅰt.102 ?S -OCH(CH 3) 2
Ⅰt.103 ?O -OCH 2-CH 2-C 2H 5
Ⅰt.104 ?S -OCH 2-CH 2-C 2H 5
Ⅰt.105 ?O -OCH(CH 3)-C 2H 5
Ⅰt.106 ?S -OCH(CH 3)-C 2H 5
?No. Z -R 8
Ⅰt.107 ?O -OCH 2-CH(CH 3) 2
Ⅰt.108 ?S -OCH 2-CH(CH 3) 2
Ⅰt.109 ?O -OC(CH 3) 3
Ⅰt.110 ?S -OC(CH 3) 3
Ⅰt.111 ?O -OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.112 ?S -OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.113 ?O -OCH 2-CH 2-OCH 3
Ⅰt.114 ?S -OCH 2-CH 2-OCH 3
Ⅰt.115 ?O -OCH 2-CH 2-OC 2H 5
?Ⅰt.116 ?S -OCH 2-CH 2-OC 2H 5
Ⅰt.117 ?O -OCH 2-CO-OCH 3
Ⅰt.118 ?S -OCH 2-CO-OCH 3
Ⅰt.119 O -OCH 2-CO-OC 2H 5
Ⅰt.120 ?S -OCH 2-CO-OC 2H 5
Ⅰt.121 ?O -OCH 2-CO-OCH 2-C 2H 5
Ⅰt.122 ?S -OCH 2-CO-OCH 2-C 2H 5
Ⅰt.123 ?O -OCH 2-CO-OCH(CH 3) 2
Ⅰt.124 ?S -OCH 2-CO-OCH(CH 3) 2
Ⅰt.125 ?O -OCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.126 ?S -OCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.127 ?O -OCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.128 ?S -OCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.129 ?O -OCH 2-CO-OCH 2-CH(CH 3) 2
Ⅰt.130 ?S -OCH 2-CO-OCH 2-CH(CH 3) 2
Ⅰt.131 ?O -OCH 2-CO-OC(CH 3) 3
Ⅰt.132 ?S -OCH 2-CO-OC(CH 3) 3
Ⅰt.133 ?O -OCH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.134 ?S -OCH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.135 ?O -OCH(CH 3)-CO-OCH 3
Ⅰt.136 ?S -OCH(CH 3)-CO-OCH 3
Ⅰt.137 ?O -OCH(CH 3)-CO-OC 2H 5
Ⅰt.138 ?S -OCH(CH 3)-CO-OC 2H 5
Ⅰt.139 ?O -OCH(CH 3)-CO-OCH 2-C 2H 5
Ⅰt.140 ?S -OCH(CH 3)-CO-OCH 2-C 2H 5
Ⅰt.141 ?O -OCH(CH 3)-CO-OCH(CH 3) 2
Ⅰt.142 ?S -OCH(CH 3)-CO-OCH(CH 3) 2
Ⅰt.143 ?O -OCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰt.144 ?S -OCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰt.145 ?O -OCH(CH 3)-CO-OCH(CH 3)-C 2H 5
?No. Z -R 8
Ⅰt.146 ?S -OCH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰt.147 ?O -OCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰt.148 ?S -OCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰt.149 ?O -OCH(CH 3)-CO-OC(CH 3) 3
Ⅰt.150 ?S -OCH(CH 3)-CO-OC(CH 3) 3
Ⅰt.151 ?O -OCH(CH 3)-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.152 ?S -OCH(CH 3)-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.153 ?O -OCH 2-CH=CH 2
Ⅰt.154 ?S -OCH 2-CH=CH 2
Ⅰt.155 ?O -OCH(CH 3)-CH=CH 2
Ⅰt.156 ?S -OCH(CH 3)-CH=CH 2
Ⅰt.157 ?O -OCH 2-C(CH 3)=CH 2
Ⅰt.158 ?S -OCH 2-C(CH 3)=CH 2
Ⅰt.159 ?O -OCH 2-CH=CH-CH 3
Ⅰt.160 ?S -OCH 2-CH=CH-CH 3
Ⅰt.161 ?O -OCH 2-CH 2-CH=CH 2
Ⅰt.162 ?S -OCH 2-CH 2-CH=CH 2
Ⅰt.163 ?O -OCH 2-CH=C(CH 3) 2
Ⅰt.164 ?S -OCH 2-CH=C(CH 3) 2
Ⅰt.165 ?O -OCH 2-C≡CH
Ⅰt.166 ?S -OCH 2-C≡CH
Ⅰt.167 ?O -OCH(CH 3)-C≡CH
Ⅰt.168 ?S -OCH(CH 3)-C≡CH
Ⅰt.169 ?O -OCH 2-C≡C-CH 3
Ⅰt.170 ?S -OCH 2-C≡C-CH 3
Ⅰt.171 ?O -SH
Ⅰt.172 ?S -SH
Ⅰt.173 ?O -SCH 3
Ⅰt.174 ?S -SCH 3
Ⅰt.175 ?O -SC 2H 5
Ⅰt.176 ?S -SC 2H 5
Ⅰt.177 ?O -SCH 2-C 2H 5
Ⅰt.178 ?S -SCH 2-C 2H 5
Ⅰt.179 ?O -SCH(CH 3) 2
Ⅰt.180 ?S -SCH(CH 3) 2
Ⅰt.181 ?O -SCH 2-CH 2-C 2H 5
Ⅰt.182 ?S -SCH 2-CH 2-C 2H 5
Ⅰt.183 ?O -SCH(CH 3)-C 2H 5
Ⅰt.184 ?S -SCH(CH 3)-C 2H 5
?No. Z -R 8
Ⅰt.185 ?O -SCH 2-CH(CH 3) 2
Ⅰt.186 ?S -SCH 2-CH(CH 3) 2
Ⅰt.187 ?O -SC(CH 3) 3
Ⅰt.188 ?S -SC(CH 3) 3
Ⅰt.189 ?O -SCH 2-CH 2-CH 2-C 2H 5
Ⅰt.190 ?S -SCH 2-CH 2-CH 2-C 2H 5
Ⅰt.191 ?O -SCH 2-CH=CH 2
Ⅰt.192 ?S -SCH 2-CH=CH 2
Ⅰt.193 ?O -SCH(CH 3)-CH=CH 2
Ⅰt.194 ?S -SCH(CH 3)-CH=CH 2
Ⅰt.195 ?O -SCH 2-C(CH 3)=CH 2
Ⅰt.196 ?S -SCH 2-C(CH 3)=CH 2
Ⅰt.197 ?O -SCH 2-CH=CH-CH 3
Ⅰt.198 ?S -SCH 2-CH=CH-CH 3
Ⅰt.199 ?O -SCH 2-CH 2-CH=CH 2
Ⅰt.200 ?S -SCH 2-CH 2-CH=CH 2
Ⅰt.201 ?O -SCH 2-CH=C(CH 3) 2
Ⅰt.202 ?S -SCH 2-CH=C(CH 3) 2
Ⅰt.203 ?O -SCH 2-C≡CH
Ⅰt.204 ?S -SCH 2-C≡CH
Ⅰt.205 ?O -SCH(CH 3)-C≡CH
Ⅰt.206 ?S -SCH(CH 3)-C≡CH
Ⅰt.207 ?O -SCH 2-C≡C-CH 3
Ⅰt.208 ?S -SCH 2-C≡C-CH 3
Ⅰt.209 O -SCH 2-CO-OCH 3
Ⅰt.210 ?S -SCH 2-CO-OCH 3
Ⅰt.211 ?O -SCH 2-CO-OC 2H 5
Ⅰt.212 ?S -SCH 2-CO-OC 2H 5
Ⅰt.213 ?O -SCH 2-CO-OCH 2-C 2H 5
Ⅰt.214 ?S -SCH 2-CO-OCH 2-C 2H 5
Ⅰt.215 ?O -SCH 2-CO-OCH(CH 3) 2
Ⅰt.216 ?S -SCH 2-CO-OCH(CH 3) 2
Ⅰt.217 ?O -SCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.218 ?S -SCH 2-CO-OCH 2-CH 2-C 2H 5
Ⅰt.219 ?O -SCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.220 ?S -SCH 2-CO-OCH(CH 3)-C 2H 5
Ⅰt.221 ?O -SCH 2-CO-OCH 2-CH(CH 3) 2
Ⅰt.222 ?S -SCH 2-CO-OCH 2-CH(CH 3) 2
?Ⅰt.223 ?O -SCH 2-CO-OC(CH 3) 3
?No. Z -R 8
Ⅰt.224 ?S -SCH 2-CO-OC(CH 3) 3
Ⅰt.225 ?O -SCH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.226 ?S -SCH 2-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.227 ?O -SCH(CH 3)-CO-OCH 3
Ⅰt.228 ?S -SCH(CH 3)-CO-OCH 3
Ⅰt.229 ?O -SCH(CH 3)-CO-OC 2H 5
Ⅰt.230 ?S -SCH(CH 3)-CO-OC 2H 5
Ⅰt.231 ?O -SCH(CH 3)-CO-OCH 2-C 2H 5
Ⅰt.232 ?S -SCH(CH 3)-CO-OCH 2-C 2H 5
Ⅰt.233 ?O -SCH(CH 3)-CO-OCH(CH 3) 2
Ⅰt.234 ?S -SCH(CH 3)-CO-OCH(CH 3) 2
Ⅰt.235 ?O -SCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰt.236 ?S -SCH(CH 3)-CO-OCH 2-CH 2-C 2H 5
Ⅰt.237 ?O -SCH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰt.238 ?S -SCH(CH 3)-CO-OCH(CH 3)-C 2H 5
Ⅰt.239 ?O -SCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰt.240 ?S -SCH(CH 3)-CO-OCH 2-CH(CH 3) 2
Ⅰt.241 ?O -SCH(CH 3)-CO-OC(CH 3) 3
Ⅰt.242 ?S -SCH(CH 3)-CO-OC(CH 3) 3
Ⅰt.243 ?O -SCH(CH 3)-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.244 ?S -SCH(CH 3)-CO-OCH 2-CH 2-CH 2-C 2H 5
Ⅰt.245 ?O -NH 2
Ⅰt.246 ?S -NH-CH 3
Ⅰt.247 ?O -N(CH 3) 2
Ⅰt.248 ?S -NH-C 2H 5
Ⅰt.249 ?O -N(C 2H 5) 2
Ⅰt.250 ?S -NH-CH 2-CH=CH 2
Ⅰt.251 ?O -NH-CH 2-C≡CH
Ⅰt.252 ?S -NH 2
Ⅰt.253 ?O -NH-CH 3
Ⅰt.254 ?S -N(CH 3) 2
Ⅰt.255 ?O -NH-C 2H 5
Ⅰt.256 ?S -N(C 2H 5) 2
Ⅰt.257 ?O -NH-CH 2-CH=CH 2
Ⅰt.258 ?S -NH-CH 2-C≡CH
Ⅰt.259 ?O -NH-CH 2-C 6H 5
Ⅰt.260 ?S -NH-CH 2-C 6H 5
Ⅰt.261 ?O -NH-CH 2-CO-OCH 3
Ⅰt.262 ?S -NH-CH 2-CO-OCH 3
?No. Z -R 8
Ⅰt.263 ?O -NH-CH 2-CO-OC 2H 5
Ⅰt.264 ?S -NH-CH 2-CO-OC 2H 5
Ⅰt.265 ?O -N(CH 3)-CH 2-CO-OC 2H 5
Ⅰt.266 ?S -N(CH 3)-CH 2-CO-OC 2H 5
Ⅰt.267 ?O -N(CH 3)-CH 2-CO-OCH 3
Ⅰt.268 ?S -N(CH 3)-CH 2-CO-OCH 3
Ⅰt.269 ?O -NH-CH(CH 3)-CO-OCH 3
Ⅰt.270 ?S -NH-CH(CH 3)-CO-OCH 3
Ⅰt.271 ?O -NH-CH(CH 3)-CO-OC 2H 5
Ⅰt.272 ?S -NH-CH(CH 3)-CO-OC 2H 5
Ⅰt.273 ?O -N(CH 3)-CH(CH 3)-CO-OCH 3
Ⅰt.274 ?S -N(CH 3)-CH(CH 3)-CO-OCH 3
Ⅰt.275 O -N(CH 3)-CH(CH 3)-CO-OC 2H 5
Ⅰt.276 ?S -N(CH 3)-CH(CH 3)-CO-OC 2H 5
Ⅰt.277 ?O -Cl
Ⅰt.278 ?S -Cl
Ⅰt.279 ?O -Br
Ⅰt.280 ?S -Br
Ⅰt.281 ?O -CH 2-CH(CH 3)-COOH
Ⅰt.282 ?S -CH 2-CH(CH 3)-COOH
Ⅰt.283 ?O -CH 2-CH(CH 3)-CO-OCH 3
Ⅰt.284 ?S -CH 2-CH(CH 3)-CO-OCH 3
Ⅰt.285 ?O -CH 2-CH(CH 3)-CO-OC 2H 5
Ⅰt.286 ?S -CH 2-CH(CH 3)-CO-OC 2H 5
Ⅰt.287 ?O -CH 2-CH(Cl)-COOH
Ⅰt.288 ?S -CH 2-CH(Cl)-COOH
Ⅰt.289 ?O -CH 2-CH(Cl)-CO-OCH 3
Ⅰt.290 ?S -CH 2-CH(Cl)-CO-OCH 3
Ⅰt.291 ?O -CH 2-CH(Cl)-CO-OC 2H 5
Ⅰt.292 ?S -CH 2-CH(Cl)-CO-OC 2H 5
Ⅰt.293 ?O -CH=CH-COOH
Ⅰt.294 ?S -CH=CH-COOH
Ⅰt.295 ?O -CH=CH-CO-OCH 3
Ⅰt.296 ?S -CH=CH-CO-OCH 3
Ⅰt.297 ?O -CH=CH-CO-OC 2H 5
Ⅰt.298 ?S -CH=CH-CO-OC 2H 5
Ⅰt.299 ?O -CH=C(CH 3)-COOH
Ⅰt.300 ?S -CH=C(CH 3)-COOH
Ⅰt.301 ?O -CH=C(CH 3)-CO-OCH 3
?NO. ?Z -R 8
Ⅰt.302 ?S -CH=C(CH 3)-CO-OCH 3
Ⅰt.303 ?O -CH=C(CH 3)-CO-OC 2H 5
Ⅰt.304 ?S -CH=C(CH 3)-CO-OC 2H 5
Ⅰt.305 ?O -CH=C(Cl)-COOH
Ⅰt.306 ?S -CH=C(Cl)-COOH
Ⅰt.307 ?O -CH=C(Cl)-CO-OCH 3
It.308 ?S -CH=C(Cl)-CO-OCH 3
It.309 ?O -CH-C(Cl)-CO-OC 2H 5
It.310 ?S -CH-C(Cl)-CO-OC 2H 5
And, the 6-aryl-3-sulfo--5-oxo-2,3,4 of the replacement shown in the special preferred structure formula I u-I y, 5-tetrahydrochysene-1,2, the 4-triazine, particularly
-chemical compounds I u.1-I u.310, itself and corresponding compounds I t.1-I difference t.310 only are R 3Be chlorine:
Figure A9980768700491
-chemical compounds I v.1-I v.310, itself and corresponding compounds I t.1-I difference t.310 only are R 3Be hydrogen:
Figure A9980768700492
-chemical compounds I w.1-I w.310, itself and corresponding compounds I t.1-I difference t.310 only are that Ar is Ar 4:
-chemical compounds I x.1-I x.310, itself and corresponding compounds I t.1-I difference t.310 only are that Ar is Ar 4And R 3Be chlorine:
-chemical compounds I y.1-I y.310, itself and corresponding compounds I t.1-I difference t.310 only are that Ar is Ar 4And R 3Be hydrogen:
Figure A9980768700502
The 6-aryl of the replacement shown in the structural formula I-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, the 4-triazine can prepare by variety of way, particularly prepares by one of following method:
A) 2, thiocarboxyl group hydrazides IV and aryl Glyoxylic acid hydrate or its C that dibasic thiosemicarbazide of 4-or 2-replace 1-C 6-alkyl ester (V) carries out ring-closing condensation reaction:
Figure A9980768700511
R 25Be hydrogen or C 1-C 6-alkyl.I{x=O}
Reaction is carried out in inert solvent/thinner usually, acetate for example, and lower alcohol is as methyl alcohol, ethanol, n-propyl alcohol and Virahol, ether such as t-butyl methyl ether, tetrahydrofuran (THF) diox and 1,2-diethoxyethane, aprotonic solvent such as dimethyl formamide, dimethyl sulfoxide (DMSO) and pyridine.Except that t-butyl methyl ether, the mixture of above-mentioned solvents/diluents and water also can use.
Reaction is generally carried out to the boiling temperature of above-mentioned reaction mixture at 20 ℃.
The condensation reaction of IV and V is carried out under the catalysis of acid usually, and the acid that is fit to is carboxylic acid such as formic acid and acetate particularly, sulfonic acid such as Phenylsulfonic acid and tosic acid, or mineral acid example hydrochloric acid, sulfuric acid and phosphoric acid.
Ring-closure reaction from IV to I is carried out under the catalysis of alkali usually.Being fit to the alkali of this purpose, for example is alkaline carbonate such as yellow soda ash, alkali metal hydrocarbonate such as sodium bicarbonate and alkali metal hydroxide such as sodium hydroxide, and nitrogenous organic bases such as triethylamine, dicyclohexyl ethamine, pyridine and 4-dimethylaminopyridine.
Such reaction is known, H.Neunhoeffer A.R.Katritzky for example, ComprehensiveHeterocyclic Chemistry, Vol.3, p.430 and the reference J.Gut and M.Prystas that quotes, Coll.Czech.Chem.Commun.24,2986 (1959); M.Tisler and Z.Vrbaski, J.Org.Chem.25,770 (1960); V.J.Ram and M.Nath, Ind.J.Chem.Vol.34B, p.423-426 (1995); WO 94/03454.
The alkyl ester (V) of aryl Glyoxylic acid hydrate and they be known or by the currently known methods preparation (reference, for example, J.S.Nimitz﹠H.S.Mosher, J.Org.Chem.46 (1981), 211-213; W.M.P.Johnson﹠G.Holan, Aust.J.Chem.34 (1981), 2363 and X.Creary, J.Org.Chem.52 (1987), 5026).
According to the active compound I of particularly preferred wherein A=Ar1, particularly advantageous is compound V a
R wherein particularly 4=chlorine and R 5=OR 18 'Those compounds, R wherein 18 'Be hydrogen, methyl or-CH (CH 3)-COOCH 3
B) 6-aryl-triazine true tumor VII and alkylogen or dialkylsulfates R 1The alkylated reaction of-L:
L is a chlorine, bromine, iodine or O-SO 2-OR 1
Particularly suitable solvents/diluents is non-proton transfer solvent such as N, dinethylformamide, dimethyl sulfoxide (DMSO), acetonitrile, acetone, tetrahydrofuran (THF), diox and 1,2-diethoxyethane.
Reaction is generally carried out to the boiling temperature of above-mentioned reaction mixture at 0 ℃.
This alkylated reaction is normally known, for example: M.Prystas and J.Gut, Coll.czech.Chem.Commun.27,1898 (1962); J.Daunis etc., ull.Soc.Chim.Fr.10,3658 (1971) and Bull.Soc.Chim.Fr.11,1511 (1972); A.K.Mansour and Y.A.Ibrahim, Journal f.prakt.Chemie 315,221 (1973).
6-aryl-triazine derivative VII preferred class is similar to method A) by thiocarboxyl group hydrazides (R 2=NH 2) or the condensation reaction preparation of 4 monobasic thiosemicarbazide IX and V:
Most of thiosemicarbazide and thiocarboxyl group hydrazides IV and IX are known, but they also can prepare by currently known methods (referring to, KAJensen etc. for example, Acta Chemica Scandinayica22 (1968), 1 and C.-J.Kroger etc., Liebigs Ann.Chem.643 (1961), 121).
C) 6-aryl-3-sulfo--5-oxo-2,3,4,5-tetrahydrochysene-1,2, the mercaptanization of 4-triazine referring to, for example, M.Prystas﹠J.Gut, Coll.Czech.Chem.Commun.27 (1962), 1898; J.Jonas﹠J.Gut, Coll.Czech.Chem.Commun.27 (1962), 1886; C.Tzeng etc., J.Org.Chem.48 (1983), 1271}:
Figure A9980768700532
Sulfuration generally is to carry out in inert solvent/thinner, for example at aromatic hydrocarbons such as toluene and dimethylbenzene, or carries out in organic amine such as the pyridine.
Particularly suitable vulcanizing agent is phosphoric sulfide (V) and 2, two (the 4-p-methoxy-phenyls)-1 of 4-, and 3-dithio-2,4-diphosphetan 2,4-disulphide (" Lawesson reagent ").
Usually, { quantity of the initiator I of X=O}, the vulcanizing agent of 1-5 times of molar weight is in fact enough finished reaction according to need sulfurations.
Usually temperature of reaction is 20 ℃ of boiling temperatures to above-mentioned reaction mixture.
Except as otherwise noted, above-mentioned all methods preferably under atmospheric pressure or under the inherent pressure of above-mentioned reaction mixture are carried out.
Usually, the 6-of replacement aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2,4-triazine I can be by above-mentioned any synthetic method preparation.Yet, consider that economy or technical reason are more preferably by similar 6-aryl-3-sulfo--5-(sulfo-) oxo-2,3; 4,5 tetrahydrochysenes-1,2; 4-triaizine compounds (they are the definition difference of the group of each on Ar particularly) prepares some chemical compounds I with currently known methods, for example by nitrification, and sulfurization; sulfochlorination, halogenation, alkylating; acylation; the acetal hydrolytic action, acetalization, amidation; esterolysis; condensation reaction, oxygenizement, Peterson olefination; reductive action; etherification, esterification, Wittig reaction or Meerwein reaction.
The initiator that every kind of method is used all is known or by currently known methods or be similar to above-mentioned either party's method preparation.
Reaction mixture for example, also then passes through to filter by the dilute with water reaction soln usually with the currently known methods aftertreatment, crystallization or solvent extraction and product separation, or by removing solvent, in water and appropriate organic solvent mixture, distribute residuum and handle organic phase, obtain product.
The 6-aryl that can obtain to replace during preparation-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, the isomer mixture of 4-triazine I; Yet,, can use ordinary method such as crystallization or chromatographic process to comprise that the enterprising circumstances in which people get things ready for a trip spectrum of optical activity adsorptive is to be separated into pure isomer basically with said mixture as needs.Preferably the optical activity initiator preparation of pure optically active isomer from being fit to.
The salt of the chemical compounds I that uses on the agricultural can by with corresponding positively charged ion alkali, preferred alkali metal hydroxide or hydride reaction make, or make with the preferred spirit of salt of corresponding anionic acid, Hydrogen bromide, sulfuric acid, phosphoric acid or nitric acid reaction.
Wherein metal ion is not that the salt of the chemical compounds I of alkalimetal ion also can use ordinary method to pass through the cationic exchange method preparation of corresponding alkali metal salt, is similar to by ammonia, phosphorus, sulfonium or hydroxide sulfonium and makes ammonium salt, phosphorus, sulfonium and sulfoxonium.
Chemical compounds I and their agricultural goes up available salt-as the isomer mixture form with pure isomer form-be fit to as weedicide.The herbicidal composition that contains chemical compounds I especially provides under height is used ratio the effectively control of plant-growth on the farming area not.Their anti-crop such as wheats, rice, corn, broadleaf weeds in soybean and the cotton and turf weeds are to crop not injury basically.This effect especially takes place under low amount of application.
Depend on various application processes, for rooting out unwanted plant, chemical compounds I or the herbicidal composition that contains them also can use in more crop.For example, following crop is suitable:
Onion, pineapple, peanut, the officinalis Radix Asparagi, the altissima beet, beet kind rape, turnip mutation napus, turnip mutation napobrassica, the silvestris blister beetle, tea, safflower, pecan tree, lemon, sweet orange, fruitlet coffee (middle fruit coffee, big fruit coffee), cucumber, Bermuda grass, Radix Dauci Sativae, oil palm, sow-tit, the big shield beans, upland cotton (tree cotton, cotton, the vitifolium cotton), Sunflower Receptacle, rubber tree, barley, hops, sweet potato, English walnut, Lens culinaris, flax, the lycopersicum tomato, the apple kind, cassava, alfalfa, Musa, tobacco (rustica), olea, rice, Sieve Bean, Kidney bean, European spruce, Pinus, pea, the sweet cherry tree, peach, European pear, the sylvestre tea foot of a hill or mountain, castor-oil plant, the saccharum noble cane, rye, potato, Chinese sorghum, cocoa, red clover, wheat, Triticum durum, broad bean, grape and corn.
In addition, chemical compounds I also can be used in by comprising the inoculation method of gene engineering method, makes it weedicide is produced in the crop of tolerance effect.
By spraying, atomisation, the mode of dusting, broadcasting sowing or watering, chemical compounds I or contain their herbicidal composition can be so that for example directly the sprayable aqueous solution, pulvis, suspension comprise spissated water, oil or other suspension or dispersion liquid, emulsion, oily dispersion liquid, paste, pulvis, the form of broadcasting sowing agent or granule uses.Using method depends on required purpose; No matter in any case, should guarantee that all activeconstituents most probable of the present invention carefully disperses.
Suitable inert additive mainly contains: medium to the mineral oil fractions of high boiling point such as the oil in kerosene and diesel oil and coal tar and plant and animal source, aliphatic series, ring family and aromatic hydrocarbon be paraffin for example, naphthane, alkylnaphthalene and its derivative, alkylbenzene and its derivative, pure as methyl alcohol, ethanol, propyl alcohol, butanols and hexalin, ketone such as pimelinketone, intensive polar solvent, for example amine such as N-Methyl pyrrolidone and water.
Moisture administration form can be by to concentrated emulsion, suspension, and paste, but add entry in wettable powder or the water discrete particles and prepare.For emulsion, the preparation of paste or oily dispersion liquid, substrate with himself form be dissolved in oil or solvent in, and by wetting agent, adhesive agent, dispersion agent or emulsifying agent homogenizing in water.Also can be by containing active compound, wetting agent, adhesive agent, dispersion agent or emulsifying agent and, as being fit to, solvent or oil prepare concentrated solution, their concentrated solution is suitable for thin up.
Suitable tensio-active agent is an aromatic sulfonic acid, for example lignin-, phenol-, naphthalene-and the dibutyl naphthene sulfonic acid, with lipid acid, alkyl-and alkyl aryl sulfonate, alkyl sulfuric ester, the an alkali metal salt of bay ether sulfuric ester and fatty alcohol sulfate, alkaline earth salt and ammonium salt, with sulfation 16-, 17-and stearyl alcohol salt, and Fatty Alcohol(C12-C14 and C12-C18) glycol ether salt, the condenses of sulfonated naphthalene and its derivative and formaldehyde, the condenses of naphthalene or naphthene sulfonic acid and phenol and formaldehyde, polyoxyethylene octyl phenol ether, the iso-octyl of ethoxyquin-, octyl group-or nonylphenol, alkyl phenyl or tributyl phenyl polyglycol ether, alkyl aryl polyether alcohol, different tridecyl alcohol, Fatty Alcohol(C12-C14 and C12-C18)/ethylene oxide condensate, the Viscotrol C of ethoxyquin, polyoxyethylene-or the polyoxypropylene alkyl oxide,, polyoxyethylene glycol ether acetic acid lauryl alcohol ester, sorbitol ester, lignin sulfite waste liquor or methylcellulose gum.
Pulvis, broadcasting sowing agent and dust agent can prepare by active compound and solid carrier being mixed together or grinding bonding.
Particle for example dressing, the passing through of dipping with active compound and the bonding preparation of solid carrier with the particle of homogenizing.Solid carrier is that mineral are native as silica, silica gel, silicate, talcum, kaolin, Wingdale, lime, chalk, bole, loess, clay, rhombspar, diatomite, calcium sulfate, sal epsom, magnesium oxide, plastics, fertilizer such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea, with plant prod such as flour, tree bark powder, wood powder and nutshell powder, cellulose powder and other solid carrier.
In the preparation of now with the current form, the concentration of active compound I can change in wide scope.It is about 0.001 to 98% that preparation contains usually, at least a active compound of preferred 0.01 to 95% weight.Active compound is preferred with 90% to 100%, and 95% to 100% purity is used (according to the NMR spectrum).
Following preparation embodiment has described the preparation of this preparation:
A.167, the compound N o. I of I .20 weight part is dissolved in the alkylated benzenes that contains 80 weight parts, the adducts by 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-single ethanol amide of 10 weight parts is in the mixture by the adducts of 40 moles of ethylene oxide and 1 mole of castor oil of 5 weight part calcium dodecylbenzene sulphonates and 5 weight parts.This solution is poured in the water of 100,000 weight parts and it is distributed, obtain containing the aqueous dispersions of 0.02% weight active compound.
C.1, the compound N o. I of II .20 weight part is dissolved in and contains 40 weight part pimelinketone, the isopropylcarbinol of 30 weight parts is in the adducts and the mixture of 10 weight parts by the adducts of 40 moles of ethylene oxide and 1 mole of castor oil of 20 weight parts by 7 moles of ethylene oxide and 1 mole of different hot phenol.This solution is poured in the water of 100,000 weight parts, and it is distributed, obtain containing the aqueous dispersions of 0.02% weight active compound.
A.167, the active compound No. I of III .20 weight part is dissolved in and contains 25 weight part pimelinketone, and the boiling range of 65 weight parts is at 210 to 280 ℃ mineral oil fractions, in the mixture of 10 weight parts by 40 moles of ethylene oxide and 1 mole of castor oil adducts.Pour solution into 100,000 heavy parts water, and it is distributed, obtain containing the aqueous dispersions of 0.02% weight active compound.
The active compound No. I of IV 20 weight parts c.154 with the sodium salt of the diisobutyl naphthalene-α-sulfonic acid of 3 weight parts, 17 weight parts mix well from the sodium salt of the lignosulfonic acid of sulfite waste liquor and the silica-gel powder of 60 weight parts, mixture grinds in hammer mill.This mixture is distributed in the water of 20,000 weight parts well, obtain containing the spraying fluid of 0.1% weight active compound.
G.167, the active compound No. I of V 3 weight parts is mixed with the kaolin of 97 weight part good distribution.Obtain containing the pulvis of 3% weight active compound in this way.
VI 20 weight part active compound No. I c.172 with the calcium salt of dodecylbenzene sulfonate of 2 weight parts, the fatty alcohol polyglycol ether of 8 weight parts, the paraffin base mineral oil of the sodium salt of the phenol/urea of 2 weight parts/formaldehyde condensation products and 68 weight parts mixes well.Obtain stable oily dispersion liquid.
G.167, the compound N o. I of VII 1 weight part is dissolved in the pimelinketone that contains 70 weight parts, in the mixture of the Viscotrol C of the isooctyl phenol of 20 weight part ethoxylations and 10 weight part ethoxylations.Obtain stable missible oil.
C.2, the compound N o. I of VIII .1 weight part is dissolved in and contains 80 weight part pimelinketone, the Wettol  EM 31 of 20 weight parts (=based on the nonionic emulsifier of the Viscotrol C of ethoxylation; BASF AG) in the mixture.Obtain stable missible oil.
Active compound I or herbicidal composition can be used by method before the seedling or behind the seedling.If active compound is to the less tolerance of certain crop, use spraying plant weed sprays agent composition, when active compound arrive be grown in below or when being exposed on the leaf that does not need plant on surface, soil (fixed after each, last is all over the field operation) with the least possible contacting of the blade of sensitive crop.
According to preventing and treating purpose, season, target crop and growth phase, the amount of application of active compound I is 0.001-3.0, preferred 0.01-1.0kg/ha.
In order to enlarge action spectrum and to reach synergistic effect, the 6-aryl of replacement-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2,4-triazine I and many other weedicide or growth regulating-activity compound, and can use jointly with it.Suitable blending ingredients is for example 1; 2; the 4-thiadiazole; 1; 3; the 4-thiadiazole; acid amides; phosphoramidic acid and its derivative; the aminotriazole class; phenyl amines; virtue oxygen/assorted fragrant oxygen paraffinic acid and its derivative; phenylformic acid and its derivative; the benzothiadiazine ketone; 2-(4-hetaroylpyrazol/aroyl)-1; the hydroresorcinol class; the heteroaryl aryl ketones; Bian isoxazoline ketone; between-the CF3-phenyl derivatives; carbamate; quinoline carboxylic acid and its derivative; chloroacetanilide; hexanaphthene-1; the 3-derovatives; diazine; Tripon and its derivative; Dihydrobenzofuranes; dihydrofuran-3-ketone; dinitroaniline; the dinitrobenzene phenols; diphenyl ether; dipyridyl; halogenated carboxylic acid class and its derivative; urea; 3-phenyl uracils class; imidazoles; imidazolone type; N-phenyl-3; 4; 5,6-tetrahydric phthalimide class oxadiazole class; oxyethane; phenol; aryloxy-and heteroaryloxy phenoxy propionic acid ester class; phenylacetic acid and its derivative; 2-phenylpropionic acid and its derivative; pyrazoles; phenyl pyrazoles; pyridazine class; pyridine carboxylic acid and its derivative; pyrimidine ether; sulfonamides; sulfonylurea; triazines; Triazinone; triazolineone; triazole carboxyl acylamide and uracil.
In addition, chemical compounds I separately or with other combinations of herbicides and with other crop protection agents for example the medicament of sterilant or controlling plant pathogenic fungi or bacterium mix that to use also may be useful.With as having additional nutrients and trace element supplement is not enough and the miscibility mineral salt solution that adds also is favourable.The oil of plant-less toxicity and dense finish also can add.
Preparation embodiment:
1. phenyl glyoxalic acid derivative
Embodiment 1
2-(4-chloro-2-fluoro-5-p-methoxy-phenyl)-2-oxo ethyl acetate
All operations all carries out under anhydrous and N2 shielding gas condition.
20-25 ℃, the tetrahydrofuran solution of the isopropylmagnesium chloride (0.4mol) of 200ml 2 volumetric molar concentrations is dropwise joined in the solution of 5-bromo-2-chloro-4-fluoroanisole in the 350ml tetrahydrofuran (THF) of 95.8g (0.4mol).After the adding, continue to stir the mixture 20 minutes (at the most! ).Down this solution is dropwise joined in the solution of 64.2g (0.44mol) diethyl oxalate in the 300ml tetrahydrofuran (THF) in (50) ℃ then.Stop cryostat and gained suspension stirred spending the night.Under the ice bath cooling, 200ml water and 200ml 10% strength hydrochloric acid are dropwise added continuously then.Water also concentrates with the saturated organic phase of separating then of salt, dried over sodium sulfate.Crude product silica gel chromatography purifying (moving phase hexanaphthene/t-butyl methyl ether=100: 5).Output: 66.2g (white crystals); Fusing point: 42-45 ℃.
Embodiment 2
2-(4-chloro-2-fluoro-5-p-methoxy-phenyl)-2-oxo acetate
75.9g (0.291mol) 2-(4-chloro-2-fluoro-5-p-methoxy-phenyl)-2-oxo ethyl acetate was refluxed 7 hours in the strong HBr aqueous solution of 1.0l47%.After the cooling, reaction mixture is poured in the 3l frozen water.Mixture t-butyl methyl ether extracting three times subsequently, each 300ml.The organic phase that merges washes twice again with less water, and dried over sodium sulfate concentrates then.Output: 63.1g (white crystals); Fusing point: 134-137 ℃.
Embodiment 3
2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-oxo acetate
63.1g 2-(4-chloro-2-fluoro-5-p-methoxy-phenyl)-2-oxo acetate was refluxed 8 hours in the strong HBr heated in water solution of 1.0l47% at reflux temperature, continue to stir 3 days in room temperature then.Then mixture is poured in the 3l frozen water.Products therefrom ethyl acetate extracting three times, each 300ml.The organic phase that merges also concentrates with a small amount of washing twice, dried over sodium sulfate.Output: 53.5g (white crystals); Fusing point: 137-139 ℃.
Embodiment 4
(R)-2-[4-chloro-2-fluoro-5-(1-methoxycarbonyl oxyethyl group) phenyl]-2-oxo acetate washes 1.8g 80% sodium hydride mineral oil suspension with dimethyl formamide, so that sodium hydride dissociates out from mineral oil, be suspended in the dimethyl formamide of 20ml and under 5-10 ℃, dropwise add 6.0g 2-(4-chloro-2-fluoro-5-the hydroxyphenyl)-solution of 2-oxo acetate in the 30ml dimethyl formamide.The mixture stirring was also dropwise added 4.0g (S)-2-methyl chloropropionate in 15 minutes.Then mixture was stirred 7 hours and stirred 12 hours at 20 ℃ for 65 ℃.Pour into then in the frozen water of 200ml, also use ethyl acetate extracting three times, each 50ml with the dilute hydrochloric acid acidifying.The organic phase that merges is at every turn with 20ml washing twice, and dried over sodium sulfate also concentrates.Output: 7.4g light yellow oil; 1H NMR (270 MHz, (CD 3) 2SO): δ [ppm]=1.59 (d, 3H), 3.72 (s, 3H), 5.27 (q, 1H), 7.43 (d, 1H), 7.78 (d, 1H).
Embodiment 5
2-(4-chloro-3-tolyl)-2-oxo ethyl acetate
Use 2-chloro-5-toluene iodide, by the method acquisition useful products of embodiment 1.1H?NMR(270MHz,CDCl 3):δ[ppm]=1.42(t,3H),2.44(s,3H),4.46(q,2H),7.48(d,1H),7.80(dd,1H),7.90(d,1H)。
Embodiment 6
2-(4-chloro-3-tolyl)-2-oxo acetate
10g (44mmol) 2-(4-chloro-3-the tolyl)-solution of 2-oxo ethyl acetate in 390ml acetate and 98ml 2M hydrochloric acid was heated 4 hours for 80 ℃.Enriched mixture then.Residuum mixes with water and uses the ethyl acetate extracting.The extract that merges washes with water, dried over sodium sulfate and final concentrating.Output: 7.5g; Fusing point: 85-86 ℃.
Embodiment 7
2-(4-chloro-2-fluorophenyl)-2-oxo acetate
Use 2-(4-chloro-2-fluorophenyl)-2-oxo ethyl acetate, by the method acquisition useful products of embodiment 2. 1H?NMR(270?MHz,CDCl 3):δ[ppm]=6.48(s,1H),7.20-7.35(m,2H),8.02(t,1H)。
Embodiment 8
2-(4-chloro-3-nitrophenyl)-2-oxo ethyl acetate
In being cooled to 131.3g (0.62mol) 2-(4-the chloro-phenyl-)-solution of 2-oxo ethyl acetate in the 350ml vitriol oil of 0 ℃, dropwise add 38.9g (0.62mol) nitric acid, then mixture was stirred 5 hours.Subsequently solution is poured in the frozen water.Use the t-butyl methyl ether extract product then.The extract that merges washes with water, dried over mgso and last concentrating.Output: 148.6g; MS (m/z): 258[M+H] +
Embodiment 9
2-(4-methoxyl group-3-nitrophenyl)-2-oxo acetate
In ice bath, 75g (0.29mol) 2-(4-chloro-3-the nitrophenyl)-solution of 2-oxo ethyl acetate in 150ml methyl alcohol is joined in the solution of 35g (0.87mol) sodium hydroxide in 250ml methyl alcohol.Then reaction mixture was stirred 16 hours, then use the dilute hydrochloric acid acidifying.Distill most of low-boiling point material subsequently.Residuum mixes with water.Use ethyl acetate to obtain useful products from the extracting of gained aqueous phase.Washing organic phase, dried over sodium sulfate and last concentrating.Output: 69.5g; MS[m/z]: 226 (M+H) +
2. thiosemicarbazide
Embodiment 10:
2,4-dimethylamino thiocarbamide
Under the room temperature 9.5g methylhydrazine dropwise is added in the solution of 15.0g Trapex in the anhydrous t-butyl methyl ether of 200ml.Mixture stirred spends the night, remove solvent and with residuum with ethanol/water (2: 1) recrystallization.Output: 21.5g (white crystals); Fusing point: 139-140 ℃.
1H NMR (270 MHz, (CD 3) 2Among the SO): δ [ppm]=2.87 (d, 3H), 3.43 (s, 3H), 4.80 (s, 2H), 8.13 (br., 1H).
Embodiment 11
2-(4-chloro-phenyl-)-4-methylamino thiocarbamide
The solution of 2.08g (29mmol) Trapex in the 20ml t-butyl methyl ether is added 4.08g (29mmol) 4-chlorophenyl hydrazine in the solution of 60ml acetate.Mixture was stirred 16 hours and concentrated.Residuum mixes with water.Use methylene dichloride to go out useful products from the aqueous phase extracting.The organic phase that merges washes with water, dried over sodium sulfate and last concentrating.Crude product silica gel chromatography (moving phase: cyclohexane/ethyl acetate) purifying.Output: behind the first cut 0.6g1-(4-chloro-phenyl-)-4-methylamino thiocarbamide, obtain 2.5g purpose product.Fusing point: 114-115 ℃.
3.1,2, the 4-triazine
Embodiment 12
6-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
With 19.7g (90mmol) 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-oxo acetate and 10.7g (90mmol) 2, the solution of 4-dimethylamino thiocarbamide in 50ml acetate was 85-90 ℃ of heating 7 hours.Dilute with water reaction mixture subsequently, isolate useful solid product after, washing is also dry.Output: 15.4g; Fusing point: 166-167 ℃.
Embodiment 13
(R)-2-[2-chloro-4-fluoro-5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl) phenoxy group]-methyl propionate (the No. I is a.167)
With 15g (50mmol) 6-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the suspension of 4-triazine and 17.2g (124mmol) salt of wormwood in the 100ml dimethyl formamide and 6.7g (55mmol) (S)-the 2-methyl chloropropionate mixes.During heating was fallen back in 4 hours under 60-65 ℃ with mixture.Solid product water that gained is useful and sherwood oil are washed and are dry.Output: 18.8g; Fusing point: 123-124 ℃.
Embodiment 14
(R)-2-(5-(4-amino-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2-chloro-4-fluorophenoxy) methyl propionate
With 6.9g (23mmol) (R)-2-(4-chloro-2-fluoro-5-[(1-methoxycarbonyl) oxyethyl group] phenyl)-2-oxo acetate and 2.4g (23mmol) thiocarbohydrazide stirred 6 hours at 85 ℃.Subsequently mixture is concentrated and residuum is added small amounts of ether, filter and obtain useful solid product and use the toluene recrystallization.Output: 3.9g; Fusing point: 176-178 ℃.
Embodiment 15
(R)-2-[5-(4-amino-2-methyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2-chloro-4-fluorophenoxy]-methyl propionate (the No. I is g.167)
3.4g (11mmol) 6.9g (R)-2-[5-(4-amino-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2-chloro-4-fluorophenoxy]-methyl propionate and the suspension of 2.2g (16mmol) salt of wormwood in the 50ml tetrahydrofuran (THF) mixes with 1.5g (11mmol) methyl-iodide.Reaction mixture was stirred 3 days and concentrated.Residuum mixes with ethyl acetate.The gained organic phase washes with water, dried over sodium sulfate and last concentrating.Crude product silica gel chromatography purifying (moving phase: cyclohexane/ethyl acetate=1: 1).Output: at first obtain 0.6g purpose product (fusing point: 89-91 ℃),, obtain 2.3g (R)-2-[5-(4-amino-3-methylthio group-5-oxo-4,5-dihydro-1,2,4 triazines-6-yl)-2-chloro-4-fluorophenoxy then as second cut]-methyl propionate.
Embodiment 16
6-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-oxo-2-phenyl-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-oxo acetate and 4-methyl-2-phenyl amino thiocarbamide, by the useful purpose product of method acquisition of embodiment 12.Fusing point: 168-169 ℃.
Embodiment 17
6-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-(4-chloro-phenyl-)-4-methyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-oxo acetate and 2-(4-chloro-phenyl-)-4-methylamino thiocarbamide, by the useful purpose product of method acquisition of embodiment 12.Fusing point: 215-216 ℃.
Embodiment 18
(R)-2-(2-chloro-4-fluoro-5-(4-methyl-5-oxo-2-phenyl-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-phenoxy group) methyl propionate
Use 6-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-oxo-2-phenyl-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine is by the useful purpose product of method acquisition of embodiment 13.MS[m/z]：449(M) +。
Embodiment 19
(R)-2-(2-chloro-5-[2-(4-chloro-phenyl-)-4-methyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl]-4-fluoro-phenoxy group) methyl propionate
Use 6-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-(4-chloro-phenyl-)-4-methyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine is by the useful purpose product of method acquisition of embodiment 13.Fusing point: 80-84 ℃.
Embodiment 20
4-amino-6-(4-chloro-phenyl-)-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4 triazines
Use 2-(4-chloro-phenyl-)-2-oxo acetate, by the useful purpose product of method acquisition of embodiment 14.Fusing point: 273-274 ℃.
Embodiment 21
4-amino-6-(4-chloro-phenyl-)-2-methyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
(No.Ⅰi.1)
Use 4-amino-6-(4-chloro-phenyl-)-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine is by the useful purpose product of method acquisition of embodiment 15.Fusing point: 157-158 ℃.
Embodiment 22
6-(4-chloro-phenyl-)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
(No.Ⅰc.1)
89.4g (0.42mol) 2-(4-chloro-phenyl-)-2-oxo ethyl acetate, 50.1g (0.42mol) 2, the solution of 4-dimethylamino thiocarbamide and 17.6g (0.44mol) sodium hydroxide in 300ml ethanolic soln and 800ml water was reflux temperature heating 7 hours.Subsequently mixture is used the dilute hydrochloric acid acidifying, leached after the solid crude product and usefulness silica gel chromatography purifying (moving phase: cyclohexane/ethyl acetate=9: 1).Output: 21.1g; Fusing point: 130-131 ℃.
Embodiment 23
6-(4-chloro-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine (the No. I is c.168)
Use 6-(4-chloro-phenyl-)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine is by the useful purpose product of method acquisition of embodiment 8.Fusing point: 184-185 ℃.
Embodiment 24
6-(3-amino-4-chloro-phenyl-)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine (the No. I is c.170)
The suspension of 39.7g (0.71mol) iron powder in 200ml methyl alcohol and 870ml acetate is heated to reflux temperature, in batches with 55.5g (0.18mol) 6-(4-chloro-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine is mixed.Subsequently mixture was stirred 3 hours, after this leach solid.Filtrate concentrates.The gained residuum mixes with water.Use ethyl acetate to obtain useful product then from the aqueous phase extracting.Organic phase concentrates with dried over sodium sulfate is also last.Crude product silica gel chromatography (moving phase: cyclohexane/ethyl acetate=2: 1) purifying.Output: 12.8g; MS[m/z]: 282 (M) +
Embodiment 25
2-chloro-3-[2-chloro-5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl) phenyl]-methyl propionate (the No. I is c.154)
With solution and 12.8g (0.15mol) methyl acrylate of 2.3g (22mmol) nitrite tert-butyl in the 50ml acetonitrile, 2.5g (19mmol) cupric chloride (II) and 4.2g (15mmol) 6-(3-amino-4-chloro-phenyl-)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4 triazines are mixed.Mixture was stirred 16 hours and concentrated.Gained crude product silica gel chromatography (moving phase: cyclohexane/ethyl acetate=10: 1) purifying.Output: 0.6g; MS[m/z]: 387 (M) +
Embodiment 26
6-[3-two (methyl sulphonyl) amino-4-chloro-phenyl-]-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine (the No. I is c.180)
4.3g (15mmol) 6-(3-amino-4-chloro-phenyl-)-2,4 dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the solution of 4-triazine in the 100ml methylene dichloride mixes with 3.4g (35mmol) triethylamine and 3.6g (32mmol) methylsulfonyl chloride, then this mixture is stirred 4 hours.Reaction mixture washes with water subsequently, and dried over sodium sulfate also concentrates.Output: quantitative; Fusing point: 225-235 ℃.
Embodiment 27
2,4-dimethyl-6-[3-(methyl sulphonyl) amino-4-chloro-phenyl-]-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine (the No. I is c.172)
The sodium methylate of catalytic amount is added 4.5g (10mmol) 6-[3-two (methyl sulphonyls)-amino-4-chloro-phenyl-]-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2 is in the solution of 4-triazine in 200ml methyl alcohol.The mixture stirring was concentrated in 3 hours then.Residual residuum mixes with water.Use ethyl acetate to go out useful product from the extracting of gained aqueous phase.Organic phase washes with water, dried over sodium sulfate and last concentrating.Crude product is by the methylene dichloride recrystallization purifying.Output: 1.7g; MS[m/z]: 360 (M) +
Embodiment 28
6-(4-chloro-3-tolyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine (the No. I is c.2)
Use 2-(4-chloro-3-tolyl)-2-oxo acetate, by the useful purpose product of method acquisition of embodiment 12.Fusing point: 133-135 ℃.
Embodiment 29
6-(4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 2-(4-hydroxyphenyl)-2-oxo acetate, by the useful purpose product of method acquisition of embodiment 12.Fusing point: 214-215 ℃.
Embodiment 30
2,4-dimethyl-5-oxo-3-sulfo--6-[4-(4-trifluoromethoxy benzyloxy) phenyl]-2,3,4,5-tetrahydrochysene-1,2,4-triazine
0.62g (18mmol) suspension and 4g (16mmol) 6-(4-hydroxyphenyl)-2 of sodium hydride (60%) in dimethyl formamide, 4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the solution of 4-triazine in the 20ml dimethyl formamide mixes.Reaction mixture was stirred 10 minutes, add 4.5g (18mmol) 4-trifluoro-methoxybenzyl bromine then.Subsequently mixture was stirred 3 days.The gained mixture mixes with frozen water.Leach the gained solid crude product and pass through silica gel chromatography (moving phase: cyclohexane/ethyl acetate=3: 1) purifying.Output: 5.1g; Fusing point: 134-135 ℃.
Embodiment 31
6-[4-(4-chlorine benzyloxy) phenyl]-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 4-chlorine bromotoluene, by the useful purpose product of method acquisition of embodiment 30.Fusing point: 162-164 ℃.
Embodiment 32
6-(3-chloro-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 2-(3-chloro-4-hydroxyphenyl)-2-oxo acetate, by the useful purpose product of method acquisition of embodiment 12. 1H?NMR(270?MHz,SO(CD 3) 2):δ[ppm]=3.60(s,3H),3.98(s,3H),7.06(d,1H),7.85(dd,1H),8.03(d,1H),10.84(s,1H)。
Embodiment 33
(R)-and 2-[3-chloro-4-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl) phenoxy group] methyl propionate
Use 6-(3-chloro-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine obtains useful purpose product by embodiment 13 methods.Fusing point: 67 ℃.
Embodiment 34
6-(3-chloro-4 alkynes propoxy-phenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 6-(3-chloro-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine and propargyl bromide obtain useful purpose product by embodiment 13 methods.Fusing point: 172 ℃.
Embodiment 35
6-[3-chloro-4-(2-propylene-1-base oxygen base) phenyl]-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 6-(3-chloro-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine and allyl bromide 98 obtain useful purpose product by embodiment 13 methods.Fusing point: 175 ℃.
Embodiment 36
6-(3-chloro-4-isopropyl phenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 6-(3-chloro-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine and isopropyl iodide obtain useful purpose product by embodiment 13 methods.Fusing point: 81 ℃.
Embodiment 37
6-(4-methoxyl group-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 2-(4-methoxyl group-3-nitrophenyl)-2-oxo acetate, obtain useful purpose product by embodiment 12 methods.Fusing point: 218-219 ℃.
Embodiment 38
6-(4-hydroxyl-3 nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
53g (0.17mol) 6-(4-methoxyl group-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the solution of 4-triazine and 21.9g (0.51mol) lithium chloride in the 610ml dimethyl formamide was reflux temperature heating 7 hours.Subsequently mixture is poured into and also used the dilute hydrochloric acid acidifying in the frozen water.Leach the solid product of useful acquisition then, water and ethyl acetate are washed and final drying subsequently.Output: 45.5g; Fusing point: 219-221 ℃.
Embodiment 39
6-(3-amino-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine
Use 6-(4-hydroxyl-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine obtains useful purpose product by embodiment 24 methods.Fusing point: 202-208 ℃.
Embodiment 40
6-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2H-1,4-benzoxazine-3 (4H)-ketone (the No. I is p.1)
8.2g (31mmol) 6-(3-amino-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the 4-triazine, 4.6g (40mmol) chloroacetyl chloride and the suspension of 6.5g (47mmol) salt of wormwood in the 70ml dimethyl formamide begin to stir 3 hours in stirring at room 85 ℃ of stirrings then in 2.5 hours.Subsequently reaction mixture is mixed with frozen water.Leach the gained solid crude product and use silica gel chromatography (moving phase: cyclohexane/ethyl acetate=2: 1) purifying.Output: 4g. 1H NMR (400MHz, SO (CD 3) 2In): δ [ppm]=3.60 (s, 3H), 3.95 (s, 3H), 4.65 (s, 2H), 7.03 (d, 1H), 7.60 (dd, 1H), 7.64 (d, 1H), 10.86 (s, 1H).
Embodiment 41
6-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-4-(2-propylene-1-yl)-2H-1,4-benzoxazine-3 (4H)-ketone (the No. I is p.10)
Use 6-(4-hydroxyl-3-nitrophenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine and allyl bromide 98 obtain useful purpose product by embodiment 30 methods.Fusing point: 169-170 ℃.
Embodiment 42
5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2 (3H)-benzoxazolones (the No. I s.1)
8.2g (31mmol) 6-(3-amino-4-hydroxyphenyl)-2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2, the solution of 4-triazine and 7.6g (46mmol) phosphinylidyne diimidazole in the 70ml tetrahydrofuran (THF) was reflux temperature heating 4 hours.Enriched mixture subsequently.Stir residuum with dilute hydrochloric acid and leach solid crude product then.Output: 5.6g; Fusing point: 242 ℃.
Embodiment 43
5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-3-propargyl-2 (3H)-benzoxazolones (the No. I s.17)
Use 5-(2,4-dimethyl-5-oxo-3 sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2 (3H)-benzoxazolones and propargyl bromide, by the useful purpose product of method acquisition of embodiment 30. 1H?NMR(400?MHz,SO(CD 3) 2):δ[ppm]=3.50(t,1H),3.63(s,3H),4.01(s,3H),4.78(d,2H),7.51(d,1H),7.88(dd,1H),7.93(d,1H)。
Embodiment 44
(R)-and 2-[5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl)-2 (3H)-benzoxazolones-3-yl] methyl propionate (the No. I is s.64)
Use 5-(2,4-dimethyl-5-oxo-3-sulfo--2,3,4,5-tetrahydrochysene-1,2,4-triazine-6-yl) 2 (3H) ,-benzoxazolones and (S)-2-methyl chloropropionate, obtain useful purpose product by embodiment 30 methods.Fusing point: 149-150 ℃.
Application Example
6-aryl-3-sulfo--5-(sulfo-) oxo-2,3,4 that replaces, 5-tetrahydrochysene-1,2, the weeding activity of 4-triazine I experimental results show that by following surface green house:
The culture vessel that uses is to contain the plastic flowerpot of about 3.0% soil ulmin as the loamy sand of substrate fertilizer.The seed of test plants is sowed respectively by kind.
In the seedling pre-treatment, after the sowing, suspension or emulsive activeconstituents are directly used by the nozzle of good distribution in water.Be stratification and growth, water container carefully, cover to plant with transparent plastic cloth then and begin to take root.Unless this covering influences active ingredient conversely, it can make the germination of test plants homogeneous.
For the seedling aftertreatment, according to plant habit, at first grow to 3-15cm when high in test plants, suspend in the water again or the emulsive active ingredient is handled.For this purpose, test plants can directly be sowed and be grown in the identical container, or a few days ago is transplanted in the test container handling being cultured to respectively to emerge then.The amount of application of seedling aftertreatment is 31.2,15.6,7.8 and 3.9g/haa.s. (active substance).
According to kind, plant remains on 10-25 ℃ or 20-35 ℃.Testing period extends to 2-4 week.
During this period, look after plant, and assessed the reaction of each processing.
Grade scale according to 0-100 is assessed.100 refer to not germination of plant, or over-ground part damages fully at least, and 0 refers to not injury or growth normally.
The plant of using in greenhouse test is following kind:
The Latin formal name used at school Chinese name
Abutilon?theophrasti Piemarker
Echinochloa?crus-galli Barnyard grass
Galium?aparine Tender Catchweed Bedstraw Herb
Polygonum?persicaria Lady's thumb
Setaria?faberii Herba Setariae viridis
Triticum?aestivum Wheat
Veronica?species Veronica
When using behind the seedling, compound N o. I g.167 amount of application be 31.2 and during 15.6g/ha a.s. to Tender Catchweed Bedstraw Herb, lady's thumb, the weeding activity that Herba Setariae viridis and veronica are done well.
When using behind the seedling, compound N o. I a.167 amount of application only is 7.8 and during 3.9g/ha a.s., and to the piemarker in the summer wheat crop, barnyard grass and Herba Setariae viridis have showed very high selection weeding activity.On the contrary, disclosed control compounds A does not show selectivity among the JP-A 10/053,508 under same amount of application
Figure A9980768700701
Application Example (dehydration/disleave activity)
The test plants of using is the cotton seedling with 4 leaves (not having cotyledon) (the atmospheric moisture 50-70% that is grown under the greenhouse experiment; 27/20 ℃ of temperature day/night).
The aqueous compositions of active compound I (in spraying liquid, adds the oxyalkylated fatty alcohol Plurafac of 0.15% weight RLF 700 1)) handle the cotton seedling blade to moistening fully.The usage quantity of water is 1000l/ha (conversion).After 13 days, blade quantity and disleave degree that statistics has come off are represented with %.
Untreated control plant is not observed disleave.
1) the low foam nonionogenic tenside of BASF AG production

Claims (13)

1. the 6-of the replacement of formula I aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5 tetrahydrochysenes-1,2, applicable salt on the agricultural of 4-triazine and chemical compounds I;
Figure A9980768700021
Wherein: X is oxygen or sulphur; R 1Be C 1-C 6-alkyl, C 1-C 6-haloalkyl or as need to have one to three substituent phenyl, each substituting group is selected from following group: nitro, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl and C 1-C 6-alkoxyl group;
R 2Be amino, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 2-C 6-alkenyl, C 3-C 6-alkynyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, C 1-C 6-alkylthio-C 1-C 6-alkyl or C 3-C 6-cycloalkyl;
Ar is general formula Ar 1-Ar 4The aryl that replaces:
R 3It is hydrogen or halogen;
R 4Be cyano group, halogen ,-CS-NH 2, hydroxyl, C 1-C 6-alkoxyl group, C 1-C 6-halogenated alkoxy, C 2-C 4-alkenyloxy, C 2-C 4-alkynyloxy group, (C 1-C 4-alkoxyl group) carbonyl-C 1-C 4-alkoxyl group or do not replace or phenyl ring on have one to three substituent benzyloxy, each substituting group is selected from following group: halogen, C 1-C 6-alkyl, C 1-C 6-alkoxyl group and C 1-C 6-halogenated alkoxy;
R 5Be hydrogen, nitro, cyano group, amino, hydroxylamino, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, formyl radical ,-CH=N-OR 9,-CH (OR 10) 2,
Figure A9980768700031
R 11, R 12,-CO-Cl ,-CO-OR 13,-CO-OR 14-CO-OR 13,-CO-N (R 15)-R 16,-CO-OR 14-CO-N (R 15)-R 16,-CH 2-CH (R 17)-CO-OR 13,-CH=C (R 17)-CO-OR 13,-OCH (CH 3)-COOH ,-OCH (CH 3)-COOCH 3,-N (R 20)-R 19,-SO 2-Cl ,-SO 2-N (R 15)-R 16,-CO-NH-OR 15, -CO-N (R 22)-OR 15
Or and R 4Represent chain O-CH together 2-CH 2-O wherein can have cyano group, halogen, C 1-C 6-alkyl, oxo, hydroxycarbonyl group or (C 1-C 6-alkoxyl group) carbonyl substituted base;
R 6Be hydrogen, hydroxyl, C 1-C 6-alkyl, C 1-C 6-alkoxyl group, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkoxyl group-(C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group)-carbonyl-C 1-C 6-alkoxyl group, C 3-C 6-alkenyl, C 3-C 6-alkynyl, C 3-C 6-alkenyloxy or C 3-C 6-alkynyloxy group;
R 7Be hydrogen, C 1-C 6-alkyl or (C 1-C 6-alkoxyl group) carbonyl;
R 8Be hydrogen, hydroxyl, sulfydryl, halogen, C 1-C 6-alkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, hydroxycarbonyl group, hydroxycarbonyl group-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl, C 1-C 6-alkoxyl group, C 1-C 6-alkoxy-C 1-C 6-alkoxyl group, C 3-C 6-alkenyloxy, C 3-C 6-alkynyloxy group, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkoxyl group, C 1-C 6-alkylthio, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkylthio, C 3-C 6-alkenyl thio, C 3-C 6-alkynes sulfenyl ,-N (R 23)-R 24,-CH 2-CH (R 17)-CO-OR 13Or-CH=C (R 17)-CO-OR 13
N is 0 or 1;
Y is oxygen or sulphur;
Z is an oxygen, sulphur or-N (R 23)-;
R 9Be hydrogen, C 1-C 6-alkyl or (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl;
R 10Be C 1-C 6-alkyl;
R 11, R 12On 4 or 5 of dioxolane, be hydrogen independently of one another, C 1-C 6-alkyl, hydroxycarbonyl group or (C 1-C 6-alkoxyl group) carbonyl;
R 13Be hydrogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkoxy-C 1-C 6-alkyl, cyano group-C 1-C 6-alkyl, C 3-C 7-cycloalkyl, 3-oxetanyl, C 3-C 6-alkenyl, C 3-C 6-halogenated alkenyl or C 3-C 6-alkynyl;
R 14Be C 1-C 6-alkylidene group;
R 15Be hydrogen or C 1-C 6-alkyl;
R 16Be hydrogen, C 1-C 6-alkyl, C 3-C 7-cycloalkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 1-C 6-alkyl sulphonyl or and R 15Representative can be interrupted by oxo bridge and/or by (C together 1-C 6-alkoxyl group) tetramethylene of carbonyl substituted or five methene chain;
R 17Be hydrogen, halogen or C 1-C 6-alkyl;
R 19Be C 1-C 6-alkyl sulphonyl;
R 20Be hydrogen, C 1-C 6-alkyl or C 1-C 6-alkyl sulphonyl;
R 21, R 22Be C independently of one another 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 3-C 6-alkenyl, C 3-C 6-alkynyl or benzyl;
R 23Be hydrogen or C 1-C 6-alkyl;
R 24Be hydrogen, C 1-C 6-alkyl, (C 1-C 6-alkoxyl group) carbonyl-C 1-C 6-alkyl, C 3-C 6-alkenyl, C 3-C 6-alkynyl or benzyl.
2. the 6-of the replacement of the formula I of claim 1 aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, the 4-triazine, wherein:
X is an oxygen;
R 1And R 2It is methyl;
Ar is aryl Ar 1
R 4Be chlorine;
R 5Be-OCH (CH 3)-COOH or-OCH (CH 3)-CO-OCH 3
3. the 6-of the replacement of the formula I of claim 1 aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, the 4-triazine, wherein:
X is an oxygen;
R 1And R 2It is methyl;
Ar is aryl Ar 1
R 3It is fluorine;
R 4Be chlorine;
R 5Be-OCH (CH 3)-CO-OCH 3
4. the 6-of the replacement of the formula I of claim 1 aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2, the 4-triazine, wherein:
X is an oxygen;
R 1And R 2It is methyl;
Ar is aryl Ar 1
R 3And R 4Be chlorine;
R 5Be-OCH (CH 3)-CO-OCH 3
5. the 6-of the replacement of claim 1 aryl-3-sulfo--5-(sulfo-) oxo-2,3,4,5 tetrahydrochysenes-1,2,4-triazine and agricultural thereof go up the purposes of applicable salt as weedicide or plant dehydration/defoliating agent.
6. herbicidal composition, 6-aryl-3-sulfo--5-(sulfo-) oxo-2 of replacement that comprises at least a claim 1 of herbicidally effective amount, 3,4,5-tetrahydrochysene-1,2,4 triazines or its agricultural go up applicable salt, and at least a inert liq and/or solid carrier and at least a if necessary tensio-active agent.
7. plant dehydration and/or defoliant composition, 6-aryl-3-sulfo--5-(sulfo-) oxo-2 that comprises the replacement of the dehydration and/or at least a claim 1 of disleave significant quantity, 3,4,5 tetrahydrochysenes-1,2,4-triazine or its agricultural go up applicable salt, and at least a inert liq and/or solid carrier and at least a if necessary tensio-active agent.
8. weeding activity preparation of compositions method, it comprises the 6-aryl of the replacement of at least a claim 1 of herbicidally effective amount-3-sulfo--5-(sulfo-) oxo-2,3,4,5 tetrahydrochysenes-1,2,4-triazine or its agricultural goes up applicable salt and at least a inert liq and/or solid carrier and at least a if necessary tensio-active agent and mixes.
9. the dehydration and/or the preparation method of defoliant composition, it comprises 6-aryl-3-sulfo--5-(sulfo-) oxo-2 with the replacement of at least a claim 1 of dehydration and/or disleave significant quantity, 3,4,5-tetrahydrochysene-1,2,4-triazine or its agricultural goes up applicable salt and at least a inert liq and/or solid carrier and at least a if necessary tensio-active agent and mixes.
10. control does not need the method for plant-growth, and it comprises the 6-aryl of the replacement of at least a claim 1 of herbicidally effective amount-3-sulfo--5-(sulfo-) oxo-2,3,4,5-tetrahydrochysene-1,2,4-triazine or its agricultural go up applicable salt and are administered to plant, on its location or the seed.
11. the method for plant dehydration and/or disleave, it comprises 6-aryl-3-sulfo--5-(sulfo-) oxo-2,3 with the replacement of at least a claim 1 of dehydration and/or disleave significant quantity, 4,5-tetrahydrochysene-1,2,4-triazine or its agricultural go up applicable salt and are administered on the plant.
12. the method for claim 11, wherein the plant of Chu Liing is a cotton.
13. the phenyl glyoxalic acid derivative of the replacement of structural formula Va '
Wherein:
R 3It is hydrogen or halogen;
R 25Be hydrogen or C 1-C 6-alkyl;
R 18 'Be hydrogen, methyl or-CH (CH 3)-COOCH 3
CN99807687A 1998-05-20 1999-05-19 Substituted 6-aryl-3-thioxo-5-(thi) oxo-2,3,4,5-tetrahydro-1,2,4-triazines Pending CN1306523A (en)

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CN103497193B (en) * 2013-09-25 2015-09-02 武汉大学 There is derivative and the synthetic method thereof of 1,2,4-triazine skeleton structure

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CN105517995B (en) * 2013-07-08 2018-10-02 拜耳作物科学股份公司 The aromatic yl sulfide and aryl oxysulfide derivative that hexa-atomic C-N as pesticide is bonded

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