CN1299351A - Optically active substituted 2,4-diamino-1,3,5-triazines as herbicides - Google Patents

Optically active substituted 2,4-diamino-1,3,5-triazines as herbicides Download PDF

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CN1299351A
CN1299351A CN99805764A CN99805764A CN1299351A CN 1299351 A CN1299351 A CN 1299351A CN 99805764 A CN99805764 A CN 99805764A CN 99805764 A CN99805764 A CN 99805764A CN 1299351 A CN1299351 A CN 1299351A
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group
ethyl
methyl
formula
replacement
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H·J·里贝尔
R·基尔斯滕
S·莱尔
K·沃伊格特
M·多林格
M·W·德鲁斯
I·维特乔洛夫斯基
渡边幸喜
五岛敏男
R·A·迈尔斯
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Bayer AG
Bayer CropScience KK
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Bayer AG
Nihon Bayer Agrochem KK
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
    • 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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to novel optically active substituted 2,4-diamino-1,3,5-triazines of formula (I), wherein Ar represents optionally substituted aryl, aryl being a carbocyclical or heterocyclical, monocyclical or bicyclical aromatic grouping from the following series: phenyl, naphthyl, pyridinyl, pyrimidinyl, furyl, benzofuryl, thienyl and benzothienyl and the possible substituents being selected from the following series: cyano, nitro, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-halogenalkylthio, C1-C4-alkylsulfinyl, C1-C4-halogenalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-halogenalkylsulfonyl, C1-C4-alkylamino and C1-C4-alkoxy-carbonyl; R<1> represents alkyl with 1 to 4 carbon atoms, R<2> represents alkyl optionally substituted with hydroxy, cyano, halogen or C1-C4-alkoxy, with 1 to 4 carbon atoms, and R<3> represents alkyl optionally substituted with cyano, halogen or C1-C4-alkoxy, with 2 to 4 carbon atoms, the substituents on the carbon atom to which R<1> is bonded being arranged in R-configuration. The invention also relates to production for the said compound and to their use as herbicides.

Description

2 of optically active replacement, 4-diamino-1,3,5-triazines class weedicide
The present invention relates to 2 of novel optically active replacement, 4-diamino-1,3,5-triazines class, its preparation method and intermediate and as herbicide applications.
The aminotriazine class that replaces in (patent) document existing report (referring to, US3816419, US3932167, EP-273328, EP-411153/WO90/09378, WO97/00254, WO97/08156).Yet these compounds do not obtain any special importance so far as yet.
Therefore, the invention provides new logical formula I optically active replacement 2,4-diamino-1,3,5-triazines class,
Figure 9980576400061
Wherein Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape, monocycle or bicyclic aromatic group: phenyl, naphthyl, pyridyl, pyrimidyl, furyl, benzofuryl, thienyl and benzothienyl, and their possible substituting group is selected from following: cyano group, nitro, formamyl, thiocarbamoyl, halogen, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio, C 1-C 4-halogenated alkylthio, C 1-C 4-alkyl sulphinyl, C 1-C 4-haloalkyl sulfinyl, C 1-C 4-alkyl sulphonyl, C 1-C 4-halogenated alkyl sulfonyl, C 1-C 4-alkylamino and C 1-C 4-alkoxy carbonyl, R 1Expression has the alkyl of 1 to 4 carbon atom, R 2Expression optional by hydroxyl-, cyano group-, halogen-or C 1-C 4The alkyl with 1 to 4 carbon atom of-alkoxyl group-replacement, R 3Expression optional by cyano group-, halogen-or C 1-C 4The alkyl with 2 to 4 carbon atoms of-alkoxyl group-replacement,
R wherein 1Substituting group on the carbon atom that connects is the R configuration.
2 of optically active replacement of new logical formula I, 4-diaminostilbene, 3, the following acquisition of 5-triazines: if suit in the presence of the reaction auxiliary, and if suit in the presence of thinner, make 2 of optically active replacement of leading to formula II, 4-diamino-1,3,5-triazines class
Figure 9980576400071
Wherein Ar, R 1And R 1As above definition is with the acylation reaction of logical formula III
Figure 9980576400072
R wherein 2As above definition and X represent halogen or group-O-CO-R 3
2 of optically active replacement of new logical formula I, 4-diamino-1,3,5-triazines class have by force and weeding activity selectively.
In its definition, hydrocarbon chain is as alkyl-comprise and heteroatomic combination such as alkoxyl group-be straight or branched under each situation.
Halogen ordinary representation fluorine, chlorine, bromine or iodine are preferably represented fluorine, chlorine or bromine, particularly represent fluorine or chlorine.
The present invention preferably provides the formula I compound; wherein Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape; monocycle or bicyclic aromatic group: phenyl; naphthyl; pyridyl; pyrimidyl; furyl; benzofuryl; thienyl and benzothienyl; and their possible substituting group is selected from following: cyano group; nitro; formamyl; thiocarbamoyl; halogen; methyl; ethyl; just or sec.-propyl; just-; different-; secondary-or the tertiary butyl; trifluoromethyl; methoxyl group; oxyethyl group; just or isopropoxy; difluoro-methoxy; trifluoromethoxy; the chlorine difluoro-methoxy; fluorine dichloro methoxyl group; methylthio group; ethylmercapto group; just or the iprotiazem base; the difluoro methylthio group; trifluoromethylthio; chlorine difluoro methylthio group; fluorine dichloromethane sulfenyl; methylsulfinyl; the ethyl sulfinyl; the trifluoromethyl sulphinyl base; methyl sulphonyl; ethylsulfonyl; trifluoromethyl sulfonyl; dimethylamino; diethylamino; methoxycarbonyl and ethoxy carbonyl, R 1Expression methyl, ethyl, just or sec.-propyl, just-, the exclusive OR sec-butyl, R 2Represent each optional by hydroxyl-, cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just or sec.-propyl, just-, the exclusive OR sec-butyl, and R 3Represent each optional by cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or the ethyl of oxyethyl group-replacements, just or sec.-propyl, just-, different-, the second month in a season-or the tertiary butyl, wherein R 1Substituting group on the carbon atom that connects is the R configuration.
In particular, the present invention relates to the formula I compound; wherein Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape; monocycle or bicyclic aromatic group: phenyl; naphthyl; pyridyl; pyrimidyl; furyl; benzofuryl; thienyl and benzothienyl; and their possible substituting group is selected from following: cyano group; nitro; formamyl; thiocarbamoyl; fluorine; chlorine; bromine; methyl; ethyl; trifluoromethyl; methoxyl group; oxyethyl group; difluoro-methoxy; trifluoromethoxy; methylthio group; ethylmercapto group; the difluoro methylthio group; trifluoromethylthio; methylsulfinyl; the ethyl sulfinyl; the trifluoromethyl sulphinyl base; methyl sulphonyl; ethylsulfonyl; trifluoromethyl sulfonyl; dimethylamino; diethylamino; methoxycarbonyl and ethoxy carbonyl, R 1Expression methyl, ethyl, just or sec.-propyl, R 2Represent each optional by hydroxyl-, cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or methyl of oxyethyl group-replacement, ethyl, just or sec.-propyl, and R 3Represent each optional by cyano group-, the ethyl of fluoro-, chloro-or methoxyl group-replacement, just or sec.-propyl,
R wherein 1Substituting group on the carbon atom that connects is the R configuration.
General or preferred group definition above-mentioned is suitable for the formula I end product, and correspondingly, also is suitable for starting raw material or intermediate required under each preparation situation.These group definition can mutually combine as required,, comprise the combination between preferable range above-mentioned that is.
The particularly preferred example grouping of the logical formula I compound of the present invention is listed in hereinafter.Group 1
Figure 9980576400091
Wherein, R 2Has for example following meanings: methyl, ethyl, just or sec.-propyl, just-, different-, secondary-or the tertiary butyl, 1-hydroxyl-ethyl, cyano methyl, 1-cyano group-ethyl, 2-cyano group-ethyl, 1-cyano group-1-methyl-ethyl, methyl fluoride, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, the chlorine methyl fluoride, the chlorine brooethyl, chlorodifluoramethyl-, the fluorine dichloromethyl, bromine difluoro methyl, trichloromethyl, 1-fluoro-ethyl, 2-fluoro-ethyl, 1-chloro-ethyl, 2-chloro-ethyl, 1-chloro-1-fluoro-ethyl, 1-fluoro-propyl group, 2-fluoro-propyl group, 3-fluoro-propyl group, 1-fluoro-1-methyl-ethyl, 2-fluoro-1-methyl-ethyl, 1-chloro-1-methyl-ethyl, 1-fluoro-1-methyl-propyl group, 1-chloro-1-ethyl-propyl group, 1-fluoro-1-ethyl-propyl group, 1-chloro-1-ethyl-propyl group, 1-fluoro-2-methyl-propyl group, 1-chloro-2-methyl-propyl group, 1-chloro-propyl group, 2-chloro-propyl group, 3-chloro-propyl group, 1-chloro-1-methyl-ethyl, 2-chloro-1-methyl-ethyl, 1,1-two fluoro ethyls, 1,2-two fluoro-ethyls, 1,1-two chloro-ethyls, 2,2,2-three fluoro-ethyls, 1,2,2,2-tetrafluoro ethyl, the perfluor ethyl, 1,1-two fluoro-propyl group, 1,1-two chloro-propyl group, perfluoro propyl, 1-fluoro-butyl, 1-chloro-butyl, methoxymethyl, 1,1-dimethoxy-methyl, 1-methoxyl group-ethyl, 2-methoxyl group-ethyl, 1,1-dimethoxy-ethyl, ethoxyl methyl, the 1-ethoxyethyl group, the 2-ethoxyethyl group, 2-methoxyl group-1-methyl-ethyl, 2-methoxyl group-1-ethyl-ethyl, 2-oxyethyl group-1-methyl-ethyl or 2-oxyethyl group-1-ethyl-ethyl.Group 2
Figure 9980576400092
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 3
Figure 9980576400101
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 4
Figure 9980576400102
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 5
Figure 9980576400103
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 6 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 7 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 8
Figure 9980576400113
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 9 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 10 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 11
Figure 9980576400123
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 12
Figure 9980576400131
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 13
Figure 9980576400132
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 14 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 15 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 16 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 17
Figure 9980576400143
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 18 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 19
Figure 9980576400152
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 20 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 21
Figure 9980576400161
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 22
Figure 9980576400162
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 23
Figure 9980576400163
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 24
Figure 9980576400171
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 25 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 26 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 27
Figure 9980576400181
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 28 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 29
Figure 9980576400183
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 30
Figure 9980576400191
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 31 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 32
Figure 9980576400193
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 33 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 34 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 35
Figure 9980576400203
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 36
Figure 9980576400211
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 37 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 38 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 39 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 40
Figure 9980576400222
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 41
Figure 9980576400223
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 42
Figure 9980576400231
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 43
Figure 9980576400232
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 44
Figure 9980576400233
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 45 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 46 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 47
Figure 9980576400243
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 48
Figure 9980576400251
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 49
Figure 9980576400252
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 50
Figure 9980576400253
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 51
Figure 9980576400261
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 52
Figure 9980576400262
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 53
Figure 9980576400263
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 54 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 55 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 56 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 57 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 58
Figure 9980576400282
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 59
Figure 9980576400283
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 60
Figure 9980576400291
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 61 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 62
Figure 9980576400293
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 63 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 64
Figure 9980576400302
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 65
Figure 9980576400303
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 66
Figure 9980576400311
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 67 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 68 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 69 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 70
Figure 9980576400322
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 71 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 72
Figure 9980576400331
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 73 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 74 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 75
Figure 9980576400341
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 76
Figure 9980576400342
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 77
Figure 9980576400343
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 78
Figure 9980576400351
Wherein, R 2Have and for example above organize the implication that provides in 1.Group 79 Wherein, R 2Have and for example above organize the implication that provides in 1.Group 80 Wherein, R 2Have and for example above organize the implication that provides in 1.
Use that for example (R)-2-amino-4-(1-methyl-3-phenyl propyl amino)-6-(1-fluoro ethyl)-1,3,5-triazines and propionyl chloride are as starting raw material, the reaction path of the inventive method can be illustrated by following reaction formula:
Formula II be provided at the preparation formula I compound of the present invention the inventive method in be used as starting raw material optically active replacement 2, the General Definition of 4-diamino-1,3,5-triazines class.In formula II, Ar, R 1And R 2Each preferably or particularly has Ar, the R that had mentioned already in the relevant description of formula I compound of the present invention above 1And R 2Preferred or particularly preferred implication.
Logical formula II starting raw material is not open in the literature so far; As novel substance, the theme of their formation patent applications more early (referring to, DE-19641693/LeA31975, DE-19641694/LeA31994).
2 of optically active replacement of logical formula II, the 4-diaminostilbene, 3, the following acquisition of 5-triazines: exist down if (a) be adapted at reacting auxiliary such as sodium methylate, if with suit at thinner for example in the presence of the methyl alcohol, under the temperature between 0 ℃ to 100 ℃, make the biguanides of optically active replacement of logical formula IV
Figure 9980576400362
Wherein Ar and R 1As above definition ,-and/or the sour affixture of logical formula IV compound, for example, corresponding hydrochloride-react with the alxoxycarbonyl compounds of general formula (V) (referring to, DE19641693/LeA31975; DE19641694/LeA31994; Also referring to, WO97/08156; Preparation embodiment)
R 2-CO-OR (V) is R wherein 2As above definition and R represent alkyl.
Need are open in the literature so far as the biguanides of optically active replacement of the logical formula IV of precursor; As novel substance, the theme of their formation patent applications more early (referring to, DE-19641693/LeA31975, DE-19641694/LeA31994).
The following acquisition of biguanides of optically active replacement of logical formula IV: if be adapted at reacting under auxiliary such as the hydrogenchloride existence, if with suit at thinner n-decane and 1 for example, 2-two chloro-benzene exist down, under the temperature between 100 ℃ to 200 ℃, make the amino compounds of optically active replacement of logical formula VI
Figure 9980576400371
Wherein Ar and R 1As above definition ,-and/or the sour affixture of logical formula VI compound, for example, corresponding hydrochloride-with the dicyanodiamide reaction of general formula (VII) (referring to, EP492615 prepares embodiment)
Figure 9980576400372
To need amino compounds as optically active replacement of the logical formula VI of this purpose precursor be known and/or can be with known method preparation itself (referring to, DE3426919; DE4000610; DE4332738; EP320898; EP443606; Tetrahedron:Asymmetry5 (1994), 817-820; Tetradedron Lett.29 (1988), 223-224; The same, 36 (1995), 3917-3920).
Logical formula III provides in the methods of the invention, and another is used as the General Definition of the acylating agent of starting raw material.In formula III, R preferably or particularly has the preferred or particularly preferred implication of the R that had mentioned already in the relevant description of formula I compound of the present invention above; X preferably represents fluorine, chlorine, bromine, acetoxyl group, propionyloxy, just or isobutyl acyloxy, particularly chlorine, acetoxyl group or propionyloxy.
The formula III starting raw material is the synthetic known organic chemicals of.
If suitable, the inventive method of the logical formula I compound of preparation is to use the reaction auxiliary to carry out.Inorganic or organic bases or acid acceptor that the reaction auxiliary that is fit to is normally conventional.These materials preferably include the acetate of basic metal or alkaline-earth metal, amide, carbonate, supercarbonate, hydride, oxyhydroxide or alkoxide, as sodium acetate, potassium acetate or lime acetate, lithamide, ammonification sodium, ammonification potassium or ammonification calcium, yellow soda ash, salt of wormwood or lime carbonate, sodium bicarbonate, saleratus or Calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride KH or hydrolith, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, methyl alcohol, ethanol, just or Virahol, just-, different-, secondary-or the sodium salt or the methyl alcohol of the trimethyl carbinol, ethanol, just-or Virahol, just-, different-, secondary-or the sylvite of the trimethyl carbinol; Also has alkaline organic nitrogen compound in addition, as, Trimethylamine 99, triethylamine, tripropyl amine, Tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclo-hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, accelerine, N, N-dimethyl-benzyl amine, pyridine, the 2-methyl-, the 3-methyl-, the 4-methyl-, 2, the 4-dimethyl-, 2, the 6-dimethyl-, 3, the 4-dimethyl-and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidines, 1,4-diazabicylo [2,2,2]-octane (DABCO), 1,5-diazabicylo [4,3,0]-ninth of the ten Heavenly Stems-5-alkene (DBN) or 1,8-diazabicylo [5,4,0]-11-7-alkene (DBU).
If suitable, the inventive method of the logical formula I compound of preparation is to use thinner to carry out.The thinner that is fit to is inert organic solvents particularly.These materials comprise the optional halogenated hydrocarbon of aliphatics particularly, alicyclic or aromatics, such as, for example gasoline, benzene,toluene,xylene, chlorobenzene, dichlorobenzene, sherwood oil, hexane, hexanaphthene, methylene dichloride, chloroform, tetracol phenixin; Ethers is as ether, Di Iso Propyl Ether, diox, tetrahydrofuran (THF) or glycol dimethyl ether or ethylene glycol diethyl ether; Ketone is as acetone, butanone or mibk; Nitrile is as acetonitrile, propionitrile or butyronitrile; Amides, as N, dinethylformamide, N,N-dimethylacetamide, N-methyl-formylaniline, N-Methyl pyrrolidone or HMPA; The ester class is as methyl acetate or ethyl acetate; The sulfoxide class is as dimethyl sulfoxide (DMSO); Alcohols, as methyl alcohol, ethanol, just-or Virahol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, the mixture of they and water, or pure water.
When carrying out the inventive method, temperature of reaction can be carried out in wide relatively scope.Usually, reaction is at 0 ℃ to 200 ℃, preferably carries out under the temperature between 10 ℃ to 150 ℃.
Method of the present invention is normally carried out under normal pressure.Yet, the inventive method also can the pressurization or the decompression under---normally 0.1 the crust to 10 the crust between pressure under carry out.
When carrying out the inventive method, adopt the roughly starting raw material of equimolar amount usually.One of yet, also can excessive relative to the earth employing reactive component.Reaction is randomly carried out in the presence of the reaction auxiliary normally randomly in the thinner that is fit to, and reaction mixture stirring several hours under required temperature usually.Aftertreatment be with ordinary method carry out (referring to, the preparation embodiment).
Active compound of the present invention can be used as defoliating agent, siccative, kill the cane agent and in particular as weedicide.So-called weeds with regard to it the most in the broadest sense, are interpreted as being grown in all plants in the place that should not grow.Material of the present invention is as steriland herbicide or selective herbicide depends on used amount basically.
The compounds of this invention can relevant use with for example following plants:
The broadleaf weed of following dependent of dead military hero: mustard belongs to, the grass of walking alone belongs to, Bedstraw, Stellaria, Matricaria, Anthemis, Achyranthes, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, japanese bearbind belongs to, sweet potato genus, Polygonum, Daubentonia, Ambrosia, Cirsium, bristlethistle, sonchus L, Solanum Han Lepidium, Herba Clinopodii Polycephali belongs to, Vandellia, lamium, Veronica, abutilon, the thorn Rumex, Datura, Viola, the weasel hemp nettle belongs to, papaver, bachelor's-button, Trifolium, Ranunculus and Dandelion.
The dicotyledonous crops of following dependent of dead military hero: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, linum, sweet potato genus, vetch, Nicotiana, tomato genus, Arachis, Btassica, Lactuca, Cucumis and Cucurbita.
The monocotyledon weed of following dependent of dead military hero: Echinochloa, setaria, Panicum, knotgrass, ladder forage spp, annual bluegrass genus, festuca, yard grass genus, Brachiaria, lolium, Brome, Avena, Cyperus, jowar genus, Agropyron, Cynodon, Monochoria, genus fimbristylis, arrowhead genus, Eleocharis, sugarcane grass genus, Paspalum, ischaemum, cusp Pittosporum, talon eria, Agrostis, amur foxtail genus and wind grass belong to.
The monocot crops of following dependent of dead military hero: Oryza, Zea, Triticum, Hordeum, Avena, Secale, jowar genus, Panicum, saccharum, Ananas, Asparagus and allium.
Yet the application of active compound of the present invention never is limited to these genus, and also can extend to other plant in an identical manner.
Depend on compound concentrations, the compound natural disposition controlling weeds that is suitable for going out, for example industrial region and railway line, and the road and the square that have or do not have the plantation woods.Equally, compound can be used for preventing and treating the weeds of perennial crop, for example the weeds in forest, the decoration woods, orchard, vineyard, citrus woods, nut garden, any of several broadleaf plants plantation, cafetal, tea place, rubber plantation, oil palm plantation, cocoa plantation, mushy fruit woods and hops field, grassland, stadium and the pasture.And The compounds of this invention can also be used for optionally preventing and treating the weeds of annual crop.
Formula I compound of the present invention is particularly suitable for optionally preventing and treating unifacial leaf and broadleaf weed in unifacial leaf or the dicotyledonous crops in two kinds of modes before the bud and behind the bud.
Active compound can change into conventional preparation, as solution, emulsion, wettable powder, suspension agent, pulvis, the agent of dusting, paste, soluble powder, granule, suspended emulsion agent, with the natural or synthetic materials of active compound dipping, and wrap in micro-fine capsule in the polymkeric substance.
These preparations can be produced in a known manner, for example, with active compound with expand agent, i.e. liquid and/or mixes, and optional use tensio-active agent, i.e. emulsifying agent and/or dispersion agent and/or pore forming material with solid carrier.
Using water as under the situation that expands agent, also can make solubility promoter with organic solvent.The liquid solvent that is fit to mainly contains: aromatic substance, and as dimethylbenzene, toluene or alkylnaphthalene, chloro aromatic substance or chlorinated aliphatic hydrocarbon are as chlorinated benzene class, polyvinyl chloride-base or methylene dichloride, aliphatic hydrocrbon, as hexanaphthene or paraffin, for example petroleum cuts, mineral and vegetables oil, alcohols, as butanols or ethylene glycol with and ether and ester, ketone is as acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or pimelinketone, intensive polar solvent, as dimethyl formamide or dimethyl sulfoxide (DMSO), and water.
The solid carrier that is fit to is: for example ammonium salt and ground natural mineral matter, as kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite, with ground synthetic mineral matter, as high dispersive silicon-dioxide, alumina and silicate, the solid carrier that is suitable for granule has: for example crush and fractionated natural mineral matter such as calcite, marble, float stone, sepiolite and rhombspar, and the synthetic particle of organic and inorganic powder and following organic particle: wood sawdust, coconut husk, corn cob and tobacco stem; The emulsifying agent and/or the pore forming material that are fit to are: for example nonionic and anionic emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example, the alkaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate and albumin hydrolysate; The dispersion agent that is fit to is: for example, and lignin sulfite waste liquor and methylcellulose gum.
Can use the natural and synthetic polymer of tackiness agent such as carboxymethyl cellulose and powdery, particle or latex form in the preparation, as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipid, as kephalin and Yelkin TTS, and synthetic phospholipid.Other tackiness agent can be mineral oil and vegetables oil.
Also may use tinting material, as mineral dye, for example ferric oxide, titanium oxide and Prussian blue, and organic dye are as the salt of alizarine dyestuff, azoic dyestuff and metal phthalocyanine dyestuff and micronutrient element such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Usually contain 0.1 to 95% active compound by weight in the preparation, preferred 0.5 to 90%.
Be controlling weeds, active compound of the present invention, its former state or with its dosage form, the mixture that also can be used as with known weedicide uses, and can be whole preparation or the mixed thing of bucket.
The possible common component of mixture is known weedicide, for example, acetochlor, acifluorfen (sodium salt), aclonifen, alachlor, alloxydim (sodium salt), ametryn, amidochlor, the acyl ethyl methyl, anilofos, the spirit of sulphur grass, atrazine, azafenidin, the tetrazolium ethyl methyl, benazolin, benfuresate, benzyl ethyl methyl (methyl esters), bentazone, benzofenap, benzoylpropethyl (ethyl ester), two alanyl phosphorus, bifenox, two careless ethers, bromobutide, bromofenoxim, bromoxynil, Butachlor technical 92, butroxydim, the fourth grass is special, cafenstrole, caloxydim, carbetamide, carfentrazone (methyl), chlomethoxyfen, weed eradication is flat, pyrazon, chlorimuron (ethyl ester), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin, ether is yellow grand, clethodim, alkynes oxalic acid clomazone, clomeprop, difluoro pyridine acid, clopyrasulfuron (methyl), cloransulam (methyl), cumyluror, cyanazine, the weed eradication spy, AC322140, cycloxydim, cyhalofop-butyl, 2,4-drips, 2, the 4-Embutox, 2,4-drips propionic acid, desmedipham, di_allate, dicamba 98, diclofop-methyl (methyl esters), diclosulam, acetyl alachlor, difenzoquat, diflufenican, diflufenzopyr, azoles is grand, dimepiperate, dimethachlor, isoamyl is clean, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, dithiopyr, Diuron Tech, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, Ethanetsulfuron (methyl esters), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid oxazole diclofop-methyl ethyl ester, wheat straw volt (isopropyl ester), the wheat straw volt (isopropyl ester-L), wheat straw volt (methyl esters), the pyridine ethyl methyl, fluazifop (butyl ester), flumetsulam, methylarsonic acid, flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofenethyl, amine grass azoles, flupropacil, flurpyrsulfuron (methyl, sodium), flurenol, the fluorine butanone, fluroxypyr, flurprimidol, flurtamone, fluthiacet (methyl), fluthiamid, Fomesafen, Glufosinate (ammonium salt), glyphosate (isopropyl ammonium salt), halosafen, pyrrole fluorine chlorine standing grain spirit (ethoxy ethyl ester), pyrrole fluorine chlorine standing grain spirit (P-methyl esters), hexazinone, miaow grass ester (methyl esters), imazamethapyr, imazamox, the weed eradication cigarette, the weed eradication quinoline, Imazethapyr, imidazoles is yellow grand, ioxynil, isopropalin, isoproturon Yi Evil swells Yi Evil acyl grass, isoxaflutole Evil grass ether, lactofen, lenacil, methoxydiuron, 2 first, 4 chlorine, Vi par, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (α-) metolachlor, metosulam, metoxuron, the piperazine humulone, metsulfuron-methyl, Hydram, monolinuron, naproanilide, napropamide, neburon, nicoculsfuron, norflurazon, orbencarb, oryzalin, oxadiargyl Evil humulone, oxasulfuron, oxaziclomefone, oxyfluorfen, Paraquat, pelargonicacid, pendimethalin, pentoxazone, phenmedipham, piperophos, the third careless amine, Fluoropyrimidinesulfuron (methyl esters), prometryn, propachlor, Stam F-34 Evil oxalic acid, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen (ethyl), pyrazolate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (methyl), pyrithiobacsodium, quinclorac, quinmerac, the weed eradication quinone, quizalofop (ethyl ester), quizalofop (tetrahydrochysene chaff ester), the sulfone ethyl methyl, sethoxydim, simazine, simetryn, sulcitrione, sulfentrazone, the first ethyl methyl, sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthylazine, terbutryn, P DimethenamidP, thiafluamide, thrizopyr, thidiazimin, thifensulfuron methyl, thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl, TRICLOPYR ACID, tridiphane, trifluralin and fluorine amine are yellow grand.
It also can be mixture with other known activity compound such as mycocide, sterilant, miticide, nematocides, bird repellent, plant food and soil conditioner.
Active compound can with itself, with its preparation or by further dilution and the type of service of preparation uses of warp, as direct available solution, suspension, emulsion, pulvis, paste and granule.They use with ordinary method, for example pour, spraying, atomizing or spread fertilizer over the fields or the like.
Active compound of the present invention can be used before or after plant germination.They also can mix in the soil prior to seeding.
The amount of used active compound can change in quite wide scope.Consumption depends on required effect basically.Usually, usage quantity is between per hectare soil surface-area restrains to 10 kilograms with 1, and preferred per hectare 5 grams are to 5 kilograms.
The preparation of active compound of the present invention and use can be referring to the following example.
Preparation embodiment:
Embodiment 1
Figure 9980576400431
With 3.4g (11mmol) (R)-2-amino-4-(1-methyl-3-phenyl-propyl group amino)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazines and 10g (77mmol) propionic anhydride stirred 2 hours down at 120 ℃.Behind cool to room temperature (about 20 ℃), mixture is diluted with 200ml water, and at room temperature stirred 15 hours.Decant water, resistates digests with methylene dichloride, washes with water, with dried over sodium sulfate and filtration.Under pump vacuum, solvent is carefully distilled from filtrate.
Thus as armorphous resistates obtain 3.0g (theoretical value 76%) (R)-2-propionyl amino-4-(1-methyl-3-phenyl-propyl group amino)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazines.
[α] D 20=-5.0°。
Be similar to preparation embodiment 1, and the general description of method produced according to the present invention can be prepared the formula I compound of for example listing in the table 1 hereinafter.
Figure 9980576400432
Table 1: formula I examples for compounds
Figure 9980576400441
The formula II starting raw material:
Embodiment (II-1)
With 18g (66mmol) (R)-1-(1-methyl-3-phenyl-propyl group)-biguanide hydrochloride, 3.6g (66mmol) sodium methylate and 50ml methanol mixture stirred 30 minutes down in room temperature (about 20 ℃), mix with 8.2g (61mmol) 2-fluoro-ethyl isobutyrate subsequently.Reaction mixture at room temperature stirred 18 hours afterwards, was diluted to three times of its original volume with methylene dichloride, washed with water, with dried over sodium sulfate and filter.From filtrate, under pump vacuum, carefully solvent is distilled.
Thus as the amorphous resistates provide 6.5g (theoretical value 34%) (R)-2-amino-4-(1-methyl-3-phenyl-propyl group-amino)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazines.
The formula IV starting raw material
Preparation embodiment (IV-1)
Figure 9980576400452
With 17.9g (96mmol) (R)-1-methyl-3-phenyl-propylamin hydrochloride and 8.1g (96mmol) dicyanodiamide are in 160 ℃ (interior temperature) heating three hours down.After the melts of gained under described temperature with about 100ml 1,2-two chloro-benzene and-at room temperature afterwards-mix with the ether of about same amount.The crystalline product of gained separates by suction filtration.
Provide thus 18.0g (theoretical value 70%) (R)-1-(1-methyl-3-phenyl-propyl group)-biguanide hydrochloride.
Application Example
Embodiment A
Test before the bud
Solvent: 5 parts of weight acetones
Emulsifying agent: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
The seed of test plant is broadcast in the common soil, and after 24 hours, soil is by a certain amount of required active agent preparations of unit surface spray application.Select the concentration of spraying fluid, the specified quantitative of required compound is used with the amount of 1,000 premium on currency/hectare.
After three weeks, the degree of damage of plant and the developmental phase of untreated control are compared, infringement % is made in range estimation.
The implication of numerical value is as follows:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, for example, preparation embodiment 1 pair of weeds demonstrate strong activity, and they some can be tolerated well by crop such as Sunflower Receptacle.Table A-1: the active compound (g ai./ha) of the following preparation embodiment application dosage amur foxtail Herba Setariae Viridis piemarker amaranth mustard of test before the greenhouse bud *
Figure 9980576400471
(1) 1,000 100 100 95 100 100 *Gram number/hectare the Table A-2 of activeconstituents: the active compound (g ai./ha) of the following preparation embodiment application dosage Sunflower Receptacle barnyard grass lamb's-quarters eggplant of test before the greenhouse bud (1) 250 10 100 100 100
Embodiment B
Test behind the bud
Solvent: 5 parts of weight acetones
Emulsifying agent: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
Press a certain amount of required active agent preparations of unit surface spray application to plant height 5-15 centimetre test plant.Select the concentration of spraying fluid, the specified quantitative of required compound is used with the amount of 1,000 premium on currency/hectare.
After three weeks, the degree of damage of plant is compared with untreated control, make infringement %.
The implication of numerical value is as follows:
0%=do not have effect (be untreated identical)
The 100%=completely destroy
In this test, for example, 1 pair of weeds of preparation embodiment demonstrate strong activity.Table B: the active compound (g ai./ha) of the following preparation embodiment application dosage amur foxtail wild avena sativa Herba Setariae Viridis piemarker amaranth mustard Siberian cocklebur of test behind the greenhouse bud (1) 1,000 90 90 90 95 100 100 90

Claims (9)

1. 2 of the replacement of the active optical of logical formula I, 4-diamino-1,3,5-triazines class
Figure 9980576400021
Wherein Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape, monocycle or bicyclic aromatic group: phenyl, naphthyl, pyridyl, pyrimidyl, furyl, benzofuryl, thienyl and benzothienyl, and their possible substituting group is selected from following: cyano group, nitro, formamyl, thiocarbamoyl, halogen, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy, C 1-C 4-alkylthio, C 1-C 4-halogenated alkylthio, C 1-C 4-alkyl sulphinyl, C 1-C 4-haloalkyl sulfinyl, C 1-C 4-alkyl sulphonyl, C 1-C 4-halogenated alkyl sulfonyl, C 1-C 4-alkylamino and C 1-C 4-alkoxy carbonyl, R 1Expression has the alkyl of 1 to 4 carbon atom, R 2Expression optional by hydroxyl-, cyano group-, halogen-or C 1-C 4The alkyl with 1 to 4 carbon atom of-alkoxyl group-replacement, R 3Expression optional by cyano group-, halogen-or C 1-C 4The alkyl with 2 to 4 carbon atoms of-alkoxyl group-replacement, wherein R 1Substituting group on the carbon atom that connects is the R configuration.
2. according to (I) compound of claim 1; it is characterized in that; Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape; monocycle or bicyclic aromatic group: phenyl; naphthyl; pyridyl; pyrimidyl; furyl; benzofuryl; thienyl and benzothienyl; and their possible substituting group is selected from following: cyano group; nitro; formamyl; thiocarbamoyl; halogen; methyl; ethyl; just or sec.-propyl; just-; different-; secondary-or the tertiary butyl; trifluoromethyl; methoxyl group; oxyethyl group; just or isopropoxy; difluoro-methoxy; trifluoromethoxy; the chlorine difluoro-methoxy; fluorine dichloro methoxyl group; methylthio group; ethylmercapto group; just or the iprotiazem base; the difluoro methylthio group; trifluoromethylthio; chlorine difluoro methylthio group; fluorine dichloromethane sulfenyl; methylsulfinyl; the ethyl sulfinyl; the trifluoromethyl sulphinyl base; methyl sulphonyl; ethylsulfonyl; trifluoromethyl sulfonyl; dimethylamino; diethylamino; methoxycarbonyl and ethoxy carbonyl, R 1Expression methyl, ethyl, just or sec.-propyl, just-, the exclusive OR sec-butyl, R 2Represent each optional by hydroxyl-, cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or the methyl of oxyethyl group-replacement, ethyl, just or sec.-propyl, just-, the exclusive OR sec-butyl, and R 3Represent each optional by cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or the ethyl of oxyethyl group-replacements, just or sec.-propyl, just-, different-, the second month in a season-or the tertiary butyl,
R wherein 1Substituting group on the carbon atom that connects is the R configuration.
3. according to the formula I compound of claim 1; it is characterized in that; Ar represents the following aryl that is selected from of optional replacement; wherein aryl is represented carbocyclic ring shape or heterocycle shape; monocycle or bicyclic aromatic group: phenyl; naphthyl; pyridyl; pyrimidyl; furyl; benzofuryl; thienyl and benzothienyl; and their possible substituting group is selected from following: cyano group; nitro; formamyl; thiocarbamoyl; fluorine; chlorine; bromine; methyl; ethyl; trifluoromethyl; methoxyl group; oxyethyl group; difluoro-methoxy; trifluoromethoxy; methylthio group; ethylmercapto group; the difluoro methylthio group; trifluoromethylthio; methylsulfinyl; the ethyl sulfinyl; the trifluoromethyl sulphinyl base; methyl sulphonyl; ethylsulfonyl; trifluoromethyl sulfonyl; dimethylamino; diethylamino; methoxycarbonyl and ethoxy carbonyl, R 1Expression methyl, ethyl, just or sec.-propyl, R 2Represent each optional by hydroxyl-, cyano group-, fluoro-, chloro-, bromo-, methoxyl group-or methyl of oxyethyl group-replacement, ethyl, just or sec.-propyl, and R 3Represent each optional by cyano group-, the ethyl of fluoro-, chloro-or methoxyl group-replacement, just or sec.-propyl, wherein R 1Substituting group on the carbon atom that connects is the R configuration.
4. according to (R)-2-propionyl amino-4-(1-methyl-3-phenyl propyl amino)-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazines of the formula (1) of claim 1
Figure 9980576400041
5. the method for formula I compound of preparation claim 1 is characterized in that, if suit in the presence of the reaction auxiliary, and if suit in the presence of thinner, make 2 of optically active replacement of leading to formula II, 4-diamino-1,3,5-triazines class Wherein Ar, R 1And R 2As defined in claim 1, with the acylation reaction of logical formula III
Figure 9980576400043
R wherein 3As above define in the claim 1 and X represents halogen or group-O-CO-R 3
6. herbicidal composition is characterized in that, they comprise the formula I compound of at least a claim 1.
7. the formula I compound of claim 1 is prevented and treated the application of undesired plant.
8. method of controlling weeds is characterized in that, the formula I compound effects that makes claim 1 is in weeds or its dried rhizome of rehmannia of dwelling.
9. prepare the method for herbicidal composition, it is characterized in that, with the formula I compound of claim with expand agent and/or tensio-active agent and mix.
CN99805764A 1998-03-05 1999-02-20 Optically active substituted 2,4-diamino-1,3,5-triazines as herbicides Pending CN1299351A (en)

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