CN1225086A - Substituted aromatic carbonyl compounds and their derivatives - Google Patents

Substituted aromatic carbonyl compounds and their derivatives Download PDF

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Publication number
CN1225086A
CN1225086A CN 97196302 CN97196302A CN1225086A CN 1225086 A CN1225086 A CN 1225086A CN 97196302 CN97196302 CN 97196302 CN 97196302 A CN97196302 A CN 97196302A CN 1225086 A CN1225086 A CN 1225086A
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group
bases
amino
alkyl
methyl
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R·安德雷
M·W·德雷韦斯
W·哈斯
A·伦德尔
K·-H·林克
O·沙尔纳
M·多林格尔
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Bayer AG
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Bayer AG
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Abstract

The invention relates to novel substituted aromatic carbonyl compounds of formula (I), preparation method thereof and appliance as herbicide, wherein Q represents oxygen, sulfur or imino (NH), R1 represents hydrogen or halogen, R<2> represnets following groups as A<1>, A<2>, A<3>, wherein A<1>, A<2>, A<3> are defined as description.

Description

The aromatic carbonyl compounds and the derivative thereof that replace
The present invention relates to the aromatic carbonyl compounds and the derivative thereof of novel substituted, its preparation method and its are as herbicide applications.
Some aromatic carbonyl compounds with replacement of the heterocyclic radical group that connects through nitrogen be known (referring to, DE-2102848, DE-2119260, DE-2166456, DE-2342934).Yet, the weeding activity of unexposed these compounds still.
Therefore, the invention provides the aromatic carbonyl compounds and the derivative thereof of the replacement of novel logical formula I
Figure A9719630200101
Wherein Q represents oxygen, sulphur or imino-(NH), R 1Represent hydrogen or halogen, R 2Represent following radicals
-A 1-A 2-A 3
Wherein
A 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-,
R wherein 4Represent hydrogen, hydroxyl or be selected from following group: alkyl, alkoxyl group, aryl,
Alkyl sulphonyl and aryl sulfonyl,
A 1Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl
Two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-,
R wherein 5Represent hydrogen, hydroxyl or be selected from following group: alkyl, aryl, alkoxyl group,
Alkyl sulphonyl and aryl sulfonyl,
A 2Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl
Two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A 3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl,
Formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen, or representative
Be selected from following group: alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl
Alkylsulfonyl, alkylamino, dialkyl amido, alkoxy carbonyl, the basic phosphorus of dialkoxy (sulphur)
Acyl group, alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy
Carbonyl, alkynyl, alkynyloxy group, alkynyl amino, alkynyloxy group carbonyl, cycloalkyl, cycloalkyl
Oxygen base, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy
Carbonyl, cycloalkyl alkoxy carbonyl, aryl, aryloxy, aralkyl, aralkoxy,
Aryloxycarbonyl, aromatic alkoxy carbonyl, heterocyclic radical, heterocyclic radical alkyl, heterocyclic radical alcoxyl
Base or heterocyclic radical alkoxy carbonyl, they each can choose wantonly and be substituted R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they each can choose wantonly be substituted and
Z representative is selected from following monocycle or double-ring is saturated or unsaturated group: heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they each can choose wantonly and be substituted,
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
The aromatic carbonyl compounds and the following acquisition of derivative thereof of the replacement of novel logical formula I: in the presence of the reaction auxiliary, make the aromatics nitrile of the replacement of logical formula II if suit
Figure A9719630200111
Wherein
R 1, R 2With Z each as defined above
With water, hydrogen sulfide or ammonia react, and the general formula of gained (aromatic carboxylic acid's or derivatives thereof of I replacement a) Wherein Q, R 1, R 2With Z each as defined above
If suit, change into the aromatic carbonyl compounds or derivatives thereof of the replacement consistent by ordinary method with the above-mentioned definition of leading to the formula I compound.
The aromatic carbonyl compounds of the replacement of novel logical formula I has strong weeding activity.
In definition, saturated or aliphatic unsaturated hydrocarbon as alkyl, alkane two bases, alkenyl or alkynyl, also comprises and the heteroatoms combination, as the situation of alkoxyl group, alkylthio or alkylamino, is straight or branched under each situation.
Halogen is represented fluorine, chlorine, bromine or iodine usually, preferably represents fluorine, chlorine or bromine and special representative's fluorine or chlorine.
The present invention preferably provides the formula I compound, wherein
Q represents oxygen, sulphur or imino-(NH),
R 1Represent hydrogen, fluorine, chlorine or bromine,
R 2Represent following radicals
-A 1-A 2-A 3A wherein 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-, R wherein 4Represent hydrogen, hydroxyl or be selected from following group: C 1-C 4-alkyl, C 1-C 4-alkoxyl group, phenyl, C 1-C 4-alkyl sulphonyl and phenyl sulfonyl, A 1Also representative is selected from following group: C 1-C 6-alkane two bases, C 2-C 6-alkene two bases, C 2-C 6-alkynes two bases, C 3-C 6-cycloalkyl two bases, C 3-C 6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace A by fluorine or chlorine 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-, R wherein 5Represent hydrogen, hydroxyl or be selected from following group: C 1-C 4-alkyl, C 1-C 4-alkoxyl group, phenyl, C 1-C 4-alkyl sulphonyl and phenyl sulfonyl, A 2Also representative is selected from following group: C 1-C 6-alkane two bases, C 2-C 6-alkene two bases, C 2-C 6-alkynes two bases, C 3-C 6-cycloalkyl two bases, C 3-C 6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace A by fluorine or chlorine 3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl, formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen; or representative is selected from following group: the basic phosphoryl of alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylamino, dialkyl amido, alkoxy carbonyl and dialkoxy (sulphur), they each have 1 to 6 carbon atom and each can be chosen wantonly by halogen, C at moieties 1-C 4-alkoxyl group or C 1-C 4-Alkoximino replaces, A 3Also representative is selected from following group: alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy carbonyl, alkynyl, alkynyloxy group, alkynyl amino and alkynyloxy group carbonyl, they respectively have 2 to 6 carbon atoms in alkenyl, alkylidene group or alkynyl and each is optional by halogen replacement, A 3Also representative is selected from following group: cycloalkyl, cycloalkyl oxy, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy carbonyl and cycloalkyl alkoxy carbonyl, they each on alkyl group, have 1 to 4 carbon atom and each is optional by halogen, cyano group, carboxyl, C having 3 to 6 carbon atoms on the group of naphthene base and choose wantonly 1-C 4-alkyl and/or C 1-C 4-alkoxyl group-carbonyl substituted,
A 3Also represent each can choose wantonly by nitro, cyano group, carboxyl, halogen, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy and/or C 1-C 4-alkoxyl group-carbonyl substituted be selected from following group: phenyl, phenoxy group, phenyl-C 1-C 4-alkyl, phenyl-C 1-C 4-alkoxyl group, phenyloxycarbonyl and phenyl-C 1-C 4-alkoxy carbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, pyrazolyl-C 1-C 4-alkyl, furyl-C 1-C 4-alkyl, thienyl-C 1-C 4-alkyl, oxazolyl-C 1-C 4-alkyl, isoxazolyl-C 1-C 4-alkyl, thiazolyl-C 1-C 4-alkyl, pyridyl-C 1-C 4-alkyl, pyrimidyl-C 1-C 4-alkyl, pyrazolyl methoxyl group, furyl methoxyl group are represented perhydro pyranyl methoxyl group or pyridyl methoxyl group, R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they respectively have 1 to 6 carbon atom on alkyl and each is optional by hydroxyl, cyano group, halogen, C 1-C 4-alkoxyl group or C 1-C 4It respectively is monocycle or the saturated or unsaturated group of two ring-types that-alkoxyl group-carbonyl substituted and Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 6 carbon atoms and 1 to 4 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional at the most three be selected from-CO-,-CS-,-SO-and/or SO 2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, halogen, C 1-C 6(it can choose wantonly by halogen or C again-alkyl 1-C 4The replacement of-alkoxyl group), C 2-C 6-alkenyl and C 2-C 6-alkynyl (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkoxyl group and C 1-C 6(they respectively can choose wantonly by halogen or C again-alkoxyl group-carbonyl 1-C 4The replacement of-alkoxyl group), C 2-C 6-alkenyloxy and C 2-C 6-alkynyloxy group (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkylthio, C 2-C 6-alkenyl thio and and C 2-C 6-alkynes sulfenyl (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkylamino and two-(C 1-C 4-alkyl) amino, C 3-C 6-cycloalkyl and and C 3-C 6-cycloalkyl-C 1-C 4(they respectively can choose wantonly by halogen and/or C again-alkyl 1-C 4The replacement of-alkyl), (they respectively can be chosen wantonly by nitro, cyano group, halogen, C again for phenyl, phenoxy group, thiophenyl, phenyl sulfinyl, phenyl sulfonyl and phenyl amino 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy and/or C 1-C 4-alkoxyl group-carbonyl substituted),
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
The present invention provides the compound of logical formula I especially, wherein
Q represents oxygen, sulphur or imino-(NH),
R 1Represent hydrogen, fluorine or chlorine,
R 2Represent following radicals:
-A 1-A 2-A 3A wherein 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-, R wherein 4Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl and ethylsulfonyl, A 1Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases, A 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-, R wherein 5Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl, ethylsulfonyl, just-or sec.-propyl alkylsulfonyl and phenyl sulfonyl, A 2Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases, A 3Represent hydrogen; hydroxyl; amino; cyano group; nitro; carboxyl; formamyl; sulfo group; fluorine; chlorine; bromine; representative is selected from following group: methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; just-; different-; secondary-or tert-pentyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; just-; different-; secondary-or uncle's pentyloxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; just-or the sec.-propyl sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the sec.-propyl alkylsulfonyl; methylamino; ethylamino; just-or sec.-propyl amino; just-; different-; secondary-and tertiary butyl amino; dimethylamino; diethylamino; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; the dimethoxy phosphoryl; the diethoxy phosphoryl; dipropoxy phosphoryl and diisopropoxy phosphoryl; they each can choose wantonly by fluorine; chlorine; methoxyl group; oxyethyl group; methoxyimino or ethoxy imino replace, A 3Also representative is selected from following group: propenyl, butenyl, propenyloxy group, butenyloxy, propenyl amino, butenyl amino, propylidene amino, butylidene amino, propenyloxy group carbonyl, butenyloxy carbonyl, proyl, butynyl, third alkynyloxy group, fourth alkynyloxy group, proyl amino, butynyl amino, the third alkynyloxy group carbonyl and fourth alkynyloxy group carbonyl, they each can choose wantonly by fluorine or chlorine and replace A 3Also representative is selected from following group: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl oxygen base, cyclobutyl oxygen base, cyclopentyloxy, cyclohexyl oxygen base, the cyclopropyl methyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexyl methyl, cyclo propyl methoxy, cyclobutyl methoxy base, the cyclopentyl methoxyl group, the cyclohexyl methoxyl group, cyclopentylidene amino, cyclohexylidene amino, the cyclopentyloxy carbonyl, cyclohexyl oxygen base carbonyl, cyclopentyl methoxycarbonyl and cyclohexyl methoxycarbonyl, they each can choose wantonly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just-or sec.-propyl, methoxycarbonyl or ethoxy carbonyl replace, A 3Also representative is selected from following group: phenyl, phenoxy group, benzyl, styroyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl oxazolyl isoxazolyl, thiazolyl, isothiazolyl oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, the pyrazolyl methyl, furyl methyl, thienyl methyl oxazolyl methyl isoxazolyl methyl, the thiazolyl methyl, pyridylmethyl, Pyrimidylmethyl, the pyrazolyl methoxyl group, furyl methoxyl group and pyridyl methoxyl group, they each can choose wantonly by nitro, cyano group, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl, trifluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, difluoro-methoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxy carbonyl replace, R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or propoxy-, methylthio group, ethylmercapto group, just-or the iprotiazem base, methylamino, ethylamino, just-or sec.-propyl amino, they each can choose wantonly by hydroxyl, cyano group, fluorine, chlorine, methoxyl group, oxyethyl group, methoxycarbonyl or ethoxy carbonyl replace and the Z representative to be selected from following respectively be monocycle shape or the saturated and unsaturated group of two ring-types: in the heterocycle ring system, respectively have 2 to 5 carbon atoms and 1 to 3 nitrogen-atoms and also optionally contain aerobic or sulphur atom and/or optionally be selected from-CO-to too many by two,-CS-,-SO-and/or SO 2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, fluorine, chlorine, bromine; Methyl, ethyl, just-or sec.-propyl, just-, different-, secondary-or the tertiary butyl, (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyl, butenyl, proyl and butynyl (each can be chosen wantonly again by fluorine or chlorine and replace); Methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-and tert.-butoxy, methoxycarbonyl and ethoxy carbonyl (they each can choose wantonly again replace) by fluorine, chlorine, methoxyl group and oxyethyl group; Propenyloxy group, butenyloxy, third alkynyloxy group and fourth alkynyloxy group (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methylthio group, ethylmercapto group, just-or the iprotiazem base, just-, different-, secondary-or uncle's butylthio, propylene sulfenyl, butylene sulfenyl, propine sulfenyl and butine sulfenyl (they each can choose wantonly again replace) by fluorine or chlorine; Methylamino, ethylamino, just-or sec.-propyl amino, just-, different-, secondary-or tertiary butyl amino, dimethylamino and diethylamino; Cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; the cyclopropyl methyl; cyclobutylmethyl; (they respectively can be chosen wantonly again by fluorine for cyclopentyl-methyl and cyclohexyl methyl; chlorine; methyl; ethyl; just-or the sec.-propyl replacement); phenyl; phenoxy group; thiophenyl; the phenyl sulfinyl; (they respectively can be chosen wantonly again by nitro for phenyl sulfonyl and phenyl amino; cyano group; fluorine; chlorine; bromine; methyl; ethyl; just-or and propyl group; trifluoromethyl; methoxyl group; oxyethyl group; just-or different-propoxy-; difluoro-methoxy; trifluoromethoxy; methoxycarbonyl or ethoxy carbonyl replace)
Except prior art compound: 5-chloro-4-(1,3-dihydro 1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
In logical formula I, the Z special representative lists in heterocyclic group hereinafter:
Figure A9719630200171
Figure A9719630200181
Figure A9719630200191
Q under each situation wherein 1Representative is selected from following group :-CO-,-CS-,-CH 2-,-CH (OH)-,-CHCl-,-CHBr-,-C (=CH 2)-,-C (=CHF)-,-C (=CF 2)-,-C (=CHCl)-,-C (=CHBr)-,-C (=CHOCHF 2)-,-C (=CHOCF 3)-,-C (=CHOCH 2CF 3)-, Q 2Represent oxygen, sulphur or be selected from following group :-CO-,-CS-,-CH 2-,-CHF-,-CF 2-,-CHCl-,-CHBr-,-CHOCHF 2-,-CHOCF 3-,-CHOCH 2CF 3-, R 6Represent hydrogen; amino; nitro; cyano group; carboxyl; formamyl; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; cyclopropyl; difluoromethyl; trifluoromethyl; one chlorodifluoramethyl-; methoxyl group; oxyethyl group; just-or isopropoxy; difluoro-methoxy; trifluoromethoxy; one chlorine difluoro-methoxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; the difluoro methylthio group; trifluoromethylthio; one chlorine difluoro methylthio group; methylamino; ethylamino; just-or sec.-propyl amino; dimethylamino; diethylamino; methoxycarbonyl or ethoxy carbonyl, and R 7Represent hydrogen, hydroxyl, amino, cyano group, methyl, ethyl, just-or sec.-propyl, difluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, or wherein, if suitable, two adjacent groups---R 6And R 6Or R 7And R 7Or R 6And R 8-representative respectively has alkane two bases or alkene two bases of four carbon atom at the most together, they each optional by fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl replace and choose wantonly in beginning (or at the end of) or in hydrocarbon chain, insert oxygen, sulphur or be selected from following group :-SO-, SO 2-,-N (CH 3)-and-N (C 2H 5)-.
Above-mentioned general or preferred group definition is suitable for the end product of formula I, and correspondingly is suitable for every kind and prepares starting raw material or the intermediate that needs under the situation.These group definition can make up on demand mutually, promptly comprise the combination between scope of providing of preferred compound.
Formula I examples for compounds grouping of the present invention is listed in hereinafter.Group 1
Figure A9719630200201
Q, R 1, R 2And R 3Respectively have the implication that provides in the form hereinafter:
Q ????R 1 ????R 2 ????R 3 ????Q ????R 1 ????R 2 ????R 3
O ????H ????F ????OH ????O ????F ????F ????OH
O ????F ????Cl ????OH ????O ????Cl ????F ????OH
O ????Cl ????Cl ????OH ????O ????F ????Br ????OH
O ????H ????F ????OCH 3 ????O ????F ????F ????OCH 3
O ????F ????Cl ????OCH 3 ????O ????Cl ????F ????OCH 3
O ????Cl ????Cl ????OCH 3 ????O ????F ????Br ????OCH 3
O ????H ????F ????SCH 3 ????O ????F ????F ????SCH 3
O ????F ????Cl ????SCH 3 ????O ????Cl ????F ????SCH 3
O ????Cl ????Cl ????SCH 3 ????O ????F ????Br ????SCH 3
S ????H ????F ????OH ????S ????F ????F ????OH
S ????F ????Cl ????OH ????S ????Cl ????F ????OH
S ????Cl ????Cl ????OH ????S ????F ????Br ????OH
S ????H ????F ????OCH 3 ????S ????F ????F ????OCH 3
S ????F ????Cl ????OCH 3 ????S ????Cl ????F ????OCH 3
S ????Cl ????Cl ????OCH 3 ????S ????F ????Br ????OCH 3
S ????H ????F ????SCH 3 ????S ????F ????F ????SCH 3
S ????F ????Cl ????SCH 3 ????S ????Cl ????F ????SCH 3
?Q ?R 1 ?R 2 ?R 3 Q ?R 1 ?R 2 R 3
?S ?Cl ?Cl ?SCH 3 S ?F ?Br SCH 3
?NH ?H ?F ?NH 2 NH ?F ?F NH 2
?NH ?F ?Cl ?NH 2 NH ?Cl ?F NH 2
?NH ?Cl ?Cl ?NH 2 NH ?F ?Br NH 2
?NH ?H ?F ?SCH 3 NH ?F ?F SCH 3
?NH ?F ?Cl ?SCH 3 NH ?Cl ?F SCH 3
?NH ?Cl ?Cl ?SCH 3 NH ?F ?Br SCH 3
?O ?H ?COOH ?OH O ?F ?COOH OH
?O ?F ?COOH ?OH O ?Cl ?COOH OH
?O ?Cl ?COOH ?OH O ?F ?COOH OH
?O ?H ?COOCH 3 ?OCH 3 O ?F ?COOCH 3 OCH 3
?O ?F ?COOCH 3 ?OCH 3 O ?Cl ?COOCH 3 OCH 3
?O ?Cl ?COOCH 3 ?OCH 3 O ?F ?COOCH 3 OCH 3
?O ?H ?OH ?OH O ?F ?SH OH
?O ?F ?OH ?OH O ?Cl ?SH OH
?O ?Cl ?OH ?OH O ?F ?NH 2 OH
?O ?H ?OH ?OCH 3 O ?F ?SH OCH 3
?O ?F ?OH ?OCH 3 O ?Cl ?SH OCH 3
?NH ?Cl ?NH 2 ?NH 2 NH ?F ?NH 2 NH 2
?NH ?H ?OH ?SCH 3 NH ?F ?SH SCH 3
?NH ?F ?OH ?SCH 3 NH ?Cl ?SH SCH 3
?NH ?Cl ?OH ?SCH 3 NH ?F ?NH 2 SCH 3
?O ?H ?CH 3 ?OCH 3 O ?F ?OCH 3 OCH 3
?O ?F ?CH 3 ?OCH 3 O ?Cl ?OCH 3 OCH 3
?O ?Cl ?CH 3 ?OCH 3 O ?F ?SCH 3 OCH 3
?O ?H ?SCH 3 ?OCH 3 O ?F ?NHCH 3 OCH 3
Figure A9719630200231
Figure A9719630200241
Figure A9719630200251
Group 2
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 3
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 4
Figure A9719630200261
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 5
Figure A9719630200262
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 6
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 7
Figure A9719630200271
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 8
Figure A9719630200272
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 9
Figure A9719630200273
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 10
Figure A9719630200281
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 11
Figure A9719630200282
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 12
Figure A9719630200283
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 13
Figure A9719630200291
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 14
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
Group 15
Figure A9719630200293
Q, R 1, R 2And R 3Respectively have and for example organize the implication that provides in 1.
For example, use 2-(2-fluoro-4-cyano group-5-methoxyl group-phenyl)-4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazole-3-ketone and water are as starting raw material, and the reaction path of the inventive method can illustrate with following reaction formula:
Figure A9719630200301
Formula II is provided at the General Definition of the aromatics nitrile that needs the replacement used as starting raw material in the inventive method of preparation formula I compound.In formula II, R 1, R 2Each preferably or particularly has those indicated R in the description of formula I compound of the present invention with Z 1, R 2Preferred or particularly preferred implication with Z.
The starting raw material formula II be known and/or can by the preparation of known method (referring to, EP-370332, EP-648749, DE-4238125, DE-4303376, US-5084084, WO95/29168).
The inventive method for preparing novel formula I compound is preferably carried out in the presence of the reaction auxiliary.These reaction auxiliarys comprise water and conventional organic thinner, oxygenant such as hydrogen peroxide or Textone, and thionamic acid.
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 20 ℃ 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 straw 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 belongs to, 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 belongs to, festuca, yard grass belongs to, Brachiaria, lolium, Brome, Avena, Cyperus, jowar belongs to, Agropyron, Cynodon, Monochoria, genus fimbristylis, arrowhead belongs to, Eleocharis, the Fischer grass belongs to, Paspalum, ischaemum, the cusp Pittosporum, talon eria, Agrostis, amur foxtail belongs to and the wind grass belongs to the monocot crops of following dependent of dead military hero: Oryza, Zea, Triticum, Hordeum, Avena, Secale, jowar belongs to, 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.
According to compound concentrations, the compound natural disposition controlling weeds that is suitable for going out, for example at 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 and 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, suspension emulsion, 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 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 protein hydrolysate; The dispersion agent that is fit to is: for example, and lignin sulfite waste liquor and methylcellulose gum.
Can use the carboxymethyl cellulose and the natural and synthetic polymer of tackiness agent such as 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 can 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 also can be used as the mixture with known weedicide, whole preparation or the possible mixed thing of bucket and uses.
The possible common component of mixture is known weedicide, for example, acetochlor, acifluorfen (sodium salt), aclonifen, alachlor, alloxydim (sodium salt), ametryn, amidochlor, amidosulfuron, the spirit of sulphur grass, atrazine, azimsulfuron, benazolin, benfuresate, benzyl ethyl methyl (methyl esters), bentazone, benzofenap, benzoylpropethyl (ethyl ester), two alanyl phosphorus, bifenox, bromobutide, bromofenoxim, bromoxynil, Butachlor technical 92, the fourth grass is special, cafenstrole, block careless amine, chlomethoxyfen, weed eradication is flat, pyrazon, chlorimuron (ethyl ester), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin, ether is yellow grand, clethodim, clodinafop (propargyl) clomazone, difluoro pyridine acid, clopyrasulfuron, cloransulam (methyl), cumyluron, cyanazine, the weed eradication spy, cyclosulfamuron, cycloxydim, cyhalofop (butyl), 2,4-drips, 2, the 4-Embutox, 2,4-drips propionic acid, desmedipham, di_allate, dicamba 98, diclofop-methyl (methyl esters), two benzene azoles are fast, diflufenican Ding Evil is grand, dimepiperate, dimethachlor, diformazan third second is clean, dimethenamid, the spirit of amino second fluorine, diphenamide, diquat, dithiopyr, Diuron Tech, daimuron, EPTC, esprocarb, ethalfluralin, Ethanetsulfuron (methyl esters), ethofumesate, ethoxyfen, 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, flumiclorac (pentyl), flumioxazin, flumipropyn, fluometuron, the fluorine cisanilide, fluoroglycofenethyl (ethyl ester), amine grass azoles, flupropacil, the fluorenes butyric acid, the fluorine butanone, fluroxypyr, flurprimidol, flurtamone, Fomesafen, Glufosinate (ammonium salt), glyphosate (isopropyl ammonium salt), halosafen, pyrrole fluorine chlorine standing grain spirit (ethoxy ethyl ester), hexazinone, miaow grass ester (methyl esters), imazamethapyr, imazamox, the weed eradication cigarette, the weed eradication quinoline, Imazethapyr, imidazoles is yellow grand, ioxynil, isopropalin, isoproturon, isoxaben, isoxaflutole 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, Hydram, monolinuron, naproanilide, napropamide, neburon, nicoculsfuron, norflurazon, orbencarb, oryzalin Evil humulone, oxyfluorfen, Paraquat, pendimethalin, phenmedipham, piperophos, the third careless amine, Fluoropyrimidinesulfuron (methyl esters), prometryn, propachlor, Stam F-34, propaquizafop, pentyne grass amine, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (ethyl ester), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (sodium), quinclorac, quinmerac, quizalofop (ethyl ester), quizalofop (tetrahydrochysene chaff ester), rimsulfuron, rare uncertain, simazine, simetryn, sulcitrione, sulfentrazone, ethyl methyl (methyl esters), grass sulphur phosphorus, tebutam, terbufos benzthiazuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thiophene methyl (methyl esters), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl (methyl esters), TRICLOPYR ACID, tridiphane, trifluralin and fluorine amine yellow grand (triflusulfuron).
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 plant sprout or behind the bud.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 activeconstituents of the present invention and use can be referring to the following example.
Preparation embodiment:
Embodiment 1
Figure A9719630200341
Under about 45 ℃; 1-(4-cyano group-2-fluoro-5-formyl radical-phenyl)-3 with 1.0g (2.93mmol); 6-dihydro-2, the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 150ml water, 0.58g (6mmol) thionamic acid and 0.54g (6mmol) Textone stirred about 24 hours.With mixture and ethyl acetate jolting, isolate organic phase afterwards afterwards, with dried over sodium sulfate and filtration.Solvent evaporated from filtrate carefully under pump vacuum.
Provide the 1-(4,5-is two-carboxyl-2-fluoro-phenyl)-3 of 0.90g (theoretical value 82%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine is the amorphous residue.
Embodiment 2
1-(4 with 0.80g (2.24mmol), 5-pair-carboxyl-2-fluoro-phenyl)-3,6-dihydro-2, the methyl-sulfate of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 0.70g (5mmol) salt of wormwood, 0.64g (5mmol) and the mixture of 20ml acetone boil about 20 hours of heating down in backflow.Under pump vacuum mixture is concentrated afterwards, residue is used the 2N hcl acidifying with the digestion of 50ml water, reclaims with the 4ml ether afterwards, and under agitation slowly dilutes with sherwood oil.The crystalline product of gained separates by suction filtration.
Provide the 1-(4,5-bi-methoxy carbonyl-2-fluoro-phenyl)-3 of 0.38g (theoretical value 42%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 141 ℃ of fusing points.
Embodiment 3
Figure A9719630200352
Elder generation is with the 1-(3-oxyethyl group sulfuryl amino-2-fluoro-4-thiocarbamoyl-phenyl)-3 of 4.5g (1.0mmol); 6-dihydro-2; 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine is added in the 50ml methylene dichloride, drips 1.5g (1.2mmol) methyl-sulfate and mixes.About 3 hours of reaction mixture reflux, and (about 20 ℃) restir 15 hours at room temperature.After adding other 0.5ml methyl-sulfate, the mixture reheat refluxed 5 hours, concentrated under pump vacuum subsequently.Residue stirs with ether, and the crystalline product of gained is separated by suction filtration.
Provide 1-(3-ethylsulfonyl amino-2-fluoro-4-(S-methyl-sulfo-imido acyl group-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 212 ℃ of the fusing points of 4.4g (theoretical value 94%) thus.
Be similar to preparation embodiment 1 to 3, and the general description of method produced according to the present invention, also make the formula I compound of for example listing in the table 1.
Figure A9719630200361
Table 1: formula I examples for compounds
Figure A9719630200362
Figure A9719630200381
The formula II starting raw material
Embodiment (II-1)
Figure A9719630200382
Step 1
Figure A9719630200383
Under agitation; the pivalyl chloride of 0.17g (1.2mmol) is joined the 1-(4-cyano group-2-fluoro-5-trifluoroacetyl group amino-phenyl)-3 of 0.50g (1.2mmol); 6-dihydro-2; in the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 1ml triethylamine and 50ml acetonitrile; and reaction mixture stirred 18 hours down at 20 ℃, and 60 ℃ of following restir 15 hours.Afterwards mixture is concentrated under pump vacuum, residue is with 1N hydrochloric acid/ethyl acetate jolting, and isolates organic phase, with dried over sodium sulfate and filter.Filtrate concentrates under pump vacuum, and residue is by column chromatography aftertreatment (silica gel, chloroform/ethyl acetate, volume ratio 1: 1).
Except unreacted 1-(4-cyano group-2-fluoro-5-trifluoroacetyl group amino-phenyl)-3; 6-dihydro-2; 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine (first step part: 0.30g); also obtain the 1-(4-cyano group-2-fluoro-5-amino-phenyl)-3 of second stage part 0.2g (theoretical value 50%); 6-dihydro-2; 6-oxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, fusing point: 195 ℃.
Step 2
Figure A9719630200391
The nitrite tert-butyl of 1.8g (21mmol) methyl acrylate, 1.6g (15.5mmol), the cupric chloride (II) of 1.6g (12mmol) and the mixture of 50ml acetonitrile are cooled to about 0 ℃, and under this temperature, drip the 1-(5-amino-4-cyano group-2-fluoro-phenyl)-3 of 3.3g (10mmol), 6-dihydro-2, the 20ml acetonitrile solution of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine.Allow this reaction mixture be warming up to room temperature, and under this temperature, stirred 18 hours.Behind the 1N hydrochloric acid that adds 20ml, with the mixture ethyl acetate extraction, the organic phase dried over sodium sulfate, and filter.Filtrate is concentrated, and residue is by the column chromatography aftertreatment.Provide 1-[4-cyano group-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl of 2.8g (theoretical value 65%) thus]-3,6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 46 ℃ of fusing points.
Stir down, to the 1-[4-cyano group that is cooled to 0 ℃ 2.0g (4.6mmol)-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-3, the N of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine and 30ml, add 0.22g sodium hydride (concentration 60%) in the mixture of dinethylformamide, and reaction mixture stirred 15 minutes down at 0 ℃ earlier, under 20 ℃, stirring about 60 minutes afterwards, and stirring 6 hours down at 60 ℃ at last.Afterwards mixture is concentrated under pump vacuum, residue stirs with isopropyl ether, and the crystalline product of gained separates with suction filtration.
Provide 1-[4-cyano group-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl-3 of 1.1g (theoretical value 60%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 154 ℃ of fusing points.
Step 3
To the 1-[4-cyano group that is cooled to the 8.7g (22mmol) under-70 ℃-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl]-3,6-dihydro-2 continues in the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine and 600ml methylene dichloride to import ozone 45 minutes.Remove cooling bath afterwards, and mixture is mixed with the 10ml dimethyl sulfide.After mixture is warming up to greenhouse (about 20 ℃), phase-splitting, organic phase washes with water, with dried over sodium sulfate and filtration.Filtrate concentrates under pump vacuum, and residue digests with ether, isolates crystalline product by suction filtration.
Provide the 1-(4-cyano group-2-fluoro-5-formyl radical-phenyl)-3 of 7.4g (theoretical value 99%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 177 ℃ of fusing points.Application Example: test solvent before the embodiment A bud: 5 parts of weight acetone emulsifying agents: 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.After about 24 hours, active agent preparations is sprayed on the soil with the required active compound amount of per unit area.Select the concentration of spraying fluid, active compound amount required under each situation is used with the 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, make infringement %.
Numerical value is meant:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, for example, under the amount of application of 60g/ha, for example prepare embodiment 2 compounds weeds are demonstrated very strong activity, belong to (100%) as wild avena sativa (80%), setaria (95%), abutilon (100%), Amaranthus (100%), Bedstraw (95%) and mustard.Test solvent behind the Embodiment B bud: 5 parts of weight acetone emulsifying agents: 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 test plant that highly is 5-15cm is sprayed with the required active compound amount of per unit area with active agent preparations.Select the concentration of spraying fluid, active compound amount required under each situation is used with the 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, make infringement %.
Numerical value is meant:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, for example, under the amount of application of 60g/ha, for example prepare embodiment 2 compounds weeds are demonstrated very strong activity, belong to (100%) as abutilon (100%), Amaranthus (100%), Bedstraw (90%) and mustard.

Claims (8)

1. the aromatic carbonyl compounds and the derivative thereof that lead to formula I
Figure A9719630200021
Wherein Q represents oxygen, sulphur or imino-(NH), R 1Represent hydrogen or halogen, R 2Represent following radicals
-A 1-A 2-A 3
Wherein
A 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-, R wherein 4Represent hydrogen, hydroxyl or be selected from following group: alkyl, alkoxyl group, aryl, alkyl sulphonyl and aryl sulfonyl,
A 1Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-, R wherein 5Represent hydrogen, hydroxyl or be selected from following group: alkyl, aryl, alkoxyl group, alkyl sulphonyl and aryl sulfonyl,
A 2Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A 3Represent hydrogen; hydroxyl; amino; cyano group; isocyano-; thiocyano; nitro; carboxyl; formamyl; thiocarbamoyl; sulfo group; chlorosulfonyl; halogen; or representative is selected from following group: alkyl; alkoxyl group; alkylthio; alkyl sulphinyl; alkyl sulphonyl; alkylamino; dialkyl amido; alkoxy carbonyl; the basic phosphoryl of dialkoxy (sulphur); alkenyl; alkenyloxy; alkenyl amino; alkylidene amino; the alkenyloxy carbonyl; alkynyl; alkynyloxy group; alkynyl amino; the alkynyloxy group carbonyl; cycloalkyl; cycloalkyl oxy; cycloalkylalkyl; cycloalkyl alkoxy; cycloalkylidene amino; the cycloalkyl oxy carbonyl; cycloalkyl alkoxy carbonyl; aryl; aryloxy; aralkyl; aralkoxy; aryloxycarbonyl; aromatic alkoxy carbonyl; heterocyclic radical; the heterocyclic radical alkyl; heterocyclic radical alkoxyl group or heterocyclic radical alkoxy carbonyl; they each can choose wantonly and be substituted
R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they each can choose wantonly be substituted and
Z representative is selected from following monocycle or double-ring is saturated or unsaturated group: heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they each can choose wantonly and be substituted,
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
2. according to the aromatic carbonyl compounds of the logical formula I of claim 1, it is characterized in that,
Q represents oxygen, sulphur or imino-(NH),
R 1Represent hydrogen, fluorine, chlorine or bromine,
R 2Represent following radicals
-A 1-A 2-A 3
Wherein
A 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-, R wherein 4Represent hydrogen, hydroxyl or be selected from following group: C 1-C 4-alkyl, C 1-C 4-alkoxyl group, phenyl, C 1-C 4-alkyl sulphonyl and phenyl sulfonyl,
A 1Also representative is selected from following group: C 1-C 6-alkane two bases, C 2-C 6-alkene two bases, C 2-C 6-alkynes two bases, C 3-C 6-cycloalkyl two bases, C 3-C 6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace by fluorine or chlorine,
A 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-, R wherein 5Represent hydrogen, hydroxyl or be selected from following group: C 1-C 4-alkyl, C 1-C 4-alkoxyl group, phenyl, C 1-C 4-alkyl sulphonyl and phenyl sulfonyl,
A 2Also representative is selected from following group: C 1-C 6-alkane two bases, C 2-C 6-alkene two bases, C 2-C 6-alkynes two bases, C 3-C 6-cycloalkyl two bases, C 3-C 6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace by fluorine or chlorine,
A 3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl, formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen; or representative is selected from following group: the basic phosphoryl of alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylamino, dialkyl amido, alkoxy carbonyl and dialkoxy (sulphur), they each have 1 to 6 carbon atom and each can be chosen wantonly by halogen, C at moieties 1-C 4-alkoxyl group or C 1-C 4-Alkoximino replaces,
A 3Also representative is selected from following group: alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy carbonyl, alkynyl, alkynyloxy group, alkynyl amino and alkynyloxy group carbonyl, they each have on alkenyl, alkylidene group or alkynyl that 2 to 6 carbon atoms and each are optional to be replaced by halogen
A 3Also representative is selected from following group: cycloalkyl, cycloalkyl oxy, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy carbonyl and cycloalkyl alkoxy carbonyl, they each on alkyl group, have 1 to 4 carbon atom and each is optional by halogen, cyano group, carboxyl, C having 3 to 6 carbon atoms on the group of naphthene base and choose wantonly 1-C 4-alkyl and/or C 1-C 4-alkoxyl group-carbonyl substituted,
A 3Also represent each can choose wantonly by nitro, cyano group, carboxyl, halogen, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy and/or C 1-C 4-alkoxyl group-carbonyl substituted be selected from following group: phenyl, phenoxy group, phenyl-C 1-C 4-alkyl, phenyl-C 1-C 4-alkoxyl group, phenyloxycarbonyl and phenyl-C 1-C 4-alkoxy carbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, pyrazolyl-C 1-C 4-alkyl, furyl-C 1-C 4-alkyl, thienyl-C 1-C 4-alkyl, oxazolyl-C 1-C 4-alkyl, isoxazolyl-C 1-C 4-alkyl, thiazolyl-C 1-C 4-alkyl, pyridyl-C 1-C 4-alkyl, pyrimidyl-C 1-C 4-alkyl, pyrazolyl methoxyl group, furyl methoxyl group are represented perhydro pyranyl methoxyl group or pyridyl methoxyl group,
R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they respectively have 1 to 6 carbon atom on alkyl and each is optional by hydroxyl, cyano group, halogen, C 1-C 4-alkoxyl group or C 1-C 4-alkoxyl group-carbonyl substituted and
It respectively is monocycle or the saturated or unsaturated group of two ring-types that Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 6 carbon atoms and 1 to 4 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional at the most three be selected from-CO-,-CS-,-SO-and/or SO 2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they optional by-or a plurality ofly be selected from following group and replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, halogen, C 1-C 6(it can choose wantonly by halogen or C again-alkyl 1-C 4The replacement of-alkoxyl group), C 2-C 6-alkenyl and C 2-C 6-alkynyl (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkoxyl group and C 1-C 6(they respectively can choose wantonly by halogen or C again-alkoxyl group-carbonyl 1-C 4The replacement of-alkoxyl group), C 2-C 6-alkenyloxy and C 2-C 6-alkynyloxy group (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkylthio, C 2-C 6-alkenyl thio and and C 2-C 6-alkynes sulfenyl (they respectively can be chosen wantonly again by halogen and replace), C 1-C 6-alkylamino and two-(C 1-C 4-alkyl) amino, C 3-C 6-cycloalkyl and C 3-C 6-cycloalkyl-C 1-C 4(they respectively can choose wantonly by halogen and/or C again-alkyl 1-C 4The replacement of-alkyl), (they respectively can be chosen wantonly by nitro, cyano group, halogen, C again for phenyl, phenoxy group, thiophenyl, phenyl sulfinyl, phenyl sulfonyl and phenyl amino 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl group, C 1-C 4-halogenated alkoxy and/or C 1-C 4-alkoxyl group-carbonyl substituted),
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
3. according to the aromatic carbonyl compounds of the logical formula I of claim 1, it is characterized in that,
Q represents oxygen, sulphur or imino-(NH),
R 1Represent hydrogen, fluorine or chlorine,
R 2Represent following radicals:
-A 1-A 2-A 3
Wherein
A 1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 4-, R wherein 4Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl and ethylsulfonyl,
A 1Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases
A 2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO 2-,-CO-or group-N-R 5-, R wherein 5Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl, ethylsulfonyl, just-or sec.-propyl alkylsulfonyl and phenyl sulfonyl,
A 2Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases
A 3Represent hydrogen; hydroxyl; amino; cyano group; nitro; carboxyl; formamyl; sulfo group; fluorine; chlorine; bromine; representative is selected from following group: methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; just-; different-; secondary-or tert-pentyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; just-; different-; secondary-or uncle's pentyloxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; just-or the sec.-propyl sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the sec.-propyl alkylsulfonyl; methylamino; ethylamino; just-or sec.-propyl amino; just-; different-; secondary-and tertiary butyl amino; dimethylamino; diethylamino; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; the dimethoxy phosphoryl; the diethoxy phosphoryl; dipropoxy phosphoryl and diisopropoxy phosphoryl; they each can choose wantonly by fluorine; chlorine; methoxyl group; oxyethyl group; methoxyimino or ethoxy imino replace
A 3Also representative is selected from following group: propenyl, butenyl, propenyloxy group, butenyloxy, propenyl amino, butenyl amino, propylidene amino, butylidene amino, propenyloxy group carbonyl, butenyloxy carbonyl, proyl, butynyl, third alkynyloxy group, fourth alkynyloxy group, proyl amino, butynyl amino, the third alkynyloxy group carbonyl and fourth alkynyloxy group carbonyl, they each can choose wantonly by fluorine or chlorine and replace
A 3Also representative is selected from following group: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl oxygen base, cyclobutyl oxygen base, cyclopentyloxy, cyclohexyl oxygen base, the cyclopropyl methyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexyl methyl, cyclo propyl methoxy, cyclobutyl methoxy base, the cyclopentyl methoxyl group, the cyclohexyl methoxyl group, cyclopentylidene amino, cyclohexylidene amino, the cyclopentyloxy carbonyl, cyclohexyl oxygen base carbonyl, cyclopentyl methoxycarbonyl and cyclohexyl methoxycarbonyl, they each can choose wantonly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just-or sec.-propyl, methoxycarbonyl or ethoxy carbonyl replace
A 3Also representative is selected from following group: phenyl, phenoxy group, benzyl, styroyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl oxazolyl isoxazolyl, thiazolyl, isothiazolyl oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, the pyrazolyl methyl, furyl methyl, thienyl methyl oxazolyl methyl isoxazolyl methyl, the thiazolyl methyl, pyridylmethyl, Pyrimidylmethyl, the pyrazolyl methoxyl group, furyl methoxyl group and pyridyl methoxyl group, they each can choose wantonly by nitro, cyano group, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl, trifluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, difluoro-methoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxy carbonyl replace
R 3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methylthio group, ethylmercapto group, just-or iprotiazem base, methylamino, ethylamino, just-or sec.-propyl amino, they each can choose wantonly by hydroxyl, cyano group, fluorine, chlorine, methoxyl group, oxyethyl group, methoxycarbonyl or ethoxy carbonyl replace and
It respectively is monocycle shape or the saturated and unsaturated group of two ring-types that Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 5 carbon atoms and 1 to 3 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional to too many by two be selected from-CO-,-CS-,-SO-and/or SO 2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, fluorine, chlorine, bromine; Methyl, ethyl, just-or sec.-propyl, just-, different-, secondary-or the tertiary butyl, (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyl, butenyl, proyl and butynyl (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-and tert.-butoxy, methoxycarbonyl and ethoxy carbonyl (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyloxy group, butenyloxy, third alkynyloxy group and fourth alkynyloxy group (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methylthio group, ethylmercapto group, just-or the iprotiazem base, just-, different-, secondary-or uncle's butylthio, propylene sulfenyl, butylene sulfenyl, propine sulfenyl and butine sulfenyl (they each can choose wantonly again replace) by fluorine or chlorine; Methylamino, ethylamino, just-or sec.-propyl amino, just-, different-, secondary-or tertiary butyl amino, dimethylamino and diethylamino; Cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; the cyclopropyl methyl; cyclobutylmethyl; (they respectively can be chosen wantonly again by fluorine for cyclopentyl-methyl and cyclohexyl methyl; chlorine; methyl; ethyl; just-or the sec.-propyl replacement); phenyl; phenoxy group; thiophenyl; the phenyl sulfinyl; (they respectively can be chosen wantonly again by nitro for phenyl sulfonyl and phenyl amino; cyano group; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; trifluoromethyl; methoxyl group; oxyethyl group; just-or different-propoxy-; difluoro-methoxy; trifluoromethoxy; methoxycarbonyl or ethoxy carbonyl replace)
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
4. the method for the aromatic carbonyl compounds of formula I is led in preparation,
Figure A9719630200081
R wherein 1, R 2, R 3, Q and Z each as defined in claim 1, described method is characterised in that, makes the aromatics nitrile of logical formula II
Figure A9719630200082
R wherein 1, R 2With Z each as defined in claim 1
With water, hydrogen sulfide or ammonia react, and the general formula of gained (aromatic carboxylic acid's or derivatives thereof of I replacement a)
Figure A9719630200091
Wherein
Q, R 1, R 2With define in each claim 1 of Z
Change into the aromatic carbonyl compounds or derivatives thereof of the replacement consistent with the above-mentioned definition of formula I compound by ordinary method.
5. herbicidal composition is characterized in that, they contain the aromatic carbonyl compounds of the formula I of at least a claim 1.
6. prevent and treat the method for undesired plant, it is characterized in that, the formula I compound effects that makes claim 1 is in undesired plant and/or its dried rhizome of rehmannia of dwelling.
7. the formula I compound of claim 1 is prevented and treated the application of undesired plant.
8. prepare the method for herbicidal composition, it is characterized in that, with the formula I aromatic carbonyl compounds of claim 1 with expand agent and/or tensio-active agent and mix.
CN 97196302 1996-07-11 1997-07-01 Substituted aromatic carbonyl compounds and their derivatives Pending CN1225086A (en)

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