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CN1294584A - Substituted aminoalkylidenamino triazines as herbicides - Google Patents

Substituted aminoalkylidenamino triazines as herbicides Download PDF

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Publication number
CN1294584A
CN1294584A CN99804348A CN99804348A CN1294584A CN 1294584 A CN1294584 A CN 1294584A CN 99804348 A CN99804348 A CN 99804348A CN 99804348 A CN99804348 A CN 99804348A CN 1294584 A CN1294584 A CN 1294584A
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group
alkyl
base
methyl
representative
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Inventor
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·维特肖洛夫斯基
渡边幸喜
城户佳织
五岛敏男
峰岸夏子
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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (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 substituted aminoalkylidenamino triazines of formula (I), wherein R<1> represents the grouping A-Z, wherein A represents optionally substituted straight-chain or branched alkane diyl, which contains oxygen, sulphur, imino (NH) or alkylimino either initially or finally or inside the akane diyl chain, and Z represents an optionally substituted monocyclic or bicyclic, carbocyclic or heterocyclic grouping such as phenyl, naphthyl, benzofuryl, dihydrobenzofuryl, pyridyl and thienyl, R<2> represents hydrogen, cyano, halogen or respectively and optionally substituted alkyl, alkoxy, alkyl carbonyl, alkoxy carbonyl, alkythio, alkyl sulfinyl, alkenyl, alkinyl or cycloalkyl, R<3> represents hydrogen or alkyl, R<4> represents hydrogen or alkyl and R<5> represents alkyl. The invention also relates to a method for the production and use thereof as herbicides.

Description

Be used as the aminoalkylidenamino triazines of the replacement of weedicide
The present invention relates to the aminoalkylidenamino triazines and preparation method thereof of new replacement and as the purposes of weedicide.
Having known from (patent) document has 2 of many replacements, 4-diamino compound in triazine class (referring to US 3816419, US 3932167, EP 191496, EP 273328, EP411153/WO 90/09378, WO 97/00254, WO 97/08156).But, do not find up to now what special importance these compounds have.
Therefore, the invention provides the aminoalkylidenamino triazines of the replacement of new logical formula I R wherein 1Represent group-A-Z, wherein the alkane 2 basis of substituted straight or branched is chosen in the A representative wantonly, this group is randomly in the beginning of alkane 2 basis, Sauerstoffatom is contained in ending or centre, sulphur atom, imino-(NH) or alkyl imino (N-alkyl), substituted monocycle or double-ring are chosen in representative wantonly with Z, carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl, cyclohexyl, phenyl, naphthyl, 1,2,3, the 4-tetralyl, the decahydro naphthyl, 1, the 2-indanyl, indenyl, furyl, benzofuryl, dihydro benzo furyl, thienyl, benzothienyl, the dihydrobenzo thienyl, isobenzofuran-base, the dihydroisobenzofuran base, isobenzo-thienyl, the dihydro isobenzo-thienyl, pyrryl, indyl, pseudoindoyl, indolinyl, iso-dihydro-indole-group, benzo dioxolyl (benzdioxolyl) oxazolyl benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl-, indazolyl oxadiazole base, thiadiazolyl group, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolines base and 2, the 3-phthalazinyl, R 2Represent hydrogen, cyano group, halogen, or the optional separately substituted alkyl of representative, alkoxyl group, alkyl-carbonyl, alkoxy carbonyl, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkenyl, alkynyl or cycloalkyl, R 3Represent hydrogen or alkyl, R 4Represent hydrogen or alkyl, and R 5Represent alkyl.
When, if suitably in the presence of thinner, when making the aminocompound reaction of replacement of the amino triazines of replacement of formula II and formula III, then obtain the aminoalkylidenamino triazines of the replacement of formula I
Figure 9980434800081
R wherein 1And R 2Have top definition,
Figure 9980434800082
R wherein 3, R 4And R 5Have top definition and R and represent alkyl.
The aminoalkylidenamino triazines of the new replacement of formula I has strong and weeding activity optionally.
On certain degree, the formula I compound also has fungicidal and insecticidal activity.
Formula I compound of the present invention can contain the carbon atom of asymmetric replacement, and in this case, they can exist with different enantiotopic (forms of R-and S-configuration) and diastereoisomeric form.The present invention had both related to various possible single enantiotopic or diastereoisomeric form of logical formula I compound, also related to the mixture of these isomeric compounds.
In described definition, hydrocarbon chain such as alkyl-comprise and heteroatoms bonded situation are as the situation in alkoxyl group or alkylthio-all be straight or branched in all cases.
Halogen typically refers to fluorine, chlorine, bromine or iodine, preferred fluorine, chlorine or bromine, particularly fluorine or chlorine.
The present invention preferably provides each group definition following formula I compound, wherein R 1Represent group-A-Z, wherein the A representative is optional by the alkane 2 basis with 1-6 carbon atom of the straight or branched of cyano group or halogen replacement, and this group randomly contains Sauerstoffatom, sulphur atom, imino-(NH) or C in beginning, ending or the centre of alkane 2 basis 1-4Alkyl imino; substituted monocycle or double-ring are chosen in representative wantonly with Z; carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl; cyclohexyl; phenyl; naphthyl; 1; 2; 3; the 4-tetralyl; the decahydro naphthyl; 1; the 2-indanyl; indenyl; furyl; benzofuryl; dihydro benzo furyl; thienyl; benzothienyl; the dihydrobenzo thienyl; isobenzofuran-base; the dihydroisobenzofuran base; isobenzo-thienyl; the dihydro isobenzo-thienyl; pyrryl; indyl; pseudoindoyl; indolinyl; iso-dihydro-indole-group; benzo dioxolyl oxazolyl benzoxazolyl; thiazolyl; benzothiazolyl; benzimidazolyl-; indazolyl oxadiazole base; thiadiazolyl group; pyrazolyl; pyridyl; pyrimidyl; pyrazinyl; pyridazinyl; quinolyl; isoquinolyl; quinoxalinyl; cinnolines base and 2; the 3-phthalazinyl; wherein, the possible substituting group of these groups is preferably selected from separately: hydroxyl; cyano group; nitro; halogen; optional separately by hydroxyl; alkyl that has 1-6 carbon atom separately or alkoxyl group that cyano group or halogen replace; choose the alkyl-carbonyl that has 1-6 carbon atom in each the comfortable alkyl that is replaced by halogen separately wantonly; alkoxy carbonyl; alkylthio; alkyl sulphinyl or alkyl sulphonyl; optional separately by hydroxyl; cyano group; nitro; halogen; C 1-4Alkyl, C 1-4Haloalkyl, C 1-4Alkoxyl group or C 1-4Phenyl that halogenated alkoxy replaces or phenoxy group and optional separately methylene-dioxy or the ethylenedioxy that is replaced by halogen, R 2Represent hydrogen, cyano group, halogen, representative is optional separately by hydroxyl, cyano group, nitro, halogen, C 1-4Alkoxyl group, C 1-4Alkylthio, C 1-4Alkyl sulphinyl or C 1-4The alkyl, alkoxyl group, alkyl-carbonyl, alkoxy carbonyl, alkylthio, alkyl sulphinyl or the alkyl sulphonyl that have 1-6 carbon atom in each comfortable alkyl that alkyl sulphonyl replaces; representative is optional separately by the alkenyl that has 2-6 carbon atom separately or the alkynyl of cyano group or halogen replacement, and perhaps representative is optional separately by cyano group, halogen or C 1-4The cycloalkyl that alkyl replaces with 3-6 carbon atom, R 3Represent hydrogen or have the alkyl of 1-6 carbon atom, R 4Represent hydrogen or have the alkyl of 1-6 carbon atom, and R 5Representative has the alkyl of 1-6 carbon atom.
In the preferred defined formula I compound of above-mentioned conduct, the following array of lay special stress on: (A) wherein A, R 2, R 3, R 4And R 5Have that top definition, Z representative is optional is separately got
The phenyl or naphthyl in generation and wherein possible substituting group be formula I chemical combination as defined above
Thing; (B) wherein A, R 2, R 3, R 4And R 5It is optional substituted to have top definition, Z representative
Heterocyclic radical and wherein possible substituting group be the formula I compound as defined above.
The formula I compound that The present invention be more particularly directed to be defined as follows, wherein R 1Represent group-A-Z, wherein the optional separately methylene radical (CH that is replaced by cyano group, fluorine or chlorine of A representative 2-), dimethylene (ethane-1,2-two bases ,-CH 2-CH 2-), ethylidene (ethane-1,1-two bases ,-CH (CH 3)-), trimethylene (propane-1,3-two bases ,-CH 2CH 2CH 2-), propylidene (propane-1,1-two bases ,-CH (C 2H 5)-), propane-2,3-two bases (CH (CH 3) CH 2-), 2-methyl-propane-1,3-two base (CH 2CH (CH 3) CH 2-), 3-oxa--propane-1,3-two base (CH 2CH 2O-), 2-oxa--propane-1,3-two base (CH 2OCH 2-), tetramethylene (butane-1,4-two bases ,-CH 2CH 2CH 2CH 2-), butane-2,4-two bases (CH (CH 3) CH 2CH 2-), butane-2,3-two bases (CH (CH 3) CH (CH 3)-), 3-methyl-butane-2,4-two bases (CH (CH 3) CH (CH 3) CH 2-), 4-oxa--butane-2,4-two bases (CH (CH 3) CH 2O-), pentane-3,5-two bases (CH (C 2H 5) CH 2CH 2-), 5-oxa--pentane-3,5-two bases (CH (C 2H 5) CH 2O-), 4-oxa--pentane-2,5-two bases (CH (CH 3) CH 2OCH 2-) or 5-oxa--hexane-3,6-two bases (CH (C 2H 5) CH 2OCH 2-); substituted monocycle or double-ring are chosen in representative wantonly with Z; carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl; cyclohexyl; phenyl; naphthyl; 1; 2; 3; the 4-tetralyl; the decahydro naphthyl; 1; the 2-indanyl; indenyl; furyl; benzofuryl; dihydro benzo furyl; thienyl; benzothienyl; the dihydrobenzo thienyl; isobenzofuran-base; the dihydroisobenzofuran base; isobenzo-thienyl; the dihydro isobenzo-thienyl; pyrryl; indyl; pseudoindoyl; indolinyl; iso-dihydro-indole-group; benzo dioxolyl oxazolyl benzoxazolyl; thiazolyl; benzothiazolyl; benzimidazolyl-; indazolyl oxadiazole base; thiadiazolyl group; pyrazolyl; pyridyl; pyrimidyl; pyrazinyl; pyridazinyl; quinolyl; isoquinolyl; quinoxalinyl; cinnolines base and 2; the 3-phthalazinyl; wherein; the possible substituting group of these groups is preferably selected from separately: hydroxyl; cyano group; nitro; fluorine; chlorine; bromine; optional separately by hydroxyl; cyano group; the methyl that fluorine or chlorine replaces; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; optional separately by the methyl carbonyl of fluorine and/or chlorine replacement; the ethyl carbonyl; just-or the sec.-propyl carbonyl; just-; different-; secondary-or tertiary butyl carbonyl; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; just-; different-; secondary-or tert-butoxycarbonyl; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; methyl sulphonyl or ethylsulfonyl; optional separately by hydroxyl; cyano group; nitro; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; trifluoromethyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; phenyl or phenoxy group that difluoro-methoxy or trifluoromethoxy replace; optional separately by the methylene-dioxy or the ethylenedioxy of fluorine and/or chlorine replacement, R 2Represent hydrogen; cyano group; fluorine; chlorine; bromine; representative is optional separately by hydroxyl; cyano group; nitro; fluorine; chlorine; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; methylsulfinyl; the ethyl sulfinyl; just-or different third sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the methyl that replaces of different third alkylsulfonyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; ethanoyl; propionyl; just-or different-butyryl radicals; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; methylthio group; ethylmercapto group; just-or the iprotiazem base; methylsulfinyl; the ethyl sulfinyl; just-or different third sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or different third alkylsulfonyl; representative is optional separately by cyano group; fluorine; the vinyl that chlorine or bromine replaces; propenyl; butenyl; ethynyl; proyl or butynyl; perhaps representative is optional separately by cyano group; fluorine; chlorine; bromine; the cyclopropyl that methyl or ethyl replace; cyclobutyl; cyclopentyl or cyclohexyl, R 3Represent hydrogen, methyl or ethyl, R 4Represent hydrogen, methyl, ethyl, just-or sec.-propyl, just-, the exclusive OR sec-butyl, and R 5Represent methylidene, ethyl, just-or sec.-propyl, just-, the exclusive OR sec-butyl.
Above-mentioned general or preferred definition is applicable to the end product of formula I and correspondingly is applicable to required raw material and the intermediate of preparation under every kind of situation.The definition of these groups can optionally mutually combine, and promptly comprises the combination between each given preferable range.
The logical formula I examples for compounds of the present invention is listed in following each group.Group 1
Figure 9980434800121
Wherein, R 2Has meaning for example given below: methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; methyl fluoride; difluoromethyl; trifluoromethyl; chloromethyl; dichloromethyl; the chlorine methyl fluoride; the chlorine brooethyl; chlorodifluoramethyl-; the fluorine dichloromethyl; bromine difluoro methyl; trichloromethyl; the 1-fluoro ethyl; the 2-fluoro ethyl; the 1-chloroethyl; the 2-chloroethyl; the 1-bromotrifluoromethane; 1-chloro-1-fluoro ethyl; the 1-fluoropropyl; the 2-fluoropropyl; the 3-fluoropropyl; the 1-chloropropyl; the 2-chloropropyl; the 3-chloropropyl; the 1-bromopropyl; 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-fluoro-2-methyl-propyl group; 1-chloro-2-methyl-propyl group; 2-chloro-1-methyl-propyl group; 1,1-two fluoro ethyls; 1,2-two fluoro ethyls; 1; the 1-Dichloroethyl; 2,2, the 2-trifluoroethyl; 1; 2,2,2-tetrafluoro ethyl; the perfluor ethyl; 1; 1-two fluoropropyls; 1,1-two chloropropyls; perfluoro propyl; 1-fluorine butyl; the 1-chlorobutyl; perfluoro butyl; the perfluor amyl group; perfluoro hexyl; the 1-hydroxyethyl; 1-hydroxyl-1-methylethyl; the 1-hydroxypropyl; methoxyl methyl; ethoxymethyl; dimethoxy-methyl; the 1-methoxy ethyl; the 2-methoxy ethyl; 1, the 1-dimethoxy-ethyl; the 1-ethoxyethyl group; the 2-ethoxyethyl group; 2; the 2-dimethoxy-ethyl; 2,2-diethoxy ethyl; 2-methoxyl group-1-methylethyl; 2-methoxyl group-1-ethyl diethyldithiocarbamate; 2-oxyethyl group-1-methylethyl; 2-oxyethyl group-1-ethyl diethyldithiocarbamate; 2, the 2-dimethoxy-methyl; methylthiomethyl; the ethylmercapto group methyl; the 1-methylthiomethyl; 2-methylmercaptoethyl; 1-ethylmercapto group ethyl; 2-ethylmercapto group ethyl; the methylsulfinyl methyl; ethyl sulfinyl methyl; the sulfonyloxy methyl ylmethyl; the ethylsulfonyl methyl; vinyl; the 1-chlorovinyl; the 2-chlorovinyl; 1-is fluoride-based; 2-is fluoride-based; the 1-bromo vinyl; the 2-bromo vinyl; 1; the 2-dichloroethylene; 1; 2-difluoroethylene base; 1, the 2-dibromo vinyl; 2, the 2-dichloroethylene; 2; 2-difluoroethylene base; 2; the 2-dibromo vinyl; 2-is fluoride-based for the 1-chloro-; 1-fluoro-2-chlorovinyl; 2-bromo-1-chlorovinyl; 2-bromo-2-chlorovinyl; 2-is fluoride-based for the 1-bromo-; 1-fluoro-2-bromo vinyl; 1-bromo-2-chlorovinyl; trichloro-vinyl; trifluoro vinyl; the tribromo-ethylene base; 1-fluoro-2, the 2-dichloroethylene; 1-bromo-2, the 2-dichloroethylene; 1-fluoro-2; the 2-dibromo vinyl; 1-chloro-2; 2-difluoroethylene base; 1-chloro-2, the 2-dibromo vinyl; 1-bromo-2,2-difluoroethylene base; 2-fluoro-1; the 2-dichloroethylene; 2-chloro-1; 2-difluoroethylene base; 2-bromo-1,2-difluoroethylene base; 2-bromo-1,2-dichloroethene base; 2-chloro-1; the 2-dibromo vinyl; 2-fluoro-1; the 2-dibromo vinyl; 2-is fluoride-based for 2-bromo-1-chloro-; 2-methoxy-ethylene base; 2-vinyl ethyl ether base; allyl group; the 2-chlorallyl; the 3-chlorallyl; 3,3-two chlorallyls; propylene-1-base; propylene-2-base; 1-propenyl chloride-1-base; 1-bromopropylene-1-base; 1-fluorine propylene-2-base; 1-propenyl chloride-2-base; 1-bromopropylene-2-base; 2-methoxyl group propylene-1-base; 2-ethoxy propylene-1-base; 3,3; 3-trifluoro propene-1-base; 3; 3,3-trifluoro propene-2-base; 1-propenyl chloride-2-base; 1-fluorine propylene-2-base; 1-bromopropylene-2-base; 1,2-dichloropropylene-1-base; 1; 2-propylene bromide-1-base; 1; 2-difluoro propylene-1-base; 1,1-dichloropropylene-2-base; 1,1-propylene bromide-2-base; 1; 1-difluoro propylene-2-base; 1-chloro-2-fluorine propylene-1-base; 1-chloro-2-bromopropylene-1-base; 1-bromo-2-propenyl chloride-1-base; 1-bromo-2-fluorine propylene-1-base; 1-chloro-3; 3,3-trifluoro propene-2-base; 1-bromo-3,3; 3-trifluoro propene-2-base; 1-fluoro-3; 3,3-tri chloropropene-1-base; 1,3; 3; 3-tetrafluoeopropene-1-base; 1,3,3; 3-tetrafluoeopropene-2-base; 1-bromo-2-chloro-3; 3,3-trifluoro propene-1-base; 1,1; 3; 3,3-five fluorine propylene-2-base; 1,2; 3; 3,3-five fluorine propylene-1-base; 1,1-two chloro-3; 3; 3-trifluoro propene-2-base; 1,2-two chloro-3,3; 3-trifluoro propene-2-base; 1; 1-two bromo-3,3,3-trifluoro propene-2-base; 1; 2-two bromo-3; 3,3-trifluoro propene-2-base; 1-chloro-2,3; 3; 3-tetrafluoro-1-propylene-1-base; 2-methacrylic-1-base; 1-chloro-2-methacrylic-1-base; 1-bromo-2-methacrylic-1-base; 1-fluoro-2-methacrylic-1-base; 1-bromo-2-methyl-3,3,3-trifluoro propene-1-base; 1-chloro-3; 3; 3-three fluoro-2-trifluoromethyl propylene-1-bases; 1-bromo-3,3,3-three fluoro-2-trifluoromethyl propylene-1-bases; 1-chloro-3; 3; 3-trifluoro propene-1-base; 1-bromo-3,3,3-trifluoro propene-1-base; 1-chloro-2; 3; 3,3-tetrafluoeopropene-1-base; 1-chloro-2-bromo-3,3; 3-trifluoro propene-1-base; 1-chloro-2-methyl-3; 3,3-trifluoro propene-1-base; 1-bromo-2-fluorine propylene-1-base; 1-butylene-1-base; 1-butylene-2-base; 2-butylene-1-base; 2-butylene-2-base; 1-chloro-1-butylene-1-base; 1-bromo-1-butylene-1-base; 1-fluoro-1-butylene-1-base; 1-chloro-1-butylene-2-base; 1-fluoro-1-butylene-2-base; 1-bromo-1-butylene-2-base; 1,2-two fluoro-1-butylene-1-base; 1; 2-two chloro-1-butylene-1-base; 1; 2-two bromo-1-butylene-1-base; 1-bromo-2-fluoro-1-butylene-1-base; 3-methyl-2-butene-2-base; 1-chloro-2-fluoro-1-butylene-1-base; 1-bromo-2-chloro-1-butylene-1-base; 1,1,1-three fluoro-2-methyl-2-butene-2-bases; 4; 4; 4-three fluoro-2-methyl-butene-2-Ji; 4,4,4-three fluoro-3-trifluoromethyl-2-butylene-2-bases; 1-chloro-2-methyl-3; 3; 3-trifluoro propene-1-base; 3-chloro-2-butylene-2-base; 3-bromo-2-butylene-2-base; 3-fluoro-2-butylene-2-base; 1-chloro-2-methyl-1-butene alkene-1-base; 1-bromo-2-methyl-1-butene alkene-1-base; 1-fluoro-2-methyl-1-butene alkene-1-base; 1-fluoro-3-methyl-1-butene-1-base; 1-chloro-3-methyl-1-butene-1-base; 2-methoxyl group-1-butylene-1-base; 2-oxyethyl group-1-butylene-1-base; 1,1-two chloro-1-butylene-2-base; 1,1-two bromo-1-butylene-2-base; 1; 1-two fluoro-1-butylene-2-base; 1-chloro-2-fluoro-1-butylene-1-base; 1-chloro-2-bromo-1-butylene-1-base; 1-chloro-2-Trifluoromethyl-1-butene-1-Ji; 1; 1,1-three fluoro-2-butylene-2-base; 4,4; 4-three fluoro-2-butylene-2-base; 4; 4,4-three fluoro-3-methyl-2-butene-2-bases; 1,1; 1-three fluoro-3-methyl-2-2-pentenyls; 1; 1,1-three fluoro-3-ethyl-2-2-pentenyls; 1,1; 1; 4,4,4-hexafluoro-2-butylene-2-base; 1-chloro-2-ethyl-1-butylene-1-base; 1-bromo-2-ethyl-1-butylene-1-base; 1-fluoro-2-ethyl-1-butylene-1-base; the 2-2-pentenyl; 2-amylene-3-base; 2-chloro-2-amylene-3-base; 2-bromo-2-amylene-3-base; 2-fluoro-2-amylene-3-base; 3-chloro-2-2-pentenyl; 3-bromo-2-2-pentenyl; 3-fluoro-2-2-pentenyl; 3-trifluoromethyl-2-2-pentenyl; 1; 1; 1-three fluoro-2-amylene-3-bases; 1,1,1-three fluoro-2-2-pentenyls; 1; 1; 1-three fluoro-3-methyl-2-2-pentenyls; 2-methyl-2-amylene-3-base; 3-methyl-2-2-pentenyl; 1,1,1-three fluoro-2-trifluoromethyls-2-amylene-3-base; 4-methyl-3-hexene-3-base; 4-fluoro-3-hexene-3-base; 4-chloro-3-hexene-3-base; 4-bromo-3-hexene-3-base; 1; 1; 1-three fluoro-2-methyl-2-hexene-3-base; 4-ethyl-3-hexene-3-base; ethynyl; 2-chloroethene alkynyl; 2-bromoacetylene base; propine-1-base; propine-3-base; 3,3,3-trifluoropropyne-1-base; ethyl acetylene-1-base; ethyl acetylene-3-base; 3-methyl isophthalic acid-butine-1-base; 1-pentyne-1-base; cyclopropyl; 1-cyano group cyclopropyl; 1-fluorine cyclopropyl; 1-chlorine cyclopropyl; 2-cyano group cyclopropyl; 2-fluorine cyclopropyl; 2-chlorine cyclopropyl; 2; 2-difluoro cyclopropyl; 2; 2-dichloro cyclopropyl; cyclobutyl; 2,2-difluoro cyclobutyl; 2,2; 3-trifluoro cyclobutyl; 2,2-two fluoro-3-chlorine cyclobutyl; cyclopentyl; cyclohexyl.Group 2
Figure 9980434800151
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 3
Figure 9980434800152
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 4
Figure 9980434800153
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 5 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 6
Figure 9980434800162
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 7
Figure 9980434800163
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 8 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 9
Figure 9980434800172
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 10
Figure 9980434800173
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 11
Figure 9980434800174
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 12
Figure 9980434800181
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 13 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 14
Figure 9980434800183
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 15 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 16 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 17
Figure 9980434800193
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 18
Figure 9980434800201
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 19
Figure 9980434800202
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 20
Figure 9980434800203
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 21
Figure 9980434800211
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 22 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 23 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 24
Figure 9980434800221
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 25
Figure 9980434800222
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 26 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 27 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 28
Figure 9980434800232
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 29 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 30
Figure 9980434800241
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 31
Figure 9980434800242
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 32
Figure 9980434800243
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 33 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 34
Figure 9980434800252
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 35
Figure 9980434800253
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 36
Figure 9980434800261
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 37 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 38
Figure 9980434800263
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 39
Figure 9980434800271
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 40
Figure 9980434800272
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 41
Figure 9980434800273
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 42 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 43 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 44 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 45 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 46 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 47 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 48
Figure 9980434800301
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 49 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 50 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 51 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 52
Figure 9980434800312
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 53
Figure 9980434800313
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 54
Figure 9980434800321
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 55 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 56 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 57 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 58
Figure 9980434800332
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 59
Figure 9980434800333
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 60
Figure 9980434800341
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 61
Figure 9980434800342
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 62
Figure 9980434800343
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 63
Figure 9980434800351
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 64
Figure 9980434800352
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 65
Figure 9980434800353
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 66 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 67 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 68 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 69 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 70 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 71 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 72
Figure 9980434800381
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 73 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 74 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 75
Figure 9980434800391
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 76
Figure 9980434800392
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 77
Figure 9980434800393
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 78 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 79
Figure 9980434800402
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 80
Figure 9980434800403
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 81
Figure 9980434800411
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 82 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 83 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 84 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 85
Figure 9980434800422
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 86 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 87 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 88 Wherein, R 2The meaning that provides in the group 1 above for example having.Group 89
Figure 9980434800433
Wherein, R 2The meaning that provides in the group 1 above for example having.Group 90
Figure 9980434800441
Wherein, R 2The meaning that provides in the group 1 above for example having.
Use, for example, 2-amino-4-(1-phenylethyl amino)-6-Trifluoromethyl-1,3,5-triazine and N, N-diethyl acetamide diethyl acetal is as starting raw material, and the reaction path of the inventive method can illustrate with following reaction formula:
Figure 9980434800442
Formula II is provided at the General Definition of the aminotriazine of the replacement that is used as starting raw material in the inventive method for preparing formula I compound of the present invention.In formula II, R 1And R 2Each preferably or particularly has 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.
The formula II starting raw material be known and/or can by known method preparation itself (referring to, US 3816419, US 3932167, EP 191496, EP 273328, EP 411153, WO 90/09378, WO 97/00254, WO 97/08156, DE 19641691, DE19641692, DE 19641693, DE 19711825, DE 19744232, DE 19744711).
Logical formula III provides in the methods of the invention another General Definition as the aminocompound of the replacement of starting raw material.In formula III, R 3, R 4And R 5Each preferably or particularly has the R that had mentioned already in the relevant description of formula I compound of the present invention above 3, R 4And R 5Preferred or particularly preferred implication; R preferably represents the alkyl with 1-4 carbon atom, particularly methyl or ethyl.
The formula III starting raw material is the synthetic known organic chemicals of.
The present invention prepares logical formula I method and uses thinner to carry out when suitable.Suitable diluent is inert organic solvents especially.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, isopropyl 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-formanilide, 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.
When carrying out the inventive method, temperature of reaction can change in the scope of broad.Usually, reaction is at 0 ℃ to 150 ℃, preferably carries out under the temperature between 10 ℃ to 120 ℃.
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 carry out in the presence of the reaction auxiliary, and reaction mixture was stirred several hours under required temperature usually normally in the thinner that is fit to.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, the weldering 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, Fischer 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 the monocot 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 of extender, 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 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 additive 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 they 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), bialaphos, bifenox, two careless ethers, bromobutide, bromofenoxim, bromoxynil, Butachlor technical 92, butroxydim, butylate, cafenstro1e, caloxydim, carbetamide, carfentrazone (ethyl), chlomethoxyfen, the weed eradication fear, chloridazon, chlorimuron (ethyl ester), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin, ether is yellow grand, clethodim, alkynes oxalic acid clomazone, clomeprop, difluoro pyridine acid, clopyrasulfuron (methyl), cloransulam (methyl), cumyluron, 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, diclosulam, acetyl alachlor, difenzoquat, diflufenican, diflufenzopyr, azoles is grand, dimepiperate, dimethachlor, diformazan third second 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, 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, the fluorine cisanilide, fluoroglycofenethyl (ethyl ester), amine grass azoles, flupropacil, flurpyrsulfuron (methyl ,-sodium), flurenol, fluridone, fluroxypyr, the phonetic alcohol of fluorine, the fluorine humulone, fluthiacet (methyl), fluthiamide, Fomesafen, Glufosinate (ammonium salt), glyphosate (isopropyl ammonium salt), halosafen, pyrrole fluorine chlorine standing grain spirit (ethoxy ethyl ester), haloxyfop-P-methyl, hexazinone, miaow grass ester (methyl esters), imazamethapyr, imazamox, imidazoles nicotinic acid, imazaquin, imazethapyr, the azoles pyrazosulfuron, ioxynil, isopropalin, the grand Yi Evil acyl grass of isoproturon Yi Evil amine, isoxafluto1e Yi Evil grass ether, lactofen, lenacil, methoxydiuron, 2 first, 4 chlorine, Vi par, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metsulfuron-methyl (methyl esters), the piperazine humulone, molinate, monolinuron, naproanilide, napropamide, neburon, nicoculsfuron, norflurazon, orbencarb, the peace nitralin, oxadiargyl Evil humulone, oxasulfuron, oxaziclomefone, oxyfluorfen, Paraquat, pelargonicacid, pendimethalin, pentoxazone, sweet grass is peaceful, piperophos, the third careless amine, Fluoropyrimidinesulfuron (methyl esters), prometryn, propachlor, Stam F-34 Evil oxalic acid, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen (ethyl), pyrazolate, pyrazosulfuron (ethyl ester), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (methyl), pyrithiobacsodium, quinclorac, quinmerac, quinoclamine, quizalofopPethyl, quizalofopPtefuryl, the sulfone ethyl methyl, sethoxydim, simazine, simetryn, the sulphur humulone, sulfentrazone, the first ethyl methyl, sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthylazine, terbutryn, P DimethenamidP, thifluzamide, thrizopyr, thidiazimin, thifensulfuron methyl, thiobencarb, tiocarbazil, tralkoxydim, tri_allate, triasulfuron, tribenuron-methyl (methyl esters), TRICLOPYR ACID, trichlopyr, 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 9980434800491
2-amino-4-(1-fluoro-1-methylethyl)-6-(1-thiophene-2-base propyl group amino)-1 with 2.0g (0.8mmol), 3,5-triazine, 1.0g (0.8mmol) N, dinethylformamide dimethylacetal and 50ml methanol mixture stirred 5 hours at 50-60 ℃.Under pump vacuum, steam volatile constituent subsequently carefully.
Obtain 2.4g (theoretical amount 99%) 2-dimethylamino methene amido-4-(1-fluoro-1-methylethyl)-6-(1-thiophene-2-base propyl group amino)-1,3,5-triazines, be the oily residue, refractive index n D 20=1.5995.
Be similar to embodiment 1, and the generality of method produced according to the present invention describes, for example also made listed formula I compound in the following table 1.
Figure 9980434800501
Stereochemistry explanation in the table 1 is meant R 1Following defined group.
Table 1: formula I examples for compounds
Figure 9980434800511
Table 1 (continuing)
Figure 9980434800521
Table 1 (continuing)
Figure 9980434800531
Table 1 (continuing)
Figure 9980434800541
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800561
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800581
Table 1 (continuing)
Figure 9980434800591
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800611
Table 1 (continuing)
Table 1 (continuing)
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800651
Table 1 (continuing)
Figure 9980434800661
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800681
Table 1 (continuing)
Figure 9980434800691
Table 1 (continuing)
Figure 9980434800701
Table 1 (continuing)
Figure 9980434800711
Table 1 (continuing)
Figure 9980434800721
Table 1 (continuing)
Table 1 (continuing)
Figure 9980434800741
The logP value that provides in the table 1 goes up at reversed-phase column (C18) by HPLC (high performance liquid chromatography) according to EEC Directive 79/831 Annex V.A8 and measures temperature: 43 ℃.
(a) be used for the interior moving phase of measuring of acid range: 0.1% phosphate aqueous solution, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile--corresponding test-results is used a) mark table 1.
(b) be used for the interior moving phase of measuring of neutral range: 0.01 mole of branch water-bearing phosphate salt buffer solution, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile--corresponding test-results is used b table 1) mark.
Correction is (the logP value is to measure by retention time with the linear interior polarization between two successive alkane ketone) of using the alkane-2-ketone (having 3-16 carbon atom) of the non-branching with known logP value to carry out.
It is spectrometric to the UV of 400nm that λ max value is used in the maximum value of chromatographic signal 200nm.The 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 about 24 hours, soil waters with active agent preparations, uses the activeconstituents of specified quantitative on per unit area.Select the concentration of spraying fluid, the specified quantitative of required active compound is used with the spray amount of 1000 premium on currency/hectares.
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, the compound of preparation embodiment 2 demonstrates strong activity to weeds, good consistency is arranged (referring to Table A with crop such as wheat simultaneously; " ai "=activeconstituents).Table A: test/greenhouse before the bud 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, preparation embodiment 1,2 and 6 compound demonstrate strong activity to weeds, and in them some can be tolerated (referring to table B1 and B2) well by crop such as wheat.Table B1: test/greenhouse behind the bud Table B2: test/greenhouse behind the bud
Figure 9980434800791

Claims (10)

1. the aminoalkylidenamino triazines that leads to the replacement of formula I
Figure 9980434800021
R wherein 1Represent group-A-Z, wherein the alkane 2 basis of substituted straight or branched is chosen in the A representative wantonly, this group is randomly in the beginning of alkane 2 basis, Sauerstoffatom is contained in ending or centre, sulphur atom, imino-(NH) or alkyl imino (N-alkyl), substituted monocycle or double-ring are chosen in representative wantonly with Z, carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl, cyclohexyl, phenyl, naphthyl, 1,2,3, the 4-tetralyl, the decahydro naphthyl, 1, the 2-indanyl, indenyl, furyl, benzofuryl, dihydro benzo furyl, thienyl, benzothienyl, the dihydrobenzo thienyl, isobenzofuran-base, the dihydroisobenzofuran base, isobenzo-thienyl, the dihydro isobenzo-thienyl, pyrryl, indyl, pseudoindoyl, indolinyl, iso-dihydro-indole-group, benzo dioxolyl oxazolyl benzoxazolyl, thiazolyl, benzothiazolyl, benzimidazolyl-, indazolyl oxadiazole base, thiadiazolyl group, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolines base and 2, the 3-phthalazinyl, R 2Represent hydrogen, cyano group, halogen, or the optional separately substituted alkyl of representative, alkoxyl group, alkyl-carbonyl, alkoxy carbonyl, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkenyl, alkynyl or cycloalkyl, R 3Represent hydrogen or alkyl, R 4Represent hydrogen or alkyl, and R 5Represent alkyl.
2. the compound of the formula I of claim 1 is characterized in that R 1Represent group-A-Z, wherein the A representative is optional by the alkane 2 basis with 1-6 carbon atom of the straight or branched of cyano group or halogen replacement, and this group randomly contains Sauerstoffatom, sulphur atom, imino-(NH) or C in beginning, ending or the centre of alkane 2 basis 1-4Alkyl imino; substituted monocycle or double-ring are chosen in representative wantonly with Z; carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl; cyclohexyl; phenyl; naphthyl; 1; 2; 3; the 4-tetralyl; the decahydro naphthyl; 1; the 2-indanyl; indenyl; furyl; benzofuryl; dihydro benzo furyl; thienyl; benzothienyl; the dihydrobenzo thienyl; isobenzofuran-base; the dihydroisobenzofuran base; isobenzo-thienyl; the dihydro isobenzo-thienyl; pyrryl; indyl; pseudoindoyl; indolinyl; iso-dihydro-indole-group; benzo dioxolyl oxazolyl benzoxazolyl; thiazolyl; benzothiazolyl; benzimidazolyl-; indazolyl oxadiazole base; thiadiazolyl group; pyrazolyl; pyridyl; pyrimidyl; pyrazinyl; pyridazinyl; quinolyl; isoquinolyl; quinoxalinyl; cinnolines base and 2; the 3-phthalazinyl; wherein, the possible substituting group of these groups is preferably selected from separately: hydroxyl; cyano group; nitro; halogen; optional separately by hydroxyl; alkyl that has 1-6 carbon atom separately or alkoxyl group that cyano group or halogen replace; choose the alkyl-carbonyl that has 1-6 carbon atom in each the comfortable alkyl that is replaced by halogen separately wantonly; alkoxy carbonyl; alkylthio; alkyl sulphinyl or alkyl sulphonyl; optional separately by hydroxyl; cyano group; nitro; halogen; C 1-4Alkyl, C 1-4Haloalkyl, C 1-4Alkoxyl group or C 1-4Phenyl that halogenated alkoxy replaces or phenoxy group and optional separately methylene-dioxy or the ethylenedioxy that is replaced by halogen, R 2Represent hydrogen, cyano group, halogen, representative is optional separately by hydroxyl, cyano group, nitro, halogen, C 1-4Alkoxyl group, C 1-4Alkylthio, C 1-4Alkyl sulphinyl or C 1-4The alkyl, alkoxyl group, alkyl-carbonyl, alkoxy carbonyl, alkylthio, alkyl sulphinyl or the alkyl sulphonyl that have 1-6 carbon atom in each comfortable alkyl that alkyl sulphonyl replaces; representative is optional separately by the alkenyl that has 2-6 carbon atom separately or the alkynyl of cyano group or halogen replacement, and perhaps representative is optional separately by cyano group, halogen or C 1-4The cycloalkyl that alkyl replaces with 3-6 carbon atom, R 3Represent hydrogen or have the alkyl of 1-6 carbon atom, R 4Represent hydrogen or have the alkyl of 1-6 carbon atom, and R 5Representative has the alkyl of 1-6 carbon atom.
3. the compound of the formula I of claim 1 is characterized in that, wherein A, R 2, R 3, R 4And R 5As defined in claim 2, and the unsubstituted separately or substituted phenyl or naphthyl of Z representative, possible substituting group wherein is as defined in claim 2.
4. the compound of the formula I of claim 1 is characterized in that, wherein A, R 2, R 3, R 4And R 5As defined in claim 2, and the unsubstituted or substituted heterocyclic radical of Z representative, possible heterocyclic radical wherein and possible substituting group are as defined in claim 2.
5. the compound of the formula I of claim 1 is characterized in that, R 1Represent group-A-Z, wherein the optional separately methylene radical (CH that is replaced by cyano group, fluorine or chlorine of A representative 2-), dimethylene (ethane-1,2-two bases ,-CH 2-CH 2-), ethylidene (ethane-1,1-two bases ,-CH (CH 3)-), trimethylene (propane-1,3-two bases ,-CH 2CH 2CH 2-), propylidene (propane-1,1-two bases ,-CH (C 2H 5)-), propane-2,3-two bases (CH (CH 3) CH 2-), 2-methyl-propane-1,3-two base (CH 2CH (CH 3) CH 2-), 3-oxa--propane-1,3-two base (CH 2CH 2O-), 2-oxa--propane-1,3-two base (CH 2OCH 2-), tetramethylene (butane-1,4-two bases ,-CH 2CH 2CH 2CH 2-), butane-2,4-two bases (CH (CH 3) CH 2CH 2-), butane-2,3-two bases (CH (CH 3) CH (CH 3)-), 3-methyl-butane-2,4-two bases (CH (CH 3) CH (CH 3) CH 2-), 4-oxa--butane-2,4-two bases (CH (CH 3) CH 2O-), pentane-3,5-two bases (CH (C 2H 5) CH 2CH 2-), 5-oxa--pentane-3,5-two bases (CH (C 2H 5) CH 2O-), 4-oxa--pentane-2,5-two bases (CH (CH 3) CH 2OCH 2-) or 5-oxa--hexane-3,6-two bases (CH (C 2H 5) CH 2OCH 2-); substituted monocycle or double-ring are chosen in representative wantonly with Z; carbocyclic ring or assorted cyclic are selected from following group: cyclopentyl; cyclohexyl; phenyl; naphthyl; 1; 2; 3; the 4-tetralyl; the decahydro naphthyl; 1; the 2-indanyl; indenyl; furyl; benzofuryl; dihydro benzo furyl; thienyl; benzothienyl; the dihydrobenzo thienyl; isobenzofuran-base; the dihydroisobenzofuran base; isobenzo-thienyl; the dihydro isobenzo-thienyl; pyrryl; indyl; pseudoindoyl; indolinyl; iso-dihydro-indole-group; benzo dioxolyl oxazolyl benzoxazolyl; thiazolyl; benzothiazolyl; benzimidazolyl-; indazolyl oxadiazole base; thiadiazolyl group; pyrazolyl; pyridyl; pyrimidyl; pyrazinyl; pyridazinyl; quinolyl; isoquinolyl; quinoxalinyl; cinnolines base and 2; the 3-phthalazinyl; wherein; the possible substituting group of these groups is preferably selected from separately: hydroxyl; cyano group; nitro; fluorine; chlorine; bromine; optional separately by hydroxyl; cyano group; the methyl that fluorine or chlorine replaces; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; optional separately by the methyl carbonyl of fluorine and/or chlorine replacement; the ethyl carbonyl; just-or the sec.-propyl carbonyl; just-; different-; secondary-or tertiary butyl carbonyl; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; just-; different-; secondary-or tert-butoxycarbonyl; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; methyl sulphonyl or ethylsulfonyl; optional separately by hydroxyl; cyano group; nitro; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; trifluoromethyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; phenyl or phenoxy group that difluoro-methoxy or trifluoromethoxy replace; optional separately by the methylene-dioxy or the ethylenedioxy of fluorine and/or chlorine replacement, R 2Represent hydrogen; cyano group; fluorine; chlorine; bromine; representative is optional separately by hydroxyl; cyano group; nitro; fluorine; chlorine; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; methylsulfinyl; the ethyl sulfinyl; just-or different third sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the methyl that replaces of different third alkylsulfonyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; ethanoyl; propionyl; just-or different-butyryl radicals; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; methylthio group; ethylmercapto group; just-or the iprotiazem base; methylsulfinyl; the ethyl sulfinyl; just-or different third sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or different third alkylsulfonyl; representative is optional separately by cyano group; fluorine; the vinyl that chlorine or bromine replaces; propenyl; butenyl; ethynyl; proyl or butynyl; perhaps representative is optional separately by cyano group; fluorine; chlorine; bromine; the cyclopropyl that methyl or ethyl replace; cyclobutyl; cyclopentyl or cyclohexyl, R 3Represent hydrogen, methyl or ethyl, R 4Represent hydrogen, methyl, ethyl, just-or sec.-propyl, just-, the exclusive OR sec-butyl, and R 5Represent methylidene, ethyl, just-or sec.-propyl, just-, the exclusive OR sec-butyl.
6. the method for compound of the formula I of preparation claim 1 is characterised in that, if suitably in the presence of thinner, the aminocompound of the aminotriazine of the replacement of formula II and the replacement of formula III reacts,
Figure 9980434800051
R wherein 1, R 2As defined in claim 1,
Figure 9980434800061
R wherein 3, R 4And R 5As defined in claim 1, R represents alkyl.
7. herbicidal composition is characterized in that, they contain the compound of the formula I of at least a claim 1.
8. the purposes of the compound controlling undesired plants of the formula I of claim 1.
9. method of controlling weeds is characterized in that, with the compound effects of the formula I of claim 1 in weeds or its vegetatively.
10. prepare the method for herbicidal composition, be characterised in that, with the compound of the formula I of claim 1 with expand agent and/or tensio-active agent and mix.
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