CN1894220A - Herbicidal pyrimidines - Google Patents
Herbicidal pyrimidines Download PDFInfo
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- CN1894220A CN1894220A CNA200480037819XA CN200480037819A CN1894220A CN 1894220 A CN1894220 A CN 1894220A CN A200480037819X A CNA200480037819X A CN A200480037819XA CN 200480037819 A CN200480037819 A CN 200480037819A CN 1894220 A CN1894220 A CN 1894220A
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Abstract
Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein R<1> is cyclopropyl optionally substituted with 1-5 R<5>, isopropyl optionally substituted with 1-5 R<6>, or phenyl optionally substituted with 1-3 R<7>; R<2> is ((O)jC(R<15>)(R<16>))kR; R is CO2H or a herbicidally effective derivative of CO2H; R<3> is halogen, cyano, nitro, OR<20>, SR<21> or N(R<22>)R<23>; R<4> is -N(R<24>)R<25> or -NO2; j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0; and R<5>, R<6>, R<7>, R<15>, R<16>, R<20>, R<21>, R<22>, R<23>, R<24> and R<25> are as defined in the disclosure. Also disclosed are compositions comprising the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I. Also disclosed are compositions comprising a compound of Formula I and at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.
Description
Invention field
The present invention relates to the salt that is fit on some pyrimidine, their the N-oxide compound, agricultural and composition and they are used to prevent and treat the method for unwanted plant.
Background of invention
The control of unwanted plant is very important in the process that realizes high crop yield.Wherein, especially in above-mentioned useful crop such as rice, soybean, sugar beet, corn, potato, wheat, barley, tomato and plantation crops, realize that optionally the growth of controlling weeds is in demand.Weeds uncontrolled growth in above-mentioned useful crop can cause the serious underproduction, thereby causes human consumer's cost to increase.The unwanted plant of non-crop zone control equally also is important.It is commercially available being used for the many products of above-mentioned purpose, but still needs more effective, cheap, low toxicity, environmentally safe or new compound with different modes of action.
The open text WO 92/05159-A of international patent application discloses the pyrimidine as plant protection product, particularly mycocide.The open text EP-136976-A2 of european patent application discloses the pyrimidine as plant-growth regulator.United States Patent (USP) 5,324,710 disclose the sulfonation heterocyclic carboxamide derivative of pyrimidine, as weedicide and growth regulator.
Summary of the invention
The present invention relates to a kind of formula I compound, comprise all geometrical isomers and steric isomer, the salt that their N-oxide compound or agricultural go up to be fit to contains their agricultural composition and they are as the purposes of weedicide.
Wherein
R
1Be randomly by 1-5 R
5The cyclopropyl that replaces is randomly by 1-5 R
6The sec.-propyl that replaces, or randomly by 1-3 R
7The phenyl that replaces;
R
2Be ((O)
iC (R
15) (R
16))
kR;
R is CO
2H or CO
2The effective derivative of the weeding of H;
R
3Be halogen, cyano group, nitro, OR
20, SR
21Or N (R
22) R
23
R
4Be-N (R
24) R
25Or-NO
2
Each R
5And R
6Be halogen, C independently
1-C
6Alkyl, C
1-C
6Haloalkyl, C
2-C
6Alkenyl, C
2-C
6Halogenated alkenyl, C
1-C
3Alkoxyl group, C
1-C
2Halogenated alkoxy, C
1-C
3Alkylthio or C
1-C
2Halogenated alkylthio;
Each R
7Be halogen, cyano group, nitro, C independently
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
6Cycloalkyl, C
3-C
6Halogenated cycloalkyl, C
1-C
4Hydroxyalkyl, C
2-C
4Alkoxyalkyl, C
2-C
4Halogenated alkoxy alkyl, C
2-C
4Alkenyl, C
2-C
4Halogenated alkenyl, C
3-C
4Alkynyl, C
3-C
4Halo alkynyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
2-C
4Alkenyl oxy, C
2-C
4Halogenated alkenyl oxy, C
3-C
4Alkynyloxy group, C
3-C
4Halo alkynyloxy group, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Halogenated alkyl sulfonyl, C
2-C
4Alkenyl thio, C
2-C
4Halogenated alkenyl sulfenyl, C
2-C
4Alkenyl sulfinyl, C
2-C
4Halogenated alkenyl sulfinyl, C
2-C
4Alkenyl alkylsulfonyl, C
2-C
4Halogenated alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfenyl, C
3-C
4Halo alkynyl sulfenyl, C
3-C
4Alkynyl sulfinyl, C
3-C
4Halo alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, C
3-C
4Halo alkynyl alkylsulfonyl, C
1-C
4Alkylamino, C
2-C
8Dialkyl amido, C
3-C
6Cycloalkyl amino, C
4-C
6(alkyl) cycloalkyl amino, C
2-C
6Alkyl-carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkyl amino carbonyl, C
3-C
6Trialkylsilkl, phenyl, phenoxy group and 5-or 6-unit hetero-aromatic ring, each phenyl, phenoxy group and 5-or 6-unit hetero-aromatic ring randomly are independently selected from R by 1-3
45Substituting group replace; Or
The R of two vicinities
7Lump together and be-OCH
2O-,-CH
2CH
2O-,-OCH (CH
3) O-,-OC (CH
3)
2O-,-OCF
2O-,-CF
2CF
2O-,-OCF
2CF
2O-or-CH=CH-CH=CH-;
R
15Be H, halogen, C
1-C
4Alkyl, C
1-C
4Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group or C
2-C
4The alkyl-carbonyl oxygen base;
R
16Be H, halogen, C
1-C
4Alkyl or C
1-C
4Haloalkyl; Or
R
15And R
16Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
R
20Be H, C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
21Be H, C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
22And R
23Be H or C independently
1-C
4Alkyl;
R
24Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl, randomly by 1-2 R
31The C that replaces
2-C
4Alkenyl or randomly by 1-2 R
32The C that replaces
2-C
4Alkynyl; Or R
24Be C (=O) R
33, nitro, OR
34, S (O)
2R
35, N (R
36) R
37Or N=C (R
62) R
63
R
25Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl or C (=O) R
33Or
R
24And R
25Lump together to being selected from-(CH
2)
4-,-(CH
2)
5-,-CH
2CH=CH-CH
2-and-(CH
2)
2O (CH
2)
2-group, each group is randomly by 1-2 R
38Replace; Or
R
24And R
25Lump together and be=C (R
39) N (R
40) R
41Or=C (R
42) OR
43
Each R
30, R
31And R
32Be halogen, C independently
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl;
Each R
33Be H, C independently
1-C
14Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenyl, phenoxy group or benzyloxy;
R
34Be H, C
1-C
4Alkyl, C
1-C
3Haloalkyl or CHR
66C (O) OR
67
R
35Be C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
36Be H, C
1-C
4Alkyl or C (=O) R
64
R
37Be H or C
1-C
4Alkyl;
Each R
38Be halogen, C independently
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl;
R
39Be H or C
1-C
4Alkyl;
R
40And R
41Be H or C independently
1-C
4Alkyl; Or
R
40And R
41Lump together and be-(CH
2)
4-,-(CH
2)
5-,-CH
2CH=CH-CH
2-or-(CH
2)
2O (CH
2)
2-;
R
42Be H or C
1-C
4Alkyl;
R
43Be C
1-C
4Alkyl;
Each R
45Be halogen, cyano group, nitro, C independently
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
6Cycloalkyl, C
3-C
6Halogenated cycloalkyl, C
2-C
4Alkenyl, C
2-C
4Halogenated alkenyl, C
3-C
4Alkynyl, C
3-C
4Halo alkynyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylamino, C
2-C
8Dialkyl amido, C
3-C
6Cycloalkyl amino, C
4-C
6(alkyl) cycloalkyl amino, C
2-C
4Alkyl-carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkyl amino carbonyl or C
3-C
6Trialkylsilkl;
R
62Be H, C
1-C
4Alkyl or randomly by 1-3 R
65The phenyl that replaces;
R
63Be H or C
1-C
4Alkyl; Or
R
62And R
63Lump together and be-(CH
2)
4-or-(CH
2)
5-;
R
64Be H, C
1-C
14Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenyl, phenoxy group or benzyloxy;
Each R
65Be CH independently
3, Cl or OCH
3
R
66Be H, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
R
67Be H, C
1-C
4Alkyl or benzyl;
J is 0 or 1; With
K is 0 or 1;
Condition is:
(a) when k is 0, j is 0 so;
(b) work as R
2Be CH
2OR
a, R wherein
aBe H, randomly when substituted alkyl or benzyl, R so
3Not cyano group;
(c) work as R
1During phenyl that to be each position replaced by Cl, so phenyl in contraposition also by R
7Replace;
(d) work as R
1Be by R in the contraposition
7During the phenyl that replaces, this R
7Not the tertiary butyl, cyano group or randomly substituted phenyl;
(e) work as R
1It is cyclopropyl or randomly by 1-5 R
6During the sec.-propyl that replaces, R is not C (=W) N (R so
b) S (O)
2-R
c-R
d, wherein W is O, S, NR
eOr NOR
eR
bBe hydrogen, C
1-C
4Alkyl, C
2-C
6Alkenyl or C
2-C
6Alkynyl; R
cBe direct key or CHR
f, O, NR
eOr NOR
eR
dBe randomly substituted heterocycle or the isocyclic aryl with 5-6 annular atoms, this group randomly condenses with fragrance or non-fragrant 5-or 6-unit ring; Each R
eBe H, C independently
1-C
3Alkyl, C
1-C
3Haloalkyl or phenyl; And R
fBe H, C
1-C
3Alkyl or phenyl; With
(f) formula I compound is not 6-amino-5-nitro-2-phenyl-4-pyrimidine diethyl malonate.
More specifically, the present invention relates to formula I compound, comprise that all geometry and steric isomer, its N-oxide compound or agricultural go up the salt that is fit to.The invention still further relates to the formula I compound that comprises herbicidally effective amount and the herbicidal composition of at least a tensio-active agent, solid diluent or liquid diluent.The invention still further relates to and comprise the method for preventing and treating undesired plant growth with formula I compound (for example, with composition as herein described) contact plant or its environment of herbicidally effective amount.The invention still further relates to a kind of Herbicidal mixture, comprise the formula I compound of herbicidally effective amount and significant quantity another is selected from the activeconstituents of other weedicides and herbicides and safeners at least.The invention still further relates to a kind of herbicidal composition, comprise the formula I compound of herbicidally effective amount, significant quantity another is selected from activeconstituents and at least a tensio-active agent, solid diluent or the liquid diluent of other weedicides and herbicides and safeners at least.
Detailed Description Of The Invention
Term used herein " comprises ", " containing ", " containing " " comprise ", " having ", " having " or any other variant, and the meaning is the mode that comprises that covers non-removing property.For example, the composition, process, method, article or the equipment that comprise a series of key elements needn't only limit to above-mentioned key element, also can comprise other key elements of the inherent of that other are not clearly listed or above-mentioned composition, process, method, article or equipment own.In addition, unless opposite statement is clearly arranged, " or " refer to comprising property rather than removing property.For example, it is that correct (or existence) and B are wrong (or non-existent) that condition A or B satisfy following arbitrary condition: A, and A is that wrong (or non-existent) and B are correct (or existence), and A and B are correct (or existence).
In addition, the indefinite article " " of above-mentioned key element of the present invention or component and " a kind of " meaning is nonrestrictive example about key element or the component number of (promptly existing).Therefore, " one " and " a kind of " should be understood to comprise a kind of or at least a, and the singulative of key element or component also comprise the plural number situation, unless the meaning of this numerical value is evident as odd number.
In statement above, term " alkyl " can use separately, also can use in as " alkylthio " or " haloalkyl " at portmanteau word, it comprises the straight or branched alkyl, as methyl, ethyl, n-propyl, sec.-propyl or different butyl, amyl group or hexyl isomer." alkenyl " comprises the alkene of straight or branched, as vinyl, 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomer." alkenyl " also comprises polyenoid, as 1, and 2-propadiene base and 2,4-hexadienyl." alkynyl " comprises the alkynes of straight or branched, as 1-proyl, 2-propynyl and different butynyl, pentynyl and hexin base isomer." alkynyl " also comprise and contain a plurality of triple-linked groups, as 2, and 5-hexadiyne base." alkoxyl group " comprise, for example methoxyl group, oxyethyl group, positive propoxy, isopropoxy and different butoxy, pentyloxy and hexyloxy isomer.The alkoxyl group that " alkoxyalkyl " refers on the alkyl replaces.The example of " alkoxyalkyl " comprises CH
3OCH
2, CH
3OCH
2CH
2, CH
3CH
2OCH
2And CH
3CH
2OCH
2CH
2" alkenyl oxy " comprises the alkenyl oxy part of straight or branched.The example of " alkenyl oxy " comprises H
2C=CHCH
2O, (CH
3) CH=CHCH
2O and CH
2=CHCH
2CH
2O." alkynyloxy base " comprises the alkynyloxy base section of straight or branched.The example of " alkynyloxy base " comprises HC ≡ CH
2O and CH
3C ≡ CCH
2O." alkylthio " comprises the alkylthio part of side chain or straight chain, for example methylthio group, ethylmercapto group and different rosickyite base and butylthio isomer." alkyl sulphinyl " comprises whole two kinds of enantiomorphs of alkyl sulphinyl.The example of " alkyl sulphinyl " comprises CH
3S (O), CH
3CH
2S (O), CH
3CH
2CH
2S (O), (CH
3)
2CHS (O) and different butyl sulfinyl isomer.The example of " alkyl sulphonyl " comprises CH
3S (O)
2, CH
3CH
2S (O)
2, CH
3CH
2CH
2S (O)
2, (CH
3)
2CHS (O)
2With different butyl alkylsulfonyl isomer." alkylamino ", " dialkyl amido ", " alkenyl thio ", " alkenyl sulfinyl ", " alkenyl alkylsulfonyl ", " alkynyl sulfenyl ", " alkynyl sulfinyl ", " alkynyl alkylsulfonyl " etc. define similarly according to above-mentioned example." cycloalkyl " comprise, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.The example of " cycloalkylalkyl " comprises cyclopropyl methyl, cyclopentyl ethyl and is bonded to other cycloalkyl moieties on the straight or branched alkyl.The alkyl that " alkyl-cycloalkyl " refers on the cycloalkyl moiety replaces.Example comprises 4-methylcyclohexyl and 3-ethyl cyclopentyl.Term " hetero-aromatic ring " comprises the heterocycle of complete fragrance." fragrance " or " virtue " refers to each annular atoms basically on same plane, and has the p track perpendicular to plane of a loop, wherein meets H ü ckel rule with relevant (4n+2) individual πDian Zi of ring (n be 0 or positive integer).The aryl of term isocyclic aryl and term carbocyclic ring type is a synonym.Multiple synthetic method is known in this area, in order to prepare fragrant heterocycle; Summary is referring to the Comprehensive Heterocyclic Chemistry of eight volumes, one cover, editor-in-chief A.R.Katritzky and C.W.Rees, Pergamon Press, Oxford, 1984, ComprehensiveHeterocyclic Chemistry II with 12 volumes, one cover, editor-in-chief A.R.Katritzky, C.W.Rees and E.F.V.Scriven, Pergamon Press, Oxford, 1996.Statement R
75-or 6-unit hetero-aromatic ring generally comprise 1-4 heteroatomic ring member, described heteroatoms member is selected from 0-4 N, a 0-1 O and 0-1 S atom.Row group 1 has been listed the example of hetero-aromatic ring; H-1 to H-55 is interpreted as illustration, rather than the hetero-aromatic ring in the restriction scope of the invention.
Row group 1
Wherein
Each R
71Be R independently
45
R
71a, R
72And R
73Be H or R independently
45
P is the integer of 0-3; With
Q is the integer of 0-2.
This paper relates to R
7The H-1 to H-55 of group refers to those groups shown in the row group 1.
Skilled person in the art will appreciate that not every nitrogen heterocyclic ring can form the N-oxide compound, because nitrogen-atoms needs the available lone-pair electron that are oxidized to oxide compound; Those skilled in the art will know that those can form the nitrogen heterocyclic ring of N-oxide compound.Those skilled in the art know that also tertiary amine can form the N-oxide compound.The synthetic method of the N-oxide compound of preparation heterocycle and tertiary amine is that those skilled in the art know very much, comprise heterocycle and tertiary amine peroxy acid such as Peracetic Acid and metachloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxide such as tert-butyl hydroperoxide, Sodium peroxoborate and dioxirane class such as the oxidation of dimethyl dioxirane.The method of the above-mentioned N-of preparation oxide compound has had in the literature to be described widely and summarizes, referring to for example: T.L.Gilchrist, Comprehensive Organic Synthesis, vol.7, pp 748-750, S.V.Ley, Ed., Pergamon Press; M.Tisler and B.Stanovnik, Comprehensive Heterocyclic Chemistry, vol.3, pp 18-20, A.J.Boulton and A.McKillop, Eds., Pergamon Press; M.R.Grimmett and B.R.T.Keene, Advances in Heterocyclic Chemistry, vol.43, pp 149-161, A.R.Katritzky, Ed., Academic Press; M.Tisler and B.Stanovnik, Advancesin Heterocyclic Chemistry, vol.9, pp 285-291, A.R.Katritzky and A.J.Boulton, Eds., Academic Press; And G.W.H.Cheeseman and E.S.G.Werstiuk, Advances in Heterocyclic Chemistry, vol.22, pp 390-392, A.R.Katritzky and A.J.Boulton, Eds., Academic Press.
Term " halogen ", independent or portmanteau word as " haloalkyl " in, comprise fluorine, chlorine, bromine or iodine.And when portmanteau word used in as " haloalkyl ", described alkyl can partially or even wholly be replaced by halogen atom, and halogen atom can be identical or different.The example of " haloalkyl " comprises F
3C, ClCH
2, CF
3CH
2And CF
3CCl
2The definition of term " halogenated alkenyl ", " halo alkynyl ", " halogenated alkoxy ", " halogenated alkylthio " etc. is similar with " haloalkyl ".The example of " halogenated alkenyl " comprises (Cl)
2C=CHCH
2And CF
3CH
2CH=CHCH
2The example of " halo alkynyl " comprises HC ≡ CCHCl, CF
3C ≡ C, CCl
3C ≡ C and FCH
2C ≡ CCH
2The example of " halogenated alkoxy " comprises CF
3O, CCl
3CH
2O, HCF
2CH
2CH
2O and CF
3CH
2O.The example of " halogenated alkylthio " comprises CCl
3S, CF
3S, CCl
3CH
2S and ClCH
2CH
2CH
2S.The example of " haloalkyl sulfinyl " comprises CF
3S (O), CCl
3S (O), CF
3CH
2S (O) and CF
3CF
2S (O).The example of " halogenated alkyl sulfonyl " comprises CF
3S (O)
2, CCl
3S (O)
2, CF
3CH
2S (O)
2And CF
3CF
2S (O)
2
The sum of the carbon atom in the substituting group " C
i-C
j" prefix represents that wherein i and j are the numerical value of 1-14.C for example
1-C
3Alkyl sulfonyl basis representation methylsulfonyl to the third alkylsulfonyl; C
2Alkoxyalkyl is represented CH
3OCH
2C
3Alkoxyalkyl represents, for example CH
3CH (OCH
3), CH
3OCH
2CH
2Or CH
3CH
2OCH
2And C
4Alkoxyalkyl represents to contain altogether the various isomer of the alkyl that the alkoxyl group of 4 carbon atoms replaces, and example comprises CH
3CH
2CH
2OCH
2And CH
3CH
2OCH
2CH
2The example of " alkyl-carbonyl " comprises C (O) CH
3, C (O) CH
2CH
2CH
3And C (O) CH (CH
3)
2The example of " alkoxy carbonyl " comprises CH
3OC (=O), CH
3CH
2OC (=O), CH
3CH
2CH
2OC (=O), (CH
3)
2CHOC (=O) with different butoxy or pentyloxy carbonyl isomer.In statement above, when formula I compound comprised one or more heterocycle, all substituting groups were connected on the above-mentioned ring by described carbon or nitrogen by replacing the hydrogen on any available carbon or the nitrogen.
When compound is had subscript (for example, (R
d)
1-3) substituting group when replacing, the numerical value of represent this substituent example (i.e. existence) can change or before use numerical range (1-3 R for example
d) represent that the substituting group of this substituting group example value can change, so when the value of this example greater than 1 the time, each example is independently selected from the defined group of this substituting group.In addition, when subscript is represented a scope, for example, (R
d)
I-j, the integer of (containing end value) between optional comfortable i of the numerical value of substituting group example and the j so.
When containing in the group can be for the substituting group of hydrogen the time, R for example
15Or R
34, when this substituting group is hydrogen, can think that it is unsubstituted being equivalent to described group so.
Can there be one or more steric isomers in The compounds of this invention.Various steric isomers comprise enantiomorph, diastereomer, atropisomer and geometrical isomer.Skilled person in the art will appreciate that when a kind of steric isomer more or when from other isomer, separating with respect to other content of isomer, this isomer can have higher active and/or show favourable effect.In addition, those skilled in the art also know how to separate, concentrate and/or optionally prepare described steric isomer.Therefore, the present invention includes the compound, its N-oxide compound and the agricultural thereof that are selected from formula I and go up the salt that is fit to.Compound of the present invention can be the mixture of steric isomer, single steric isomer, or exists to have optically active form.
Wherein R is CO
2The formula I compound of H (being carboxylic acid functional) is considered to cause in conjunction with the avtive spot of plant enzyme or acceptor the compound of the herbicidal effect of plant.Other substituent R wherein is that can be converted into carboxylic acid functional in plant materials or in the environment be CO
2The formula I compound of H also has similar herbicidal effect, comprises within the scope of the invention.Therefore, when being used for describing the substituent R of formula I, " CO
2The effective derivative of the weeding of H " be defined as arbitrary salt, ester, carboxylic acid amides, hydrazides, imidate, thioimidate, amidine, acyl halide, acyl cyanide, acid anhydrides, ether, acetal, ortho ester, carboxylic aldehyde, oxime, hydrazone, thioic acid sulfoacid, thioesters, dithioesters (dithiolester), nitrile or known in the art can not reduce the weeding activity of formula I compound and can be hydrolyzed in plant materials or in the soil, oxidation, reduction or other metabolism obtain carboxylic acid functional arbitrary other carboxylic acid derivative; according to pH, can be to dissociate or non-dissociated form.
The salt that is fit on the agricultural of The compounds of this invention is by contacting with acid or alkali or by the salt that ion-exchange forms, make institute's deutero-salt keep enough solvabilities that is used for biological utilisation, thereby keep herbicidal effect, making the counter ion of salt be suitable for agricultural application.The salt that is fit on the agricultural of The compounds of this invention comprises and mineral acid or organic acid acid salt, as Hydrogen bromide, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetate, butyric acid, fumaric acid, lactic acid, toxilic acid, propanedioic acid, oxalic acid, propionic acid, Whitfield's ointment, tartrate, 4-toluenesulphonic acids or valeric acid.The salt that is fit on the agricultural of The compounds of this invention also comprises the salt that those and highly basic (for example, sodium hydroxide, potassium hydroxide, lithium hydroxide or ammonium hydroxide) or amine form.One skilled in the art will appreciate that the salt of The compounds of this invention and their corresponding salt-independent shapes are equilibrated because under environment and physiological condition, the salt that is fit on the agricultural has been shared the biological effectiveness of salt-independent shape.
Useful especially is that wherein R is CO
2H (comprises R wherein
2Be CO
2H) salt that is fit on the agricultural that formula I compound and highly basic or amine form.Known in this field, hydroxy-acid group (CO
2H) contact with alkali and slough proton and obtain corresponding carboxylic acid radical ion (CO
2 _), the general counter ion that from alkali, derive positively charged.The R that a large amount of counter ion form wherein is CO
2The salt that is fit on the agricultural of the formula I compound of H, most of institute deutero-salt has the solvability of enough biological utilisations.It is CO that illustrative and particularly importantly following wherein R are arranged
2The salt of the formula I compound of H, counter ion wherein are alkali metal cation such as lithium, sodium or potassium, quaternary ammonium such as tetramethyl-ammonium, and ternary sulfonium such as trimethylsulfonium, or derive by amine such as dimethyl amine, diethanolamine, trolamine.
Also useful especially is that wherein R is CO
2The ester and the thioes derivatives of the formula I compound of H.Known in this field, ester group (is CO
2R
AL) by carboxylic acid functional (CO
2H) (be R with alcohol
ALOH) condensation, wherein R
ALBe by pure deutero-group; The method of the above-mentioned ester of multiple preparation is known.Similarly, formula C (O) SR
ALThioester group at conceptive carboxylic acid functional and the formula R of can be considered
ALThe condensation product of the mercaptan of SH; The method of the above-mentioned thioesters of multiple preparation is known.Because wherein R is CO
2The formula I compound of H has weeding activity, and its deutero-ester and thioesters are easy to hydrolysis (for R is CO
2H), especially in the presence of lytic enzyme, so, R wherein
1Be that ester (is CO
2R
AL) or thioesters (be C (O) SR
AL) formula I compound generally be used as weedicide.At CO
2In the effective derivative of the weeding of H, ester and thioes derivatives, particularly ester derivative are to be easy to most prepare with useful.If radicals R
ALHave more than one OH or SH functional group, this group can be CO with R so
2Pyrimidine ring system condensation in the formula I compound of H above one.The derivative hydrolyzable of the multiple esterification of institute's deutero-is that R is CO
2The formula I compound of H, the derivative of this multiple esterification are the effective CO of weeding
2The derivative of H.The ester and the thioesters of illustrative and importantly following formula I compound are arranged, and wherein are CO
2The R of H and methyl alcohol, ethanol, butanols, butoxy ethanol, 2-Ethylhexyl Alcohol, Virahol, 2-methylpropanol (isopropylcarbinol), octanol isomer (isooctyl alcohol) and sulfur alcohol esterification form methyl esters, ethyl ester, butyl ester, 2-butoxy ethyl ester, 2-ethylhexyl, isopropyl ester, 2-methyl propyl ester, monooctyl ester and sulfur alcohol ester respectively.Particularly importantly methyl esters and ethyl ester.
Embodiment of the present invention comprise:
The compound of embodiment 1. formula I, wherein j is 0.
The compound of embodiment 2. formula I, wherein k is 0.
The compound of embodiment 3. formula I, wherein R
15Be H.
The compound of embodiment 4. embodiments 3, wherein R
16Be H.
The compound of embodiment 5. formula I, wherein
R is CO
2R
12, CH
2OR
13, CH (OR
46) (OR
47), CHO, C (=NOR
14) H, C (=NNR
48R
49) H, C (=O) N (R
18) R
19, C (=S) OR
50, C (=O) SR
51, C (=S) SR
52Or C (=NR
53) YR
54
R
12Be H ,-CH_C (O) O (CH
2)
m_ ,-N=C (R
55) R
56Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl, C
2-C
14Alkynyl and phenyl groups, each group are randomly by 1-3 R
27Replace; Or
R
12Be each the CO of carboxylicesters functional group in two pyrimidine ring systems among the bonded I
2R
12Divalent group, this divalent group is selected from-CH
2-,-(CH
2)
2-,-(CH
2)
3-and-CH (CH
3) CH
2-;
R
13Be H, randomly by 1-3 R
28The C that replaces
1-C
10Alkyl or benzyl;
R
14Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl or benzyl;
R
18Be H, C
1-C
4Alkyl, hydroxyl, C
1-C
4Alkoxyl group or S (O)
2R
57
R
19Be H or C
1-C
4Alkyl;
Each R
27Be halogen, cyano group, hydroxycarbonyl group, C independently
2-C
4Alkoxy carbonyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido ,-CH_O (CH
2)
n_ or randomly by 1-3 R
44The phenyl that replaces; Or
Two R
27Lump together for-OC (O) O-or-O (C (R
58) (R
58))
1-2O-; Or
Two R
27Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
28Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido; Or
Two R
28Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
44Be halogen, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or nitro;
R
46And R
47Be C independently
1-C
4Alkyl or C
1-C
3Haloalkyl; Or
R
46And R
47Lump together and be-CH
2CH
2-,-CH
2CH (CH
3)-or-(CH
2)
3-;
R
48Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
2-C
4Alkyl-carbonyl, C
2-C
4Alkoxy carbonyl or benzyl;
R
49Be H, C
1-C
4Alkyl or C
1-C
4Haloalkyl;
R
50, R
51And R
52Be H; Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl and C
2-C
14The group of alkynyl, each group are randomly by 1-3 R
27Replace;
Y is O, S or NR
61
R
53Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, C
2-C
4Alkoxyalkyl, OH or C
1-C
3Alkoxyl group;
R
54Be C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl; Or
R
53And R
54Lump together and be-(CH
2)
2-,-CH
2CH (CR
3)-or-(CH
2)
3-;
R
55And R
56Be C independently
1-C
4Alkyl;
R
57Be C
1-C
4Alkyl, C
1-C
3Haloalkyl or NR
59R
60
Each R
58Be independently selected from H and C
1-C
4Alkyl;
R
59And R
60Be H or C independently
1-C
4Alkyl;
R
61Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl;
M is the integer of 2-3; With
N is the integer of 1-4.
The compound of embodiment 6. formula I is wherein worked as R
1When being randomly substituted cyclopropyl, R so
2Not alkoxyalkyl or alkylthio alkyl.
The compound of embodiment 7. formula I, wherein R
2Not alkoxyalkyl or alkylthio alkyl.
The compound of embodiment 8. embodiments 5, wherein
R
2Be CO
2R
12, CH
2OR
13, CH (OR
46) (OR
47), CHO, C (=NOR
14) H, C (=NNR
48R
49) H, (O)
jC (R
15) (R
16) CO
2R
17, C (=O) N (R
18) R
19, C (=S) OR
50, C (=O) SR
51, C (=S) SR
52Or C (=NR
53) YR
54
R
17Be randomly by 1-3 R
29The C that replaces
1-C
10Alkyl, or benzyl; With
Each R
29Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido.
The compound of embodiment 9. embodiments 8 is wherein worked as R
3Be CH
2OR
13The time, R so
13It or not alkyl.
The compound of embodiment 10. embodiments 8 is wherein worked as R
3Be CH
2OR
13The time, R so
13It or not randomly substituted alkyl.
The compound of embodiment 11. embodiments 8, wherein R
3Not CH
2OR
13
The compound of embodiment 12. embodiments 8, wherein j is 0.
The compound of embodiment 13. embodiments 12, wherein R
2Be CO
2R
12, CH
2OR
13, CHO or CH
2CO
2R
17
The compound of embodiment 14. embodiments 13, wherein R
2Be CO
2R
12
The compound of embodiment 15. embodiments 14, wherein R
12Be H, C
1-C
8Alkyl or the C that is replaced by phenyl
1Alkyl, this phenyl are randomly by 1-3 R
44Replace.
The compound of embodiment 16. embodiments 15, wherein R
12Be H, C
1-C
4Alkyl or the C that is replaced by phenyl
1Alkyl, this phenyl are randomly by 1-3 R
44Replace.
The compound of embodiment 17. embodiments 16, wherein R
12Be H, C
1-C
4Alkyl or benzyl.
The compound of embodiment 18. formula I, wherein R
2Be CO
2H, its agricultural goes up salt or its ester or the thioes derivatives that is fit to.
The compound of embodiment 19. embodiments 18, wherein R
2Be CO
2H, its agricultural goes up salt or the ester derivative that is fit to.
The compound of embodiment 20. formula I, wherein R
1Be randomly by 1-5 R
5The cyclopropyl that replaces.
The compound of embodiment 21. formula I, wherein R
1Be randomly by 1-5 R
6The sec.-propyl that replaces.
The compound of embodiment 22. formula I, wherein R
1Be randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 23. formula I, wherein R
1Be randomly by 1-5 R
5The cyclopropyl that replaces or randomly by 1-5 R
6The sec.-propyl that replaces.
The compound of embodiment 24. formula I, wherein R
1Be randomly by 1-5 R
5The cyclopropyl that replaces or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 25. formula I, wherein R
1Be randomly by 1-5 R
6The sec.-propyl that replaces or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 26. formula I, wherein R
1It or not cyclopropyl.
The compound of embodiment 27. formula I, wherein R
1Be randomly by 1-2 R
6The cyclopropyl that replaces or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 28. embodiments 27, wherein R
1Be randomly by 1-2 R
6The cyclopropyl that replaces.
The compound of embodiment 29. embodiments 27, wherein R
1Be cyclopropyl, or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 30. embodiments 28, wherein R
1It is cyclopropyl.
The compound of embodiment 31. embodiments 27, wherein R
1Be randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 32. embodiments 27, wherein R
1Be cyclopropyl, or in contraposition by R
7Group replace and randomly in other positions by 1-2 R
7The phenyl that replaces.
The compound of embodiment 33. embodiments 32, wherein R
1Be cyclopropyl, or contraposition replaced by halogen, methyl or methoxy and randomly in other positions by 1-2 the phenyl that group replaced that is selected from halogen and methyl.
The compound of embodiment 34. embodiments 33, wherein R
1Be cyclopropyl, or replaced and randomly be selected from by 1-2 the phenyl that group replaced of halogen and methyl in contraposition by halogen in other positions.
The compound of embodiment 35. embodiments 34, wherein R
1Be cyclopropyl, or contraposition replaced by Br or Cl and randomly in other positions by 1-2 the phenyl that group replaced that is selected from halogen and methyl.
The compound of embodiment 36. embodiments 35, wherein R
1It is the phenyl that is replaced by Br or Cl and randomly replaced by 1-2 group that is selected from halogen and methyl in contraposition in other positions.
The compound of embodiment 37. embodiments 35, wherein R
1Be cyclopropyl or the phenyl that in contraposition, replaced by Br or Cl.
The compound of embodiment 38. embodiments 37, wherein R
1Be by the phenyl of Br or Cl replacement in contraposition.
The compound of embodiment 39. formula I, wherein R
7Not cyano group.
The compound of embodiment 40. formula I, wherein R
7It or not randomly substituted phenyl, phenoxy group and 5-and 6-unit hetero-aromatic ring.
The compound of embodiment 41. formula I, wherein each R
7Be independently selected from halogen, C
1-C
2Alkyl, C
1-C
2Haloalkyl, C
1-C
2Alkoxyl group or C
1-C
2Halogenated alkoxy; Or the R of two vicinities
7Lump together and be-OCH
2O-,-CH
2CH
2O-,-OCH (CH
3) O-,-OC (CH
3)
2O-,-OCF
2O-,-CF
2CF
2O-,-OCF
2CF
2O-or-CH=CH-CH=CH-.
The compound of embodiment 42. embodiments 41, wherein each R
7Be independently selected from halogen, C
1-C
2Alkyl, C
1-C
2Haloalkyl, C
1-C
2Alkoxyl group or C
1-C
2Halogenated alkoxy; Or the R of two vicinities
7Lump together and be-OCH
2O-,-CH
2CH
2O-,-OCH (CH
3) O-or-OCF
2O-.
The compound of embodiment 43. embodiments 42, wherein each R
7Be independently selected from halogen, C
1-C
2Alkyl, C
1Fluoro-alkyl, C
1-C
2Alkoxyl group or C
1Fluoroalkyl.
The compound of embodiment 44. formula I, wherein each R
7Be independently selected from halogen, methyl and methoxyl group.
The compound of embodiment 45. embodiments 44, wherein each R
7Be independently selected from halogen and methyl.
The compound of embodiment 46. embodiments 45, wherein each R
7Be independently selected from F, Cl and Br.
The compound of embodiment 47. embodiments 46, wherein each R
7Be independently selected from Cl and Br.
The compound of embodiment 48. formula I, wherein R
3Not cyano group.
The compound of embodiment 49. formula I, wherein R
3It or not nitro.
The compound of embodiment 50. formula I, wherein R
3Be halogen, nitro, OR
20, SR
21Or N (R
22) R
23
The compound of embodiment 51. embodiments 50, wherein R
3It is halogen.
The compound of embodiment 52. embodiments 51, wherein R
3Be Br or Cl.
The compound of embodiment 53. embodiments 52, wherein R
3Be Cl.
The compound of embodiment 54. formula I, wherein R
4Be-N (R
24) R
25
The compound of embodiment 55. formula I, wherein R
24Not randomly by 1-2 R
32The C that replaces
2-C
4Alkynyl.
The compound of embodiment 56. formula I, wherein R
24Be H, C (O) R
33Or randomly by R
30The C that replaces
1-C
4Alkyl; R
25Be H or C
1-C
2Alkyl; Or R
24And R
25Lump together and be=C (R
39) N (R
40) R
41
The compound of embodiment 57. embodiments 56, wherein R
24Be H, C (O) CH
3Or randomly by R
30The C that replaces
1-C
4Alkyl; And R
25Be H or C
1-C
2Alkyl.
The compound of embodiment 58. embodiments 57, wherein R
24And R
25Be H or methyl independently.
The compound of embodiment 59. embodiments 58, wherein R
24And R
25Be H.
The compound of embodiment 60. formula I, wherein R
30Be halogen, methoxyl group, C
1Fluoroalkyl, methylthio group, C
1Fluoroalkane sulfenyl, amino, methylamino, dimethylamino or methoxycarbonyl.
The compound of embodiment 61. formula I, wherein R
33Be H or C
1-C
3Alkyl.
The compound of embodiment 62. embodiments 61, wherein R
33Be CH
3
The compound of embodiment 63. formula I, wherein R
39Be H or C
1-C
2Alkyl.
The compound of embodiment 64. formula I, wherein R
40And R
41Be H or C independently
1-C
2Alkyl.
The compound of embodiment 65. formula I, wherein R
3Not OH.
The compound of embodiment 66. formula I, wherein R
3Not OR
20
The compound of embodiment 67. formula I, wherein working as j is 1, and R
1By at least one is the R of halogen
6During the sec.-propyl that replaces, R so
24And R
25Be H.
The compound of embodiment 68. formula I, wherein working as j is 1, and R
1When being randomly substituted sec.-propyl, R so
24And R
25Be H.
The compound of embodiment 69. formula I, wherein when j is 1, R so
24And R
25Be H.
The compound of embodiment 70. formula I, wherein when j is 1, R so
6It or not halogen.
The compound of embodiment 71. formula I, wherein when j is 1, R so
1It or not randomly substituted sec.-propyl.
The compound of embodiment 72. formula I, wherein when j is 1, R so
1Be randomly by 1-5 R
5The cyclopropyl that replaces, sec.-propyl, or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 73. formula I, wherein when j is 1, R so
1Be cyclopropyl, sec.-propyl or randomly by 1-3 R
7The phenyl that replaces.
The compound of embodiment 74. formula I is wherein worked as R
1Be randomly by 1-3 R
7During the phenyl that replaces, R is not a cyano group.
The compound of embodiment 75. formula I, wherein R is not a cyano group.
The compound of embodiment 76. embodiments 5 is wherein worked as R
1Be randomly by 1-3 R
7During the phenyl that replaces, R is CO so
2R
12
The compound of embodiment 77. embodiments 5, wherein R is CO
2R
12
The compound of embodiment 78. embodiments 8 is wherein worked as R
1Be randomly by 1-3 R
7During the phenyl that replaces, R so
2Be CO
2R
12
The compound of embodiment 79. embodiments 8, wherein R
2Be CO
2R
12
The compound of embodiment 80. formula I is wherein worked as R
1Be randomly by 1-3 R
7During the phenyl that replaces, R so
24Be H, C (=O) R
33, nitro, OR
34, S (O)
2R
35Or N (R
36) R
37, and R
25Be H or C (=O) R
33
The compound of embodiment 81. formula I is wherein worked as R
1Be randomly by 1-3 R
7During the phenyl that replaces, R so
24And R
25Be H.
The compound of embodiment 82. formula I, wherein R
24Be H, C (=O) R
33, nitro, OR
34, S (O)
2R
35Or N (R
36) R
37, and R
25Be H or C (=O) R
33
The compound of embodiment 83. formula I, wherein R
24And R
25Be H.
The compound of embodiment 84. formula I is wherein worked as R
1It is cyclopropyl or randomly by 1-5 R
6During the sec.-propyl that replaces, R is not C (=W so
l) N (R
Bl) S (O)
2-R
Cd, wherein W comprises at least one atom; R
BlComprise at least one atom and R
CdComprise at least one atom.
The compound of embodiment 85. formula I is wherein worked as R
1Be randomly by 1-5 R
5The cyclopropyl that replaces or randomly by 1-5 R
6During the sec.-propyl that replaces, R is not C (=W so
l) N (R
Bl) S (O)
2-R
Cd, wherein W comprises at least one atom; R
BlComprise at least one atom and R
CdComprise at least one atom.
The compound of embodiment 86. formula I, wherein R is not C (=W
l) N (R
Bl) S (O)
2-R
Cd, wherein W comprises at least one atom; R
BlComprise at least one atom and R
CdComprise at least one atom.
The compound of embodiment 87. embodiments 5, wherein R
18Be H, C
1-C
4Alkyl, hydroxyl or C
1-C
4Alkoxyl group.
The compound of embodiment 88. embodiments 8, wherein R
18Be H, C
1-C
4Alkyl, hydroxyl or C
1-C
4Alkoxyl group.
The compound of embodiment 89. formula I, wherein each R
5And R
6Be halogen, C independently
1-C
2Alkyl or C
1-C
2Haloalkyl.
The compound of embodiment 90. formula I, wherein R
15Be H, halogen, C
1-C
4Alkyl, C
1-C
4Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group or C
2-C
4The alkyl-carbonyl oxygen base.
The compound of embodiment 91. formula I, wherein R
16Be H, halogen, C
1-C
4Alkyl or C
1-C
4Haloalkyl.
The compound of embodiment 92. formula I, wherein R
24Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl, randomly by 1-2 R
31The C that replaces
2-C
4Alkenyl or randomly by 1-2 R
32The C that replaces
2-C
4Alkynyl; Or R
24Be C (=O) R
33, nitro, OR
34, S (O)
2R
35Or N (R
36) R
37
The compound of embodiment 93. formula I, wherein each R
33Be H, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenoxy group or benzyloxy.
The compound of embodiment 94. formula I, wherein R
34Be H, C
1-C
4Alkyl or C
1-C
3Haloalkyl.
The compound of embodiment 95. formula I, wherein R
36Be H or C
1-C
4Alkyl.
The compound of embodiment 96. embodiments 5, wherein R
12Be H; Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl and C
2-C
14The group of alkynyl, each group are randomly by 1-3 R
27Replace; Or-N=C (R
55) R
56
The compound of embodiment 97. embodiments 5, wherein each R
27Be halogen, hydroxycarbonyl group, C independently
2-C
4Alkoxy carbonyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido ,-CH_O (CH
2)
n_ or randomly by 1-3 R
44The phenyl that replaces; Or two R
27Lump together for-OC (O) O-or-O (C (R
58) (R
58))
1-2O-; Or two R
27Lump together and be Sauerstoffatom, the carbon atom that is connected with them formation carbonyl moiety.
The compound of embodiment 98. embodiments 5, wherein R
53Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl.
Illustrate the combination of embodiment 1-98:
The compound of embodiment A. formula I, wherein
R
2Be CO
2R
12, CH
2OR
13, CH (OR
46) (OR
47), CHO, C (=NOR
14) H, C (=NNR
48R
49) H, (O)
iC (R
15) (R
16) CO
2R
17, C (=O) N (R
18) R
19, C (=S) OR
50, C (=O) SR
51, C (=S) SR
52Or C (=NR
53) YR
54
R
12Be H ,-CH_C (O) O (CH
2)
m_ ,-N=C (R
55) R
56Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl, C
2-C
14Alkynyl and phenyl groups, each group are randomly by 1-3 R
27Replace; Or
R
12Be each the CO of carboxylicesters functional group in two pyrimidine ring systems among the bonded I
2R
12Divalent group, this divalent group is selected from-CH
2-,-(CH
2)
2-,-(CH
2)
3-and-CH (CH
3) CH
2-;
R
13Be H, randomly by 1-3 R
28The C that replaces
1-C
10Alkyl or benzyl;
R
14Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl or benzyl;
R
17Be randomly by 1-3 R
29The C that replaces
1-C
10Alkyl, or benzyl;
R
18Be H, C
1-C
4Alkyl, hydroxyl, C
1-C
4Alkoxyl group or S (O)
2R
57
R
19Be H or C
1-C
4Alkyl;
Each R
27Be halogen, cyano group, hydroxycarbonyl group, C independently
2-C
4Alkoxy carbonyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido ,-CH_O (CH
2)
n_ or randomly by 1-3 R
44The phenyl that replaces; Or
Two R
27Lump together for-OC (O) O-or-O (C (R
58) (R
58))
1-2O-; Or
Two R
27Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
28Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido; Or
Two R
28Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
29Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido;
Each R
44Be halogen, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or nitro;
R
46And R
47Be C independently
1-C
4Alkyl or C
1-C
3Haloalkyl; Or
R
46And R
47Lump together and be-CH
2CH
2-,-CH
2CH (CH
3)-or-(CH
2)
3-;
R
48Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
2-C
4Alkyl-carbonyl, C
2-C
4Alkoxy carbonyl or benzyl;
R
49Be H, C
1-C
4Alkyl or C
1-C
4Haloalkyl;
R
50, R
51And R
52Be H; Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl and C
2-C
14The group of alkynyl, each group are randomly by 1-3 R
27Replace;
Y is O, S or NR
61
R
53Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, C
2-C
4Alkoxyalkyl, OH or C
1-C
3Alkoxyl group;
R
54Be C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl; Or
R
53And R
54Lump together and be-(CH
2)
2-,-CH
2CH (CH
3)-or-(CH
2)
3-;
R
55And R
56Be C independently
1-C
4Alkyl;
R
57Be C
1-C
4Alkyl, C
1-C
3Haloalkyl or NR
59R
60
Each R
58Be independently selected from H and C
1-C
4Alkyl;
R
59And R
60Be H or C independently
1-C
4Alkyl;
R
61Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl;
M is the integer of 2-3; With
N is the integer of 1-4.
The compound of embodiment B. embodiment A, wherein R
3It is halogen.
The compound of embodiment C. embodiment B, wherein R
1Be cyclopropyl, or the phenyl that is replaced by halogen, methyl or methoxy and randomly replaced by 1-2 group that is selected from halogen and methyl in other positions in contraposition; And R
4Be-N (R
24) R
25
The compound of embodiment D. embodiment C, wherein R
2Be CO
2R
22, CH
2OR
12, CHO or CH
2CO
2R
17
The compound of embodiment E. embodiment D, wherein R
24Be H, C (O) R
33Or randomly by R
30The C that replaces
1-C
4Alkyl; R
25Be H or C
1-C
2Alkyl; Or R
24And R
25Lump together and be=C (R
39) N (R
40) R
41
The compound of embodiment F. embodiment E, wherein R
2Be CO
2R
12And R
24And R
25Be H.
The compound of embodiment G. embodiment F, wherein R
12Be H, C
1-C
4Alkyl or benzyl.
Specific embodiment comprises following formula I compound:
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid phenyl methyl esters,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid list sodium salt,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid phenyl methyl esters,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid list sodium salt,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid,
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid methyl esters and
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid.
Noticeable in addition embodiment is a herbicidal composition of the present invention, comprises the compound of above-mentioned embodiment.
The invention still further relates to the method for the unwanted plant of control, comprise The compounds of this invention (for example with composition forms as herein described) from herbicidally effective amount to the location of plant that use.The embodiment that relates to using method that should be noted that is to comprise those of above-mentioned embodiment compound.
Importantly following formula I compound comprises all geometry and steric isomer, and the salt that its N-oxide compound or agricultural go up to be fit to contains their agricultural composition and as the purposes of weedicide, wherein R
2Be CO
2R
12, CH
2OR
13, CHO, C (=NOR
14) H, C (R
15) (R
16) CO
2R
17Or C (=O) N (R
18) R
19Each R
7Be halogen, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, C
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio or C
1-C
3Halogenated alkylthio; R
12Be H; Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl and C
2-C
14The group of alkynyl, each group are randomly by 1-3 R
27Replace; R
13Be H, randomly by 1-3 R
28The C that replaces
1-C
10Alkyl or benzyl; R
14Be H, C
1-C
4Alkyl or C
1-C
4Haloalkyl; R
15And R
16Be H, halogen, C independently
1-C
4Alkyl, C
1-C
4Haloalkyl, hydroxyl or C
1-C
4Alkoxyl group; R
17Be randomly by 1-3 R
29The C that replaces
1-C
10Alkyl or benzyl; R
18And R
19Be H or C independently
1-C
4Alkyl; Each R
27Be halogen, hydroxycarbonyl group, C independently
2-C
4Alkoxy carbonyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido ,-CH_O (CH
2)
n_ or randomly by 1-3 R
44The phenyl that replaces; Or two R
27Lump together the carbon atom that is connected with them and form carbonyl moiety; Each R
28And R
29Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido; Each R
30, R
31And R
32Be halogen, hydroxyl, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl; Each R
38Be halogen, C independently
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl; Each R
44Be halogen, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or nitro; M is the integer of 2-5; With n be the integer of 1-4.In addition, important compound is following formula I compound, comprises all geometry and steric isomer, and the salt that its N-oxide compound or agricultural go up to be fit to contains their agricultural composition and as the purposes of weedicide, wherein each R
5And R
6Be halogen, C independently
1-C
2Alkyl or C
1-C
2Haloalkyl; R
15Be H, halogen, C
1-C
4Alkyl, C
1-C
4Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group or C
2-C
4The alkyl-carbonyl oxygen base; R
16Be H, halogen, C
1-C
4Alkyl or C
1-C
4Haloalkyl; R
24Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl, randomly by 1-2 R
31The C that replaces
2-C
4Alkenyl or randomly by 1-2 R
32The C that replaces
2-C
4Alkynyl; Or R
24Be C (=O) R
33, nitro, OR
34, S (O)
2R
35Or N (R
36) R
37Each R
33Be H, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenoxy group or benzyloxy; R
34Be H, C
1-C
4Alkyl, C
1-C
3Haloalkyl; And R
36Be H or C
1-C
4Alkyl.
Formula I compound can prepare by one or more following scheme 1-7 and the described method of the text of enclosing and modification.The hereinafter R of Chinese style I to 12 compound, R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
12, R
13, R
14, R
15, R
16, R
17, R
18, R
19, R
20, R
21, R
22, R
23, R
24, R
25, R
27, R
28, R
29, R
30, R
31, R
32, R
33, R
34, R
35, R
36, R
37, R
38, R
39, R
40, R
41, R
42, R
43, R
44, R
45, R
46, R
47, R
48, R
49, R
50, R
51, R
52, R
53, R
54, R
55, R
56, R
57, R
58, R
59, R
60, R
61, Y, j, k and n definition identical with during summary of the invention and embodiment are described, unless indicate in addition.
Formula I compound can by the muriate of formula 2 by with the amine of formula 3, randomly in the presence of alkali such as triethylamine or salt of wormwood, react and prepare, shown in scheme 1.This reaction can comprise in tetrahydrofuran (THF), para-dioxane, ethanol and the methyl alcohol at all kinds of SOLVENTS, carries out under the optimal temperature of room temperature to 200 ℃.The method of scheme 1 is set forth among the step B of the step D1 of embodiment 2 and D2 and embodiment 4 at the step C of embodiment 1.
Scheme 1
The compound of formula 2 can by the oxy-compound of formula 4 (can keto-acid exist) by with chlorination reagent such as phosphoryl chloride or thionyl chloride, randomly at alkali such as N, react under the existence of accelerine and prepare, shown in scheme 2.This reaction can be independent, or at solvent N, carries out under the temperature of room temperature to 120 ℃ under the existence of dinethylformamide.The method of scheme 2 is set forth among the step B of the step C1 of embodiment 2 and C2 and embodiment 4 at the step C of embodiment 1.
Scheme 2
But the amidine of the compound through type 5 of formula 4 and the ketone ester of formula 6 carry out condensation under in room temperature to the temperature of solvent refluxing temperature in solvent such as methyl alcohol or ethanol prepares, shown in scheme 3.Can randomly use alkali such as metal alkoxide or 1,1,3, the 3-tetramethyl guanidine.The method of scheme 3 is set forth among the steps A 1 among steps A and the embodiment 2 and the A2 in embodiment 1 and 4.
Scheme 3
R wherein
80Be carbon residue such as alkyl, preferred C
1-C
2Alkyl.
R wherein
3Formula 4 compounds that are halogen can be by R wherein
3Formula 4 compounds that are hydrogen are by comprising acetate, N with halogen such as bromine or halide reagent such as N-halo succinimide or sulfonic acid halide at all kinds of SOLVENTS, under 0-100 ℃ temperature, react in dinethylformamide, methylene dichloride and the tetracol phenixin and prepare, shown in scheme 4.The method of scheme 4 is set forth in the step B1 of the step B of embodiment 1 and embodiment 2 and B2.
Scheme 4
In addition, R wherein
3The formula I compound that is halogen can be by R wherein
3Be that the formula I compound of hydrogen reacts by the halide reagent similar to scheme 4 methods and prepares.This alternative method is set forth in the step C of embodiment 4.
R wherein
3Be halogen and R
2Be CO
2R
12The useful especially preparation of formula 4 compounds are R wherein
3Be hydrogen and R
2Be CH (OR
12)
2Formula 4 compounds and halide reagent and oxidising agent such as N-halo succinimide or bromine (work as R
3Be bromine) reaction in solvent such as methylene dichloride, trichloromethane or tetrachloromethane, carried out under in room temperature to the temperature of solvent refluxing temperature.Shown in scheme 5.
Scheme 5
Formula 5 and 6 compound are commercially availablely maybe can prepare by known method.(for example referring to P.J.Dunn, Comprehensive Organic Functional GroupTransformations, A.R.Katritzky, O.Meth-Cohn, C.W.Rees Eds, Pergamon Press; Oxford, 1995; Vol.5, pp.741-782; T.L.Gillchrist, Comprehensive Organic Functional Group Transformations, A.R.Katritzky, O.Meth-Cohn, C.W.Rees Eds., Pergamon Press; Oxford, 1995; Vol.6, pp.601-637 and B.R.Davis, P.J.Garratt, ComprehensiveOrganic Synthesis, B.M.Trost Ed., Pergamom Press; Oxford, 1991; Vo.2, pp.795-803.)
Alternatively, formula I compound can be prepared by formula 7 compounds that corresponding X1 wherein is leavings group such as halogen or alkyl sulphonyl (for example, methylsulfonyl, trifyl, benzenesulfonyl), shown in scheme 6.
Scheme 6
M wherein
1Be B (OH)
2, Sn (n-Bu)
3, MgX
1Or ZnX
1R
1Be randomly substituted cyclopropyl, randomly substituted sec.-propyl or randomly substituted phenyl; And X
1It is leavings group.This method comprises that the compound of formula 7 and formula 8 compounds are with boric acid (M for example
1Be B (OH)
2), organotin reagent (M for example
1Be Sn (n-Bu)
3), Grignard reagent (for example, M
1Be MgX
1) or organic zinc reagent (M for example
1Be ZnX
1) the palladium catalyzed reaction of form.(for example referring to N.Ali, A.McKillop, M.Mitchell, R.Rebelo, A.Ricardo, P.Wallbank, Tetrahedron, 1992,48,8117-8126; J.Solberg, K.Undheim, Acta Chem.Scand., 1989,43,62-68, V.Bonnet, F.Mongin, F.Tr é court, G.Qu é guiner and P.Knochel, Tetrahedron, 2002,58,4429-4438.)
X wherein
1Formula 7 compounds that are halogen can be by the dihalo compound of formula 12 and the amine of formula 3, randomly by alkali such as triethylamine or salt of wormwood catalysis, comprise in tetrahydrofuran (THF) and the methylene dichloride reacting to the temperature of solvent refluxing temperature at all kinds of SOLVENTS preparing, shown in scheme 7 in 0 ℃.
Scheme 7
The compound of formula 12 can prepare by known method.(for example, referring to H.Gershon, J.Org.Chem., 1962,27,3507-3510.)
Shown in scheme 8, R wherein
2Be CO
2R
12Formula I compound also can prepare by carbonylation reaction by the compound of formula 13.General condition is a 1-10 atmospheric carbon monoxide, in the presence of palladium catalyst, at pure and mild another kind of solvent such as N, in the mixture of dinethylformamide, N-Methyl pyrrolidone or tetrahydrofuran (THF), in the temperature of room temperature to 150 ℃.
Scheme 8
Shown in scheme 9, the compound of formula 13 can be by the compound of formula 14 by being prepared with the reaction similar to the method for scheme 1 to the amine of formula 3.
Scheme 9
Shown in scheme 10, the compound of formula 14 can be by the glycol of formula 15 by preparing with the reaction similar to the method for scheme 2 to halide reagent such as phosphoryl chloride or phosphoryl bromide.(referring to H.Gershon, R.Braun, A.Scala and R.Rodin, J.Med.Chem 1964,7,808-811 and M.H.Norman, N.Chen, Z.Chen, C.Fotsch, N.Han, R.Hurt, T.Jenkins J.Kincaid, L.Liu, Y.Lu, O.Moreno, V.J.Santora, J.D.Sonnenberg and W.Karbon, J.Med.Chem, 2000,43,4288-4312 is as the example and preparation formula 15 examples for compounds of this method.)
Scheme 10
R wherein
2Comprise (for example, the CO of ester functional group
2R
12, R wherein
12Be not H) formula I compound can be by the carboxylic acid cpd of corresponding formula I compound (for example, R wherein
12Be H) prepare by multiple esterification process known in the art.A kind of method is set forth in embodiment 3.On the contrary, the carboxylic acid cpd of formula I can prepare as saponification by corresponding ester cpds by multiple method for hydrolysis known in the art.
Will be appreciated that some reagent of above-mentioned preparation I compound and reaction conditions may be incompatible with some functional group of existing in the intermediate.In these cases, protect/go defence program or functional group's change to join and to help to obtain desired product in the building-up process.Protecting group use and select technician to the chemosynthesis aspect be conspicuous (referring to, T.W.Greene for example, P.G.M.Wuts, Protective Groups in Organic Synthesis2nd ed.; Wiley:New York, 1991).Those skilled in the art will know that in some cases, one given introduce as the reagent described in arbitrary independent scheme after, also must finish the additional conventional synthesis step of not introducing in detail, synthetic with perfect I compound.Those skilled in the art also know, to hint that with the specific degrees that is used for preparation I compound by elaboration it may be necessary that the different order of order is finished the step combination that such scheme sets forth.
Those of skill in the art also will appreciate that formula I compound as herein described and intermediate can carry out multiple parent's electricity, nucleophilic, free radical, organo-metallic, oxidation and reduction reaction to be increased substituting group or change existing substituting group.
Need not further weigh, can believe, those skilled in the art utilize content described above the present invention can be used its most complete degree.Therefore, the following examples just are used for explaining, rather than limit the present invention by any way.Step among the following embodiment has been set forth the process in each step in whole synthetic conversion, and the raw material in each step needn't prepare by concrete preparation feedback, if its process is described in other embodiment or step.Percentage ratio is weight percentage, only chromatographic solvent mixture or other explanations are arranged in addition.Unless other explanations are arranged, and the umber of chromatographic solvent mixture and percentage ratio are volume parts and percent by volume.
1H NMR spectrum is carried out record with ppm according to the downfield from tetramethylsilane; " s " is unimodal, and " d " is bimodal, and " t " is triplet, and " q " is quartet, " m " is multiplet, and " dd " is double doublet, and " ddd " is doublet in pairs, and " dt " is two triplets, " bq " is two quartets, and " br s " is wide unimodal, and " br d " is wide doublet.
Embodiment 1
Preparation 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester (compound 1) and
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters (compound 2)
Steps A: preparation 2-cyclopropyl-6-(diethoxymethyl)-4 (1H)-pyrimidone
To 4, and 4-diethoxy-ethyl 3-oxobutanoate (according to E.Graf, R.Troschutz, Synthesis, the method preparation in 1999,7,1216; 10.0g, 46mmol) and cyclopropane carbonamidine (carboximidamide) mono-hydrochloric salts (Lancaster Synthesis, 5.0g, add in methyl alcohol 41mmol) (100mL) mixture sodium methylate methanol solution (5.4M, 8.4mL, 46mmol).This reaction mixture stirring is spent the night.Utilize Rotary Evaporators to remove solvent.Add methylene dichloride and filter this mixture.Solvent in the filtrate is removed with Rotary Evaporators.Resistates obtains title compound, white solid (4.67g) with medium pressure liquid chromatography method (MPLC) purifying (hexane solution of 35 → 100% ethyl acetate is made eluent).
1H NMR(CDCl
3)δ6.55(s，1H)，5.10(s，1H)，3.61(m，4H)，1.91(m，1H)，1.23(m，8H)，1.09(m，2H)。
Obtain the product that 3.24g does not dewater in addition.This material can be in methyl alcohol refluxes with the tosic acid pyridine of catalytic amount and is converted into title compound.
Step B: preparation 5-bromo-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid ethyl ester
To 2-cyclopropyl-6-(diethoxymethyl)-4 (1H)-pyrimidone (being the title product of steps A) (2.9g, add in methylene dichloride 12.1mmol) (75mL) solution N-bromosuccinimide (4.76g, 26.8mmol).This reaction mixture stirring is spent the night.Remove solvent with Rotary Evaporators.Resistates obtains title compound by MPLC purifying (dichloromethane solution of 1 → 4% methyl alcohol is made eluent), white solid (2.68g).
1H NMR(CDCl
3)δ4.43(q，2H)，1.90(m，1H)，1.41(t，3H)，1.30(m，2H)，1.20(m，2H)。
Step C: preparation 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester and 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters
To 5-bromo-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid ethyl ester (being the product of step B) (1.07g, N 3.7mmol), add in dinethylformamide (15mL) solution thionyl chloride (0.54mL, 7.5mmol).This reaction mixture was stirred 2 hours.Remove solvent with Rotary Evaporators.Resistates is dissolved in the methylene dichloride, with saturated sodium bicarbonate aqueous solution washing and dry (Na
2SO
4).Remove solvent with Rotary Evaporators.Resistates is dissolved in the tetrahydrofuran (THF) (2mL), and the methanol solution of adding ammonia (7N, 2mL).With reaction mixture place sealing bottle and microwave reactor in 125 ℃ the heating 2 hours.With reaction mixture sat whole weekend.Add methylene dichloride and filter reaction mixture.Remove solvent with Rotary Evaporators.Resistates obtains title compound, a kind of compound of the present invention, white solid (0.52g) by MPLC purifying (hexane solution of 10 → 30% ethyl acetate is made eluent).
1H NMR(CDCl
3)δ5.40(br s，2H)，4.44(q，2H)，2.05(m，1H)，1.01(t，3H)，1.05(m，2H)，0.99(m，2H)。
Also from the MPLC purifying, isolate corresponding methyl esters in addition, i.e. 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters, another compound of the present invention, white solid (0.06g).
1H NMR(CDCl
3)δ5.40(br s，2H)，3.97(s，3H)，2.05(m，1H)，1.05(m，2H)，0.99(m，2H)。
Embodiment 2
Preparation 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (compound 135)
Steps A 1: preparation 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
To the diethyl oxaloacetate sodium salt (150g that is warming up to 30 ℃, sodium hydroxide (the 56g of adding 50% in 30 minutes in methyl alcohol 714mmol) (300mL) and water (150mL) mixture, 700mmol) water (60mL) solution, during temperature remain on 25-30 ℃, pH is at 11-12.Then with the mixture that is stirred 35 ℃ of reheat 30 minutes.In this mixture, add in batches in 15 minutes the cyclopropane carboxamidine monohydrochloride (64g, 530mol).Orange solution was heated to 50 ℃ in 30 minutes, and kept 3 hours in this temperature.Reaction mixture is cooled to 35 ℃, and (about 70g 0.7mol) (causes foam) and is about 1.5-2.5 up to pH to add concentrated hydrochloric acid at 30-40 ℃ step by step in 30 minutes.Concentrate this mixture with Rotary Evaporators at 35-40 ℃ and remove alcohol, and stir 3-4 hour to finish the crystallization of product at 25 ℃.After this mixture is cooled to 0 ℃, solid collected by filtration.This solid water (blot, and obtains title compound at 60 ℃ in the vacuum oven inner drying then, beige solid (about 60g) by 2 * 60mL) washings.
1H NMR(DMSO-d
6)δ6.58(s，1H)，1.95(m，1H)，1.0(m，4H)。
Steps A 2: preparation 2-cyclopropyl-1, the other method of 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
To the diethyl oxaloacetate sodium salt (210g, add in 30 minutes in methyl alcohol 950mmol) (500mL) and water (400mL) mixture 50% sodium hydroxide (80g, 1.0mol) water (60mL) solution, during temperature remain on 25-30 ℃, pH is at 11-12.Then with the mixture that is stirred 30 ℃ of reheat 30 minutes.Adding cyclopropane carboxamidine monohydrochloride in this mixture (110g, 910mol).Orange solution was heated to 50 ℃ in 30 minutes, and kept 5 hours in this temperature.This reaction mixture is cooled to 30 ℃, is evaporated to half volume at 35-40 ℃, (140g 1.4mol) (causes foam) and is about 1-2 up to pH to add concentrated hydrochloric acid at 25-30 ℃ step by step in 30 minutes.This mixture is stirred 1 hour to finish the crystallization of product at 5 ℃.After this mixture is cooled to 0 ℃, solid collected by filtration.This solid water (blot, and obtains title compound at 70 ℃ of vacuum oven inner dryings then, beige solid (100g) by 3 * 60mL) washings; M.p.235-236 ℃ (decomposition).
1H NMR(DMSO-d
6)δ6.58(s，1H)，1.95(m，1H)，1.0(m，4H)。
Step B1: preparation 5-chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
At 15 ℃ to 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (being the product of steps A 1 or A2) (9.2g, (30mL) solution of water 52mmol) and concentrated hydrochloric acid (22g, the aqueous solution (11% that dropwise adds clorox in mixture 220mmol) in 15 minutes, 40g, 59mmol), thus be accompanied by the cooling make this mixture maintain 15-20 ℃.Then this mixture was kept 1 hour at 20-25 ℃.Add solid sodium bisulfite (about 2g), (50%, 8g 0.10mol), makes this reaction mixture maintain about 25 ℃ thereby be accompanied by cooling dropwise to add aqueous sodium hydroxide solution then.This mixture is cooled to 10 ℃,, uses the cold water washing of minimum by the product that filtering separation suspends.Then with this product 50 ℃ in the vacuum oven inner drying to constant weight, obtain title compound (7.5g).
1H NMR(DMSO-d
6)δ13.4(br s，1H)，1.95(m，1H)，1.0(m，4H)。
Step B2: preparation 5-chloro-2-cyclopropyl-1, the other method of 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
At 8-12 ℃ to 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (being the product of steps A 1 or A2) (184g, 1.02mol) water (45mL) solution and concentrated hydrochloric acid (292g, the aqueous solution (8.4% that dropwise adds clorox in mixture 3mol) in 2 hours, 1.02kg, 1.15mol), make this mixture maintain 8-10 ℃ thereby be accompanied by cooling.Then this mixture was kept 1 hour at 10-12 ℃.Monitor this conversion by HPLC.When the raw material residue is less than 5%, adds the sodium bisulfite solid and arrive negative up to the test of KI starch paper.This mixture is cooled to 5 ℃,, uses the cold water washing of minimum by the product that filtering separation suspends.Then with this product 50 ℃ in the vacuum oven inner drying to constant weight, obtain title compound (194g); M.p.189-190 ℃.
1H NMR(DMSO-d
6)δ13.4(br s，1H)，1.95(m，1H)，1.0(m，4H)。
Step C1: preparation 5,6-two chloro-2-cyclopropyl-4-pyrimidinecarboxylic acids
(0.15mol) with 5-chloro-2-cyclopropyl-1, (75g 300mmol) and at 85 ℃ heated 3 hours 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (being the product of step B1 or B2) for 14mL, 23g to mix phosphoryl chloride.Reaction mixture be cooled to 30 ℃ and in 30 minutes, join acetonitrile (50mL) and the mixture of frozen water (80mL) in, simultaneous temperature maintains 5-10 ℃, by adding ammonia soln (28%) simultaneously pH is maintained 1-3.PH is adjusted to about 2, this mixture concentrates with Rotary Evaporators at 25 ℃ and removes acetonitrile, (2 * 25mL) washings of sedimentary product of filtering separation and water.This solid drying in vacuum oven is obtained title compound (about 7.0g).
1H NMR(DMSO-d
6)δ2.23(m，1H)，1.2(m，2H)，1.0(m，2H)。
Step C2: preparation 5, the other method of 6-two chloro-2-cyclopropyl-4-pyrimidinecarboxylic acids
(2.14mol) with 5-chloro-2-cyclopropyl-1, (96.8g 451mmol) and at 90 ℃ heated 5 hours 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (being the product of step B1 or B2) for 200mL, 328g to mix phosphoryl chloride.Reaction mixture is cooled to 50-60 ℃ and be evaporated to half volume.After being cooled to 30 ℃, this reaction mixture was added in 60 minutes in the mixture of the trimethyl carbinol (200mL) and water (300mL), and simultaneous temperature maintains 8-10 ℃.In mixture, add crystal seed, add entry (300mL) step by step, and this mixture was stirred 1 hour at 10-15 ℃.After being cooled to 5 ℃, (3 * 50mL) washings of sedimentary product of filtering separation and water.This solid drying in vacuum oven is obtained title compound (93g).
1H NMR(DMSO-d
6)δ2.23(m，1H)，1.2(m，2H)，1.0(m，2H)。
Step D1: preparation 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid
With 5,6-two chloro-2-cyclopropyl-4-pyrimidinecarboxylic acids (being the product of step C1 or C2) (5.1g, 22mmol), water (30mL) and ammonia soln (28%, 8g, mixture 130mmol) was 80 ℃ of heating 3 hours.50 ℃ and 70 holder (9.3kPa) pressure down with this solution concentration to half volume of pact to remove most of excess of ammonia.The soup compound of gained is acidified to pH 2 20 ℃ of stirrings with aqueous hydrochloric acid, is cooled to 5 ℃ and filtration.The isolating solid of institute drying in vacuum oven obtains title compound (4.2g), a kind of compound of the present invention.
1H NMR(DMSO-d
6)δ13.4(br s，1H)，1.95(m，1H)，1.0(m，4H)。
Step D2: preparation 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid
With 5,6-two chloro-2-cyclopropyl-4-pyrimidinecarboxylic acids (being the product of step C1 or C2) (280g, 1.2mol), water (1.26L) and ammonia soln (28%, 350g, mixture 5.76mol) was 80 ℃ of heating 5 hours.50 ℃ and 70 holder (9.3kPa) pressure down with this solution concentration to half volume of pact to remove most of excess of ammonia.The soup compound of gained is acidified to pH 1-2 20 ℃ of stirrings with aqueous hydrochloric acid, is cooled to 5 ℃ and filtration.The isolating solid of institute drying in vacuum oven obtains title compound (270g), a kind of compound of the present invention.
1H NMR(DMSO-d
6)δ13.4(br s，1H)，1.95(m，1H)，1.0(m，4H)。
Embodiment 3
Preparation 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters (compound 9)
To 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (being the step D1 of embodiment 2 or the product of D2) (2.0g, dropwise add in methyl alcohol 8.5mmol) (20mL) solution thionyl chloride (4mL, 70mmol).This mixture was heated 24 hours at reflux temperature.Add the vitriol oil (5), this reaction mixture was heated 16 hours at reflux temperature.After the cooling of this mixture, add entry (30mL) and dropwise add ammonia soln (28%, 10mL).This mixture is cooled to 5 ℃, this solid of filtering separation, wash with water and 40 ℃ in vacuum oven drying obtain title product (2.3g), a kind of compound of the present invention.
1H NMR(CDCl
3)δ5.41(br s，2H)，3.98(s，3H)，2.06(m，1H)，1.04(m，2H)，1.00(m，2H)。
The other method of preparation 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters
To 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (being the step D1 of embodiment 2 or the product of D2) (8.5g, dropwise add in methyl alcohol 40mmol) (120mL) solution cooling thionyl chloride (15mL, 200mmol).This mixture was heated 24 hours at 60 ℃.This mixture is concentrated into 25% of original volume, and water (100mL) dilution.Add phenolphthalein pH indicator, be accompanied by cooling at 10-20 ℃ and dropwise add 10% aqueous sodium hydroxide solution, make pH reach 8-10.This solid of filtering separation, wash with water and 50-60 ℃ in vacuum oven drying obtain title product (7.3g), a kind of compound of the present invention.
1H NMR(CDCl
3)δ5.41(br s，2H)，3.98(s，3H)，2.06(m，1H)，1.04(m，2H)，1.00(m，2H)。
Embodiment 4
Preparation 6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid (compound 65)
Steps A: preparation 2-(4-chloro-phenyl-)-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
To the diethyl oxaloacetate sodium salt (123.2g, water 586mmol) (750mL) mixture add lentamente aqueous sodium hydroxide solution (50%, 47g, 586mmol).After 1 hour, this solid dissolving.Add then 4-spanon mono-hydrochloric salts (111.95g, 586mmol), with this mixture 70 ℃ of heated overnight.After being cooled to room temperature, adding concentrated hydrochloric acid (causing foam) lentamente and be reduced to 1.5 up to pH.This solid of filtering separation, and water and methanol wash.This solid develops twice with hot methanol then, and with the hydrochloric acid repeated washing of 1N, then with methanol wash once, drying obtains title compound (66.07g).
1H NMR(DMSO-d
6)δ8.23(d，2H)，7.65(d，2H)，6.90(s，1H)。
Step B: preparation 6-amino-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid
In phosphoryl chloride (180mL), add 2-(4-chloro-phenyl-)-1, and 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (being the product of steps A) (81.81g, 326mmol).This mixture be heated to 90 ℃ 2.5 hours.After being cooled to room temperature, this reaction mixture joins 1: 2 acetonitrile lentamente: in the water (1.5L), maintain the temperature at 35-45 ℃ simultaneously.In stirring at room after 30 minutes, the solid by filtration of gained is separated also and is washed with water with this reaction mixture.Then with this solid and ammonia soln (5%, 2.1L) mix and be heated to 80 ℃ 18 hours.In room temperature after 2 days, by the filtering separation solid and wash with water.Obtain the second section product by cooling filtrate with refiltering.Solid drying after the merging obtains title compound (58.8g).
1HNMR(DMSO-d
6)δ8.33(d，2H)，7.51(d，2H)，6.89(s，2H)，6.81(s，1H)。
Step C: preparation 6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid
To 6-amino-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid (being the product of step B) (75g, N 300mmol), in dinethylformamide (300) solution 50 ℃ add in batches N-chlorosuccinimide (44.1g, 330mmol).The temperature of this reaction mixture is because heat release rises to 65 ℃.This reaction mixture was 55 ℃ of heating 3 hours then.(14g 90mmol), keeps this reaction mixture 30 minutes at 55 ℃ to add N-chlorosuccinimide more in batches.Add entry after the reaction mixture cooling.The solid by filtration of gained is separated, and washes with water, is dissolved in the ethyl acetate, washes with water and drying.Utilize Rotary Evaporators to remove solvent and obtain title product, a kind of compound of the present invention, brown solid (73.68g).
1H NMR(DMSO-d
6)δ8.28(d，2H)，7.70(br s，2H)，7.58(d，2H)。
Embodiment 5
Preparation 6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid ethyl ester (compound 64)
To 6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid (being the product of embodiment 4 step C) (20.0g, 70.4mmol) ethanol (70mL) solution in add thionyl chloride (5.14mL, 70.4mmol), utilize simultaneously ice bath with temperature maintenance below 15 ℃.This reaction mixture is in the reflux temperature heated overnight then.Add entry.Be accompanied by outside cooling then and add sodium hydroxide (50%) aqueous solution, pH is adjusted to 7.The solid of gained separates after filtration and drying obtains title product, a kind of compound of the present invention, light beige solid (20.1g).
1H NMR(CDCl
3)δ8.31(d，2H)，7.42(d，2H)，5.50(br s，2H)，4.50(q，2H)，1.47(t，3H)。
In conjunction with methods known in the art, show the compound among the 1-4 according to program described herein below can preparing.The abbreviation of using in the following table is as follows: t refers to uncle, and i refers to different, Me nail base, and Et refers to ethyl, and Pr refers to propyl group, and i-Pr refers to sec.-propyl, and Bu refers to butyl, and t-Bu refers to the tertiary butyl, and CN refers to cyano group, and S (O)
2Me nail base alkylsulfonyl." _ " refers to negative formal charge and " _ " formal charge of making a comment or criticism.
Table 1
| R 1It is cyclopropyl; R 3Be Cl. R 2 | R 1It is cyclopropyl; R 3Be F. R 2 | R 1It is cyclopropyl; R 3Be Br. R 2 | R 1It is cyclopropyl; R 3Be I. R 2 |
| CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CH(OC(＝O)Me)CO 2Me CHO C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CH(OC(＝O)Me)CO 2Me CHO C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CH(OC(＝O)Me)CO 2Me CHO C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CH(OC(＝O)Me)CO 2Me CHO C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph |
| C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 2N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2O(Ch 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ | C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2C(O)O _H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3C(O)O _N _(Me) 4C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3C(O)O _K _ | C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2OCH 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ | C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2C(O)O _H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _H 2N __CH(CH 2) 2CH 2_ C(O)O _HN _(Et) 3C(O)O _N _(Me) 4C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3C(O)O _K _ |
| R 1Be 4-Cl-Ph; R 3Be Cl. R 2 | R 1Be 4-Cl-Ph; R 3Be F. R 2 | R 1Be 4-Cl-Ph; R 3Be Br. R 2 | R 1Be 4-Cl-Ph; R 3Be I. R 2 |
| CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2CO 2CH 2CH 2OMe | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe | CO 2H CO 2Me CO 2Et CO 2Pr CO 2iPr CO 2t-Bu CO 2Cyclohexyl CO 2Hexyl CO 2CH 2Cyclohexyl CO 2CH 2Ph CO 2CH(Me)Ph CO 2CH 2(4-Cl-Ph) CO 2CH 2(3-F-Ph) CO 2CH 2CH 2NMe 2 CO 2CH 2CH 2OMe |
| CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CHO CH(OC(＝O)Me)CO 2Me C(＝NOH)H C(＝NOMe)H C(＝O)HH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ | CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CHO CH(OC(＝O)Me)CO 2Me C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ | CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CHO CH(OC(＝O)Me)CO 2Me C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3N _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ | CO 2CH 2CH 2OH CO 2CH 2(3-oxetanyl) CH 2OH CH 2OMe CH 2CO 2Me CH(OH)CO 2Me CHO CH(OC(＝O)Me)CO 2Me C(＝NOH)H C(＝NOMe)H C(＝O)NH 2 C(＝O)NHMe C(＝O)NMe 2 CO 2Ph C(O)O _H 3N _Me C(O)O _H 3N _i-Pr C(O)O _H 3N _Pr C(O)O _H 3N _Butyl C (O) O _H 3XN _Hexyl C (O) O _H 3N _Octyl group C (O) O _H 3N _Hexadecyl C (O) O _H 3N _Octadecyl C (O) O _H 3N _Cyclohexyl C (O) O _H 2N _(Et) 2 C(O)O _ H 2N __(CH 2) 2O(CH 2) 2_ C(O)O _ H 2N __CH 2(CH 2) 2CH 2_ C(O)O _HN _(Et) 3 C(O)O _N _(Me) 4 C(O)O _N _(Me) 3CH 2Ph C(O)O _S _(Me) 3 C(O)O _K _ |
Table 2
| R 2Be CO 2H；R 3Be Cl. R 1 | R 2Be CO 2Me；R 3Be Cl. R 1 | R 2Be CO 2Et；R 3Be Cl. R 1 |
| I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4-Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe | I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4-Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe | I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4-Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe |
| R 2Be CO 2H；R 3Be Br. R 1 | R 2Be CO 2Me；R 3Be Br. R 1 | R 2Be CO 2Et；R 3Be Br. R 1 |
| I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4-Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe | I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4-Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe | I-Pr 1-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2,2-two-F-cyclopropyl 2,2-two-Cl-cyclopropyl 1,2-two-F-cyclopropyl 2,2,3,3-four-F-cyclopropyl 1,2,2,3,3-five-F-cyclopropyl Ph 4-Cl-Ph 4-F-Ph 3-OMe-Ph 4-Br-Ph 4-I-Ph 4-CF 3-Ph 4-OCHF 2-Ph 4-OCF 3-Ph 4-SCF 3-Ph 4-SCHF 2-Ph 4-CN-Ph 4-CO 2Me-Ph 2,4-two-Cl-Ph 2-F-4Cl-Ph 3,4-two-Cl-Ph 2-MeO-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH 2OMe |
Table 3
| R 1It is cyclopropyl; R 2Be CO 2Me. R 3 | R 1It is cyclopropyl; R 2Be CO 2Et. R 3 |
| CN NO 2 OMe SMe NH 2 NHMe NMe 2 | CN NO 2OMe SMe NH 2NHMe NMe 2 |
Table 4
| R 1It is cyclopropyl; R 2Be CO 2Me；R 3Be Cl. R 4 | R 1It is cyclopropyl; R 2Be CO 2Me；R 3Be Br. R 4 | R 1It is cyclopropyl; R 2Be CO 2Et；R 3Be Cl. R 4 | R 1It is cyclopropyl; R 2Be CO 2Et；R 3Be Br. R 4 |
| NO 2 NHMe NMe 2 N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2 NHNO 2 N＝CHNMe 2 NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2NHMe NMe 2N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2NHNO 2N＝CHNMe 2NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2NHMe NMe 2N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2NHNO 2N＝CHNMe 2NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2NHMe NMe 2N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2NHNO 2N＝CHNMe 2NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 |
| R 1Be 4-Cl-Ph; R 2Be CO 2Me；R 3Be Cl. R 4 | R 1Be 4-Cl-Ph; R 2Be CO 2Me；R 3Be Br. R 4 | R 1Be 4-Cl-Ph; R 2Be CO 2Et；R 3Be Cl. R 4 | R 1Be 4-Cl-Ph; R 2Be CO 2Et；R 3Be Br. R 4 |
| NO 2 NHMe NMe 2 N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2 NHNO 2 N＝CHNMe 2 NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2 NHMe NMe 2 N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2 NHNO 2 N＝CHNMe 2 NHOH NHOMe NHCR 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2NHMe NMe 2N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2NHNO 2N＝CHNMe 2NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 | NO 2NHMe NMe 2N_CH 2CH 2OCH 2CH 2_ NHC(＝O)Me NHC(＝O)OMe NHS(O) 2Me NHNH 2NHNO 2N＝CHNMe 2NHOH NHOMe NHCH 2CO 2Me NHCH 2CO 2Et NHCH 2CH 2OH NHCH 2CH 2OMe NHCH 2CH 2NMe 2 |
Preparation/application
The compounds of this invention is general goes up the carrier that is fit to agricultural, comprises at least a liquid diluent, solid diluent or tensio-active agent, uses with the form of preparation or composition.The selection of preparation or composition components should with the physical properties of activeconstituents, method of application and environmental factors such as soil type, humidity and temperature adapt.Useful preparation comprises liquor such as solution (comprising emulsifiable concentrate), suspension agent, emulsion (comprising microemulsion and/or suspended emulsion agent) etc., and they can randomly be condensed to gelling material.Useful preparation also comprises solid preparation such as dust, powder, granule, pill, tablet, film (comprising seed pelleting) etc., and they can be (" wettable ") of water dispersible or water miscible.Activeconstituents can be by (little) encapsulated suspension agent or the solid preparation further made again; Alternatively, the whole preparation of activeconstituents also can be by encapsulated (or " bag quilt ").The encapsulated release that can control or delay activeconstituents.Sprayable preparation can expand in suitable medium, uses by per hectare about to the sprayed volume of several hectolitres.The composition of high density is mainly as the intermediate of further processing.
Preparation generally contains effective amount of actives, thinner and tensio-active agent, and by following about scope, summation is 100% weight.
Weight percentage
| Activeconstituents | Thinner | Tensio-active agent | |
| Water dispersible and water miscible granule, tablet and powder suspension agent, emulsion, solution (comprising emulsifiable concentrate) powder particle agent and pill high concentration composition | 0.001-90 1-50 1-25 0.001-99 90-99 | 0-99.999 40-99 70-99 5-99.999 0-10 | 0-15 0-50 0-5 0-15 0-2 |
General solid diluent is described in people such as Watkins, Handbook of InsecticideDust Diluents and Carriers, and 2nd Ed., Dorland Books, Caldwell is among the NewJersey.General liquid diluent is described in Marsden, Solvents Guide, and 2ndEd., Interscience, New York is in 1950.McCutcheon ' s Detergents andEmulsifiers Annual, Allured Publ.Corp., Ridgewood, New Jersey, and Sisely and Wood, Encyclopedia of Surface Active Agents, ChemicalPubl.Co., Inc., New York has listed tensio-active agent in 1964 and uses and recommend.All preparations all can contain minor amounts of additives with minimizing foam, knot cake, burn into microbial growth etc., or thickening material is to increase viscosity.
Tensio-active agent comprises; for example; polyethoxylated alcohols, polyethoxylated alkylphenol, polyethoxylated fatty acid esters of sorbitan, sulfosuccinate dialkyl, alkyl sodium sulfate ester, alkylbenzene sulfonate, organo-siloxane, N; N-dialkyl group taurine ester (N; N-dimethyltaurates), sulfonated lignin, naphthalenesulfonate formaldehyde condensation compound, polycarboxylate, glyceryl ester, polyoxyethylene/polyoxypropylene block copolymers and alkyl polyglycoside; wherein the value of glucose unit refers to the polymerization degree (D.P.); can be 1-3, alkyl unit can be C
6To C
14(referring to Pure and Applied Chemistry 72,1255-1264).Solid diluent comprises, for example clay such as wilkinite, montmorillonite, attapulgite (attapulgite) and kaolin, starch, sugar, silicon-dioxide, talcum, diatomite, urea, lime carbonate, yellow soda ash and sodium bicarbonate, and sodium sulfate.Liquid diluent comprises, for example, water, N, dinethylformamide, methyl-sulphoxide, N-alkyl pyrrolinone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic ester, paraffin, alkylbenzene, alkylnaphthalene, glycerine, triacetin, sweet oil, Viscotrol C, linseed oil, tung oil, sesame oil, Semen Maydis oil, peanut oil, Oleum Gossypii semen, soybean oil, rapeseed oil and theobroma oil, fatty acid ester, ketone such as pimelinketone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2 pentanone, acetate esters such as hexyl acetate, heptyl acetate and octyl acetate, with alcohols such as methyl alcohol, hexalin, decyl alcohol, benzylalcohol and tetrahydrofurfuryl alcohol.
The useful preparation of the present invention also can contain the material that well known to a person skilled in the art as preparation used additives such as defoamer, membrane-forming agent and dyestuff.Defoamer can comprise the water-dispersion liquid that contains organopolysiloxane such as Rhodorsil_416.Membrane-forming agent can comprise polyvinyl acetate, polyvinyl acetate ester copolymer, Polyvinylpyrolidone (PVP)-vinyl acetate copolymer, polyvinyl alcohol, polyvinyl alcohol copolymer and wax.Dyestuff can comprise water-dispersion liquid dye compositions such as Pro-lzed_Colorant Red.Skilled person in the art will appreciate that this is enumerating of non-exhaustive preparation used additives.The example of the preparation used additives that is fit to comprises that this paper enumerates, the McCutcheon ' s 2001 that MC publishing company publishes, those cited auxiliary agents among the open text WO03/024222 of Volume 2:Functional Materials and PCT.
Solution comprises emulsifiable concentrate, can be by mixing each preparation that becomes to assign to simply.Dust and powder can be by mixing, and grind in hammer mill or fluid energy mill usually and prepare.Suspension agent prepares by wet-milling usually; Referring to, U.S.3 for example, 060,084.Granule and pill can prepare by active substance is sprayed onto on the particulate vector that is prefabricated into or by the reunion technology.Referring to Browning, " Agglomeration ", Chemical Engineering, December4,1967, pp 147-48, Perry ' s Chemical Engineer ' s Handbook, 4th Ed., McGraw-Hill, New York, 1963,8-57 page or leaf and following WO91/13546.Pill can be prepared described in 172,714 according to U.S.4.Water dispersible and water-soluble granular formulation be according to U.S.4, and 144,050, U.S.3,920,442 and DE3, the method preparation described in 246,493.Tablet can be according to U.S.5, and 180,587, U.S.5,232,701 and U.S.5, the method described in 208,030 prepares.Film can be according to GB2, and 095,558 and U.S.3, the method described in 299,566 prepares.
About the more information of formulation art referring to T.S.Woods, " The Formulator ' sToolbox-Product Forms for Modern Agriculture ", Pesticide Chemistryand Bioscience, The Food-Environment Challenge, T.Brooks and T.R.Roberts, Eds., Proceeding of the 9th International Congress on PesticideChemistry, The Royal Society of Chemistry, Cambridge, 1999, pp.120-133.Also can be referring to U.S.3,235,361,6 hurdles 16 walk to 7 hurdles, 19 row and embodiment 10-41; U.S.3,309,192,5 hurdles 43 walk to 7 hurdles 62 row and embodiment 8,12,15,39,41,52,53,58,132,138-140,162-164,166,167 and 169-182; U.S.2,891,855,3 hurdles 66 walk to 5 hurdles, 17 row and embodiment 1-4; Klingman, WeedControl as a Science, John Wiley and Sons, Inc., New York, 1961, pp81-96; People such as Hance, Weed Control Handbook, 8th Ed., BlackwellScientific Publications, Oxford, 1989; With Developments in formulationtechnology, PJB Publications, Richmond, UK, 2000.
In following examples, all percentage number averages by weight, all preparations all prepare with ordinary method.Compound number refers to the compound among the concordance list A-D.
Embodiment A
The high density enriched material
Compound 1 98.5%
Aerosil 0.5%
The unbodied fine silica 1.0% of synthetic.
Embodiment B
Wettable powder
Compound 2 65.0%
4-dodecylphenol polyglycol ether 2.0%
Sodium lignosulfonate 4.0%
Sodium silicoaluminate 6.0%
Polynite (incinerating) 23.0%.
Embodiment C
Granule
Compound 4 10.0%
The attapulgite particle (low volatile, 0.71/0.30mm,
The U.S.S.No.25-50 sieve) 90.0%.
Embodiment D
Water suspending agent
Compound 9 25.0%
Aqueous attapulgite 3.0%
Unprocessed calcium lignin sulphonate 10.0%
SODIUM PHOSPHATE, MONOBASIC 0.5%
Water 61.5%.
Embodiment E
The extruding pill
Compound 1 25.0%
Anhydrous sodium sulphate 10.0%
Unprocessed calcium lignin sulphonate 5.0%
Sodium alkyl naphthalene sulfonate 1.0%
Calcium/magnesium wilkinite 59.0%.
Embodiment F
Microemulsion
Compound 21.0%
Triacetin 30.0%
C
8-C
10Alkyl polyglycoside 30.0%
Glyceryl monooleate 19.0%
Water 20.0%.
Embodiment G
Wettable powder
Compound 9 65.0%
4-dodecylphenol polyglycol ether 2.0%
Sodium lignosulfonate 4.0%
Sodium silicoaluminate 6.0%
Polynite (incinerating) 23.0%.
Test-results shows that The compounds of this invention is (postemergent) weedicide and/or a plant-growth regulator behind (preemergent) and/or the seedling before the highly active seedling.Many zones that prevent and treat all plants fully at needs in them have before the seedling of wide spectrum and/or control of weeds effect behind the seedling, described zone be for example near the fuel storage jar, near industrial storage area, stop, drive-in theater, airport, riverbank, irrigation and other water channels, the billboard and motorway and railway construction thing.Many The compounds of this invention, because of its crop with respect to the selectivity metabolism aspect the weeds, physiology on crop and the weeds suppress the site selective active or by on crop and weeds mixture or the selectivity in its environment settle, can be used for optionally preventing and treating Gramineae and broadleaf weeds in crop/weeds mixture.The preferably combination that one skilled in the art will appreciate that these selectivity factors in a kind of compound or the one group of compound can be determined by carrying out conventional biology and/or biochemical test at an easy rate.Important farm crop, comprise, but be not limited to clover, barley, cotton, wheat, rape, sugar beet, Semen Maydis, Chinese sorghum, soybean, rice, oat, peanut, vegetables, tomato, potato, perennial plantation crops, comprise coffee, cocoa, oil palm, rubber, sugarcane, citrus, grape, fruit tree, nutwood, banana, plantain, pineapple, hops, tea and forest such as eucalyptus and pine and cypress (for example torch pine), with the turf kind (for example, English grass, Herba Stenotaphri helferi (St.Augustine gross), Kentucky fescue grass and Bermuda grass), can show tolerance to The compounds of this invention.The compounds of this invention can be used for introducing resistance to weedicide through genetic transformation or breeding, gives expression to the deleterious albumen of invertebrate pests (as the bacillus thuringiensis toxin), and/or gives expression in the crop of other useful property.Skilled person in the art will appreciate that not all compound all has the effect that is equal to all weeds.Alternatively, The compounds of this invention can be used for improving the growth of plant.
Because The compounds of this invention has before the seedling and postemergence herbicide activity, prevent and treat unwanted plant by killing or damage plant or delaying its growth, these compounds can be used by several different methods effectively, comprise the The compounds of this invention of herbicidally effective amount or comprise described compound and at least a tensio-active agent, the composition of solid diluent or liquid diluent with do not need leaf or the environment of other parts or undesired plant growth such as the soil or the water of undesired plant growth of plant, or around soil or the water contact of the seed that does not need plant or other propaguluies.
The herbicidally effective amount of The compounds of this invention is determined by many factors.These factors comprise: quantity of the preparation of selection, application process, existing plant and type, growth conditions etc.Usually, the herbicidally effective amount of The compounds of this invention is about 0.0001-20kg/ha, preferably about 0.001-5kg/ha, more preferably from about 0.004-3kg/ha.Those skilled in the art can easily determine herbicidally effective amount according to the needed level of control of weeds.
The compounds of this invention can use separately, or mixes use with other weedicides, sterilant and mycocide and other agrochemicals such as fertilizer.The mixture of mixture of the present invention and other weedicides can enlarge the activity profile to other weeds kind, suppresses the propagation of any resistance biotype.Other weedicides also comprise campelyco, as navel in the Alternariadestruens Simmons, glue born of the same parents anthrax-bacilus (Colletotrichum gloeosporiodes), barnyard grass wriggle spore bacterium (Drechsiera monoceras) (MTB-951), myrothecium verrucaria (Myrothecium verrucaria), palm mould bacterium (Phytophthora palmivora) and Xi handle rest fungus (Puccinia thlaspeos).The combination of The compounds of this invention and other weedicides can cause being higher than the additivity effect (being synergy) to weeds and/or be lower than additivity effect (being safety) to crop or other useful plants.In some cases, have similar control spectrum with other but the different combinations of herbicides of the mode of action can be particularly conducive to the prevention resistant weed generation.The herbicidally effective amount of The compounds of this invention and the herbicidally effective amount of other weedicides can be determined by simple experiment easily by those skilled in the art.
In order better to prevent and treat unwanted plant (for example lower usage quantity; the control of weeds spectrum of broad; or stronger crop safety) or in order to prevent the generation of resistant weed; the mixture of The compounds of this invention and following weedicide preferably: Diuron Tech; hexazinone; terbacil; bromacil; glyphosate (glyphosate isopropyl ammonium salt especially; sodium glyphosate; glyphosate potassium; sulphosate); glufosinates (especially careless ammonium phosphine); azimsulfuron; chlorine sulphur is grand; ethametsulfuron; chlorimuronethyl; benbbensulfuronmethyl; rimsulfuron; sulfometuronmethyl; metsulfuronmethyl; nicosulfuron; tribenuron-methyl; thifensulfuronmethyl; flupyrsulfuronmethylsodium; flupyrsulfuronmethylsodium; halosulfuronmethyl; primisulfuronmethyl; trifloxysulfuron; foramsulfuron; mesosulfuronmethyl; the iodine metsulfuronmethyl; isoproturon; ametryn; amerol; Paraquat; diquat; atrazine; the piperazine humulone; acetochlor; metolachlor; the S-metolachlor; alachlor; the third careless amine; sethoxydim; tralkoxydim; clethodim; cyhalofop-butyl; quizalofop; diclofop-methyl; alkynes grass ester; _ azoles diclofop-methyl; dimethenamid; flufenacet; picloram; prodiamine; ioxynil; 2; 4-D; 2,4-DB; dicamba 98; penoxsuam; flumetsulam; quinclorac; pendimethalin; oryzalin; MCPA (and dimethyl ammonium; sylvite and sodium salt); the different monooctyl ester of MCPA-; MCPA-sulfo-ethyl ester; mecoprop; clopyralid; the chloro amido pyridine acid; trichlopyr; fluroxypyr; diflufenzopyr; imidazoles nicotinic acid; imazethapyr; imazamox; fluorine pyrrole acyl grass amine; oxyfluorfen; _ humulone; carfentrazone; sulfentrazone; flumioxazin; diflufenican; bromoxynil; Stam F-34; thiobencarb; molinate; fluridone; mesotrione; the sulphur humulone; different _ the azoles humulone; different _ acyl grass amine; different _ the grass pine; anilofos; beflubutamid; benfuresate; bentazone; benzobicylon; benzofenap; bromobutide; Butachlor technical 92; press down careless phosphine; cafenstrole; clomeprop; dimepiperate; dimethametryn; daimuron; esprocarb; ethobenzanid; fentrazamide; indanofan; cumyluron; mefenacet; _ piperazine humulone; propine _ humulone; ring penta _ humulone; pyraclonil; pyrazolate (pyrazolate); pyributicarb; pyriftalid; KIH 6127; P DimethenamidP; two careless ethers; clefoxidim; copper sulfate; cinosulfuron; AC322140; ethoxysulfuron; epoprodan; fluorine pyridine second sulphur is grand; imazosulfuron; _ azoles acyl grass amine; pyrazosulfuronmethyl; quinclorac; the flucarbazonesodium sodium salt; the procarbazone sodium salt; amicarbazone; florasulam; triasulfuron; triaziflam; pinoxaden; tritosulfuron; amidosulfuron; metosulam; sulfosulfuron; pyrrole grass ether; HOK-201; KUH-021 and CUH-35.The compounds of this invention and the ratio of other herbicidal active components in herbicidal composition are generally 100: 1-1: 100, be more generally 10: 1-1: and 10, be generally 5 most: 1-1: 5 weight.Optimal ratio can be determined based on required control of weeds spectrum easily by those skilled in the art.
Owing to being higher than, some weeds adds and effect (being synergy), what pay special attention to is the mixture of The compounds of this invention and growth hormone conduction depressant drug (plant hormone (phytotropins)), and example is the composition of compound 1 (6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester) and diflufenzopyr.The growth hormone conduction depressant drug is the chemical substance that suppresses growth hormone in the plant materials, for example by combining with the growth hormone carrier proteins.Other examples of growth hormone conduction depressant drug comprise quinclorac (being also referred to as N-(1-naphthyl) phthalamic acid and 2-[(1-naphthyl amino) carbonyl] phenylformic acid), 9-hydroxyphenyl fluorene-9-formic acid and 2,3,5 triiodobenzoic acid.Therefore, an aspect of of the present present invention relates to the compound of the claim 1 that comprises the synergy significant quantity and the Herbicidal mixture of growth hormone conduction depressant drug.The synergy significant quantity of growth hormone conduction depressant drug and The compounds of this invention can be determined easily.
The compounds of this invention also can be used in combination to increase the security to some crop with herbicides and safeners; safener is benoxacor, BCS (1-bromo-4-[(chloro methyl) alkylsulfonyl for example] benzene), cloquitocet_mexyl, cyometrinil, dichlormide, 2-(dichloromethyl)-2-methyl isophthalic acid; 3-dioxolane (MG191), fenchlorazole, fenclorim, separate careless amine, fluxofenim, separate grass _ azoles, two benzene _ azoles acid, mefenpyrdiethyl, methoxyphenone ((4-methoxyl group-3-aminomethyl phenyl) (3-aminomethyl phenyl) ketone), naphthalic anhydride (1, the 8-naphthalic anhydride) and oxabetrinil.The herbicides and safeners of detoxifcation significant quantity can be used simultaneously with The compounds of this invention, or uses with seed treatment.Therefore, one aspect of the present invention relates to the Herbicidal mixture that comprises The compounds of this invention and detoxifcation significant quantity herbicides and safeners.Seed treatment is useful especially for the selectivity control of weeds, because it has limited the detoxifcation of crop on physiology.Therefore, the useful especially embodiment of the present invention is the method for selectivity control undesired plant growth in crop, comprise that the seed of the crop that wherein grows is handled with the safener of detoxifcation significant quantity with the place of the The compounds of this invention contact crop of herbicidally effective amount.The detoxifcation significant quantity of safener can be determined by simple experiment easily by those skilled in the art.
The compounds of this invention also can be used in combination with plant-growth regulator, and plant-growth regulator is aviglycine, N-(phenyl methyl)-1H-purine-6-amine, epocholeone, gibberic acid, Plant hormones regulators,gibberellins A for example
4And A
7, super quick albumen, casing coupling peace, transfer naphthenic acid, prohydrojasmon, nitrophenol sodium and the anti-ester that falls, and plant-growth improvement property microorganism such as bacillus cereus (Bacilluscereus) strain BP 01.
Following evidence the prevention effect of The compounds of this invention to concrete weeds.But the weeds that compound can be prevented and treated are not limited to mentioned kind.Referring to the description of concordance list A-D to compound.The abbreviation of using in the following concordance list is as follows: t refers to uncle, and s refers to the second month in a season, and n makes a comment or criticism, and i refers to different, the c finger ring, and Me nail base, Et refers to ethyl, and Pr refers to propyl group, and i-Pr refers to sec.-propyl, and Bu refers to butyl, and Ph refers to phenyl, and MeO refers to methoxyl group, and EtO refers to oxyethyl group, CN refers to cyano group." _ " refers to negative formal charge, " _ " formal charge of making a comment or criticism.Abbreviation " dec. " expression compound occurs decomposing when fusing.Abbreviation " Ex. " representative " embodiment ", numeral compound thereafter is to make in this embodiment.
Concordance list A
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 1(Ex.1) 2(Ex.1) 3 4 5 7 8 9(Ex.3) 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 | c-Pr c-Pr i-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr Ph c-Pr c-Pr c-Pr c-Pr Ph c-Pr c-Pr c-Pr c-Pr 2-Me-c-Pr | CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 CO 2H CO 2CH 3 CO 2CH 3 CH 2OCH 3 CH 2CO 2CH 2CH 3 CH 2CO 2CH 3 CO 2(i-Pr) CO 2CH 2CH 2CH 3 CO 2CH 2CH 2CH 2CH 3 CO 2(i-Bu) CO 2CH 2CH 3 CO 2CH 3 C(O)NH 2 CH 2OH CO 2CH 2Ph CO 2CH 3 CHO CO 2CH 3 CHO CH＝NOH CO 2CH 3 | Br Br Br Cl Br I Br Cl Br Br Br Br Br Br Br Br Br Br Br Br Br Br F F Br Br Br | NH 2 NH 2 NH 2 NHx NHCH 3 NH 2 NH 2 NH 2 NHCH 2CO 2CH 3 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 N＝CHN(CH 3) 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 | 107-108 148-150 107-109 87-89 * 145-146 160-162 143-145 95-96 * * * 141-142 86-90 87-90 121-123 1110-111 * * 182-185 129-131 * * * * * 132-133 |
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64(Ex.5) 65(Ex.4) | c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr t-Bu 4-Cl-Ph c-Pr c-Pr c-Pr 4-Cl-Ph c-Pr 4-F-Ph 4-CF 3-Ph c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr 4-Cl-Ph c-Pr 4-CF 3-Ph 4-H 3-Ph 4-CH 3-Ph 4-F-Ph 4-Cl-Ph 4-Cl-Ph | CO 2CH 2CH 3 CH(Cl)CO 2CH 2CH 3 CH(CH 3)CO 2CH 2CH 3 CH 2CO 2CH 2CH 3 CCl 2CO 2CH 2CH 3 CO 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CH 2CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 CH(OCH 2CH 3) 2 CH(OCH 3) 2 CH(CO 2CH 2CH 3)OC(O)CH 3 CH＝NOCH 3 CH＝NNHCH 3 CH＝NN(CH 3) 2 CH＝NNHC(O)CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 C(OH)CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2H | F Br Br Br Br Br Br Br Br Br Br Br Br Cl Cl Br F Br Br Br Br Br Br Br Br Br Br Br Cl OMe Br Br Cl Br Cl Cl | NH 2 NH 2 NH 2 N＝CHN(CH 3) 2 NH 2 NHOH NH 2 NH 2 NH(CH 2) 2N(CH 3) 2 NHCH 2CH 2OCH 3 N＝CHN(CH 3) 2 NH 2 NHNH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NHOCH 3 NHC(O)CH 3 NHOCH 2Ph NHO(t-Bu) N_CH 2(CH 2) 2CH 2_ NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 | * * * * * * 69-70 120-121 * * * * * * * * * * * * * * * * * * * * 215-218 * * * * * 132-133 158-160 dec. |
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 | 3; 4-two-Cl-Ph 2; 4-two-Cl-Ph 1; 3-benzo dioxole-5-base 2-F-4-Cl-Ph 3; 4-two-Me-Ph 3; 4-two-Me-Ph 2; 4-two-Cl-Ph 3; 4-two-Cl-Ph 1,3-benzo dioxole-5-base c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr 4-Me-Ph 4-Cl-Ph 4-Me-Ph c-Pr 3-F-4-Me-Ph 3-F-4-Me-Ph 4-Cl-Ph 4-Me-Ph 4-F-Ph 4-Me-Ph 4-F-Ph 4-F-Ph 4-Br-Ph 4-Br-Ph 4-Br-Ph 3-Me-Ph 4-MeO-Ph 4-Et-Ph 3-Cl-Ph 3-Br-5-MeO-Ph | CO 2CH 2CH 3 CO 2CH 2CH 3CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3CO 2CH 2CH 3 CO 2CH 2CH 2CH 3 CO 2CH 2CH 2CH 2CH 3 C(O)O _Na _ CO 2CH 2Ph CO 2CH 3 CO 2CH 2(4-Cl-Ph) C(O)NHCH 3 CO 2CH 3 CO 2CH 3 CO 2CH 3 C(O)NH 2 CO 2CH 3 CO 2H CO 2H CO 2H CO 2H CO 2H CO 2CH 3 CO 2H CO 2CH 2CH 3 CO 2H CO 2CH 3 CO 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 | Br Br Br Br Br Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Br Br Cl Cl Cl Cl Br Br Cl Cl Br Br Cl Cl Cl Cl Cl Cl Cl Cl | NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NHCH 3 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 | * * * * * * * * * 87-90 97-99 297dec. 126-128 * 123-125 * * * * 232-236 185-186 150dec. * * * * * * 136-137 157-158 dec. 223-224 * * * * 110-112 |
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135(Ex.2) | 4-Cl-Ph 4-CF 3O-Ph 4-CF 3-Ph 4-Cl-Ph 2-F-Ph 3-CF 3-Ph i-Pr i-Pr i-Pr 4-Cl-Ph c-Pr c-Pr 4-Cl-Ph c-Pr c-Pr 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-MeS-Ph 4-MeS(O) 2-Ph 4-MeS (O)-Ph c-Pr c-Pr c-Pr 2-naphthyl 4-I-Ph 4-Br-Ph 4-Br-Ph 4-Cl-Ph c-Pr 4-I-Ph 4-I-Ph c-Pr | CO 2(i-Pr) CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 C(O)O _Na _ CO 2CH 3 CO 2CH 3 OCH 2CO 2CH 3 C(O)O _Na _ OCH 2CO 2CH 2CH 3 OCH 2CO 2CH 2CH 3 OCH 2C(O)O _Na _ C(O)O _Na _ CO 2CH 2Ph OCH 2CO 2CH 3 CH 2CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 CO 2CH 3 CO 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 2CH 3 CO 2CH 3 CO 2CH 3 C(O)NH 2 C(O)NHSO 2CH 3 C(O)NHSO 2CH 3 CO 2CH 2CH 3 CH(OCH 3) 2 CO 2H | Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Br Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Br Br Br Cl Br Br Br Cl Cl Cl Cl Cl | NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NHCH 3 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NHN＝CHCH 3 NHOCH 2CO 2H NHNHC(O)CH 3 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 | 153-156 * 138-140 80-81 120-124 121-122 102-103 190-192 dec. 100-104 dec. 124-126 148-150 ＞300 * 164-168 264-267 dec. ＞300 150-153 129-132 * 169-173 173-175 173-175 * * * * 192-195 204-206 234-236 243-245 227-233 140-142 176-179 144-146 |
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 136 137 138 139 141 143 144 145 146 148 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 | 4-Br-Ph 4-Cl-Ph 4-I-Ph c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr c-Pr | CO 2H CO 2CH 2CH 3CH(OCH 2CH 3) 2CO 2CH 2CH 2O(n-Bu) CO 2CH 2CH 2OCH 2CH 2OCH 3CO 2CH 2CH 2CH 2OH C(O)O _(i-Pr)NH 3 _CO 2(4-Cl-Ph) CO 2N＝C(CH 3) 2CO 2CH 2CO 2CH 3C(O)O _(c-hexyl) NH 3 _C(O)O __(CH 2) 2O(CH 2) 2_NH 2 _C(O)O _(HOCH 2CH 2) 2NH 2 _C(O)O _(CH 3CH 2) 3NH _C(O)O _Pyridine-H _C(O)O _Li _C(O)O _K _C(O)O _Cs _C(O)O _(CH 3) 4N _C(O)O _(CH 3) 3S _C(O)O _HOCH 2CH 2NH 3 _C(O)O _(HOCH 2CH 2) 3NH _C(O)O _(CH 3) 2NH 2 _CO 2(CH 2) 7CH 3CO 2(i-Pr) CO 2CH(CH 3)(CH 2) 5CH 3CO 2CH 2CH(C 2H 5)(CH 2) 3CH 3 | Br I Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl | NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 NH 2 | 167-170 116-119 * 64-66 79-80 91-94 170dec. 145-147 101-103 107-108 170dec. 189-190 dec. 118-124 138-141 dec. 144-147 dec. 280dec. 273dec. 300dec. 263dec. 157dec. 168dec. 125-128 170dec. 73-74 143-144 82-85 60-62 |
* 1H NMR data are referring to concordance list D.
Concordance list B
| Compound | R 1 | R 2 | R 3 | R 4 | m.p.(℃) |
| 140 147 149 150 | c-Pr c-Pr c-Pr c-Pr | CO 2CH 2(2-Oxyranyle) CO 2CH 2(2,2-two-Me-1,3-dioxolane-4-yl) CO 2CH 2(2-oxo-1,3-dioxolane-4-yl) CO 2CH 2(tetrahydrochysene-2-furyl) | Cl Cl Cl Cl | NH 2 NH 2 NH 2 NH 2 | * 104-105 142-150 114-116 |
* 1H NMR data are referring to concordance list D.
Concordance list C
| Compound | R 1 | R 3 | R 4 | m.p.(℃) |
| 142 | c-Pr | Cl | NH 2 | 107-108 |
* 1H NMR data are referring to concordance list D.
Concordance list D
| Compound | 1H NMR data (CDCl 3Solution, unless otherwise indicated) a |
| 5 11 12 13 19 20 23 24 25 26 27 30 31 32 33 34 | δ5.60(br s，1H)，3.96(s，3H)，3.02(d，3H)，2.10(m，1H)，1.10(m，2H)，0.98(m，2H). δ5.20(br s，2H)，4.97(s，2H)，3.49(s，3H)，2.07(m，1H)，1.02(m，2H)，0.95(m，2H). δ5.20(br s，2H) 4.18(q，2H)，3.80(s，2H)，1.90(m，1H)，1.25(t，3H)，1.01-0.93(m，4H). δ5.26(br s，2H)，3.82(s，2H)，3.73(s，3H)，1.90(m，1H)，1.02-0.92(m，4H). δ8.60(s，1H)，3.97(s，3H)，3.20(s，3H)，3.19(s，3H)，2.10(m，1H)，1.08(m，2H)，0.99(m， 2H). δ7.65(br s，1H)，5.94(br s，2H)，5.8(br s，1H)，2.01(m，1H)，1.03(m，4H). δ8.35(m，2H)，7.46(m，3H)，5.61(br s，2H)，4.02(s，3H). δ10.01(s，1H)，5.31(br s，2H)，2.10(m，1H)，1.10-0.95(m，4H). δ5.15(br s，2H)，3.98(s，3H)，2.03(m，1H)，1.04-0.92(m，4H). δ9.98(s，1H)，5.60(br s，2H)，2.10(m，1H)，1.10-1.02(m，4H). δ8.19(s，1H)，1.89(m，1H)，0.92-0.87(m，4H). δ5.12(br s，2H)，4.45(q，2H)，2.13(m，1H)，1.41(t，3H)，1.04-0.92(m，4H). δ5.66(s，1H)，5.34(br s，2H)，4.30(q，2H)，1.98(m，1H)，1.30(m，3H)，1.13-0.92(m，4H). δ5.26(br s，2H)，4.21-4.07(m，3H)，1.94(m，1H)，1.45(d，2H)，1.22(t，3H)，1.08-0.90(m， 4H). δ8.57(s，1H)，4.18(q，2H)，3.88(s，2H)，3.18(s，3H)，3.16(s，3H)，2.00(m，1H)，1.24(t， 3H)，1.05-0.96(m，4H). δ5.48(br s，2H)，4.38(q，2H)，2.02(m，1H)，1.36(t，3H)，1.11-0.97(m，4H). |
| Compound | 1H NMR data (CDCl 3Solution, unless otherwise indicated) a |
| 35 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 59 60 | δ3.97(s，3H)，2.07(m，1H)，1.20-1.13(m，2H)，1.12-1.04(m，2H). δ6.20(br s，1H)，4.43(q，2H)，3.48(m，2H)，2.50(m，2H)，2.27(s，6H)，2.07(m，1H)，1.41 (t，3H)，1.07(m，2H)，0.96(m，2H). δ5.90(br s，1H)，4.43(q，2H)，3.65(m，2H)，3.54(m，2H)，3.39(s，3H)，2.08(m，1H)，1.41 (t,3H)，1.04(m，2H)，0.98(m，2H). δ8.59(s，1H)，4.44(q，2H)，3.20(s，3H)，3.18(s，3H)，2.10(m，1H)，1.41(t，3H)，1.11-1.05 (m，2H)，1.01-0.94(m，2H). δ8.27(m，2H)，7.39(m，2H)，5.39(br s，2H)，4.23(q，2H)，3.93(s，2H)，1.29(t，3H). δ6.70(br s，1H)，4.43(q，2H)，4.0(br s，2H)，2.10(m，1H)，1.41(t，3H)，1.11(m，2H)，1.01 (m，2H). δ8.35(m，2H)，7.10(dd，2H)，5.54(br s，2H)，4.02(s，3H). δ8.47(d，2H)，7.69(d，2H)，5.61(br s，2H)，4.04(s，3H). δ5.56(s，1H)，5.29(br s，2H)，3.86-3.74(m，2H)，3.71-3.58(m，2H)，2.14-2.03(m，1H)， 1.30-1.23(m，6H)，1.07-0.89(m，4H). δ5.39(s，1H)，4.96(br s，2H)，3.49(s，6H)，2.15-2.04(m，1H)，1.02-0.87(m，4H). δ6.32(s，1H)，5.34(br s，2H)，4.28(q，2H)，2.21(s，3H)，2.03-1.93(m，1H)，1.28(t，3H)， 1.11-0.91(m，4H). δ8.41(s，1H)，5.34(br s，2H)，4.12(s，3H)，2.19-2.10(m，1H)，0.90-0.80(m，4H). (DMSO-d 6)δ8.45(q，1H)，7.34(s，1H)，6.82(br s)，2.86(d，3H)，1.91-1.81(m，1H)，1.07- 0.92(m，4H). δ7.23(s，1H)，5.18(br s，2H)，3.21(s，6H)，2.19-2.08(m，1H)，1.05-0.88(m，4H). (DMSO-d 6)δ11.68+11.55(2xs，1H)，8.39+8.09(2xs，1H)，2.20+1.97(2xs，3H)， 1.97-1.86(m，1H)，0.90(d，4H). δ8.76+8.07(2xs，1H)，4.50-4.32(br s，2H)，3.94+3.89(2xs，3H)，2.26-2.11(br m，1H)， 1.40(br s，3H)，1.20-1.12(m，2H)，1.09-1.00(m，2H). δ4.49(q，2H)，2.30(s，3H)，2.3-2.2(m，1H)，1.43(t，3H)，1.27-1.09(m，4H). δ7.47-7.34(m，5H)，5.06(s，2H)，4.43(q，2H)，1.90-1.84(m，1H)，1.41(t，3H)，1.23-1.03 (m，4H). δ8.64+7.64(2xs，1H)，4.45+4.36(2xq，2H)，2.20-2.10(m，1H)，1.42+1.37(2xt.3H)， 1.34+1.32(2xs，9H)，1.18-0.98(m，4H). δ4.42(q，2H)，3.77(m，4H)，2.07-1.97(m，1H)，1.91(m，4H)，1.40(t，3H)，1.07-0.89(m， 4H). δ5.37-5.30(m，3H)，4.51(d，1H)，4.28-4.16(m，2H)，2.06-1.96(m，1H)，1.27(t，3H)，1.09- 0.94(m，4H). δ5.14(br s，2H)，3.97(s，3H)，3.84(s，3H)，2.09(m，1H)，1.00(m，2H)，0.94 (m，2H). δ8.46(d，2H)，7.69(d，2H)，5.65(br s，2H)，4.50(m，2H)，1.46(t，3H). |
| Compound | 1H NMR data (CDCl 3Solution, unless otherwise indicated) a |
| 61 62 63 66 67 68 69 70 71 72 73 74 79 81 82 83 84 88 89 90 91 92 93 97 98 99 100 103 114 120 | δ8.23(d，2H)，7.24(d，2H)，5.57+5.53(2x br s，2H)，4.49(m，2H)，2.40(s，3H)，1.45(t， 3H). δ8.23(d，2H)，7.24(d，2H)，5.53(br s，2H)，4.49(m，2H)，2.40(s，3H)，1.45(t，3H). δ8.35(m，2H)，7.11(t，2H)，5.57(br s，2H)，4.49(m，2H)，1.45(t，3H). δ8.46(d，1H)，8.20(dd，1H)，7.50(d，1H)，5.629br s，2H)，4.50(m，2H)，1.46(t，3H). δ7.67(d，1H)，7.48(d，1H)，7.32(dd，1H)，5.69(br s，2H)，4.47(m，2H)，1.43(t，3H). δ7.96(dd，1H)，7.83(d，1H)，6.85(d，1H)，6.02(s，2H)，5.53(brs，2H)，4.48(m，2H)，1.45(t， 3H). δ8.97(t，1H)，7.23-7.15(m，2H)，5.67(br s，2H)，4.48(m，2H)，1.44(t，3H). δ8.11(m，1H)，8.06(m，1H)，7.19(d，1H)，5.57(br s，2H)，4.49(m，2H)，2.32(t，3H)，2.30(t， 3H)，1.45(t，3H). δ8.11(m，1H)，8.06(m，1H)，7.20(d，1H)，5.50(br s，2H)，4.49(m，2H)，2.33(t，3H)，2.31(t， 3H)，1.45(t，3H). δ7.67(d，1H)，7.48(d，1H)，7.32(dd，1H)，5.63(br s，2H)，4.48(m，2H)，1.43(t，3H). δ8.46(d，1H)，8.20(dd，1H)，7.50(d，1H)，5.56(br s，2H)，4.50(m，2H)，1.46(t，3H). δ7.95(dd，1H)，7.83(d，1H)，6.86(d，1H)，6.02(s,2H)，5.48(br s，2H)，4.48(m，2H)，1.45(t， 3H). δ5.56(br s，1H)，3.97(s，3H)，3.04(d，3H)，2.11(m，1H)，1.10(m，2H)，0.98(m，2H). δ7.82(br s，1H)，5.48(br s，2H)，2.97(d，3H)，2.01(m，1H)，1.04(m，2H)，0.99(m，2H). δ8.22(d，2H)，7.24(d，2H)，5.57+5.52(2xbr s，2H)，4.02(s，3H)，2.40(s，3H). δ8.29(d，2H)，7.40(d，2H)，5.60(br s，2H)，4.02(s，3H). δ8.22(d，2H)，7.24(d，2H)，5.53(br s，2H)，4.02(s，3H)，2.40(s，3H). (DMSO-d 6)δ14.1-13.9(brs)，8.25(d，2H)，7.56(d，2H). (DMSO-d 6)δ8.15(d，2H)，7.29(d，2H)，2.36(s，3H). (DMSO-d 6)δ14.2-13.9(brs)，8.29(m，2H)，7.31(t，2H). δ8.18(d，2H)，7.30(d，2H)，5.84(br s，2H)，2.43(s，3H). δ8.35(m，2H)，7.11(t， 2H)，5.59(br s，2H)，4.02(s，3H). δ8.32(m，2H)，7.17(t， 2H)，5.96(br s，2H). δ8.11(m，2H)，7.31(m，2H)，5.57(br s，2H)，4.02(s，3H)，2.42(s，3H). δ8.30(d，2H)，6.94(d，2H)，5.48(br s，2H)，4.49(q，2H)，3.86(s，3H)，1.45(t，3H). δ8.24(d，2H)，7.26(d，2H)，5.51(br s，2H)，4.49(q，2H)，2.70(q，2H)1.45(t，3H)，1.26(t， 3H). δ8.35(s，1H)，8.24(d，1H)，7.46-7.34(m，2H)，5.56(br s，2H)，4.50(q，2H)，1.46(t，3H). δ8.39(d，2H)，7.27(d，2H)，5.47(br s，2H，4.50(q，2H)，1.45(t，3H). δ8.19(d，2H)，7.38(d，2H)，5.26(br s，2H)，4.98(s，2H)，4.24(q，2H)，1.26(t，3H). δ8.27(d，2H) ，739(d，2H)，5.34(br s，2H)，4.23(q，2H)，3.91(s，2H)，1.29(t，3H). |
| Compound | 1H NMR data (CDCl 3Solution, unless otherwise indicated) a |
| 124 125 126 127 138 140 | δ8.61+8.48(2xs，1H)，7.48+7.12(2xq，1H)，3.98+3.96(2xs，3H)，2.30-2.15(m，1H)， 2.14+2.00(2xd，3H)，1.19-1.12(2xm，2H)，1.06-0.97(2xm，2H). δ4.61+4.54(2xbr s，2H)，4.47-4.36(m，2H)，2.18-1.98(br m，1H)，1.44-1.34(m，3H)， 1.32-1.00(br m，4H). δ7.83(d，1H)，7.69(d，1H)，4.45(q，2H)，2.14(s，3H)，1.41(t，3H)，1.08-1.00(m，4H). δ8.89(s，1H)，8.43(d，1H)，7.97(d，1H)，7.92-7.83(m，2H)，7.57-7.46(m，2H)，5.57(br s， 2H)，4.53(q，2H)，1.48(t，3H). δ8.11(d，2H)，7.76(d，2H)，5.65(s，1H)，5.39(br s，2H)，3.88(m，2H)，3.70(m，2H)，1.30(t， 6H). 5.38(br s，2H)，4.44(dd，1H)，4.28(dd，1H)，3.35(m，1H)，2.88(dd，1H)，2.76(dd，1H)，2.07 (m，1H)，1.05(m，2H)，1.00(m，2H). |
A1H NMR data are carried out record with ppm according to the downfield from tetramethylsilane.Coupling usefulness (s)-unimodal, (d)-bimodal, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-double doublet, (dt)-two triplets, (dq)-two quartets, (br s)-wide unimodal, (br d)-and wide bimodal, (br m)-wide multiplet is represented.
Biological Examples of the present invention
Test A
The seed of barnyard grass grass (Echinochloa crus-galli), lady's-grass (Digitaria sanguinalis), Fa Shi dog hair grass (Setaria faberi), sweet potato (Ipomoea spp.), Amaranthus retroflexus (Amaranthusretroflexus) and piemarker (Abutilon theophrasti) is implanted in the mixture of loam and sand, uses directionally soil spraying the carrying out seedling pre-treatment of test chemical of the solvent mixture preparation of the plant-less toxicity that comprises tensio-active agent.Simultaneously, above-mentioned kind is also carried out the seedling aftertreatment with the test chemical of same way as preparation.
Plant length is to 2-10 centimetre high and be in the 1-2 leaf during phase, carries out the seedling aftertreatment.Handle plant and untreated control and brought up in the greenhouse about 10 days, all afterwards processing plant and untreated control compare, and the visually rank infringement.Plant reaction grade (being summarized in the Table A) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table A | Compound | |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 2000g ai/ha seedling | 1 75 80 75 100 100 85 | 57 75 30 80 80 95 80 |
| Table A | Compound |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 1000g ai/ha seedling | 43 20 30 10 45 85 50 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 1 75 65 70 95 100 95 | 20 0 0 0 40 60 55 | 57 25 10 60 70 75 50 | 58 10 10 50 80 80 85 | 59 30 10 35 100 80 85 | 60 0 0 0 20 40 40 | 61 60 5 25 30 50 100 | 62 80 35 80 35 60 95 | 63 0 0 0 25 65 70 | 64 70 70 80 95 100 100 | 65 85 80 95 95 100 100 | 66 0 0 0 30 65 75 | 67 0 5 0 60 90 75 | 68 0 0 0 35 55 60 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 69 5 40 55 90 90 90 | 70 0 20 0 10 20 60 | 71 0 5 0 0 30 55 | 72 0 30 0 70 95 85 | 73 5 35 45 65 80 75 | 74 70 60 70 30 70 80 | 75 90 90 90 90 100 100 | 76 90 70 90 95 95 100 | 77 90 90 90 100 95 100 | 78 90 80 80 90 95 90 | 79 90 75 90 95 100 95 | 80 90 70 90 95 95 90 | 81 30 10 30 80 75 75 | 82 50 0 0 40 75 90 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 83 10 10 10 75 85 90 | 84 80 10 20 20 65 90 | 85 0 0 0 75 90 60 | 86 30 0 0 20 50 85 | 87 90 10 30 15 90 95 | 88 85 85 90 85 95 95 | 89 85 10 45 30 100 95 | 90 10 20 30 65 90 85 | 91 90 15 75 30 100 95 | 92 0 5 0 75 70 70 | 93 0 0 0 55 70 80 | 94 60 50 65 75 85 90 | 95 90 80 85 80 95 95 | 96 25 20 35 65 85 85 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 97 10 0 0 50 30 70 | 98 20 10 15 0 15 45 | 99 0 0 0 0 10 35 | 100 10 0 0 55 25 70 | 101 0 0 0 0 5 15 | 102 0 10 0 15 65 70 | 103 0 0 0 0 20 70 | 104 10 30 5 40 45 80 | 105 25 45 10 70 90 95 | 106 5 0 0 35 70 55 | 107 0 5 35 0 10 65 | 108 5 0 10 90 85 65 | 109 10 10 10 80 85 80 | 110 10 10 5 85 85 65 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 111 10 30 0 50 85 85 | 112 0 0 0 50 40 35 | 113 90 55 85 90 90 95 | 114 0 0 0 55 55 5 | 115 0 0 0 60 45 40 | 116 0 0 0 60 35 40 | 117 90 90 90 90 100 100 | 118 0 20 15 70 75 95 | 119 5 0 0 35 45 10 | 120 40 5 0 55 35 65 | 121 5 0 0 10 0 0 | 122 0 0 0 0 0 0 | 123 10 0 10 20 0 0 | 127 0 0 0 0 10 80 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 128 0 0 0 80 75 80 | 129 0 0 0 70 85 90 | 130 0 0 0 0 15 30 | 131 20 30 30 20 70 60 | 132 10 10 5 50 65 60 | 133 40 55 60 85 90 85 | 134 0 0 0 0 30 55 | 135 90 65 80 100 95 100 | 136 80 70 80 80 100 95 | 137 0 0 0 30 45 60 | 138 0 0 0 20 35 70 | 139 90 70 80 90 100 90 | 140 90 80 90 90 100 90 | 141 90 80 85 90 100 100 |
| Table A | Compound | ||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 500g ai/ha seedling | 142 75 25 45 90 90 90 | 143 75 60 80 90 90 95 | 144 90 80 80 95 100 100 | 145 60 30 70 95 90 95 | 146 90 80 85 100 95 100 | 147 90 75 90 100 95 100 | 148 90 85 80 100 95 95 | 149 90 75 80 95 90 100 | 150 95 80 85 100 90 100 |
| Table A | Compound |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 250g ai/ha seedling | 43 10 10 10 20 60 50 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 20 0 0 0 20 40 10 | 58 5 5 0 55 70 70 | 59 0 0 0 90 60 60 | 60 0 0 0 0 10 30 | 61 35 0 0 10 25 70 | 62 15 0 0 10 30 90 | 63 0 0 0 20 40 55 | 64 25 50 70 80 90 95 | 65 85 55 85 75 100 95 | 66 0 0 0 20 50 50 | 67 0 5 0 50 90 65 | 68 0 0 0 15 50 60 | 69 0 20 0 75 90 85 | 70 0 0 0 0 15 35 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 71 0 0 0 0 5 40 | 72 0 10 0 55 95 85 | 73 0 15 15 50 75 70 | 74 30 30 60 40 60 70 | 75 85 80 90 90 90 85 | 76 90 45 90 90 85 80 | 77 90 70 85 95 95 95 | 78 80 70 70 80 85 75 | 79 85 40 80 90 90 90 | 80 55 30 70 90 65 65 | 81 0 0 0 50 55 50 | 82 40 0 0 20 45 90 | 83 0 0 0 55 70 90 | 84 55 0 0 5 60 75 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 85 0 0 0 20 75 25 | 86 10 0 0 0 20 70 | 87 50 0 0 0 55 90 | 88 50 60 80 60 90 90 | 89 60 0 10 0 50 70 | 90 0 0 0 20 35 65 | 91 75 5 5 5 55 75 | 92 0 0 0 45 35 45 | 93 0 0 0 40 45 65 | 94 30 35 45 70 80 90 | 95 75 70 85 75 85 90 | 96 20 5 25 60 70 80 | 97 30 0 0 45 10 60 | 98 0 0 0 0 5 35 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 99 0 0 0 0 5 0 | 100 0 0 0 40 10 50 | 101 0 0 0 0 0 0 | 102 0 10 0 0 50 45 | 103 0 0 0 0 0 45 | 104 0 15 0 25 30 70 | 105 10 20 10 50 65 85 | 106 0 0 0 20 15 25 | 107 0 0 0 0 10 35 | 108 0 0 0 70 50 35 | 109 0 0 0 70 60 25 | 110 0 0 0 70 55 40 | 111 0 5 0 20 55 75 | 112 0 0 0 55 20 20 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 113 55 25 65 90 80 80 | 114 0 0 0 40 45 0 | 115 0 0 0 35 10 30 | 116 0 0 0 40 20 15 | 117 85 75 80 90 100 100 | 118 0 10 0 65 60 90 | 119 0 0 0 40 25 0 | 120 10 0 0 25 20 50 | 121 0 0 0 0 0 0 | 122 0 0 0 0 0 0 | 123 0 0 0 0 0 0 | 127 0 0 0 0 0 60 | 128 0 0 0 55 55 65 | 129 0 0 0 60 80 80 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 130 0 0 0 0 0 0 | 131 10 10 15 0 50 35 | 132 0 5 0 45 50 50 | 133 10 30 15 70 80 80 | 134 0 0 0 0 15 50 | 135 75 65 75 90 90 85 | 136 50 35 75 70 85 85 | 137 0 0 0 5 25 45 | 138 0 0 0 0 20 60 | 139 80 60 80 80 90 85 | 140 70 65 85 85 90 90 | 141 80 25 40 90 90 85 | 142 45 15 30 90 85 80 | 143 55 5 25 90 70 75 |
| Table A | Compound | ||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker behind the 125g ai/ha seedling | 144 60 40 70 85 85 95 | 145 30 5 20 80 80 75 | 146 70 20 80 85 90 85 | 147 80 25 60 85 85 80 | 148 68 10 45 90 75 75 | 149 65 25 60 80 75 85 | 150 80 65 80 80 90 90 |
| Table A | Compound | |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 2000g ai/ha seedling | 1 80 75 85 100 100 80 | 57 80 70 70 100 100 95 |
| Table A | Compound |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 1000g ai/ha seedling | 43 10 10 10 45 75 20 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 1 60 25 40 85 85 60 | 20 0 0 0 60 70 70 | 57 25 10 10 100 90 80 | 58 0 0 10 25 60 40 | 59 15 0 0 100 70 45 | 60 0 0 0 0 0 0 | 61 10 30 10 15 30 50 | 62 45 60 0 35 75 75 | 63 40 75 35 0 80 15 | 64 60 90 70 70 100 95 | 65 90 90 80 90 100 95 | 66 0 15 0 0 10 35 | 67 0 30 30 0 75 40 | 68 0 0 0 0 15 10 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 69 15 75 50 0 85 65 | 70 0 20 5 0 10 35 | 71 0 0 0 0 15 50 | 72 0 0 0 0 100 55 | 73 30 35 15 0 60 40 | 74 50 50 40 30 40 50 | 75 95 90 90 100 95 95 | 76 90 75 85 100 90 100 | 77 100 80 95 100 95 100 | 78 75 70 65 100 90 85 | 79 80 80 95 100 100 90 | 80 80 85 70 100 90 90 | 81 20 10 10 50 70 40 | 82 15 0 0 0 70 35 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 83 5 5 0 10 50 30 | 84 25 15 20 0 80 70 | 85 0 5 0 20 60 10 | 86 0 0 0 0 5 10 | 87 20 75 0 20 100 95 | 88 55 85 50 90 100 70 | 89 50 60 10 0 100 75 | 90 35 50 15 25 80 45 | 91 80 75 25 50 100 100 | 92 0 0 0 0 45 45 | 93 30 45 35 5 90 85 | 94 40 55 40 35 95 90 | 95 80 85 90 85 100 95 | 96 10 65 10 80 80 80 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 97 0 25 5 0 70 50 | 98 0 15 0 0 0 5 | 99 0 0 0 0 0 0 | 100 0 0 0 0 0 0 | 101 0 0 0 0 0 0 | 102 0 0 0 0 15 20 | 103 0 0 0 0 10 10 | 104 5 10 5 0 10 10 | 105 0 0 0 0 0 0 | 106 5 0 0 0 30 30 | 107 0 5 0 0 0 10 | 108 15 20 0 90 75 50 | 109 25 25 5 95 80 50 | 110 15 15 0 90 65 35 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 111 0 0 0 0 0 0 | 112 10 10 0 10 30 10 | 113 80 70 80 100 90 95 | 114 0 0 0 0 0 0 | 115 20 10 0 35 40 10 | 116 20 10 0 50 50 15 | 117 85 75 85 85 100 100 | 118 10 25 15 0 55 15 | 119 10 0 0 0 0 0 | 120 15 0 0 0 0 0 | 121 0 0 0 0 0 0 | 122 0 0 0 0 0 0 | 123 0 0 0 0 0 0 | 127 0 0 0 0 0 0 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 128 0 0 0 0 0 0 | 129 0 0 0 0 15 5 | 130 0 0 0 0 0 0 | 131 0 0 0 0 0 0 | 132 0 0 0 0 65 5 | 133 15 45 30 35 65 30 | 134 0 0 0 0 0 0 | 135 90 95 85 100 100 100 | 136 40 60 60 20 100 75 | 137 0 0 0 0 0 0 | 138 0 0 0 0 0 0 | 139 90 90 90 100 100 90 | 140 90 90 85 95 95 95 | 141 75 85 85 95 85 85 |
| Table A | Compound | ||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 500g ai/ha seedling | 142 75 85 65 95 90 85 | 143 85 95 75 100 95 95 | 144 80 95 80 95 85 85 | 145 75 80 60 100 85 85 | 146 90 75 90 100 95 100 | 147 85 80 85 100 90 95 | 148 85 90 80 100 90 100 | 149 85 75 90 100 90 85 | 150 80 80 80 100 95 95 |
| Table A | Compound |
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 250g ai/ha seedling | 43 0 0 0 0 0 0 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 20 0 0 0 10 40 0 | 58 0 0 0 10 0 0 | 59 0 0 0 80 20 10 | 60 0 0 0 0 0 0 | 61 0 0 0 0 0 0 | 62 0 0 0 0 0 0 | 63 0 0 0 0 0 0 | 64 0 25 15 40 20 25 | 65 50 60 40 25 100 55 | 66 0 0 0 0 0 0 | 67 0 0 0 0 10 10 | 68 0 0 0 0 0 5 | 69 0 50 10 0 65 35 | 70 0 5 5 0 0 20 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 71 0 0 0 0 0 30 | 72 0 0 0 0 75 40 | 73 5 5 0 0 15 35 | 74 0 20 0 0 0 30 | 75 70 85 75 95 90 80 | 76 75 30 70 100 80 90 | 77 90 70 75 100 85 100 | 78 45 55 10 90 75 80 | 79 30 30 40 55 90 60 | 80 10 45 15 90 80 75 | 81 10 0 0 0 60 20 | 82 0 0 0 0 0 5 | 83 0 0 0 0 20 15 | 84 0 0 0 0 0 15 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 85 0 0 0 0 50 0 | 86 0 0 0 0 0 0 | 87 0 10 0 0 85 25 | 88 10 35 10 10 80 10 | 89 0 0 0 0 80 20 | 90 0 10 0 0 70 10 | 91 5 25 0 5 100 80 | 92 0 0 0 0 15 10 | 93 5 25 5 0 80 55 | 94 5 45 20 30 90 75 | 95 20 65 65 80 95 55 | 96 5 50 5 15 80 65 | 97 0 15 5 0 25 45 | 98 0 0 0 0 0 0 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 99 0 0 0 0 0 0 | 100 5 10 0 0 20 0 | 101 0 0 0 0 0 0 | 102 0 0 0 0 10 10 | 103 0 0 0 0 0 0 | 104 0 0 0 0 0 0 | 105 0 0 0 0 0 0 | 106 0 0 0 0 0 5 | 107 0 0 0 0 0 0 | 108 10 0 0 0 55 10 | 109 0 0 0 30 50 15 | 110 0 0 0 0 40 25 | 111 0 0 0 0 0 0 | 112 0 0 0 0 10 0 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 113 25 15 15 90 80 65 | 114 0 0 0 0 0 0 | 115 0 0 0 25 30 5 | 116 10 0 0 30 30 0 | 117 25 45 50 10 65 55 | 118 0 10 0 0 10 0 | 119 0 0 0 0 0 0 | 120 5 0 0 0 0 0 | 121 0 0 0 0 0 0 | 122 0 0 0 0 0 0 | 123 0 0 0 0 0 0 | 127 0 0 0 0 0 0 | 128 0 0 0 0 0 0 | 129 0 0 0 0 0 0 |
| Table A | Compound | |||||||||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 130 0 0 0 0 0 0 | 131 0 0 0 0 0 0 | 132 0 0 0 0 15 0 | 133 0 0 0 0 10 10 | 134 0 0 0 0 0 0 | 135 65 75 30 95 85 80 | 136 5 20 10 10 45 30 | 137 0 0 0 0 0 0 | 138 0 0 0 0 0 0 | 139 75 75 80 90 90 90 | 140 70 70 40 90 90 90 | 141 35 60 5 85 80 80 | 142 50 45 25 85 70 85 | 143 65 70 35 90 65 90 |
| Table A | Compound | ||||||
| The barnyard grass mare Fa Shi of Tang dog hair grass sweet potato Amaranthus retroflexus piemarker before the 125g ai/ha seedling | 144 65 75 35 85 75 75 | 145 30 65 0 75 65 70 | 146 65 35 60 95 75 85 | 147 70 70 40 95 80 75 | 148 65 45 40 90 80 80 | 149 70 20 35 85 70 70 | 150 65 50 50 90 70 75 |
Test B
Plantation is selected from barnyard grass grass (Echinochloa crus-galli), pitch arm shape grass (Brachiariadecumbens), Siberian cocklebur (Xanthium strumarium), corn (Zea mays), lady's-grass (Digitaria sanguinalis), Fa Shi dog hair grass (Setaria faberii), lamb's-quarters (Chenopodium album), sweet potato (Ipomoea coccinea), Amaranthus retroflexus (Amaranthusretroflexus), piemarker (Abutilon theophrasti), and the seed of common wheat (Triticumaestivum) also carries out the seedling pre-treatment with the test chemical that the solvent mixture of the plant-less toxicity that comprises tensio-active agent is prepared.
Simultaneously, be selected from the test chemical that the plant of above-mentioned crop and weeds kind and big fringe amur foxtail (Alopecurusmyosuroides) and wild avena sativa (Avena fatua) prepares with same way as and carry out the seedling aftertreatment.When plant length arrives 2-18 centimetre high (1-4 leaf phase), carry out the seedling aftertreatment.Plant variety in the rice field test that big flood is irrigated, comprise rice (Oryza sativa), Herba Cyperi Difformis (Cyperus difformis), natural pond living different stamen flower (Heteranthera limosa) and barnyard grass grass (Echinochloa crus-galli), the 2 leaf phases of growing to test.Handle plant and brought up 13-15 days impinging upon in the greenhouse, all kinds and contrast afterwards compares, and visually rank.Plant reaction grade (being summarized among the table B) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table B | Compound | |||||||||||||
| 1000g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 1 80 80 70 20 | 2 90 90 60 90 | 3 0 0 0 0 | 4 90 100 80 80 | 5 50 90 0 90 | 7 20 0 0 0 | 8 70 90 60 40 | 9 90 100 80 90 | 10 0 0 0 0 | 11 0 70 0 20 | 12 0 20 20 0 | 13 0 0 0 0 | 14 80 80 20 50 | 15 90 80 70 70 |
| Table B | Compound | |||||||||||||
| 1000g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 16 90 90 70 60 | 17 80 90 50 50 | 18 0 80 0 0 | 19 80 80 60 70 | 21 60 80 40 0 | 22 80 90 60 50 | 23 0 30 0 0 | 24 0 0 10 20 | 25 30 40 30 40 | 26 60 90 70 80 | 27 0 60 20 60 | 28 0 30 0 0 | 30 0 0 0 0 | 31 30 60 20 0 |
| Table B | Compound | |||||||||||||
| 1000g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice | 32 0 0 0 | 33 0 0 0 | 34 0 0 0 | 35 0 0 0 | 36 0 0 0 | 37 20 100 0 | 38 0 0 0 | 39 0 0 0 | 40 70 80 60 | 41 0 90 0 | 42 0 0 0 | 44 0 90 0 | 45 0 0 0 | 46 0 60 0 |
| Herba Cyperi Difformis | 0 | 0 | 0 | 0 | 0 | 90 | 0 | 0 | 70 | 80 | 0 | 80 | 0 | 30 |
| Table B | Compound | |||||
| 1000g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 47 0 80 0 70 | 48 20 20 0 0 | 49 50 60 30 70 | 50 30 40 30 0 | 51 0 0 0 0 | 124 0 0 0 0 |
| Table B | Compound | |||||||||||||
| 500g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 58 0 100 0 100 | 59 0 0 0 0 | 60 20 90 0 30 | 64 0 100 0 90 | 75 70 70 70 10 | 76 70 70 50 70 | 77 60 80 50 40 | 78 40 70 40 50 | 79 0 70 20 0 | 80 50 70 50 70 | 83 0 100 0 100 | 88 0 90 0 90 | 91 20 100 0 90 | 92 0 90 0 90 |
| Table B | Compound | |||||||||
| 500g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 94 0 100 0 90 | 95 30 100 40 90 | 961 10 100 0 90 | 13 0 0 0 0 | 117 70 100 50 90 | 128 30 100 0 100 | 129 20 100 0 100 | 133 0 90 0 90 | 135 80 90 60 80 | 136 20 90 40 90 |
| Table B | Compound |
| 250g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 64 0 100 0 70 |
| Table B | Compound | |||||||||||||
| 125g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 58 0 100 0 90 | 59 0 0 0 0 | 60 0 80 0 0 | 64 0 90 0 0 | 75 0 0 0 0 | 76 0 0 0 30 | 77 0 40 0 0 | 78 0 20 20 10 | 79 0 10 0 0 | 80 0 50 0 20 | 83 0 100 0 90 | 88 0 90 0 60 | 91 0 100 0 80 | 92 0 80 0 80 |
| Table B | Compound | |||||||||
| 125g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 94 0 100 0 90 | 95 0 90 0 90 | 96 0 100 0 90 | 113 0 0 0 0 | 117 20 100 20 80 | 128 0 90 0 90 | 129 0 100 0 90 | 133 0 90 0 90 | 135 30 60 20 70 | 136 0 90 0 90 |
| Table B | Compound |
| 62g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 64 0 80 0 0 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 500g ai/ha seedling | 2 90 80 100 80 90 80 100 100 70 100 90 100 70 | 3 10 50 100 0 40 40 100 100 30 90 30 80 20 | 5 90 80 100 90 90 50 100 100 60 100 80 90 60 | 7 30 80 100 30 30 40 100 90 70 90 20 90 80 | 8 90 0 100 90 90 90 100 100 0 100 90 100 0 | 9 90 80 100 90 90 90 100 100 70 100 90 100 70 | 10 10 0 70 0 40 10 90 80 10 90 10 80 0 | 11 90 60 90 0 70 50 100 100 10 90 50 80 40 | 12 40 0 70 0 30 30 80 80 0 80 0 60 0 | 13 10 20 40 0 30 20 70 70 0 70 0 50 0 | 14 90 60 70 70 30 50 100 100 70 90 50 70 50 | 15 90 80 100 80 60 70 100 100 70 100 90 90 70 | 16 90 70 100 80 80 80 100 100 60 100 90 90 60 | 17 90 70 100 80 50 70 100 100 50 90 80 100 60 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn of barnyard grass grass behind the 500g ai/ha seedling | 18 0 0 70 0 | 19 90 80 100 70 | 21 0 20 10 0 | 22 90 80 100 80 | 23 0 10 90 0 | 24 10 10 70 10 | 25 80 60 90 30 | 26 60 70 90 20 | 27 0 30 100 20 | 28 50 30 100 0 | 30 80 70 100 30 | 31 0 0 80 0 | 32 70 40 90 10 | 33 20 40 80 0 |
| Lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat | 0 0 90 70 0 70 0 50 0 | 80 80 100 100 70 100 90 100 60 | 0 0 20 30 0 30 0 30 20 | 90 80 100 100 60 100 90 100 70 | 0 10 80 70 10 70 10 70 20 | 40 30 80 90 0 80 10 50 0 | 80 80 90 90 20 100 70 70 30 | 70 40 80 80 40 80 60 70 30 | 10 30 90 90 30 70 0 70 30 | 50 40 90 90 10 90 50 90 10 | 90 90 100 100 70 100 80 90 60 | 30 0 70 70 0 50 0 60 0 | 20 20 80 90 30 80 10 50 30 | 20 40 70 70 20 80 0 50 20 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 500g ai/ha seedling | 34 60 70 80 0 30 50 90 70 40 80 50 60 40 | 35 90 70 100 60 50 60 100 100 60 100 80 90 60 | 36 0 40 70 0 0 10 50 70 40 30 0 40 40 | 37 90 60 100 70 80 60 100 100 0 100 70 100 60 | 38 0 0 0 0 20 0 60 40 0 30 20 50 0 | 39 70 0 50 50 40 30 90 100 0 70 30 70 0 | 40 90 60 90 60 80 60 100 100 60 100 70 90 60 | 41 70 60 - 80 20 30 90 90 0 90 10 70 40 | 42 30 60 90 0 30 0 90 90 0 90 10 80 50 | 44 50 40 100 70 80 - 90 100 0 90 50 90 30 | 46 30 10 0 0 30 10 30 90 0 80 10 0 0 | 47 60 0 100 0 60 50 90 90 0 80 20 40 0 | 48 20 20 80 0 20 10 80 80 20 80 10 60 20 | 49 70 50 100 30 80 70 90 100 60 90 60 80 40 |
| Table B | Compound | ||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat behind the 500g ai/ha seedling | 50 50 50 90 40 80 70 90 90 60 | 51 60 30 90 0 60 30 90 90 30 | 52 80 50 60 60 60 60 90 90 20 | 54 70 40 80 20 30 30 90 90 40 | 55 50 40 80 20 30 20 90 90 20 | 56 30 20 20 0 0 0 30 50 20 | 124 40 40 80 0 40 20 90 100 30 | 125 70 20 60 0 30 40 70 90 20 | 126 0 0 0 10 20 0 40 60 20 |
| Amaranthus retroflexus pitch arm shape grass piemarker common wheat | 90 60 90 60 | 90 40 80 40 | 90 30 50 20 | 90 0 60 20 | 80 0 30 0 | 70 0 0 0 | 90 0 50 30 | 60 10 50 0 | 30 70 20 0 |
| Table B | Compound | |||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters behind the 250g ai/ha seedling | 1 90 70 90 70 90 80 100 | 4 90 90 100 90 90 90 100 | 45 0 0 10 0 20 0 30 | 53 90 60 90 70 30 70 100 |
| Table B | Compound | |||
| Sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 250g ai/ha seedling | 1 100 60 100 90 90 70 | 4 100 80 100 90 100 80 | 45 60 0 50 0 20 0 | 53 90 60 100 50 80 60 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 125g ai/ha seedling | 2 90 50 100 20 90 70 100 100 40 100 90 60 40 | 3 0 20 70 0 30 20 100 80 10 80 10 50 10 | 5 50 70 80 30 50 40 100 100 40 90 50 70 50 | 7 0 60 90 0 10 20 80 80 40 0 0 50 50 | 8 90 0 100 70 80 80 100 100 0 100 80 80 0 | 9 90 60 100 70 90 90 90 100 20 100 90 100 40 | 10 0 0 60 0 30 0 80 80 0 80 10 50 0 | 11 20 20 80 0 30 10 90 80 0 80 20 60 0 | 12 0 0 40 0 10 0 60 60 0 50 0 20 0 | 13 0 10 10 0 20 10 60 50 0 50 0 40 0 | 14 30 30 50 30 10 20 100 100 20 80 10 50 20 | 15 90 70 100 50 30 40 100 100 10 80 60 80 40 | 16 70 10 90 30 30 30 100 100 10 90 60 80 30 | 17 20 0 100 0 20 10 100 100 0 70 30 60 0 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn of barnyard grass grass behind the 125g ai/ha seedling | 18 0 0 70 0 | 19 80 60 90 30 | 21 0 10 0 0 | 22 70 60 100 20 | 23 0 0 30 0 | 24 0 0 50 0 | 25 40 10 90 0 | 26 20 40 80 0 | 27 0 30 100 0 | 28 20 10 90 0 | 30 0 60 100 0 | 32 20 30 40 0 | 33 0 40 60 0 | 34 0 60 80 0 |
| Lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat | 0 0 70 20 0 20 0 20 0 | 40 20 100 100 40 90 40 70 20 | 0 0 10 10 0 0 0 10 10 | 50 70 100 90 10 100 80 100 0 | 0 0 70 40 10 30 0 40 0 | 20 20 70 60 0 70 0 40 0 | 60 50 90 90 10 90 50 60 20 | 40 30 70 70 30 70 30 40 30 | 10 20 80 70 20 60 0 60 20 | 30 20 90 90 0 80 10 70 0 | 30 0 90 90 60 90 10 50 50 | 10 10 70 40 20 80 0 10 20 | 10 10 60 40 20 60 0 40 20 | 0 20 70 60 30 50 10 30 30 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 125g ai/ha seedling | 35 40 60 30 0 20 10 90 70 60 70 20 50 20 | 36 0 0 20 0 0 0 40 10 0 20 0 20 0 | 37 0 40 100 0 60 10 100 90 0 100 20 80 0 | 38 0 0 0 0 0 0 20 10 0 30 0 0 0 | 39 0 0 30 0 0 0 70 80 0 50 0 40 0 | 40 0 50 0 0 0 0 0 0 40 0 0 0 50 | 41 20 20 70 20 10 20 80 70 0 70 0 50 30 | 42 10 30 80 0 0 0 80 80 0 80 0 50 50 | 44 40 30 90 30 70 - 90 80 0 80 - 80 0 | 46 0 0 0 0 10 0 10 80 0 70 0 0 0 | 47 20 0 90 0 10 10 80 80 0 70 0 20 0 | 48 10 0 20 0 10 10 60 30 0 60 0 10 0 | 49 30 20 90 0 30 10 80 90 30 90 10 50 30 | 50 10 30 90 0 40 20 80 90 30 80 20 70 30 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus behind the 125g ai/ha seedling | 51 20 20 80 0 30 0 80 80 20 80 | 52 30 0 40 0 0 40 80 90 0 60 | 54 0 40 20 0 20 20 80 80 0 80 | 55 0 30 20 0 0 20 70 80 0 70 | 56 0 0 0 0 0 0 20 0 0 50 | 75 90 60 100 70 80 80 100 100 60 90 | 76 90 60 90 70 90 80 100 100 60 100 | 77 90 60 100 80 80 80 100 100 60 100 | 78 90 40 100 80 70 70 100 100 70 100 | 79 80 50 60 60 60 70 100 100 40 100 | 83 80 60 100 10 60 50 100 100 40 100 | 88 90 60 100 80 80 70 100 90 50 100 | 92 10 20 80 0 20 30 90 60 0 80 | 94 90 60 100 90 80 60 90 90 30 90 |
| Pitch arm shape grass piemarker common wheat | 0 70 30 | 0 40 0 | 0 50 0 | 0 10 0 | 0 0 0 | 80 100 70 | 80 90 70 | 80 90 60 | 80 80 70 | 60 80 40 | 60 90 30 | 80 100 60 | 10 60 0 | 80 100 60 |
| Table B | Compound | ||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 125g ai/ha seedling | 95 90 - 90 90 80 80 100 100 60 100 90 100 50 | 113 80 40 90 40 40 50 90 90 50 90 80 80 50 | 117 90 70 100 90 80 80 100 100 50 100 70 100 70 | 124 0 0 30 0 10 10 40 50 0 50 0 20 0 | 125 0 0 40 0 20 0 60 70 0 60 0 0 0 | 126 0 0 0 0 0 0 30 30 0 0 0 10 0 | 128 60 50 90 70 40 50 90 90 40 90 40 80 20 | 129 70 70 100 80 70 50 100 100 40 100 70 90 20 | 133 70 70 100 80 70 70 100 100 60 100 70 100 50 | 135 90 70 100 80 70 80 100 100 60 100 80 100 60 | 136 90 70 100 70 80 70 100 100 50 100 80 90 60 |
| Table B | Compound | |||||||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 62g ai/ha seedling | 1 50 40 90 30 70 50 100 90 20 90 60 90 30 | 4 70 70 90 50 80 80 100 90 50 100 90 70 40 | 31 0 0 70 0 0 0 40 50 0 20 0 10 0 | 45 0 0 0 0 0 0 10 40 0 30 0 0 0 | 53 80 20 50 0 0 30 90 90 30 80 10 40 30 | 65 70 70 100 80 80 70 100 80 40 100 80 90 50 | 75 80 50 70 60 70 60 90 100 50 80 70 70 50 | 76 90 50 60 50 70 60 100 100 50 90 70 90 60 | 77 60 50 70 30 70 70 100 100 50 90 70 80 50 | 78 80 20 100 40 60 60 100 100 50 80 60 70 50 | 79 50 20 - 20 30 40 90 90 30 80 20 50 0 | 83 50 50 90 10 50 40 100 60 0 100 50 80 0 | 88 90 40 100 70 70 60 100 60 40 100 80 90 50 | 92 10 20 60 0 0 20 90 50 0 70 0 50 0 |
| Table B | Compound | ||||||||
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass Fa Shi dog hair grass of barnyard grass grass lamb's-quarters sweet potato wild oat Amaranthus retroflexus Brachiaria decumbens piemarker common wheat behind the 62g ai/ha seedling | 94 80 40 100 70 70 50 90 80 30 90 80 90 40 | 95 90 60 90 80 80 80 100 90 30 100 80 100 40 | 113 50 30 90 10 20 20 80 90 40 70 30 60 30 | 117 90 60 100 90 60 80 90 80 30 100 70 90 50 | 128 40 40 70 10 20 30 90 40 0 90 30 50 0 | 129 60 70 70 70 50 40 100 50 0 100 50 80 0 | 133 70 60 100 70 60 60 100 70 40 90 60 90 0 | 135 70 60 100 50 60 80 100 100 60 100 80 100 40 | 136 70 70 90 40 70 60 100 40 20 90 70 80 20 |
| Table B | Compound |
| The big fringe amur foxtail Siberian cocklebur corn lady's-grass of barnyard grass grass behind the 4g ai/ha seedling | 65 20 20 80 10 20 |
| Table B | Compound |
| Fa Shi dog hair grass lamb's-quarters sweet potato wild avena sativa Amaranthus retroflexus behind the 4g ai/ha seedling | 65 40 80 70 0 70 |
| Table B | Compound |
| Pitch arm shape grass piemarker common wheat behind the 4g ai/ha seedling | 65 20 50 0 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens Tong fiber crops before the 500g ai/ha seedling | 2 90 100 80 90 90 100 100 100 90 100 | 3 0 80 0 50 0 90 60 90 20 70 | 5 30 80 70 70 10 100 80 90 10 90 | 7 30 80 0 30 0 90 80 90 0 80 | B 90 100 90 90 90 100 100 100 90 100 | 9 90 100 80 100 80 100 100 100 90 100 | 10 50 90 0 60 20 90 90 90 0 90 | 11 10 90 0 80 70 100 90 90 70 90 | 12 80 90 30 70 50 100 90 90 - 90 | 13 80 100 30 70 40 100 100 90 - 90 | 14 80 80 70 80 80 100 100 90 80 80 | 15 90 100 80 90 80 100 100 100 90 100 | 16 90 100 70 100 80 100 100 90 80 100 | 17 80 90 60 100 70 100 100 100 90 90 |
| The Shanxi leads to wheat | 70 | 0 | 50 | 30 | 80 | 80 | 0 | 50 | 60 | 60 | 50 | 60 | 60 | 60 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 500g ai/ha seedling | 18 0 40 0 0 0 60 0 70 0 40 0 | 19 90 100 90 90 80 100 100 100 90 100 60 | 21 10 80 - 60 10 80 90 70 20 80 30 | 22 20 80 - 100 20 100 100 80 20 100 50 | 23 0 10 0 0 0 30 10 20 0 20 0 | 24 20 90 0 80 60 90 90 90 50 80 70 | 25 60 90 0 70 80 90 90 90 70 80 60 | 26 90 90 80 90 80 100 100 100 80 100 60 | 27 60 90 50 70 40 100 90 100 70 90 50 | 28 30 90 0 80 50 100 90 90 60 90 40 | 30 40 100 80 90 80 90 100 90 80 80 60 | 31 70 100 40 80 80 100 100 100 60 90 70 | 32 10 90 0 40 0 90 80 90 0 80 10 | 33 50 90 30 50 40 100 90 90 40 80 50 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 500g ai/ha seedling | 34 0 60 0 70 20 80 70 80 50 60 10 | 35 80 90 50 80 70 100 100 100 60 90 50 | 36 0 60 0 0 0 40 0 20 0 40 0 | 37 40 80 10 90 60 100 50 100 40 80 60 | 38 0 0 10 0 0 90 50 70 0 0 0 | 39 20 30 50 50 20 100 70 100 0 30 10 | 40 90 100 50 80 80 100 100 100 70 90 70 | 41 10 10 0 20 0 60 20 60 0 30 20 | 42 0 70 0 20 0 90 80 90 20 70 10 | 44 10 80 0 80 40 60 40 80 60 80 60 | 46 0 40 0 40 50 60 90 90 40 20 20 | 47 40 90 30 90 40 100 100 90 20 90 50 | 48 10 20 0 - 50 100 30 80 60 0 30 | 49 60 90 40 90 70 100 100 100 60 90 70 |
| Table B | Compound | ||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass before the 500g ai/ha seedling | 50 50 90 20 80 40 | 51 0 20 0 0 0 | 52 30 60 0 0 0 | 54 40 90 0 0 0 | 55 60 90 0 60 0 | 56 0 30 0 0 0 | 124 0 60 0 0 0 | 125 - 90 0 100 0 | 126 0 90 0 100 0 |
| Lamb's-quarters sweet potato Amaranthus retroflexus pitch arm shape grass piemarker common wheat | 100 90 90 70 90 40 | 80 40 70 0 0 0 | - 100 50 0 30 0 | - - 100 0 80 0 | - 100 100 50 90 70 | - 20 80 0 30 0 | 70 60 70 0 50 0 | - 100 90 0 90 0 | - 70 80 20 20 0 |
| Table B | Compound | |||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters before the 250g ai/ha seedling | 1 90 100 80 90 90 100 | 4 90 100 80 90 80 100 | 45 0 0 - 0 0 30 | 53 70 100 0 50 50 - |
| Table B | Compound | |||
| Sweet potato Amaranthus retroflexus pitch arm shape grass piemarker common wheat before the 250g ai/ha seedling | 1 100 100 80 100 60 | 4 100 100 90 90 70 | 45 50 50 0 0 0 | 53 100 100 30 90 40 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the seedling | 2 70 90 0 90 30 100 100 90 40 90 60 | 3 0 80 0 10 0 70 50 80 0 40 0 | 5 10 70 0 20 0 90 70 90 0 70 - | 7 0 70 0 0 0 80 70 90 0 50 0 | 8 70 90 90 80 50 90 100 100 60 80 60 | 9 50 90 50 90 70 90 100 90 70 90 40 | 10 20 80 0 20 0 - 80 80 0 80 0 | 11 0 80 0 30 10 100 80 80 10 80 0 | 12 50 80 0 20 20 90 70 80 0 80 30 | 13 40 90 - 50 20 90 90 80 0 80 40 | 14 10 60 0 10 30 90 70 80 40 60 40 | 15 40 70 20 70 40 90 70 90 30 70 40 | 16 30 70 30 70 30 100 90 90 40 80 50 | 17 20 80 0 70 20 90 100 80 30 70 40 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass before the 125g ai/ha seedling | 18 0 10 0 0 0 | 19 40 90 70 80 20 | 21 0 30 0 0 0 | 22 0 50 10 20 0 | 23 0 0 0 0 0 | 24 0 80 - 60 10 | 25 20 80 0 60 40 | 26 50 80 30 30 10 | 27 30 80 10 30 0 | 28 10 80 0 70 30 | 30 10 60 10 50 10 | 32 0 80 0 0 0 | 33 20 80 10 0 0 | 34 0 30 0 0 0 |
| Lamb's-quarters sweet potato Amaranthus retroflexus pitch arm shape grass piemarker common wheat | 10 0 0 0 0 0 | 100 90 90 60 90 50 | 70 50 50 0 10 0 | 70 100 60 0 30 10 | 0 0 0 0 0 0 | 70 50 80 10 50 30 | 90 80 80 20 70 50 | 100 90 90 10 90 30 | 90 80 90 0 80 10 | 80 80 80 - 80 10 | 80 90 50 0 10 30 | 40 40 40 0 50 0 | 90 0 80 0 70 0 | 50 20 40 10 30 0 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 125g ai/ha seedling | 35 10 60 0 30 0 90 70 80 10 70 20 | 36 0 10 0 0 0 0 0 0 0 10 0 | 37 10 20 0 50 10 100 10 100 - 40 30 | 38 0 0 0 0 0 20 0 10 0 0 0 | 39 0 10 30 0 0 50 30 70 0 0 0 | 40 50 90 0 60 20 100 90 90 50 90 40 | 41 0 0 0 0 0 30 0 0 - 10 0 | 42 0 40 0 0 0 40 20 50 0 10 10 | 44 0 10 0 40 20 - 10 70 40 30 30 | 46 0 0 0 0 0 10 50 80 0 0 0 | 47 0 80 0 20 20 90 80 80 0 60 20 | 48 0 0 0 10 30 70 0 60 30 0 0 | 49 30 80 10 80 40 90 80 90 40 80 30 | 50 30 80 20 50 10 90 80 70 20 80 20 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 125g ai/ha seedling | 51 0 0 0 0 0 - 0 10 0 0 0 | 52 0 10 - 0 0 - 10 - 0 0 0 | 54 0 50 0 0 0 - 0 100 0 10 0 | 55 0 70 0 50 0 - 80 80 0 50 0 | 56 0 0 0 0 0 - - - 0 0 0 | 75 80 90 80 90 90 100 100 100 80 100 70 | 76 90 100 80 90 80 100 100 100 90 90 70 | 77 90 100 80 90 90 100 100 100 90 100 70 | 78 70 100 70 90 70 100 100 100 90 90 70 | 79 70 80 60 70 20 90 90 100 0 80 60 | 83 30 50 0 60 10 90 10 100 10 60 50 | 88 - 90 10 70 30 - 10 - 50 90 70 | 92 30 50 0 10 10 80 0 80 0 70 30 | 94 - 50 0 70 20 - 0 - 30 70 60 |
| Table B | Compound | ||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 125g ai/ha seedling | 95 - 100 80 100 90 60 100 100 80 | 113 20 80 20 70 10 80 60 90 60 90 60 | 117 30 90 10 90 90 100 20 100 100 90 80 | 124 0 10 0 0 0 0 10 20 0 20 0 | 125 0 30 0 0 0 30 30 0 10 0 | 126 0 0 0 80 0 0 20 0 10 0 | 128 10 10 0 0 0 50 0 50 0 40 0 | 129 30 30 0 30 0 80 0 90 10 60 20 | 133 30 50 0 70 20 70 0 80 10 60 60 | 135 90 100 80 90 90 100 100 100 90 100 90 | 136 80 70 0 80 50 100 40 100 50 80 70 |
| Table B | Compound | |||||||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus Brachiaria decumbens piemarker common wheat before the 62g ai/ha seedling | 1 60 90 20 90 30 100 90 90 50 90 30 | 4 30 80 0 70 10 90 60 90 40 80 50 | 31 20 90 0 10 10 90 90 90 20 80 40 | 45 0 - 0 0 0 0 30 0 0 0 0 | 53 0 60 0 0 0 - 90 60 0 20 0 | 65 40 80 0 70 30 90 30 100 40 70 80 | 75 60 90 50 80 30 100 80 100 70 80 30 | 76 40 80 70 80 40 90 100 100 70 80 30 | 77 70 80 70 80 70 100 100 100 60 80 70 | 78 60 80 30 80 20 90 80 100 60 70 30 | 79 0 50 30 0 0 90 70 80 0 50 0 | 83 20 10 0 30 0 70 0 80 0 50 20 | 88 - 60 0 50 10 - 0 - 20 70 50 | 92 10 40 0 0 0 50 0 40 0 50 0 |
| Table B | Compound | ||||||||
| Barnyard grass grass Siberian cocklebur corn lady's-grass Fa Shi dog hair grass lamb's-quarters before the 62g ai/ha seedling | 94 - 30 0 40 0 - | 95 - 90 40 80 50 - | 113 0 70 0 40 0 70 | 117 10 50 0 90 20 90 | 128 0 0 0 0 0 10 | 129 10 10 - 10 0 - | 133 30 20 0 40 0 - | 135 70 100 50 80 60 100 | 136 30 40 0 70 10 90 |
| Sweet potato Amaranthus retroflexus pitch arm shape grass piemarker common wheat | 0 - 10 40 30 | 30 - 50 80 70 | 50 70 20 80 10 | 10 100 80 70 50 | 0 10 0 0 0 | 0 80 0 50 0 | 0 70 0 50 50 | 100 100 80 90 70 | 10 80 10 60 50 |
| Table B | Compound |
| Barnyard grass grass Siberian cocklebur corn lady's-grass before the 4g ai/ha seedling | 65 0 10 0 20 |
| Table B | Compound |
| Fa Shi dog hair grass lamb's-quarters sweet potato Amaranthus retroflexus before the 4g ai/ha seedling | 65 0 30 0 20 |
| Table B | Compound |
| Pitch arm shape grass piemarker common wheat before the 4g ai/ha seedling | 65 0 0 20 |
Test C
Plantation is selected from Bermuda grass (Cynodon dactylon), pitch arm shape grass (Brachiariadecumbens), Siberian cocklebur (Xanthium strumarium), corn (Zea mays), lady's-grass (Digitaria sanguinalis), wild broomcorn millet (Eriochloa villosa), Fa Shi dog hair grass (Setaria faberii), Herba Eleusines Indicae (Eleusine indica), Johnson grass (Sorghumhalepense), summer cypress (Kochia scoparia), lamb's-quarters (Chenopodium album), sweet potato (Ipomoea coccinea), east black nightshade (Solanum ptycanthum), tiger nuts (Cyperus esculentus), Amaranthus retroflexus (Amaranthus retroflexus), american ragweed (Ambrosia elatior), soybean (Glycine max), the seed or the fruit stone of the plant variety of (oil type) Sunflower Receptacle (Helianthus annuus) and piemarker (Abutilon theophrasti), and the test chemical of preparing with the solvent mixture of the plant-less toxicity that comprises tensio-active agent carries out the seedling pre-treatment.
Simultaneously, be selected from above-mentioned crop and weeds kind and barley (Hordeum vulgare), big fringe amur foxtail (Alopecurus myosuroides) Xiao Zi Mango grass (Phalaris minor), chickweed (Stellaria media), cheatgrass brome (Bromus tectorum), Herba Setariae Viridis (Setariaviridis), Itanlian rye (Lolium multiflorum), common wheat (Triticumaestivum), wild avena sativa (Avena fatua) He Apo draws the plant of grass (Apera spica-venti) to carry out the seedling aftertreatment with some test chemical of preparing in the same manner.When plant length arrives 2-18 centimetre high (1-4 leaf phase), carry out the seedling aftertreatment.Plant variety in the rice field test that big flood is irrigated, comprise rice (Oryza sativa), Herba Cyperi Difformis (Cyperus difformis), natural pond living different stamen flower (Heteranthera limosa) and barnyard grass grass (Echinochloa crus-galli), the 2 leaf phases of growing to test.Handle plant and brought up 12-14 days impinging upon in the greenhouse, all kinds and are carried out visually rank compared with the control afterwards.Plant reaction grade (being summarized among the table C) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table C | Compound | ||||||||||||
| 500g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 1 25 0 0 0 | 2 75 95 65 25 | 4 85 100 80 75 | 5 20 0 0 0 | 9 85 90 75 85 | 14 45 55 0 30 | 15 75 85 50 25 | 16 50 85 65 55 | 17 50 80 75 25 | 19 60 60 20 50 | 22 70 95 60 95 | 26 0 40 25 20 | 37 0 100 0 95 |
| Table C | Compound | ||||||||||||
| 250g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 1 15 0 0 0 | 2 45 90 45 0 | 4 65 90 75 65 | 5 0 0 0 0 | 9 55 80 55 15 | 14 0 45 0 0 | 15 25 50 20 10 | 16 15 75 0 50 | 17 0 80 45 20 | 19 0 60 10 50 | 22 40 90 40 75 | 26 0 40 20 20 | 37 0 100 0 90 |
| Table C | Compound | ||||||||||||
| 125g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 1 0 - 0 - | 2 20 70 25 0 | 4 60 80 40 30 | 5 0 0 0 0 | 9 15 70 30 15 | 14 0 40 0 0 | 15 0 45 0 0 | 16 0 65 0 0 | 17 0 0 0 0 | 19 0 40 0 50 | 22 0 60 20 30 | 26 0 40 0 0 | 37 0 95 0 85 |
| Table C | Compound | ||||||||||||
| 62g ai/ha big flood barnyard grass marsh is given birth to different stamen flower rice Herba Cyperi Difformis | 1 0 0 0 0 | 2 0 50 0 0 | 4 0 70 0 0 | 5 0 0 0 0 | 9 0 45 0 0 | 14 0 0 0 0 | 15 0 45 0 0 | 16 0 65 0 - | 17 0 0 0 0 | 19 0 20 0 20 | 22 0 30 20 0 | 26 0 40 0 0 | 37 0 95 0 85 |
| Table C | Compound | |||||||||||||
| The big fringe amur foxtail of barley Bermuda grass cheatgrass brome Xiao Zi Mango grass behind the 500g ai/ha seedling | 1 - 90 - - - | 4 65 80 70 70 60 | 5 - 80 - - - | 7 - 0 - - - | 8 - 75 - - - | 10 - 0 - - - | 15 - 75 - - - | 22 - 60 - - - | 27 - 30 - - - | 28 - 0 - - - | 35 45 - 65 40 55 | 37 - 20 - - - | 49 40 65 60 30 40 | 50 - 95 - - - |
| The wild broomcorn millet Fa Shi of chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | - 100 45 90 90 90 - 70 70 100 100 100 5 - 100 100 - 100 95 100 - - | 100 100 95 80 95 95 75 75 95 100 100 100 0 70 100 100 65 100 95 100 65 75 | - 100 45 80 70 60 - 50 45 100 100 100 0 - 100 100 - 100 70 95 - - | 0 30 0 25 20 10 - 0 0 80 80 65 0 - 55 75 - 60 0 40 - - | 100 100 90 75 85 75 - 60 85 100 100 100 0 - 100 100 - 100 80 95 - - | 70 75 0 0 0 0 - 0 0 100 100 95 0 - 95 90 - 100 0 90 - - | 85 100 75 80 75 70 - 55 80 100 100 100 0 - 100 95 - 100 65 90 - - | 90 100 65 85 65 60 - 25 100 100 95 100 0 - 100 90 - 100 85 95 - - | 0 25 0 30 0 0 - 0 0 60 50 85 0 - 80 50 - 95 0 30 - - | 20 100 0 20 0 15 - 15 0 95 95 95 0 - 75 95 - 95 0 75 - - | - - - - - - 65 - - - - - - 55 - - 40 - - - 45 65 | 0 95 25 60 45 45 - 0 55 95 95 95 20 - 100 95 - 100 0 95 - - - | 45 95 25 95 65 0 60 25 70 100 95 100 0 60 95 90 50 100 45 80 60 60 | 20 90 65 80 30 20 - 0 60 95 85 95 0 - 95 80 - 100 60 80 - - |
| Table C | Compound |
| The wild broomcorn millet of Bermuda grass chickweed Siberian cocklebur corn lady's-grass behind the 500g ai/ha seedling | 51 0 45 85 0 45 0 |
| Table C | Compound |
| Fa Shi dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato behind the 500g ai/ha seedling | 51 0 0 0 95 90 100 |
| Table C | Compound |
| Chufa Amaranthus retroflexus american ragweed soybean Brachiaria decumbens piemarker behind the 500g ai/ha seedling | 51 0 85 85 95 0 65 |
| Table C | Compound | |||||||||||||
| The big fringe amur foxtail of barley Bermuda grass behind the 250g ai/ha seedling | 1 - 90 - | 2 60 80 75 | 3 30 45 0 | 4 65 70 70 | 5 - 70 - | 7 - 0 - | 8 - 65 - | 9 - 80 - | 10 - 0 - | 15 - 65 - | 16 - 75 - | 17 - 0 - | 22 - 60 - | 27 - 0 - |
| The wild broomcorn millet Fa Shi of the little seed Mango grass of cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | - - 90 100 40 85 90 80 - 40 70 100 100 100 5 - 100 100 - 100 90 100 - - | 60 40 95 85 30 70 75 70 70 45 60 100 100 100 20 60 100 95 60 100 70 100 65 70 | 20 10 40 90 0 0 0 0 35 0 0 100 100 75 0 40 80 95 35 95 0 70 10 30 | 65 60 100 100 90 75 85 85 70 65 95 100 100 100 0 70 100 100 65 100 75 100 65 70 | - - 20 100 40 70 50 50 - 40 45 100 100 100 0 - 90 95 - 100 30 90 - - | - - 0 30 0 5 0 0 - 0 0 70 70 55 0 - 40 65 - 35 0 35 - - | - - 95 100 70 70 75 70 - 45 45 100 100 100 0 - 100 95 - 100 70 85 - - | - - 100 100 95 80 85 80 - 45 85 100 100 100 0 - 100 100 - 100 80 95 - - | - - 20 60 0 0 0 0 - 0 0 95 90 95 0 - 95 80 - 90 0 80 - - | - - 65 100 55 65 65 65 - 40 70 100 100 100 0 - 85 90 - 95 55 85 - - | - - 35 100 55 75 65 65 - 20 70 100 100 100 0 - 95 95 - 100 55 90 - - | - - 85 100 20 65 20 35 - 0 60 100 100 100 0 - 95 95 - 1001 0 95 - - | - - 85 100 60 85 60 50 - 20 80 100 95 95 0 - 100 90 - 00 85 90 - - | - - 0 25 0 5 0 0 - 0 0 50 25 85 0 - 30 40 - 85 0 0 - - |
| Table C | Compound | |||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass behind the 250g ai/ha seedling | 28 - 0 - - - 15 95 0 0 0 0 | 30 - 5 - - - 85 100 50 50 40 40 | 34 40 - 45 35 45 - - - - - - | 35 40 - 60 40 45 - - - - - - | 37 - 0 - - - 0 95 15 40 0 40 | 42 - 5 - - - 10 20 0 0 5 0 | 49 30 55 50 0 30 40 95 20 75 60 0 | 50 - 90 - - - - 65 60 75 15 0 | 51 - 0 - - - 0 70 0 0 0 0 | 64 100 70 50 20 10 55 - - 90 - 50 | 78 90 65 50 55 0 70 100 40 90 90 70 | 88 - 80 - - - 100 90 30 85 85 85 |
| Green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | - 0 0 95 85 95 0 - 60 90 - 95 0 70 - - | - 0 40 100 90 95 5 - 90 90 - 95 35 60 - - | 45 - - - - - - 50 - - 60 - - - 35 60 | 60 - - - - - - 45 - - 40 - - - 45 65 | - 0 - 95 95 80 0 - 100 90 - 95 0 90 - - | - 0 10 85 25 85 0 - 30 40 - 70 0 20 - - | 50 20 35 95 95 80 0 40 95 75 50 95 40 75 50 60 | - 0 - 65 80 85 0 - 85 45 - 100 0 70 - - | - 0 0 85 85 85 0 - 80 80 - 95 0 60 - - | 45 70 85 90 90 90 50 10 100 90 45 100 - 95 10 60 | 75 50 40 95 100 100 0 60 100 100 25 100 90 100 55 40 | - 80 85 95 100 85 75 - 100 100 - 100 85 95 - - |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat behind the 125g ai/ha seedling | 1 - 90 - - - - 100 15 85 80 65 - 0 30 100 100 100 0 - | 2 60 70 70 45 40 75 85 20 60 70 65 65 0 25 95 100 100 0 55 | 3 0 0 0 20 10 0 75 0 0 0 0 35 0 0 90 90 65 0 40 | 4 65 65 65 60 45 85 100 80 75 70 75 70 20 80 100 100 100 0 65 | 5 - 50 - - - 10 95 40 50 50 30 - 5 40 100 100 95 0 - | 7 - 0 - - - 0 30 0 0 0 0 - 0 0 65 60 50 0 - | 8 - 60 - - - 75 100 20 65 60 60 - 0 35 100 100 95 0 - | 9 - 70 - - - 100 100 65 75 70 75 - 40 80 100 100 100 0 - | 10 - 0 - - - 0 15 0 0 0 0 - 0 0 90 80 85 0 - | 11 - 0 - - - 0 40 0 20 0 0 - 0 0 90 80 0 0 - | 15 - 45 - - - 50 100 15 45 50 60 - 0 55 95 100 95 0 - | 16 - 60 - - - 20 100 20 45 0 55 - 0 60 100 100 100 0 - | 17 - 0 - - - 55 100 0 20 0 0 - 0 40 100 100 100 0 - | 19 45 45 65 60 65 5 90 35 70 65 55 60 0 - 90 95 85 0 65 |
| Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | 100 100 - 100 90 90 - - | 95 90 60 100 65 80 65 70 | 75 80 35 90 0 55 0 30 | 100 100 60 100 75 100 60 65 | 90 95 - 100 20 90 - - | 40 35 - 25 0 10 - - | 75 80 - 95 65 70 - - | 100 95 - 100 75 80 - - | 80 65 - 80 0 70 - - | 90 75 - 95 0 75 - - | 70 85 - 95 20 70 - - | 95 95 - 100 25 65 - - | 75 95 - 100 0 80 - - | 65 80 70 75 - 60 45 60 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass behind the 125g ai/ha seedling | 22 - 60 - - - 60 90 40 55 60 45 - 10 80 100 95 90 0 - 100 85 - 100 60 60 - - | 25 - 0 - - - 85 90 0 50 30 30 - 0 20 85 90 90 0 - 100 70 - 90 5 45 - - | 27 - 0 - - - 0 25 0 0 0 0 - 0 0 20 20 85 0 - 20 20 - 45 0 0 - - | 28 - 0 - - - 0 95 0 0 0 0 - 0 0 85 75 95 0 - 35 80 - 85 0 50 - - | 30 - 5 - - - 65 100 0 5 0 0 - 0 10 100 80 95 0 - 80 85 - 90 0 60 - - | 34 30 - 35 30 35 - - - - - - 45 - - - - - - 45 - - 45 - - - 30 50 | 35 35 - 50 30 45 - - - - - - 50 - - - - - - 45 - - 40 - - - 40 55 | 37 - 0 - - - 0 95 10 15 0 0 - 0 20 90 95 65 0 - 95 80 - 85 0 85 - - | 42 - 0 - - - 0 5 0 0 0 0 - 0 0 50 20 80 0 - 20 40 - 40 0 0 - - | 47 - 15 - - - 0 65 0 20 0 - - 0 0 100 80 65 0 - 70 80 - 75 20 0 - - | 49 20 55 40 0 20 0 95 0 65 15 0 20 0 20 45 90 70 0 40 80 65 30 95 0 70 40 40 | 50 - 75 - - - 0 40 0 60 0 0 - 0 - 55 75 80 0 - 80 45 - 95 0 55 - - | 51 - 0 - - - 0 65 0 0 0 0 - 0 - 60 75 80 0 - 70 80 - 95 0 20 - - | 64 - 65 50 20 10 0 100 50 85 65 50 40 60 85 90 90 90 50 10 100 85 35 100 60 90 10 55 |
| Table C | Compound | |||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass behind the 125g ai/ha seedling | 65 50 70 65 55 45 70 100 90 90 85 70 70 70 85 90 95 95 50 40 100 95 60 100 80 90 45 70 | 76 - 75 - - - 95 100 70 90 95 85 - 50 95 100 100 100 60 - 100 100 - 100 - 95 - - | 78 30 60 5 15 0 - 100 40 90 - 65 70 40 20 95 95 100 0 60 95 95 20 100 55 95 30 30 | 79 35 - 60 35 35 - - - - - - 60 - - - - - - 45 - - 45 - - - 40 50 | 83 - 55 - - - 30 100 60 75 60 40 - 45 70 90 100 90 75 - 100 95 - 100 65 100 - - | 88 - 70 - - - 100 90 - 80 85 80 - 75 75 95 95 85 55 - 100 100 - 100 80 95 - - | 94 - 80 - - - 95 100 60 85 90 80 - 80 90 100 100 100 75 - 100 100 - 100 100 95 - - | 117 - 90 - - - - 90 - 90 85 80 - 80 50 90 95 50 60 - 95 100 - 100 80 95 - - | 129 45 - 50 0 30 - - - - - - 60 - - - - - - 40 - - 60 - - - 35 60 | 133 - 85 - - - 45 95 80 80 70 75 - 70 95 85 100 100 80 - 100 95 - 100 70 95 - - | 135 - 75 - - - 85 100 35 75 80 75 - 55 70 95 95 95 40 - 100 95 - 100 60 95 - - | 136 55 85 65 55 65 50 100 75 75 70 85 70 80 95 90 95 100 75 60 100 95 65 100 70 95 55 65 |
| Table C | Compound | |||||||||||||
| The big fringe amur foxtail of barley Bermuda grass cheatgrass brome Xiao Zi Mango grass behind the 62g ai/ha seedling | 1 - 70 - - - | 2 35 60 65 35 40 | 3 0 0 0 20 10 | 4 30 40 65 45 35 | 5 - 5 - - - | 7 - 0 - - - | 8 - 50 - - - | 9 - 65 - - - | 10 - 0 - - - | 11 - 0 - - - | 15 - 0 - - - | 16 - 0 - - - | 17 - 0 - - - | 19 35 30 65 50 60 |
| The wild broomcorn millet Fa Shi of chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | 80 90 10 30 65 40 - 0 30 100 100 100 0 - 90 100 100 90 85 - - | 65 75 15 55 60 35 55 0 0 95 100 75 0 55 80 85 45 100 55 70 60 65 | 0 65 0 0 0 0 30 0 0 65 90 60 0 30 65 75 35 75 0 55 0 30 | 30 85 0 70 60 60 65 0 70 100 100 15 0 60 100 100 45 100 60 80 50 60 | 0 80 10 40 5 20 - 0 0 100 95 95 0 - 85 90 - 95 0 55 - - | 0 30 0 0 0 0 - 0 0 40 50 - 0 - 20 25 - 25 0 0 - - | 20 80 0 60 30 40 - 0 30 95 75 95 0 - 70 60 - 95 40 60 - - | 85 85 55 70 60 65 - 0 65 100 95 95 0 - 70 80 - 100 65 75 - - | 0 0 0 0 0 0 - 0 0 80 60 70 0 - 65 45 - 70 0 65 - - | 0 25 0 0 0 0 - 0 0 75 70 0 0 - 80 65 - 80 0 60 - - | 20 85 15 15 0 45 - 0 20 95 100 90 0 - 65 75 - 95 0 65 - - | 0 95 0 15 0 20 - 0 0 100 100 95 0 - 90 85 - 95 0 60 - - | 0 100 0 0 0 0 - 0 0 100 100 95 0 - 65 85 - 95 0 50 - - | 5 50 0 70 65 40 45 0 0 90 90 80 0 60 65 70 65 75 45 50 40 60 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica behind the 62g ai/ha seedling | 22 - 50 - - - 30 90 30 50 60 40 - 10 | 25 - 0 - - - 40 90 0 30 0 5 - 0 | 27 - 0 - - - 0 20 0 0 0 0 - 0 | 28 - 0 - - - 0 85 0 0 0 0 - 0 | 30 - 0 - - - 50 95 0 0 0 0 - 0 | 34 20 - 35 0 30 - - - - - - 40 - | 35 20 - 50 30 35 - - - - - - 40 - | 37 - 0 - - - 0 0 0 0 0 0 - 0 | 42 - 0 - - - 0 0 0 0 0 0 - 0 | 47 - 0 - - - 0 60 0 0 0 0 - 0 | 49 0 0 40 0 0 0 75 0 0 0 0 0 0 | 50 - 50 - - - 0 40 0 60 0 0 - 0 | 51 - 0 - - - 0 65 0 0 0 0 - 0 | 64 20 60 45 15 5 0 90 50 80 40 20 30 35 |
| Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | 40 95 90 90 0 - 85 80 - 95 55 55 - - | 10 85 85 90 0 - 80 65 - 90 0 45 - - | 0 0 20 20 0 - 5 5 - 30 0 0 - - | 0 75 60 80 0 - 30 65 - 75 0 45 - - | 5 90 60 90 0 - 70 80 - 90 0 10 - - | - - - - - 40 - - 40 - - - 20 40 | - - - - - 30 - - 40 - - - 35 40 | 0 0 0 0 0 - 0 0 - 20 0 0 - - | 0 30 20 50 0 - 10 10 - 30 0 0 - - | 0 20 70 40 0 - 45 40 - 65 0 0 - - | - 20 70 50 0 30 65 45 30 95 0 45 20 40 | 0 20 70 65 0 - 75 20 - 95 0 50 - - | 0 15 60 80 0 - 65 65 - 75 0 0 - - | 80 85 90 90 50 5 95 80 30 90 60 85 0 55 |
| Table C | Compound | ||||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed behind the 62g ai/ha seedling | 65 50 70 65 50 35 60 100 90 90 85 70 60 70 85 85 90 90 20 20 100 95 | 76 - 75 - - - 70 100 55 85 80 55 - 45 - 95 100 95 40 - 100 95 | 78 5 60 5 10 0 0 100 40 90 55 30 40 0 10 90 95 90 0 10 80 85 | 79 35 - 60 30 25 - - - - - - 30 - - - - - - 25 - - | 83 - 20 - - - 10 70 50 65 45 20 - 30 55 75 95 90 60 - 100 75 | 88 - 70 - - - 100 90 0 80 75 75 - 75 45 95 95 - 45 - 100 100 | 94 - 75 - - - 50 90 35 85 90 80 - 80 75 95 95 90 70 - 100 95 | 95 - 85 - - - 95 100 35 80 80 80 - 80 90 95 100 95 75 - 100 95 | 117 - 85 - - - 40 90 - 90 80 70 - 75 50 90 95 50 50 - 95 100 | 129 45 - 50 0 30 - - - - - 40 - - - - - - 40 - - | 133 - 85 - - - 20 95 60 75 60 70 - 65 90 85 95 100 75 - 95 85 | 135 - 60 - - - 25 - 20 75 60 65 - 45 65 90 90 95 15 - 100 85 | 136 50 80 65 45 55 50 100 65 75 70 75 70 75 85 90 95 90 75 55 100 90 |
| Itanlian rye soybean pitch arm shape grass piemarker common wheat A Po draws grass | 55 100 80 80 45 70 | - 95 95 95 - - | 10 100 55 80 20 30 | 40 - - - 30 45 | - 100 45 85 - - | - 100 60 90 - - | - 100 90 95 - - | - 100 75 100 - - | - 100 80 95 - - | 55 - - - 35 60 | - 100 55 85 - - | - 100 60 - - - | 60 100 65 90 45 65 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass behind the 31g ai/ha seedling | 2 0 15 60 20 30 60 65 15 40 40 0 55 0 0 85 100 70 0 20 65 65 35 100 0 65 20 65 | 3 0 0 0 20 10 0 60 0 0 0 0 20 0 0 20 75 45 0 30 60 55 35 60 0 25 0 10 | 9 - 60 - - - 15 40 45 60 40 60 - 0 55 95 90 90 0 - 55 70 - 95 45 0 - - | 11 - 0 - - - 0 0 0 0 0 0 - 0 0 65 60 0 0 - 70 45 - 60 0 50 - - | 16 - 0 - - - 0 75 0 0 0 0 - 0 0 95 95 85 0 - 85 60 - 85 0 55 - - | 17 - 0 - - - 0 95 0 0 0 0 - 0 0 100 95 95 0 - 45 65 - 85 0 25 - - | 19 25 5 60 0 60 0 25 0 40 25 5 35 0 0 90 90 55 0 40 50 40 65 55 25 40 30 40 | 25 - 0 - - - - 85 0 0 0 0 - 0 10 80 60 90 0 - 50 50 - 90 0 20 - - | 30 - 0 - - - 40 90 0 0 0 0 - 0 0 55 50 90 0 - 60 60 - 80 0 10 - - | 34 20 - - 0 20 - - - - - - 40 - - - - - - - - - 40 - - - 0 40 | 42 - 0 - - - 0 0 0 0 0 0 - 0 0 5 10 0 0 - 10 0 - 10 0 0 - - | 47 - 0 - - - 0 45 0 0 0 0 - 0 - 0 45 35 0 - 15 0 - 40 0 0 - - | 64 20 20 40 10 5 0 90 20 70 30 0 0 35 60 80 80 90 40 5 85 75 5 90 20 80 0 40 | 65 40 60 60 50 30 60 100 90 80 80 60 55 50 60 85 90 90 0 15 90 90 50 100 80 80 40 60 |
| Table C | Compound | |||||||||||
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass behind the 31g ai/ha seedling | 76 - 70 - - - 45 100 35 75 60 25 - 45 65 95 95 95 30 - 95 90 - 95 70 80 - - | 78 5 60 0 5 0 0 90 40 55 50 0 25 0 10 90 90 90 0 5 50 70 0 90 50 50 20 5 | 79 30 - 40 20 20 - - - - - - 20 - - - - - - 25 - - 35 - - - 20 40 | 83 - 5 - - - 0 70 15 45 15 0 - 10 55 75 95 85 60 - 95 70 - 90 30 85 - - | 88 - 50 - - - 80 90 0 75 70 55 - 50 30 85 90 60 40 - 95 90 - 100 45 85 - - | 94 - 70 - - - 45 80 35 80 80 65 - 60 60 90 95 80 60 - 100 90 - 100 60 90 - - | 95 - 85 - - - - 100 - 80 75 75 - 75 75 95 100 80 60 - 100 95 - 100 70 100 - - | 117 - 65 - - - - - 30 90 80 55 - 40 50 90 95 50 50 - 95 95 - 100 50 70 - - | 129 40 - 45 0 30 - - - - - - 40 - - - - - - 35 - - 55 - - - 35 45 | 133 - 85 - - - 10 85 40 75 50 60 - 55 85 80 95 90 75 - 85 80 - 95 45 85 - - | 135 - - - - - 15 100 10 75 60 60 - 35 35 90 90 90 0 - 95 80 - - 50 90 - - | 136 50 80 55 - 45 50 100 35 75 65 75 65 65 85 80 95 85 65 45 100 85 50 100 65 85 40 60 |
| Table C | Compound | |||||||||||||
| The big fringe amur foxtail of barley Bermuda grass cheatgrass brome Xiao Zi Mango grass behind the 16g ai/ha seedling | 11 - 0 - - - | 19 25 0 55 0 45 | 25 - 0 - - - | 47 - 0 - - - | 65 40 60 50 40 30 | 76 - 15 - - - | 79 0 - 20 0 0 | 83 - 0 - - - | 94 - 60 - - - | 95 - 70 - - - | 117 - 60 - - - | 129 35 - 35 0 0 | 133 - 50 - - - | 135 - 40 - - - |
| The wild broomcorn millet Fa Shi of chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | 0 0 0 0 0 0 - 0 0 40 50 0 0 - 60 15 - 45 0 20 - - | 0 25 0 20 0 0 30 0 0 80 70 - 0 40 50 35 65 45 0 30 10 40 | 0 70 0 0 0 0 - 0 0 10 30 90 0 - 50 40 - 40 0 5 - - | 0 35 0 0 0 0 - 0 - 0 0 20 0 - 0 0 - 20 0 0 - - | 60 90 5 80 60 50 50 50 45 85 85 90 0 5 90 80 10 100 60 65 40 50 | 35 100 10 55 55 15 - 30 25 90 90 95 10 - 85 80 - 95 60 45 - - | - - - - - - 20 - - - - - - 0 - - 35 - - - 0 40 | 0 60 5 25 15 0 - 10 10 65 90 70 60 - 95 65 - 85 20 70 - - | - 75 10 70 60 30 - 35 55 75 95 60 55 - 95 90 - 100 50 75 - - | - 100 20 75 75 - - 65 70 95 100 - 60 - 95 95 - 100 65 95 - - | 30 90 30 85 60 50 - 40 10 90 95 20 5 - 90 95 - 100 45 60 - - | - - - - - - 40 - - - - - - 30 - - 45 - - - 0 40 | 0 75 35 50 35 15 - 15 70 75 95 80 60 - 85 80 - 95 35 80 - - | 0 90 5 65 30 10 - 5 15 75 60 80 0 - 85 75 - 100 45 55 - - |
| Table C | Compound |
| The wild broomcorn millet Fa Shi of the little seed Mango grass of the big fringe amur foxtail of barley Bermuda grass cheatgrass brome chickweed Siberian cocklebur corn lady's-grass dog hair grass green bristlegrass eleusine indica behind the 16g ai/ha seedling | 136 40 75 40 30 40 45 95 35 60 55 65 45 50 |
| Table C | Compound |
| The wild broomcorn millet Fa Shi of Bermuda grass chickweed Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato chufa behind the 8g ai/ha seedling | 95 70 95 100 20 75 75 70 50 55 90 75 60 55 |
| Johnson grass summer cypress lamb's-quarters sweet potato chufa wild oat Amaranthus retroflexus american ragweed Itanlian rye soybean Brachiaria decumbens piemarker common wheat A Po draws grass | 60 75 95 65 60 40 90 75 45 95 55 85 20 45 |
| Amaranthus retroflexus american ragweed soybean pitch arm shape grass piemarker | 90 90 100 55 95 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 500g ai/ha seedling | 1 90 100 70 95 95 90 70 90 100 100 100 100 50 100 100 100 100 90 100 | 4 95 100 90 95 95 85 65 95 100 100 100 100 80 100 100 100 100 100 100 | 5 70 100 50 60 0 60 40 70 100 100 100 100 0 100 100 100 100 0 90 | 8 100 100 75 0 100 0 45 20 100 100 100 - 100 95 100 100 100 100 100 | 10 0 100 0 0 0 0 0 0 65 95 100 95 - 85 85 - 0 0 60 | 15 70 100 60 100 95 80 0 95 100 100 100 100 20 100 100 100 100 95 100 | 22 90 100 65 100 95 60 100 100 - 100 100 100 95 100 100 100 100 100 100 | 26 0 95 20 - 0 10 0 100 50 90 90 100 0 100 90 20 90 10 90 | 27 0 95 25 85 15 20 20 65 45 100 100 100 20 100 95 75 95 30 70 | 28 35 100 0 - 0 0 20 - 100 100 100 100 0 100 100 90 100 0 100 | 33 0 95 40 100 0 50 0 40 50 - 95 100 0 90 90 90 90 10 85 | 40 70 100 40 100 95 35 40 95 - 100 100 100 0 100 100 95 95 90 100 | 49 95 100 65 100 25 65 15 85 100 100 100 100 0 100 100 90 100 65 100 | 50 95 95 45 95 40 70 0 85 90 100 100 100 0 100 100 90 100 85 100 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 250g ai/ha seedling | 1 70 100 50 90 90 90 10 80 100 100 100 100 50 100 100 100 100 90 95 | 2 0 100 0 50 45 30 60 40 100 100 100 100 0 100 0 100 100 0 90 | 3 0 70 0 0 0 0 0 0 30 80 35 20 0 80 45 20 0 0 35 | 4 45 100 75 85 95 75 55 90 100 100 100 100 15 100 100 100 100 85 95 | 5 30 100 20 20 0 10 0 60 100 100 90 100 0 100 100 98 100 0 90 | 8 100 100 10 0 100 0 35 0 100 90 100 - 100 90 100 100 100 100 100 | 9 100 100 75 100 100 80 50 90 100 100 100 - 100 100 100 100 100 100 100 | 10 0 0 0 0 0 0 0 0 45 65 0 20 - 70 55 - 0 0 0 | 12 20 90 - 0 100 0 0 5 85 70 90 80 0 85 85 70 85 0 70 | 13 0 95 30 0 0 5 0 45 85 90 90 90 0 90 85 90 90 10 90 | 15 0 100 45 95 85 65 0 75 100 100 100 100 0 100 100 95 100 75 100 | 16 0 100 75 95 65 75 0 80 100 100 100 100 0 100 100 100 100 80 100 | 17 0 100 75 80 85 75 0 75 85 100 100 100 0 100 100 100 100 0 100 | 22 50 100 65 95 95 20 80 100 - 100 100 100 95 100 100 100 100 100 100 |
| Table C | Compound | |||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa before the 250g ai/ha seedling | 26 0 90 0 - 0 0 0 0 - - 85 100 0 | 27 0 70 15 0 10 0 0 45 30 90 95 100 0 | 28 30 95 0 - 0 0 0 0 90 100 100 100 0 | 30 0 90 0 85 50 60 50 5 90 90 100 100 0 | 31 0 85 0 0 0 0 20 5 70 80 50 - 0 | 33 0 90 30 100 0 50 0 10 50 85 90 95 0 | 40 0 90 20 - 70 30 5 80 - 100 90 100 0 | 49 85 95 15 95 20 0 0 80 100 100 100 100 0 | 50 0 95 20 95 0 0 0 65 20 100 95 100 0 | 64 20 30 30 90 40 0 75 60 70 100 10 95 10 |
| Amaranthus retroflexus american ragweed soybean Sunflower Receptacle pitch arm shape grass piemarker | 100 85 10 70 10 90 | 90 85 20 90 20 50 | 100 100 65 100 0 95 | 90 100 70 90 20 50 | 40 60 80 70 0 60 | 90 70 80 80 0 60 | 100 100 90 90 10 90 | 100 100 90 100 40 90 | 95 95 75 95 65 85 | 100 100 85 85 90 0 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 125g ai/ha seedling | 1 50 100 0 60 60 30 0 30 100 100 100 100 0 100 100 100 100 35 90 | 2 0 80 - 0 0 0 0 0 95 100 100 100 0 95 0 90 100 0 75 | 3 0 55 0 0 0 0 0 0 20 0 20 0 0 65 0 15 0 0 20 | 4 20 95 0 65 80 40 25 70 100 100 100 100 0 100 100 100 100 65 95 | 5 0 90 5 0 0 0 0 20 95 95 80 100 0 90 90 90 90 0 85 | 8 100 85 0 0 65 0 0 0 85 20 100 - 0 85 100 100 40 100 75 | 9 100 100 60 95 95 75 20 65 100 100 100 - 100 100 100 100 100 100 100 | 10 0 0 0 0 0 0 0 0 0 50 0 - 0 55 0 - 0 0 0 | 11 0 0 0 60 0 20 0 75 60 85 0 - - 90 45 55 0 100 0 | 12 0 85 60 0 10 0 0 5 50 40 60 60 0 50 20 - 0 0 50 | 13 0 90 10 0 0 0 0 5 80 90 85 90 0 85 70 90 60 0 80 | 15 0 90 15 95 20 0 0 65 100 100 100 100 0 100 95 90 100 65 95 | 16 0 95 20 65 15 0 0 65 100 100 100 95 0 100 95 100 100 15 95 | 17 0 95 35 20 20 20 0 55 25 100 100 95 0 100 95 95 100 0 100 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass before the 125g ai/ha seedling | 19 0 80 0 0 0 0 | 22 50 95 50 95 95 15 | 25 10 85 0 0 50 0 | 26 0 70 0 - 0 0 | 27 0 50 10 0 0 0 | 28 20 95 0 - 0 0 | 30 0 85 0 70 45 20 | 31 0 75 0 0 0 0 | 33 0 0 0 20 0 10 | 40 0 70 20 - 5 0 | 47 95 75 0 100 0 20 | 49 0 95 15 95 0 0 | 50 0 85 10 90 0 0 | 64 20 5 20 70 0 0 |
| Eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker | 0 55 90 100 90 100 0 95 80 90 90 10 65 | 0 100 - 100 100 100 0 100 100 95 95 90 95 | 0 0 70 50 90 75 0 85 85 65 90 40 40 | 0 - - - 5 100 0 100 10 10 20 0 10 | 0 20 0 40 70 70 0 80 65 0 20 0 0 | 0 - 80 100 100 100 0 95 95 45 50 0 55 | 35 5 70 85 90 100 0 80 90 5 90 0 15 | 0 0 50 40 10 0 0 35 60 15 5 0 0 | 0 5 - - 85 50 0 90 20 30 70 0 20 | 0 80 - 100 90 100 0 100 90 40 90 0 70 | 90 0 100 95 100 100 0 85 65 0 100 0 50 | 0 65 100 100 95 100 0 90 100 70 75 15 70 | 0 55 0 100 95 100 0 90 85 60 55 15 75 | 0 50 25 95 0 85 0 100 95 85 30 50 0 |
| Table C | Compound | ||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 125g ai/ha seedling | 65 80 90 30 80 70 60 50 70 70 100 100 80 70 100 100 100 100 80 100 | 75 20 100 65 60 60 10 30 55 100 100 100 100 0 90 90 100 100 55 100 | 76 0 90 45 60 50 10 0 50 100 80 100 100 0 90 100 95 100 45 90 | 77 0 95 35 0 0 0 0 0 80 40 75 0 0 65 55 100 100 0 90 | 78 20 90 40 45 10 0 0 50 100 80 100 70 - 95 80 95 100 75 80 | 117 65 90 25 60 50 50 30 70 60 100 50 45 50 100 98 100 100 95 90 | 135 0 100 70 5 0 0 40 40 100 90 100 50 0 100 70 100 90 0 100 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 62g ai/ha seedling | 1 0 90 0 10 0 0 0 0 95 95 90 100 0 90 95 85 80 0 80 | 2 0 - 0 0 0 0 0 0 90 100 100 20 0 95 0 75 100 0 50 | 3 0 30 0 0 0 0 0 0 0 0 0 0 0 50 0 0 0 0 0 | 4 0 80 - 40 0 0 0 50 95 95 100 100 0 95 100 95 100 0 75 | 5 0 10 5 0 0 0 0 5 80 95 50 100 0 60 85 85 60 0 85 | 8 100 - 0 0 0 0 0 0 50 0 20 - 0 65 100 100 20 0 65 | 9 100 80 5 95 90 0 0 45 95 100 100 - 100 95 100 100 100 100 95 | 10 0 - 0 0 0 0 0 0 0 0 0 - 0 20 0 0 0 - 0 | 11 0 0 0 0 0 0 0 0 0 40 0 - 0 65 20 - 0 100 0 | 12 0 50 30 0 0 0 0 0 50 10 60 50 0 50 10 50 0 - 5 | 13 0 60 5 0 0 0 0 0 60 85 65 0 0 60 60 60 50 0 60 | 15 0 65 0 0 0 0 0 20 95 95 95 95 0 90 90 75 65 15 80 | 16 0 95 15 0 0 0 0 40 95 95 95 90 0 95 90 85 85 0 90 | 17 0 90 20 0 0 0 0 0 0 95 95 80 0 100 80 90 95 0 80 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa before the 62g ai/ha seedling | 19 0 65 0 0 0 0 0 35 85 100 90 100 0 | 22 0 90 40 90 40 10 0 80 - 100 100 100 0 | 25 0 60 0 0 0 0 0 0 5 30 50 30 0 | 26 0 70 0 - 0 0 0 0 0 10 0 10 0 | 27 0 0 0 0 0 0 0 0 0 - 0 0 0 | 28 0 90 0 - 0 0 0 - 0 95 100 100 0 | 30 0 60 0 0 5 0 30 0 70 80 85 80 0 | 31 0 60 0 0 0 0 0 0 0 40 0 0 0 | 33 0 0 0 0 0 0 0 0 - - 0 0 0 | 40 0 5 0 5 5 0 0 0 - 100 - 100 0 | 47 0 70 0 100 0 0 85 0 0 85 70 95 0 | 49 0 20 - 95 0 0 0 45 100 100 90 95 0 | 50 - 70 10 90 0 0 0 0 - 95 80 95 0 | 64 0 0 0 0 0 0 0 5 20 95 0 85 0 |
| Amaranthus retroflexus american ragweed soybean Sunflower Receptacle pitch arm shape grass piemarker | 70 70 85 70 0 40 | 90 90 95 90 - 90 | 35 70 60 75 0 0 | 30 0 0 0 0 0 | 20 20 0 0 0 0 | 80 65 0 45 0 50 | 30 85 5 80 0 10 | 30 10 5 0 0 0 | 85 0 0 0 0 0 | 20 90 10 5 - 0 | 85 45 0 20 0 20 | 85 70 0 15 0 15 | 75 70 0 15 0 65 | 30 85 85 0 0 0 |
| Table C | Compound | |||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 62g ai/ha seedling | 65 70 50 0 70 5 50 0 60 50 80 20 - 30 80 90 95 95 80 80 | 75 0 95 30 20 60 0 0 50 100 80 95 70 0 80 80 100 100 55 85 | 76 0 90 35 5 20 0 0 20 95 80 100 60 0 80 80 95 100 0 70 | 77 0 80 0 0 0 0 0 0 50 - 50 0 0 65 50 100 100 0 85 | 78 0 90 20 40 0 0 0 20 100 80 85 60 0 70 80 80 100 0 70 | 95 55 60 5 35 5 35 40 80 45 100 60 75 60 100 100 100 100 10 90 | 117 30 5 20 0 15 5 0 60 20 100 5 40 50 90 90 100 90 50 65 | 135 0 95 30 0 0 0 0 5 75 70 90 35 0 80 35 95 90 0 90 |
| Table C | Compound | |||||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass before the 31g ai/ha seedling | 2 0 60 0 0 0 0 | 3 0 0 0 0 0 0 | 9 100 75 0 20 0 0 | 11 0 0 0 0 0 0 | 12 0 50 0 0 0 0 | 13 0 40 0 0 0 0 | 16 0 45 0 0 0 0 | 17 0 75 0 0 0 0 | 19 0 30 0 0 0 0 | 25 0 20 0 0 0 0 | 30 0 0 0 0 0 0 | 31 0 0 0 0 0 0 | 47 0 0 0 100 0 0 | 64 0 0 0 0 0 0 |
| Eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker | 0 0 75 90 100 0 0 90 0 15 20 0 20 | 0 0 0 0 0 0 0 20 0 0 0 0 0 | 0 15 95 95 100 - 20 95 100 100 100 95 70 | 0 0 0 0 0 - 0 0 0 - 0 0 0 | 0 0 0 0 30 - 0 10 - - 0 0 0 | 0 0 45 50 60 0 0 50 45 0 5 0 60 | 0 0 90 95 65 55 0 85 45 75 20 0 25 | 0 0 0 95 70 - 0 95 70 70 60 0 20 | 0 0 - 100 10 40 0 45 55 25 25 - 35 | 0 0 0 0 0 0 0 30 70 - 60 0 0 | 0 0 50 0 0 50 0 0 30 0 20 0 0 | 0 0 0 0 0 0 0 10 5 0 0 0 0 | 45 0 - - 0 85 0 80 - 0 0 0 20 | 0 5 20 70 0 5 0 10 85 0 0 - 0 |
| Table C | Compound | |||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 31g ai/ha seedling | 65 50 30 0 20 0 10 0 50 0 50 0 0 0 80 85 95 70 40 40 | 75 0 90 0 10 0 0 0 0 80 75 90 50 0 75 70 60 70 0 60 | 76 0 90 0 0 0 0 0 0 90 70 60 40 0 80 60 70 85 0 40 | 77 0 70 0 0 0 0 0 0 - 0 50 0 0 60 0 100 50 0 30 | 78 0 70 0 5 0 0 0 10 80 70 70 30 0 60 65 70 70 0 55 | 95 0 0 0 30 0 30 10 60 40 100 10 60 60 100 100 100 95 5 60 | 117 0 0 5 0 0 0 0 35 5 100 0 5 0 80 60 100 50 40 50 | 135 0 95 30 0 0 0 0 0 75 70 90 30 0 70 - 95 70 0 85 |
| Table C | Compound | |||||||||||
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus american ragweed soybean sunflower Brachiaria decumbens piemarker before the 16g ai/ha seedling | 11 0 0 0 0 0 0 0 0 0 0 0 - 0 0 0 - 0 0 0 | 19 0 15 0 0 0 0 0 0 35 75 10 0 0 35 55 0 10 0 25 | 25 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 5 0 0 | 47 0 0 0 20 0 0 0 0 0 0 0 80 0 0 0 0 0 0 0 | 65 0 0 0 0 0 0 0 0 0 0 0 0 0 40 85 85 40 0 0 | 75 0 55 - 0 0 0 0 0 70 70 50 0 0 70 20 55 50 0 5 | 76 0 65 0 0 0 0 0 0 70 70 40 30 0 60 50 50 50 0 30 | 77 0 55 0 0 0 0 0 0 20 0 5 0 0 60 0 40 20 0 10 | 78 0 55 0 0 0 0 0 0 70 0 0 0 0 55 10 30 50 0 10 | 95 0 0 0 0 0 0 0 50 0 100 0 0 40 90 90 90 40 0 0 | 117 0 0 0 0 0 0 0 0 0 20 0 0 0 50 60 85 0 40 0 | 135 0 85 5 0 0 0 0 0 60 0 85 0 0 70 5 85 65 0 60 |
| Table C | Compound |
| The wild broomcorn millet Fa Shi of Bermuda grass Siberian cocklebur corn lady's-grass dog hair grass eleusine indica before the 8g ai/ha seedling | 95 0 0 0 0 0 0 0 |
| Table C | Compound |
| Johnson grass summer cypress lamb's-quarters sweet potato east black nightshade chufa Amaranthus retroflexus before the 8g ai/ha seedling | 95 0 0 0 0 0 0 50 |
| Table C | Compound |
| American ragweed soybean Sunflower Receptacle pitch arm shape grass piemarker before the 3g ai/ha seedling | 95 65 90 5 0 0 |
Test D
Plantation is selected from Tender Catchweed Bedstraw Herb (Galium aparine), chickweed (Stellaria media), summer cypress (Kochia scoparia), lamb's-quarters (Chenopodium album), Amaranthus retroflexus (Amaranthusretroflexus), Herba Salsolae Collinae (Salsola kali), volume stem knotweed (Polygonum convolvulus), wild Europe sinapsis alba (Sinapis arvensis), the seed of the plant variety of barley (Hordeum vulgare) and common wheat (Triticum aestivum), and the test chemical of preparing with the solvent mixture of the plant-less toxicity that comprises tensio-active agent carries out the seedling pre-treatment.
Simultaneously, the plant that is selected from above-mentioned crop and weeds kind carries out the seedling aftertreatment with some test chemical of preparing in the same manner.When plant length arrives 2-18 centimetre high (1-4 leaf phase), carry out the seedling aftertreatment.Handle plant and to bringing up 15-25 days in the growing environment that impinges upon control, afterwards all kinds with compare, and carry out visually rank.Plant reaction grade (being summarized among the table D) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table D | Compound |
| The wild Europe of volume stem knotweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 500g ai/ha seedling | 58 100 100 100 100 100 100 80 85 |
| Table D | Compound | |||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 250g ai/ha seedling | 26 50 55 55 85 55 50 75 70 40 20 | 28 40 60 65 100 75 75 60 70 70 35 | 33 45 55 60 65 50 45 50 55 40 45 | 35 70 80 85 100 85 100 75 100 100 70 | 47 - 70 70 98 75 45 70 65 70 45 | 58 - 100 - 100 100 100 100 100 70 70 |
| Table D | Compound | |||||||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 125g ai/ha seedling | 1 - 80 85 100 100 100 75 100 100 100 | 2 - 95 85 100 100 100 80 100 100 100 | 4 - 100 100 100 100 100 90 100 100 100 | 9 - 100 100 100 100 100 95 100 100 100 | 26 45 35 45 70 35 40 60 60 40 45 | 28 40 55 65 - 75 70 60 60 70 35 | 33 45 50 50 60 50 30 50 55 40 40 | 35 65 70 80 100 85 100 75 100 100 65 | 47 - 65 65 80 65 40 65 55 65 35 | 58 - 90 - 100 100 85 100 100 70 60 |
| Table D | Compound | ||||||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 62g ai/ha seedling | 1 - 80 65 100 100 100 70 100 85 90 | 2 - 90 85 100 100 100 70 100 95 100 | 4 - 100 100 100 100 100 75 100 100 100 | 9 - 100 100 100 100 100 80 100 100 90 | 28 20 35 65 100 70 65 45 60 65 20 | 33 45 40 40 55 50 30 50 45 30 35 | 35 65 60 80 100 80 100 75 100 100 0 | 47 - 65 60 75 50 35 60 50 55 35 | 58 - 65 - 100 70 80 100 80 70 55 |
| Table D | Compound | ||||
| The wild Europe of volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 31g ai/ha seedling | 1 80 65 100 100 95 70 100 65 80 | 2 65 60 100 100 100 65 85 85 70 | 4 85 100 100 100 100 65 100 90 85 | 9 80 100 100 100 100 80 100 90 80 | 47 60 35 65 45 35 55 35 45 30 |
| Table D | Compound | |||
| The wild Europe of volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat behind the 16g ai/ha seedling | 1 50 65 95 85 95 60 60 45 40 | 2 45 60 75 75 60 65 65 65 70 | 4 80 65 100 85 95 65 85 80 80 | 9 65 60 100 85 95 65 65 65 50 |
| Table D | Compound |
| The wild Europe of volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat before the 500g ai/ha seedling | 58 100 100 100 100 100 100 100 85 70 |
| Table D | Compound | ||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat before the 250g ai/ha seedling | 26 35 95 65 100 75 65 65 100 100 35 | 28 45 60 60 100 100 60 60 80 100 35 | 33 45 65 65 100 65 65 65 90 85 55 | 35 45 65 100 100 100 80 75 85 100 50 | 58 - 100 75 100 100 100 100 100 70 60 |
| Table D | Compound | ||||||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat before the 125g ai/ha seedling | 1 - 75 75 100 100 100 90 100 100 70 | 2 - 85 90 100 100 100 85 100 100 70 | 4 - 100 100 100 100 100 85 100 100 80 | 9 - 100 100 100 100 100 85 100 100 - | 26 25 65 60 85 55 60 65 65 - 25 | 28 25 45 60 100 80 60 60 - 80 35 | 33 35 65 - 80 65 65 65 70 60 35 | 35 45 60 100 100 100 75 70 80 100 40 | 58 - 80 - 100 95 100 100 100 65 50 |
| Table D | Compound | |||||||
| The wild Europe of barley volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus before the 62g ai/ha seedling | 1 - 70 70 100 100 85 70 95 | 2 - 80 75 98 100 95 70 85 | 4 - 100 85 100 100 100 85 100 | 9 - 100 100 100 100 100 85 100 | 28 10 45 60 100 45 60 60 45 | 33 10 55 - 70 60 60 65 60 | 35 40 55 60 85 75 65 65 65 | 58 - 40 60 100 35 60 65 70 |
| The Herba Salsolae Collinae common wheat | 100 70 | 100 70 | 100 80 | 100 75 | 45 20 | 55 15 | 85 35 | 40 25 |
| Table D | Compound | |||
| The wild Europe of volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat before the 31g ai/ha seedling | 1 60 65 80 75 75 65 70 100 70 | 2 65 60 90 70 85 70 70 100 60 | 4 80 70 100 100 80 85 90 100 70 | 9 85 95 100 98 100 70 80 100 75 |
| Table D | Compound | |||
| The wild Europe of volume stem knotweed chickweed clearvers summer cypress lamb's-quarters sinapsis alba Amaranthus retroflexus salsola collina common wheat before the 16g ai/ha seedling | 1 45 60 80 65 65 50 60 100 35 | 2 45 60 80 55 - 50 65 85 45 | 4 60 65 90 85 70 65 70 90 - | 9 60 65 85 70 65 60 65 100 60 |
Test E
Three plastic tub of each dosage (the about 16cm of diameter), partly load onto the sterile sand that comprises in the basin: silt: the ratio of clay is the Tama silt loam of 35: 50: 15 and 2.6% organic matter.Plantation respectively as mentioned below in three basins each.The natural pond that derives from the U.S. is given birth to 16cm basin of each dosage plantation of seed of different stamen flower (Heteranthera limosa), Herba Cyperi Difformis (Cyperus difformis) and the Herba Ammanniae Bacciferae that comes into leaves (Ammannia coccinea).The cyperus iria (Cyperus iria) of the U.S., the seed of Semen Euphorbiae (Leptochloa fasca ssp.fascicularis) will be derived from, cluster 9 or 10 tiller water direct seeding rice seedlings (rice varieties ' Japonica-M202 '), cluster 6 tillers are transplanted each dosage of rice seedlings (rice varieties ' Japonica-M202 ') and are implanted in the basin of a 16cm.Each dosage of seed that derives from barnyard grass grass (Echinochloa crus-galli), rice field barnyard grass (Echinochloa oryzicola), paddy field barnyard grass (Echinochloa oryzoides) and the awns barnyard grass (Echinochloa colona) of the U.S. is implanted in the 16cm basin.Continued growth is the 2.0-2.5 leaf phase up to crop and weeds kind when handling.
Potted plant grows in the greenhouse, the daytime/night temperature be set in 29.5/26.7 ℃, and provide and replenish balance illumination and make the photoperiod reach 16 hours.The test basin remains in the greenhouse and finishes up to test.
During processing, the test basin is irrigated to being higher than 3 centimetres of soil surfaces, handles by directly test compound being applied in the paddy field water either, keeps the depth of water at duration of test afterwards.The effect that rice and weeds are handled after 21 days by relatively carrying out visual assessment with untreated control.The plant reaction grade is summarised among the table E, is divided into 0 to 100 grade, and wherein 0 is to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table E | Compound | ||
| 500g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice that comes into leaves | 44 10 100 - 20 75 0 | 61 65 100 95 25 100 25 | 62 100 100 100 65 100 30 |
| Table E | Compound | ||
| Barnyard grass rice field, 500g ai/ha big flood water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass | 44 20 100 95 0 20 | 61 35 100 65 25 25 | 62 60 100 75 0 20 |
| Table E | Compound | |||||||||||||
| 250g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 37 0 100 90 0 80 0 0 95 0 - 0 | 44 0 100 - 20 50 0 0 100 50 0 0 | 58 - 100 100 0 95 0 20 100 60 - 0 | 61 0 100 40 25 100 0 10 95 65 20 20 | 62 50 100 65 50 95 0 10 100 45 0 20 | 63 - 100 85 30 75 0 30 80 65 0 0 | 64 - 100 100 0 80 10 0 100 0 0 20 | 65 - 100 100 40 60 0 10 100 40 10 25 | 66 35 100 0 0 100 0 0 0 0 0 0 | 67 40 100 60 65 85 0 0 70 30 0 0 | 69 - 100 100 0 30 0 0 100 0 0 0 | 70 0 100 65 0 0 0 0 60 0 0 0 | 71 60 100 0 45 30 0 0 70 60 0 0 | 72 0 100 100 0 100 0 0 100 0 0 0 |
| Table E | Compound | |||||||||||||
| 250g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 73 100 100 45 0 100 0 0 85 70 0 | 74 0 100 95 65 25 0 0 100 0 0 | 84 85 100 80 50 100 20 30 100 40 30 | 88 0 100 100 90 65 0 0 95 95 50 | 91 10 100 - 70 50 10 20 100 30 0 | 94 0 100 100 0 100 20 10 100 40 0 | 95 0 100 0 0 80 15 15 95 0 0 | 96 0 100 100 0 100 20 10 100 0 0 | 98 0 100 100 0 40 0 0 60 0 0 | 99 0 100 100 0 45 20 20 - 0 0 | 111 0 100 0 0 75 0 0 75 0 0 | 117 0 100 100 0 30 20 0 100 0 0 | 118 0 100 100 65 85 0 0 100 85 0 | 128 0 100 80 10 90 0 0 100 80 0 |
| The rice field barnyard grass | 20 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Table E | Compound | |
| 250g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice that comes into leaves | 129 0 100 100 0 95 0 | 133 0 100 100 0 85 0 |
| Table E | Compound | |
| Barnyard grass rice field, 250g ai/ha big flood water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass | 129 0 100 70 0 0 | 133 35 100 0 0 0 |
| Table E | Compound | |||||||||||||
| 125g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 37 0 100 75 0 40 0 0 65 0 - 0 | 44 0 100 - 0 20 0 0 90 30 0 0 | 58 - 100 100 0 95 0 0 95 60 - 0 | 61 0 100 40 20 80 0 0 85 60 0 20 | 62 0 100 45 40 85 0 0 95 30 0 20 | 63 - 100 85 0 75 0 20 75 40 0 0 | 64 - 100 100 0 60 10 0 100 0 0 20 | 65 - 100 100 40 50 0 0 100 40 0 0 | 66 0 100 0 0 40 0 0 0 0 0 0 | 67 40 100 60 30 0 0 0 40 30 0 0 | 69 0 100 100 0 0 0 0 90 0 0 0 | 70 0 100 30 0 0 0 0 0 0 0 0 | 71 0 100 0 0 0 0 0 30 0 0 0 | 72 0 100 100 0 35 0 0 90 0 0 0 |
| Table E | Compound | |||||||||||||
| 125g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 73 90 100 - 0 100 0 0 35 50 0 | 74 - 100 90 0 20 0 0 95 0 0 | 84 20 100 60 50 70 0 0 90 0 20 | 88 0 100 100 0 0 0 0 85 85 0 | 91 10 100 - 0 30 0 10 100 30 0 | 94 0 100 100 0 100 10 10 100 20 0 | 95 0 100 0 0 70 0 0 95 0 0 | 96 0 100 100 0 100 10 10 100 0 0 | 98 0 100 100 0 40 0 0 60 0 0 | 99 0 100 100 0 0 0 20 - 0 0 | 111 0 100 0 0 30 0 0 0 0 0 | 117 0 100 100 0 0 0 0 100 0 0 | 118 0 100 95 65 50 0 0 100 70 0 | 128 0 100 60 0 90 0 0 100 0 0 |
| The rice field barnyard grass | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Table E | Compound | |
| 125g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice that comes into leaves | 129 0 100 100 0 80 0 | 133 0 100 95 0 75 0 |
| Table E | Compound | |
| Barnyard grass rice field, 125g ai/ha big flood water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass | 129 0 100 0 0 0 | 133 0 100 0 0 0 |
| Table E | Compound | |||||||||||||
| 64g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 37 0 100 0 0 30 0 0 50 0 - 0 | 44 0 100 0 10 0 0 90 30 0 0 | 58 - 100 100 0 85 0 0 95 60 - 0 | 61 0 100 0 20 80 0 0 75 35 0 20 | 62 0 100 0 30 85 0 0 80 0 0 20 | 63 - 65 75 0 65 0 0 75 40 0 0 | 64 - 100 90 0 60 0 0 85 0 0 0 | 65 - 100 100 0 30 0 0 85 0 0 0 | 66 - 100 0 0 0 0 0 0 0 0 0 | 67 0 100 30 0 0 0 0 0 0 0 0 | 69 0 100 100 0 0 0 0 30 0 0 0 | 70 0 100 0 0 0 0 0 0 0 0 0 | 71 0 100 0 0 0 0 0 0 - 0 0 | 72 - 100 100 0 25 0 0 75 0 0 0 |
| Table E | Compound | |||||||||||||
| 64g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 73 0 100 0 0 90 0 0 0 0 0 | 74 0 100 0 0 0 0 0 80 0 0 | 84 0 100 60 0 20 0 0 80 0 10 | 88 0 100 100 0 0 0 0 - 0 0 | 91 10 100 - 0 0 0 10 30 0 0 | 94 0 100 100 0 75 10 - 100 0 0 | 95 0 100 0 0 30 0 0 95 0 0 | 96 0 100 100 0 90 0 0 100 0 0 | 98 0 100 100 0 0 0 0 60 0 0 | 99 0 100 100 0 - 0 0 - 0 0 | 111 0 85 0 0 30 0 0 0 0 0 | 117 0 100 100 0 0 0 0 100 0 0 | 118 0 100 95 45 30 0 0 100 0 0 | 128 0 100 0 0 80 0 0 70 0 0 |
| The rice field barnyard grass | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Table E | Compound | |
| 64g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice that comes into leaves | 129 0 100 100 0 75 0 | 133 0 100 95 0 65 0 |
| Table E | Compound | |
| Barnyard grass rice field, 64g ai/ha big flood water direct seeding rice Herba Cyperi Difformis Semen Euphorbiae paddy field barnyard grass | 129 0 80 0 0 0 | 133 0 95 0 0 0 |
| Table E | Compound | |||||||||||||
| 32g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 37 0 100 0 0 0 0 0 50 0 - 0 | 44 0 100 - 0 0 0 0 20 20 0 0 | 58 - 100 100 0 80 0 0 95 40 - 0 | 61 0 100 0 0 65 0 0 20 35 0 0 | 62 0 100 0 20 75 0 0 70 0 0 0 | 63 - 30 75 0 65 0 0 75 0 0 0 | 64 - 100 85 0 60 0 0 B0 0 0 0 | 65 - 10D 80 0 30 0 0 80 0 0 0 | 66 0 100 0 0 0 0 0 0 0 0 0 | 67 0 100 0 0 0 0 0 0 0 0 0 | 69 0 100 70 D 0 0 0 0 0 0 0 | 70 0 40 0 0 0 0 0 0 0 0 0 | 71 0 100 0 0 0 0 0 0 0 0 0 | 72 0 80 100 0 25 0 0 30 0 0 0 |
| Table E | Compound | |||||||||||||
| 32g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 73 - 100 0 0 0 0 0 0 0 0 | 74 0 100 0 0 0 0 0 0 0 0 | 84 0 100 35 0 20 0 0 80 0 0 | 88 0 100 85 0 0 0 0 40 0 0 | 91 0 100 - 0 0 0 0 0 0 0 | 94 0 100 100 0 65 0 0 100 0 0 | 95 0 100 0 0 - 0 0 95 0 0 | 96 0 100 100 0 85 0 0 100 0 0 | 98 0 100 80 0 0 0 0 60 0 0 | 99 0 100 - 0 0 0 0 - 0 0 | 111 0 0 0 0 20 0 0 0 0 0 | 117 0 100 100 0 0 0 0 85 0 0 | 118 0 100 95 40 20 0 0 95 0 0 | 128 0 100 0 0 75 0 0 60 0 0 |
| The rice field barnyard grass | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Table E | Compound | |
| 32g ai/ha big flood barnyard grass marsh is given birth to the different stamen flower cyperus iria awns barnyard grass water three-coloured amaranth transplanting rice that comes into leaves | 129 0 100 100 0 60 0 | 133 0 100 65 0 20 0 |
| Table E | Compound | |
| Barnyard grass rice field, 32g ai/ha big flood water direct seeding rice Herba Cyperi Difformis Semen Euphorbiae paddy field barnyard grass | 129 0 60 0 0 0 | 133 0 0 0 0 0 |
| Table E | Compound | |||||||||||||
| 16g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 37 0 80 0 0 0 0 0 30 0 - 0 | 58 - 100 40 0 60 0 0 65 20 - 0 | 63 - 30 60 0 65 0 0 70 0 0 0 | 64 - 100 75 0 20 0 0 65 0 0 0 | 65 - 100 0 0 0 0 0 20 0 0 0 | 66 0 95 0 0 0 0 0 0 0 0 0 | 67 0 85 0 0 0 0 0 0 0 0 0 | 69 0 95 65 0 0 0 0 0 0 0 0 | 70 0 0 0 0 0 0 0 0 0 0 0 | 71 0 100 0 0 0 0 0 0 - 0 0 | 72 - 80 90 0 0 0 0 0 0 0 0 | 73 0 75 0 0 0 0 0 0 0 0 0 | 74 0 100 0 0 0 0 0 0 0 0 0 | 84 0 100 25 0 0 0 0 70 0 0 0 |
| Table E | Compound | ||||||||||||
| 16g ai/ha big flood barnyard grass marsh is given birth to different stamen flower cyperus iria awns barnyard grass barnyard grass rice field, the water three-coloured amaranth transplanting rice water direct seeding rice difformed galingale herb moleplant seed paddy field barnyard grass that comes into leaves | 88 0 95 50 0 0 0 0 40 0 0 0 | 91 0 100 - 0 0 0 0 0 - 0 0 | 94 0 100 100 0 0 0 0 100 0 0 0 | 95 0 100 0 0 30 0 0 0 0 0 0 | 96 0 100 100 0 0 0 0 100 0 0 0 | 98 0 0 80 0 0 0 0 60 0 0 0 | 99 0 95 100 0 0 0 0 - 0 0 0 | 111 0 0 0 0 0 0 0 0 0 0 0 | 117 0 100 100 0 0 0 0 60 0 0 0 | 118 0 100 85 0 0 0 0 85 0 0 0 | 128 0 95 0 0 0 0 0 0 0 0 0 | 129 0 100 100 0 30 0 0 0 0 0 0 | 133 0 100 30 0 0 0 0 0 0 0 0 |
Test F
Plantation is selected from Bermuda grass (Cynodon dactylon), English grass (Poapratensis), marsh bent grass (Agrostis palustris), fescue grass (Festuca ovina), lady's-grass (Digitaria sanguinalis), Herba Eleusines Indicae (Eleusine indica), Paspalum dilalatum (Paspalum dilatatum), annual bluegrass (Poa annua), chickweed (Stellaria media), common dandelion (Taraxacum officinale), the seed or the fruit stone of the plant variety of white clover (Trifolium repens) and tiger nuts (Cyperus esculentus), and the test chemical of preparing with the solvent mixture of the plant-less toxicity that comprises tensio-active agent carries out the seedling pre-treatment.
Simultaneously, the plant that is selected from above-mentioned crop and weeds kind carries out the seedling aftertreatment with the test chemical of same way as preparation.When plant length arrives 2-18 centimetre high (1-4 leaf phase), carry out the seedling aftertreatment.Handle plant and brought up 12-14 days impinging upon in the greenhouse, all kinds and are carried out visually rank compared with the control afterwards.Plant reaction grade (being summarized among the table F) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table F | Compound |
| Marsh bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa behind the 500g ai/ha seedling | 1 70 70 95 30 100 100 90 60 95 0 50 15 |
| Table F | Compound |
| Marsh bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa behind the 250g ai/ha seedling | 1 50 50 70 0 85 100 75 75 85 0 40 15 |
| Table F | Compound |
| Marsh bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa behind the 125g ai/ha seedling | 1 50 40 45 0 85 100 70 15 75 0 35 10 |
| Table F | Compound |
| Bent grass Bermuda grass meadow, marsh annual bluegrass behind the 62g ai/ha seedling | 1 30 20 0 |
| Table F | Compound |
| Bent grass Bermuda grass annual bluegrass in marsh behind the 31g ai/ha seedling | 1 0 0 35 |
| Table F | Compound |
| The preceding marsh of 500g ai/ha seedling bent grass Bermuda grass annual bluegrass | 1 100 90 70 |
| Chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 80 90 45 0 75 0 10 10 |
| English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 20 0 70 0 0 50 0 5 0 |
| English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 80 100 100 100 95 100 90 85 70 |
| Table F | Compound |
| The front marsh of 250g ai/ha seedling bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 1 90 80 70 40 100 100 95 70 100 60 65 25 |
| Table F | Compound |
| The front marsh of 125g ai/ha seedling bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 1 60 50 45 30 100 100 85 45 100 60 30 30 |
| Table F | Compound |
| The front marsh of 62g ai/ha seedling bent grass Bermuda grass annual bluegrass English grass chickweed white clover lady's-grass hairy flowered paspalum common dandelion fescue grass eleusine indica chufa | 1 60 40 65 30 100 100 40 35 95 60 40 15 |
| Table F | Compound |
| The preceding marsh of 31g ai/ha seedling bent grass Bermuda grass annual bluegrass English grass | 1 50 10 20 0 |
| Table F | Compound |
| Chickweed white clover lady's-grass Paspalum dilalatum before the 31g ai/ha seedling | 1 80 80 15 10 |
| Table F | Compound |
| Common dandelion fescue grass Herba Eleusines Indicae tiger nuts before the 31g ai/ha seedling | 1 35 50 30 0 |
Test G
Plantation is selected from Bermuda grass (Cynodon dactylon), pitch arm shape grass (Brachiariadecumbens), lady's-grass (Digitaria sanguinalis), Herba Setariae Viridis (Setaria viridis), Herba Eleusines Indicae (Eleusine indica), Johnson grass (Sorghum halepense), summer cypress (Kochiascoparia), wild sweet potato (Ipomoea lacunosa), Rhizoma Cyperi (Cyperus rotundus), american ragweed (Ambrosia elatior), black mustard (Brassica nigra), big broomcorn millet (Panicummaximum), Paspalum dilalatum (Paspalum dilatatum), barnyard grass grass (Echinochloacrus-galli), tribulus terrestrisl grass (Cenchrus echinatus), sonchus oleraceus (Sonchusoleraceous), Radix sidae acutae (Sida spinosa), Itanlian rye (Lolium multiflorum), purslane (Portulaca oleracea), broad-leaved arm shape grass (Brachiaria platyphylla), Herba Senecionis Vulgaris (Senecio vulgaris), chickweed (Stellaria media), meal bag grass (Commelina benghaleusis), annual bluegrass (Poa annua), cheatgrass brome (Bromustectorum), Rottboellia exaltata (Rottboellia cochinchinensis), couchgrass (Elytrigiarepens), Herba Erigerontis Canadensis (Conyza canadensis), Herba seu Flos Convolvuli arvensis (Convolvulusarvensis), Herba Bidentis Bipinnatae (Bidens bipinnata), the seed or the fruit stone of the plant variety of high mallow (Malva sylvestris) and Herba Salsolae Collinae (Salsola kali), and the test chemical of preparing with the solvent mixture of the plant-less toxicity that comprises tensio-active agent carries out the seedling pre-treatment.
Simultaneously, the plant that is selected from above-mentioned weeds kind carries out the seedling aftertreatment with some test chemical of preparing in the same manner.When plant length arrives 2-18 centimetre high (1-4 leaf phase), carry out the seedling aftertreatment.Handle plant and brought up 12-21 days impinging upon in the greenhouse, all kinds and are carried out visually rank compared with the control afterwards.
At different time, the grape of growing in the chamber of having built up (Vitus vinifera) rattan and Fructus oleae europaeae (Olea europaea) and sweet orange (Citrus sinensis) tree are handled with some test chemical of preparing in the same manner, and be administered to soil surface and be lower than 5 centimetres plant or trunk place (post-directed application is used in the back management).The height of plant is 30-100 centimetre.Utilization is sent the hand sprayer of 990L/ha volume and is used.Handle plant and brought up 28 days impinging upon in the greenhouse, all kinds and are carried out visually rank compared with the control afterwards.
At different time, the sugarcane kind (joint) of (Saccharum officinarum) grows cane, and carry out before the seedling and/or the seedling aftertreatment with the test chemical that some are prepared in the same manner, handle plant and brought up 14 days impinging upon in the greenhouse, all kinds and are carried out visually rank compared with the control afterwards.
Plant reaction grade (being summarized among the table G) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
| Table G | Compound |
| Barnyard grass grass Bermuda grass Herba seu Flos Convolvuli arvensis black mustard annual bluegrass behind the 500g ai/ha seedling | 1 75 50 95 75 50 |
| Table G | Compound |
| Barnyard grass grass Bermuda grass Herba seu Flos Convolvuli arvensis black mustard annual bluegrass behind the 375g ai/ha seedling | 1 70 40 95 75 50 |
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of cheatgrass brome lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass high mallow bur purslane couchgrass american ragweed Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 80 70 30 60 60 100 95 100 70 95 95 100 30 95 100 70 100 40 95 85 100 95 95 90 |
| The wild sweet potato rhizome of nutgrass flatsedge of cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Conyza canadensis Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 70 100 70 30 50 60 100 100 60 95 95 95 100 30 95 100 70 100 100 40 95 75 95 95 95 90 |
| Table G | Compound | ||
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass behind the 250g ai/ha seedling | 1 70 40 95 75 40 60 95 70 | 22 85 65 100 95 75 95 95 85 | 77 75 50 100 60 40 75 100 75 |
| Table G | Compound |
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass behind the 125g ai/ha seedling | 1 60 25 95 75 30 30 95 60 |
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 30 30 60 95 95 100 60 95 - 70 100 20 90 100 60 95 100 40 95 75 95 95 95 85 | 75 75 50 - 100 - 85 - 100 95 100 15 95 98 85 100 100 85 95 85 100 - 98 95 | 50 40 65 100 75 80 80 85 98 95 100 40 80 85 60 100 - 40 40 70 95 98 100 70 |
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 20 20 60 95 70 70 40 70 60 100 10 70 100 30 95 100 10 60 60 95 95 95 60 |
| Table G | Compound | |
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass behind the 125g ai/ha seedling | 22 25 40 100 95 40 95 85 85 25 50 | 77 65 35 100 60 40 65 90 75 35 40 |
| Table G | Compound | |||
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass behind the 62g ai/ha seedling | 1 60 25 90 60 20 30 - 50 10 10 | 22 15 35 100 75 15 85 50 50 15 25 | 64 20 35 90 10 0 75 - 80 20 0 | 77 40 35 98 50 0 35 90 75 15 35 |
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 35 85 95 - 75 - 100 85 95 0 95 95 75 98 100 40 85 50 100 - 95 65 | 50 95 65 80 70 85 98 85 100 0 80 70 60 98 - 30 35 60 95 98 90 65 |
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 20 60 60 - 20 70 - 50 100 - 70 80 10 75 100 0 30 20 95 80 95 30 | 25 65 65 - 50 - 98 - 85 0 90 85 65 98 100 15 40 25 95 - 85 35 | 20 0 0 60 60 0 90 90 65 35 75 60 35 100 - 35 20 30 80 90 90 10 | 50 80 65 75 65 70 98 80 90 0 80 60 40 95 - 30 10 50 90 98 75 25 |
| Table G | Compound | ||
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel behind the 31g ai/ha seedling | 22 0 35 100 75 0 65 50 35 0 15 15 65 | 64 20 35 80 0 0 40 - 70 0 0 0 0 | 77 10 20 98 40 0 20 80 70 0 0 15 75 |
| Table G | Compound | ||
| Barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel behind the 16g ai/ha seedling | 22 0 15 85 50 0 15 - 15 0 0 5 65 | 64 20 20 70 0 0 20 - 50 0 0 0 0 | 77 0 10 70 25 0 0 10 60 0 0 0 40 |
| The wild sweet potato rhizome of nutgrass flatsedge of big broomcorn millet Conyza canadensis Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 55 - 25 - 98 60 85 0 85 55 40 85 100 5 15 15 85 - 40 15 | 0 60 0 0 85 90 20 35 75 0 20 100 - 20 20 0 80 90 80 0 | 0 50 35 65 95 75 60 0 75 20 10 75 - 20 0 30 90 95 50 10 |
| The wild sweet potato rhizome of nutgrass flatsedge of big broomcorn millet Conyza canadensis Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 5 - 15 - 98 40 50 0 75 50 15 65 95 0 0 5 75 - 15 0 | 0 60 0 0 75 80 0 35 65 0 20 75 - 10 0 0 80 75 80 0 | 0 40 0 20 90 65 50 0 70 20 0 75 - 0 0 0 75 75 10 0 |
| Table G | Compound |
| The big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata behind the 8g ai/ha seedling | 64 0 0 60 0 0 0 30 0 0 0 0 0 60 0 |
| Table G | Compound | |
| Management grapefruit olive sweet orange behind the 1500g ai/ha | 1 100 50 50 | 4 100 - 75 |
| Table G | Compound |
| Manage Fructus oleae europaeae behind the 900g ai/ha | 4 50 |
| Table G | Compound | |
| Sugarcane behind the 500g ai/ha seedling | 1 38 | 9 17 |
| The wild sweet potato rhizome of nutgrass flatsedge of Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 0 65 65 0 0 40 0 0 75 0 0 0 65 65 65 0 |
| Table G | Compound | |
| Sugarcane behind the 250 g ai/ha seedlings | 1 13 | 9 7 |
| Table G | Compound | |
| Sugarcane behind the 125 g ai/ha seedlings | 1 3 | 9 0 |
| Table G | Compound | |
| Sugarcane behind the 62 g ai/ha seedlings | 1 0 | 9 0 |
| Table G | Compound | |
| Sugarcane behind the 31 g ai/ha seedlings | 1 0 | 9 0 |
| Table G | Compound | ||
| The big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress before the seedling | 1 70 70 100 100 85 95 100 90 95 90 50 100 100 100 90 75 100 | 4 100 100 100 100 100 100 100 100 100 100 90 100 100 100 95 95 - | 9 95 100 100 100 100 100 100 100 100 100 95 - 100 100 85 95 - |
| Table G | Compound |
| The big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow before the 375 g ai/ha seedlings | 1 70 70 100 100 95 100 90 95 90 50 100 100 100 85 75 100 95 |
| The wild sweet potato rhizome of nutgrass flatsedge of high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 95 100 100 100 100 95 100 100 95 85 95 100 100 100 100 | 100 100 100 100 100 100 100 100 100 100 95 100 100 100 95 | 100 100 - 100 - 100 100 - 80 95 100 - 100 100 90 |
| Wild sweet potato rhizome of nutgrass flatsedge bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 100 100 100 100 95 100 100 95 85 75 100 100 100 95 |
| Table G | Compound | ||||
| The wild sweet potato of the big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow before the 250g ai/ha seedling | 1 50 30 100 85 85 95 95 90 50 50 50 100 85 100 80 60 100 95 100 | 4 80 95 100 100 80 100 100 100 95 100 70 100 100 100 80 85 - 100 100 | 9 85 95 100 100 95 70 100 90 80 100 95 - 100 100 80 95 - 100 100 | 22 80 30 100 75 60 75 100 80 50 20 0 50 95 - 65 80 100 80 90 | 77 90 60 100 95 40 75 100 90 85 90 55 100 95 100 90 95 100 80 100 |
| Rhizome of nutgrass flatsedge bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 100 100 95 90 100 100 30 70 75 100 100 100 95 | 100 100 100 100 100 100 100 90 95 100 100 100 80 | - 100 - 70 100 - 75 90 80 - 100 100 80 | 50 95 75 30 100 100 50 85 80 100 - 100 90 | 100 95 100 80 100 100 75 100 95 100 - 100 100 |
| Table G | Compound | ||||
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane before the 125g ai/ha seedling | 1 20 20 100 80 30 20 95 30 10 10 - 100 70 95 30 40 100 80 100 100 100 60 | 4 70 90 100 95 60 70 100 75 50 70 60 95 95 100 70 75 - 100 100 100 100 100 | 9 70 95 100 75 30 50 100 90 70 85 60 - 100 100 60 80 - 100 100 - 100 - | 22 70 0 90 65 30 20 90 80 40 10 0 - 90 - 40 50 100 80 90 40 80 70 | 77 85 10 100 90 20 10 100 85 30 85 25 80 85 100 85 85 100 80 100 100 90 100 |
| Couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 60 95 100 10 30 70 100 100 100 95 | 90 100 100 60 80 70 100 100 100 60 | - 100 - 50 80 80 - 100 100 70 | 20 95 100 0 70 10 100 - 100 35 | 50 100 - 40 100 90 100 - 95 90 |
| Table G | Compound | |||||
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina before the 62g ai/ha seedling | 1 0 10 95 30 10 0 70 20 0 10 0 60 70 95 10 20 100 50 95 10 70 10 10 50 100 | 4 50 20 100 95 10 30 100 60 0 20 10 95 95 100 70 60 - 100 100 40 85 60 60 80 - | 9 30 10 95 70 10 10 - 70 10 20 10 - 90 100 30 40 - 90 70 - 95 - 70 95 - | 22 30 0 90 60 0 0 - 40 0 0 0 - 75 - 20 20 98 75 60 30 65 50 20 90 95 | 64 10 0 65 35 0 0 0 35 0 0 0 40 0 95 20 0 15 0 0 0 50 35 0 95 0 | 77 75 0 95 85 5 0 90 80 15 65 5 - 85 100 45 75 95 50 100 100 85 75 10 100 100 |
| Itanlian rye tribulus terrestris grass broad-leaved arm shape grass sonchus oleraceus beggar-ticks meal bag grass Brachiaria decumbens | 0 0 10 95 100 70 95 | 30 30 50 100 100 100 30 | 20 - 20 - 100 100 40 | 0 0 0 90 - 95 0 | 0 0 0 90 35 90 0 | 0 100 75 100 - 95 70 |
| Table G | Compound | ||
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass before the 31g ai/ha seedling | 22 20 0 75 35 0 0 50 40 0 0 0 0 35 - 0 0 70 50 50 0 50 0 0 75 75 0 0 0 | 64 0 0 0 20 0 0 0 0 0 0 0 10 0 95 0 0 10 0 0 0 30 0 0 65 0 0 0 0 | 77 55 0 90 60 0 0 70 45 5 5 5 60 70 90 10 65 95 40 90 100 75 60 0 95 - 0 20 10 |
| Table G | Compound | ||
| The wild sweet potato rhizome of nutgrass flatsedge of the big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass before the 16g ai/ha seedling | 22 10 0 65 30 0 0 0 0 0 0 0 - 0 - 0 0 35 50 20 0 50 0 0 65 65 0 0 0 | 64 0 0 0 0 0 0 - 0 0 0 0 0 0 75 0 0 0 - 0 0 0 0 0 65 - 0 0 0 | 77 50 0 80 60 0 0 - 45 0 0 0 50 30 70 0 10 85 30 70 100 70 45 0 80 85 0 0 5 |
| Sonchus oleraceus Herba Bidentis Bipinnatae meal bag grass pitch arm shape grass | 75 - 50 0 | 35 0 75 0 | 100 - 85 5 |
| Sonchus oleraceus Herba Bidentis Bipinnatae meal bag grass pitch arm shape grass | 35 - 0 0 | 0 0 50 0 | 80 - 60 0 |
| Table G | Compound |
| The big broomcorn millet Conyza canadensis of barnyard grass grass Bermuda grass field bindweed black mustard annual bluegrass cheatgrass brome chickweed lady's-grass hairy flowered paspalum green bristlegrass eleusine indica Groundsel Rottboellia exaltata Johnson grass before the 8g ai/ha seedling | 64 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
| Table G | Compound |
| The wild sweet potato rhizome of nutgrass flatsedge of summer cypress high mallow bur purslane couchgrass american ragweed salsola collina Itanlian rye tribulus terrestris grass broad-leaved arm shape grass hare's-lettuce beggar-ticks meal bag grass Brachiaria decumbens before the 8g ai/ha seedling | 64 0 0 0 0 0 0 0 65 0 0 0 0 0 0 0 0 |
| Table G | Compound |
| Sugarcane before the 375g ai/ha seedling | 1 0 |
| Table G | Compound |
| Sugarcane before the 125g ai/ha seedling | 1 0 |
| Table G | Compound |
| Sugarcane before the 250g ai/ha seedling | 1 0 |
| Table G | Compound |
| Sugarcane before the 62g ai/ha seedling | 1 0 |
Test H
This test evaluation the mixture of compound 1 and diflufenzopyr to the effect of several plant kind.Containing Redi-Earth_ culture medium for cultivating (the Scotts Company that comprises spaghnum peat moss, vermiculite, wetting agent and nutrition source, 14111 Scottslawn Road, Marysville, Ohio 43041) basin in the seed of planting experiment plant, comprise lady's-grass (DIGSA, Digitaria sanguinalis (L.) Scop.), lamb's-quarters (CHEAL, Chenopodiumalbum L.), Amaranthus retroflexus (AMARE, Amaranthus retroflnexus L.), Siberian cocklebur (XANST, Xanthium strumarium L.), barnyard grass grass (ECHCG; Echinochloacrus-galli (L.) Beauv.), corn (ZEAMD, Zea mays L. cv. ' Pioneer33G26 '), sweet potato (IPOCO, Ipomoea coccinea L.), Fa Shi dog hair grass (SETFA, Setaria faberi Herrm.) and the seed of piemarker (ABUTH, Abutilon theophrasti Medik.).The kind of seedlet plant about 1 centimetre dark; The kind of big seed plant about 2.5 centimetres dark.Plant grows in the greenhouse, utilizes additional light source to keep about 14 hours light application time; Diurnal temperature is respectively about 25-30 ℃ and 22-25 ℃.Balanced feritilizer utilizes watering system to use.Made that the plant height of plant was 2-18 centimetre (1-4 leaf phase) when handling in plant strain growth 7-11 days.Processing comprises independent compound 1 and diflufenzopyr, and combination, and its suspension or be dissolved in the water-containing solvent that comprises glycerine and tween nonionogenic tenside is adopted the volume of 541L/ha to carry out blade spraying and used.Each is handled and repeats four times.Using solvent compares with untreated control plant and does not observe effect.Processed plant and bring up impinging upon in the greenhouse is watered as required, but first the 24 hours blades of not getting wet after processing.Handle the back and about 3 weeks compare the effect of range estimation with untreated contrast plant.The plant reaction grade is calculated according to four multiple mean values, is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The Colby formula is in order to calculate the expection herbicidal effect of mixture.Colby formula (Colby, S.R. " Calculating Synergistic and Antagonistic Response ofHerbicide Combinations ", Weeds, 15 (1), pp20-22 (1967)) expection of calculating Herbicidal mixture adds and effect, adopts following formula for two kinds of activeconstituentss:
P
a+b＝P
a+P
b-(P
a P
b/100)
P wherein
A+bBe the percentage ratio that adds and contribute the effect of the mixture of expecting by independent component,
P
aBe with the effect percentage ratio of the observation of the first kind of activeconstituents that in mixture, uses same dose and
P
bBe effect percentage ratio with the observation of second kind of activeconstituents of use same dose in mixture.
Result and list among the table H by adding of Colby formula expection with effect.
Table H-by independent compound 1 and with the combination observation of diflufenzopyr to and the result that anticipates
*
| Amount of application (gai/ha) | DIGSA | CHEAL | AMARE | XANST | ECHCG | ||||||
| Compound 1 | Diflufenzopyr | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 125 | - | 81 | - | 100 | - | 100 | - | 97 | - | 90 | - |
| 62 | - | 37 | - | 100 | - | 97 | - | 98 | - | 42 | - |
| 31 | - | 7 | - | 98 | - | 91 | - | 87 | - | 25 | - |
| - | 50 | 8 | - | 80 | - | 95 | - | 68 | - | 23 | - |
| - | 25 | 1 | - | 76 | - | 91 | - | 60 | - | 10 | - |
| - | 12 | 0 | - | 61 | - | 73 | - | 43 | - | 5 | - |
| 125 | 50 | 88 | 83 | 100 | 100 | 100 | 100 | 100 | 99 | 93 | 92 |
| 62 | 25 | 77 | 38 | 100 | 100 | 100 | 100 | 92 | 99 | 85 | 48 |
| 31 | 12 | 62 | 7 | 100 | 99 | 100 | 98 | 100 | 93 | 85 | 29 |
| Amount of application (g a.i/ha) | ZEAMD | IPOCO | SETFA | ABUTH | |||||
| Compound 1 | Diflufenzopyr | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 125 | - | 22 | - | 100 | - | 65 | - | 93 | - |
| 62 | - | 5 | - | 97 | - | 4 | - | 26 | - |
| 31 | - | 2 | - | 92 | - | 2 | - | 14 | - |
| - | 50 | 0 | - | 82 | - | 59 | - | 68 | - |
| - | 25 | 0 | - | 83 | - | 58 | - | 78 | - |
| - | 12 | 0 | - | 77 | - | 41 | - | 50 | - |
| 125 | 50 | 56 | 22 | 100 | 100 | 89 | 86 | 100 | 98 |
| 62 | 25 | 32 | 5 | 100 | 99 | 72 | 60 | 92 | 84 |
| 31 | 12 | 8 | 2 | 99 | 98 | 73 | 42 | 62 | 57 |
*Amount of application is the gram number (g a.i./ha) of per hectare activeconstituents." Obsd. " is the result who observes." Exp. " is the expected results that is calculated by the Colby formula.
From the result that lists of table H as can be seen, the result that major part observes all is higher than by the desired result of Colby formula, and is high in some cases a lot.The most significant is to be higher than adding and effect that lady's-grass, barnyard grass grass, corn and Fa Shi dog hair grass are observed.For other the test kinds effect increases more not obvious, but mainly be because the test the desired effect of amount near 100%.
Test I
This test evaluation the mixture of compound 9 and metsulfuronmethyl combination grand with the chlorine sulphur of metsulfuronmethyl and 5: 1 weight ratios to the effect of several plant kind.The seed of planting experiment plant comprises common wheat (TRZAW in the mixture of loam and sand; Triticum aestivum), volume stem knotweed (POLCO; Polygonum convolvulus), Amaranthus retroflexus (AMARE; Amaranthusretroflexus), wild Europe sinapsis alba (SINAR; Sinapis arvensis), Tender Catchweed Bedstraw Herb (GALAP; Galium aparine), Herba Salsolae Collinae (SASKR; Salsola kali), chickweed (STEME; Stellaria media), summer cypress (KCHSC; Kochia scoparia) and lamb's-quarters (CHEAL; Chenopodium album).Plant grows in the greenhouse, utilizes additional light source to keep about 14 hours light application time; Diurnal temperature is respectively about 23 ℃ and 16 ℃.Balanced feritilizer utilizes watering system to use.Made that the plant height of plant was the 2-8 leaf phase when handling in plant strain growth 10-23 days.Processing comprises that independent compound 9, metsulfuronmethyl and chlorine sulphur swell-metsulfuronmethyl (5: 1), and combination.This processing is prepared with the solvent mixture of the non-plant toxicity that comprises tensio-active agent, and the volume of employing 280-458L/ha carries out blade spraying and uses.Each handles triplicate.Using solvent compares with untreated control plant and does not observe effect.Processed plant and bring up impinging upon in the greenhouse is watered as required, but first the 24 hours blades of not getting wet after processing.Handle about 17 days of back and compare the effect of range estimation with untreated contrast plant.The plant reaction grade is calculated according to three multiple mean values, is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The Colby formula is used for determining the desired herbicidal effect of mixture.Result and be listed in the Table I by Colby formula desired adding with effect.
The result that Table I-swell by independent compound 9 and with metsulfuronmethyl with chlorine sulphur-metsulfuronmethyl (5: 1) combination institute is observed and anticipates
*
| Amount of application (g a.i./ha) | POLCO | AMARE | SINAR | GALAP | KCHSC | ||||||
| Compound 9 | Metsulfuronmethyl | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 8 | - | 27 | - | 70 | - | 47 | - | 87 | - | 87 | - |
| 4 | - | 17 | - | 62 | - | 45 | - | 83 | - | 70 | - |
| - | 8 | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| - | 4 | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| 8 | 8 | 32 | 27 | 58 | 70 | 45 | 47 | 85 | 87 | 70 | 87 |
| 8 | 4 | 38 | 27 | 77 | 70 | 48 | 47 | 82 | 87 | 80 | 87 |
| 4 | 8 | 38 | 17 | 65 | 62 | 48 | 45 | 85 | 83 | 85 | 70 |
| 4 | 4 | 30 | 17 | 52 | 62 | 33 | 45 | 80 | 83 | 80 | 70 |
| Amount of application (g a.i./ha) | SASKR | STEME | CHEAL | TRZAW | |||||
| Compound 9 | Metsulfuronmethyl | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 8 | - | 73 | - | 55 | - | 83 | - | 12 | - |
| 4 | - | 50 | - | 47 | - | 45 | - | 8 | - |
| - | 8 | 0 | - | 0 | - | 0 | - | 0 | - |
| - | 4 | 0 | - | 0 | - | 0 | - | 0 | - |
| 8 | 8 | 68 | 73 | 43 | 55 | 73 | 83 | 8 | 12 |
| 8 | 4 | 67 | 73 | 55 | 55 | 88 | 83 | 7 | 12 |
| 4 | 8 | 55 | 50 | 50 | 47 | 60 | 45 | 8 | 8 |
| 4 | 4 | 55 | 50 | 52 | 47 | 48 | 45 | 3 | 8 |
| Amount of application (g a.i./ha) | TRZAW | ||
| Compound 9 | Chlorine sulphur swells metsulfuronmethyl | Obsd. | Exp. |
| 16 | - | 43 | - |
| 8 | - | 30 | - |
| - | 20 | 35 | - |
| - | 10 | 3 | - |
| 16 | 20 | 42 | 63 |
| 16 | 10 | 33 | 45 |
| 8 | 20 | 33 | 55 |
| 8 | 10 | 22 | 32 |
*Amount of application is the gram number (g a.i./ha) of per hectare activeconstituents." Obsd. " is the result who observes." Exp. " is the expected result that is calculated by the Colby formula.
The result who lists from Table I as can be seen, some observed results to weeds are higher than by the desired result of Colby formula.The most significant is to be higher than adding and effect that volume stem knotweed, summer cypress and lamb's-quarters are observed.
In addition, nearly all result that processing observed to common wheat all is lower than by the desired result of Colby formula, shows that crop is safe.
Test J
The mixture of this test evaluation compound 58 and azimsulfuron is to the effect of several plant kind.Three plastic tub of each dosage (the about 16cm of diameter), partly load onto the sterile sand that comprises in the basin: silt: the ratio of clay is the Tama silt loam of 35: 50: 15 and 2.6% organic matter.In three basins each plantation respectively as mentioned below.Different stamen flower (HETLI is given birth in the natural pond that derives from the U.S.; Heteranthera limosa), Herba Cyperi Difformis (CYPDI; Cyperusdifformis) and the Herba Ammanniae Bacciferae (AMMCO that comes into leaves; Ammannia coccinea) each dosage kind of seed is gone into a 16cm basin.Semen Euphorbiae (the LEFUF of the U.S. will be derived from; Leptochloafasca ssp.fascicularis) seed, cluster 9 or 10 tiller water direct seeding rice seedlings (ORYSW; Rice varieties ' Japonica-M202 ') and cluster 6 tillers transplant rice seedlings (ORYSP; Rice varieties ' Japonica-M202 ') each dosage is implanted in the 16cm basin.Barnyard grass grass (the ECHCG of the U.S. will be derived from; Echinochloa crus-galli), rice field barnyard grass (ECOR2; Echinochloaoryzicola), paddy field barnyard grass (ECHOR; Echinochloa oryzoides) and awns barnyard grass (ECHCO; Echinochloa colona) each dosage kind of seed is implanted in the 16cm basin.Continued growth was 2.0 to 2.5 leaf phases up to crop and weeds kind when handling.
Potted plant grows in the greenhouse, the daytime/night temperature be set in 29.5/26.7 ℃, and provide and replenish balance illumination and make the photoperiod reach 16 hours.The test basin remains in the greenhouse and finishes up to test.
During processing, the test basin is irrigated to being higher than 3 centimetres of soil surfaces, handles by directly applying in the paddy field water either with the test compound that the solvent mixture of the non-plant toxicity that comprises tensio-active agent is prepared then.In the duration of test basin, keep 3 centimetres the depth of water.Processing comprises independent compound 58 and azimsulfuron, and combination.The effect that rice and weeds are handled after 21 days by relatively carrying out visual assessment with untreated control.The plant reaction grade is calculated and is summarized among the table J according to three multiple mean values.Amount of application is based on 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.The Colby formula is used for determining the desired herbicidal effect of mixture.The result and by the Colby formula desired add with effect be listed in the table J in.
Table J-by independent compound 58 and with the combination observation of azimsulfuron to and the result that anticipates
*
| Amount of application (ga.i./ha) | ORYSW | ORYSP | AMMCO | HETLI | CYPDI | ||||||
| Compound 58 | Azimsulfuron | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 64 | - | 20 | - | 0 | - | 90 | - | 100 | - | 100 | - |
| 32 | - | 10 | - | 0 | - | 30 | - | 100 | - | 100 | - |
| 16 | - | 10 | - | 0 | - | 0 | - | 100 | - | 100 | - |
| - | 8 | 10 | - | 0 | - | 95 | - | 100 | - | 100 | - |
| - | 4 | 0 | - | 0 | - | 0 | - | 30 | - | 100 | - |
| - | 2 | 0 | - | 0 | - | 0 | - | 30 | - | 95 | - |
| 64 | 8 | 10 | 28 | 15 | 0 | 95 | 100 | 100 | 100 | 100 | 100 |
| 32 | 8 | 0 | 19 | 10 | 0 | 95 | 97 | 100 | 100 | 100 | 100 |
| 16 | 8 | 10 | 19 | 10 | 0 | 80 | 95 | 100 | 100 | 100 | 100 |
| 64 | 4 | 0 | 20 | 0 | 0 | 70 | 90 | 100 | 100 | 100 | 100 |
| 32 | 4 | 0 | 10 | 0 | 0 | 70 | 30 | 100 | 100 | 100 | 100 |
| 16 | 4 | 15 | 10 | 0 | 0 | 70 | 0 | 100 | 100 | 100 | 100 |
| 64 | 2 | 0 | 20 | 0 | 0 | 70 | 90 | 100 | 100 | 100 | 100 |
| 32 | 2 | 0 | 10 | 0 | 0 | 30 | 30 | 100 | 100 | 100 | 100 |
| 16 | 2 | 0 | 10 | 0 | 0 | 0 | 0 | 100 | 100 | 100 | 100 |
| Amount of application (g a.i./ha) | LEFUF | ECHCG | ECOR2 | ECHOR | ECHCO | ||||||
| Compound 58 | Azimsulfuron | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. | Obsd. | Exp. |
| 64 | - | 20 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| 32 | - | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| 16 | - | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| - | 8 | 0 | - | 30 | - | 50 | - | 40 | - | 40 | - |
| - | 4 | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| - | 2 | 0 | - | 0 | - | 0 | - | 0 | - | 0 | - |
| 64 | 8 | 0 | 20 | 55 | 30 | 60 | 50 | 55 | 40 | 60 | 40 |
| 32 | 8 | 0 | 0 | 45 | 30 | 45 | 50 | 65 | 40 | 55 | 40 |
| 16 | 8 | 0 | 0 | 30 | 30 | 45 | 50 | 30 | 40 | 40 | 40 |
| 64 | 4 | 0 | 20 | 35 | 0 | 50 | 0 | 20 | 0 | 30 | 0 |
| 32 | 4 | 0 | 0 | 10 | 0 | 30 | 0 | 20 | 0 | 20 | 0 |
| 16 | 4 | 0 | 0 | 20 | 0 | 0 | 0 | 20 | 0 | 20 | 0 |
| 64 | 2 | 0 | 20 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| 32 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| 16 | 2 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
*Amount of application is the gram number (g a.i./ha) of per hectare activeconstituents." Obsd. " is the result who observes." Exp. " is the expected result that is calculated by the Colby formula.
Test K
Be selected from the Tender Catchweed Bedstraw Herb (GALAP of sulfonylurea herbicide sensitivity (SU-sensitivity) and sulfonylurea herbicide resistance (SU-resistance); Galium aparine) and common wheat (TRZAW; The seed of plant variety Triticumaestivum) carries out the seedling aftertreatment with the test chemical of the solvent mixture preparation of the non-plant toxicity that comprises tensio-active agent.Handle plant in 2-3 leaf phase and 2 whorl phases respectively for common wheat and Tender Catchweed Bedstraw Herb.Handle plant and to bringing up 15 days in the growing environment that impinges upon control, all kinds and are carried out visually rank compared with the control afterwards.Plant reaction grade (being summarized among the table K) is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The no test-results of horizontal line (-) reaction expression.
Table K-is by compound 1 and 9 grand to common wheat and to the result of the Tender Catchweed Bedstraw Herb of sulfonylurea sensitivity and resistance with chlorine sulphur
| Amount of application (g a.i./ha) | TRZAW | GALAP SU-sensitivity | GALAP SU resistance | ||
| Compound 1 | Compound 9 | Chlorine sulphur is grand | |||
| 125 | - | - | 38 | 100 | 100 |
| 62 | - | - | 30 | 100 | 100 |
| 31 | - | - | 25 | 98 | 100 |
| 16 | - | - | 0 | 98 | 100 |
| 8 | - | - | 0 | 80 | 100 |
| 4 | - | - | 0 | 63 | 100 |
| - | 125 | - | 40 | 100 | 100 |
| - | 62 | - | 38 | 100 | 100 |
| - | 31 | - | 38 | 100 | 100 |
| - | 16 | - | 25 | 100 | 100 |
| - | 8 | - | 20 | 100 | 100 |
| - | 4 | - | 0 | 75 | 100 |
| - | - | 16 | 20 | 100 | 5 |
From table K as can be seen, the grand sulfonylurea resistance biotype to Tender Catchweed Bedstraw Herb of chlorine sulphur does not almost have effect in this test, and compound 1 and 9 antagonism and responsive biotype all have good prevention effect.
Test L
This piece test comprises the processing to the Silk Road Ji (Cirsium arvense) and bitter fleabane (Erigeron spp.) of independent compound 1 and nicosulfuron and combination.Near the Newark of the Delaware State, when plant height 20-30 centimetre of plant, use during May.Compound 1 is processed to contain the wettable powder of 25% weight activeconstituents.Nicosulfuron is the form of Accent_ weedicide, a kind of water dispersible granules that contains 75% weight activeconstituents.Before the processing, said preparation is dispersed in the water of atomizer jar.Utilization is calibrated to the knapsack sprayer of sending 24 gallon/acre (224L/ hectare) and handles 10ft * 30ft (plot of 3m * 9m).Each is handled and repeats twice.Handle about 56 days of back and compare the effect of range estimation with untreated contrast plant.The plant reaction grade is calculated according to twice multiple mean value, is divided into 0 to 100 grade, and the 0th, to no effect, and the 100th, control fully.The Colby formula is used for determining the desired herbicidal effect of mixture.The result and by the Colby formula desired add with effect be listed in the table L in.
Table L-by independent compound 1 and with nicosulfuron combination observe (Obsd.) and anticipate the result of (Exp.)
*
| Amount of application (ga.i./ha) | The Silk Road Ji | Bitter fleabane | |||
| Compound 1 | Nicosulfuron | Obsd. | Exp. | Obsd. | Exp. |
| 125 | - | 73 | - | 53 | - |
| - | 18 | 15 | - | 28 | - |
| 125 | 18 | 98 | 77 | 85 | 66 |
* amount of application is the gram number (g a.i./ha) of per hectare activeconstituents." Obsd. " is the result who observes." Exp. " is the expected result that is calculated by the Colby formula.
Table L shows that the synergistic effect that is combined in this test of compound 1 and nicosulfuron is tangible.
Claims (14)
1. compound, its N-oxide compound or an agricultural that is selected from formula I goes up the salt that is fit to,
Wherein
R
1Be randomly by 1-5 R
5The cyclopropyl that replaces is randomly by 1-5 R
6The sec.-propyl that replaces, or randomly by 1-3 R
7The phenyl that replaces;
R
2Be ((O)
jC (R
15) (R
16))
kR;
R is CO
2H or CO
2The effective derivative of the weeding of H;
R
3Be halogen, cyano group, nitro, OR
20, SR
21Or N (R
22) R
23
R
4Be-N (R
24) R
25Or-NO
2
Each R
5And R
6Be halogen, C independently
1-C
6Alkyl, C
1-C
6Haloalkyl, C
2-C
6Alkenyl, C
2-C
6Halogenated alkenyl, C
1-C
3Alkoxyl group, C
1-C
2Halogenated alkoxy, C
1-C
3Alkylthio or C
1-C
2Halogenated alkylthio;
Each R
7Be halogen, cyano group, nitro, C independently
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
6Cycloalkyl, C
3-C
6Halogenated cycloalkyl, C
1-C
4Hydroxyalkyl, C
2-C
4Alkoxyalkyl, C
2-C
4Halogenated alkoxy alkyl, C
2-C
4Alkenyl, C
2-C
4Halogenated alkenyl, C
3-C
4Alkynyl, C
3-C
4Halo alkynyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
2-C
4Alkenyl oxy, C
2-C
4Halogenated alkenyl oxy, C
3-C
4Alkynyloxy group, C
3-C
4Halo alkynyloxy group, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Haloalkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Halogenated alkyl sulfonyl, C
2-C
4Alkenyl thio, C
2-C
4Halogenated alkenyl sulfenyl, C
2-C
4Alkenyl sulfinyl, C
2-C
4Halogenated alkenyl sulfinyl, C
2-C
4Alkenyl alkylsulfonyl, C
2-C
4Halogenated alkenyl alkylsulfonyl, C
3-C
4Alkynyl sulfenyl, C
3-C
4Halo alkynyl sulfenyl, C
3-C
4Alkynyl sulfinyl, C
3-C
4Halo alkynyl sulfinyl, C
3-C
4Alkynyl alkylsulfonyl, C
3-C
4Halo alkynyl alkylsulfonyl, C
1-C
4Alkylamino, C
2-C
8Dialkyl amido, C
3-C
6Cycloalkyl amino, C
4-C
6(alkyl) cycloalkyl amino, C
2-C
6Alkyl-carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkyl amino carbonyl, C
3-C
6Trialkylsilkl, phenyl, phenoxy group and 5-or 6-unit hetero-aromatic ring, each phenyl, phenoxy group and 5-or 6-unit hetero-aromatic ring randomly are independently selected from R by 1-3
45Substituting group replace; Or
The R of two vicinities
7Lump together and be-OCH
2O-,-CH
2CH
2O-,-OCH (CH
3) O-,-OC (CH
3)
2O-,-OCF
2O-,-CF2CF
2O-,-OCF
2CF
2O-or-CH=CH-CH=CH-;
R
15Be H, halogen, C
1-C
4Alkyl, C
1-C
4Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group or C
2-C
4The alkyl-carbonyl oxygen base;
R
16Be H, halogen, C
1-C
4Alkyl or C
1-C
4Haloalkyl; Or
R
15And R
16Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
R
20Be H, C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
21Be H, C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
22And R
23Be H or C independently
1-C
4Alkyl;
R
24Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl, randomly by 1-2 R
31The C that replaces
2-C
4Alkenyl or randomly by 1-2 R
32The C that replaces
2-C
4Alkynyl; Or R
24Be C (=O) R
33, nitro, OR
34, S (O)
2R
35, N (R
36) R
37Or N=C (R
62) R
63
R
25Be H, randomly by 1-2 R
30The C that replaces
1-C
4Alkyl or C (=O) R
33Or
R
24And R
25Lump together to being selected from-(CH
2)
4-,-(CH
2)
5-,-CH
2CH=CH-CH
2-and-(CH
2)
2O (CH
2)
2-group, each group is randomly by 1-2 R
38Replace; Or
R
24And R
25Lump together and be=C (R
39) N (R
40) R
41Or=C (R
42) OR
43
Each R
30, R
31And R
32Be halogen, C independently
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl;
Each R
33Be H, C independently
1-C
14Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenyl, phenoxy group or benzyloxy;
R
34Be H, C
1-C
4Alkyl, C
1-C
3Haloalkyl or CHR
66C (O) OR
67
R
35Be C
1-C
4Alkyl or C
1-C
3Haloalkyl;
R
36Be H, C
1-C
4Alkyl or C (=O) R
64
R
37Be H or C
1-C
4Alkyl;
Each R
38Be halogen, C independently
1-C
3Alkyl, C
1-C
3Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or C
2-C
4Alkoxy carbonyl;
R
39Be H or C
1-C
4Alkyl;
R
40And R
41Be H or C independently
1-C
4Alkyl; Or
R
40And R
41Lump together and be-(CH
2)
4-,-(CH
2)
5-,-CH
2CH=CH-CH
2-or-(CH
2)
2O (CH
2)
2-;
R
42Be H or C
1-C
4Alkyl;
R
43Be C
1-C
4Alkyl;
Each R
45Be halogen, cyano group, nitro, C independently
1-C
4Alkyl, C
1-C
4Haloalkyl, C
3-C
6Cycloalkyl, C
3-C
6Halogenated cycloalkyl, C
2-C
4Alkenyl, C
2-C
4Halogenated alkenyl, C
3-C
4Alkynyl, C
3-C
4Halo alkynyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, C
1-C
4Alkyl sulphinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylamino, C
2-C
8Dialkyl amido, C
3-C
6Cycloalkyl amino, C
4-C
6(alkyl) cycloalkyl amino, C
2-C
4Alkyl-carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkyl amino carbonyl or C
3-C
6Trialkylsilkl;
R
62Be H, C
1-C
4Alkyl or randomly by 1-3 R
65The phenyl that replaces;
R
63Be H or C
1-C
4Alkyl; Or
R
62And R
63Lump together and be-(CH
2)
4-or-(CH
2)
5-;
R
64Be H, C
1-C
14Alkyl, C
1-C
3Haloalkyl, C
1-C
4Alkoxyl group, phenyl, phenoxy group or benzyloxy;
Each R
65Be CH independently
3, Cl or OCH
3
R
66Be H, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
R
67Be H, C
1-C
4Alkyl or benzyl;
J is 0 or 1; With
K is 0 or 1;
Condition is:
(a) when k is 0, j is 0 so;
(b) work as R
2Be CH
2OR
a, R wherein
aBe H, randomly when substituted alkyl or benzyl, R so
3Not cyano group;
(c) work as R
1During phenyl that to be each position replaced by Cl, so phenyl in contraposition also by R
7Replace;
(d) work as R
1Be by R in the contraposition
7During the phenyl that replaces, this R
7Not the tertiary butyl, cyano group or randomly substituted phenyl;
(e) work as R
1It is cyclopropyl or randomly by 1-5 R
6During the sec.-propyl that replaces, R is not C (=W) N (R so
b) S (O)
2-R
c-R
d, wherein W is O, S, NR
eOr NOR
eR
bBe hydrogen, C
1-C
4Alkyl, C
2-C
6Alkenyl or C
2-C
6Alkynyl; R
cBe direct key or CHR
f, O, NR
eOr NOR
eR
dBe randomly substituted heterocycle or the isocyclic aryl with 5-6 annular atoms, this group randomly condenses with fragrance or non-fragrant 5-or 6-unit ring; Each R
eBe H, C independently
1-C
3Alkyl, C
1-C
3Haloalkyl or phenyl; And R
fBe H, C
1-C
3Alkyl or phenyl; With
(f) formula I compound is not 6-amino-5-nitro-2-phenyl-4-pyrimidine diethyl malonate.
2. the compound of claim 1, wherein
R
2Be CO
2R
12, CH
2OR
13, CH (OR
46) (OR
47), CHO, C (=NOR
14) H, C (=NNR
48R
49) H, (O)
jC (R
15) (R
16) CO
2R
17, C (=O) N (R
18) R
19, C (=S) OR
50, C (=O) SR
51, C (=S) SR
52Or C (=NR
53) YR
54
R
12Be H ,-CH[-C (O) O (CH
2)
m-] ,-N=C (R
55) R
56Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl, C
2-C
14Alkynyl and phenyl groups, each group are randomly by 1-3 R
27Replace; Or
R
12Be each the CO of carboxylicesters functional group in two pyrimidine ring systems among the bonded I
2R
12Divalent group, this divalent group is selected from-CH
2-,-(CH
2)
2-,-(CH
2)
3-and-CH (CH
3) CH
2-;
R
13Be H, randomly by 1-3 R
28The C that replaces
1-C
10Alkyl or benzyl;
R
14Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl or benzyl;
R
17Be randomly by 1-3 R
29The C that replaces
1-C
10Alkyl, or benzyl;
R
18Be H, C
1-C
4Alkyl, hydroxyl, C
1-C
4Alkoxyl group or S (O)
2R
57
R
19Be H or C
1-C
4Alkyl;
Each R
27Be halogen, cyano group, hydroxycarbonyl group, C independently
2-C
4Alkoxy carbonyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino, C
2-C
4Dialkyl amido ,-CH_O (CH
2)
n_ or randomly by 1-3 R
44The phenyl that replaces; Or
Two R
27Lump together for-OC (O) O-or-O (C (R
58) (R
58))
1-2O-; Or
Two R
27Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
28Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido; Or
Two R
28Lump together and be the carbon atom formation carbonyl moiety of Sauerstoffatom to link to each other with them;
Each R
29Be halogen, C independently
1-C
4Alkoxyl group, C
1-C
4Halogenated alkoxy, C
1-C
4Alkylthio, C
1-C
4Halogenated alkylthio, amino, C
1-C
4Alkylamino or C
2-C
4Dialkyl amido;
Each R
44Be halogen, C independently
1-C
4Alkyl, C
1-C
3Haloalkyl, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
3Halogenated alkoxy, C
1-C
3Alkylthio, C
1-C
3Halogenated alkylthio, amino, C
1-C
3Alkylamino, C
2-C
4Dialkyl amido or nitro;
R
46And R
47Be C independently
1-C
4Alkyl or C
1-C
3Haloalkyl; Or
R
46And R
47Lump together and be-CH
2CH
2-,-CH
2CH (CH
3)-or-(CH
2)
3-;
R
48Be H, C
1-C
4Alkyl, C
1-C
4Haloalkyl, C
2-C
4Alkyl-carbonyl, C
2-C
4Alkoxy carbonyl or benzyl;
R
49Be H, C
1-C
4Alkyl or C
1-C
4Haloalkyl;
R
50, R
51And R
52Be H; Or be selected from C
1-C
14Alkyl, C
3-C
12Cycloalkyl, C
4-C
12Alkyl-cycloalkyl, C
4-C
12Cycloalkylalkyl, C
2-C
14Alkenyl and C
2-C
14The group of alkynyl, each group are randomly by 1-3 R
27Replace;
Y is O, S or NR
61
R
53Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl, C
2-C
4Alkoxyalkyl, OH or C
1-C
3Alkoxyl group;
R
54Be C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl; Or
R
53And R
54Lump together and be-(CH
2)
2-,-CH
2CH (CH
3)-or-(CH
2)
3-;
R
55And R
56Be C independently
1-C
4Alkyl;
R
57Be C
1-C
4Alkyl, C
1-C
3Haloalkyl or NR
59R
60
Each R
58Be independently selected from H and C
1-C
4Alkyl;
R
59And R
60Be H or C independently
1-C
4Alkyl;
R
61Be H, C
1-C
3Alkyl, C
1-C
3Haloalkyl or C
2-C
4Alkoxyalkyl;
M is the integer of 2-3; With
N is the integer of 1-4.
3. the compound of claim 2, wherein R
3It is halogen.
4. the compound of claim 2, wherein R
1Be cyclopropyl, or the phenyl that is replaced by halogen, methyl or methoxy and randomly replaced by 1-2 group that is selected from halogen and methyl in other positions in contraposition; And R
4Be-N (R
24) R
25
5. the compound of claim 4, wherein R
2Be CO
2R
12, CH
2OR
13, CHO or CH
2CO
2R
17
6. the compound of claim 5, wherein R
24Be H, C (O) R
33Or randomly by R
30The C that replaces
1-C
4Alkyl; R
25Be H or C
1-C
2Alkyl; Or R
24And R
25Lump together and be=C (R
39) N (R
40) R
41
7. the compound of claim 6, wherein R
2Be CO
2R
12R
24And R
25Be H.
8. the compound of claim 7, wherein R
12Be H, C
1-C
4Alkyl or benzyl.
9. the compound of claim 1 is selected from:
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid phenyl methyl esters,
6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid list sodium salt,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid phenyl methyl esters,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid list sodium salt,
6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid methyl esters,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-5-chloro-2-(4-chloro-phenyl-)-4-pyrimidinecarboxylic acid,
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid ethyl ester,
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid methyl esters and
6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid.
10. Herbicidal mixture comprises the compound of claim 1 of herbicidally effective amount and at least a other activeconstituents that is selected from other weedicides and herbicides and safeners of significant quantity.
11. a Herbicidal mixture comprises the compound and the growth hormone conduction depressant drug of the claim 1 of synergy significant quantity.
12. a herbicidal composition comprises compound and at least a tensio-active agent, solid diluent or the liquid diluent of the claim 1 of herbicidally effective amount.
13. a method of preventing and treating undesired plant growth comprises compound contact plant or its environment with the claim 1 of herbicidally effective amount.
14. a herbicidal composition comprises the compound of the claim 1 of herbicidally effective amount, at least a other activeconstituents that is selected from other weedicides and herbicides and safeners and at least a tensio-active agent, solid diluent or the liquid diluent of significant quantity.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53130003P | 2003-12-19 | 2003-12-19 | |
| US60/531,300 | 2003-12-19 | ||
| US59839704P | 2004-08-03 | 2004-08-03 | |
| US60/598,397 | 2004-08-03 | ||
| PCT/US2004/042302 WO2005063721A1 (en) | 2003-12-19 | 2004-12-16 | Herbicidal pyrimidines |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210115004.5A Division CN102675218B (en) | 2003-12-19 | 2004-12-16 | Herbicidal pyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1894220A true CN1894220A (en) | 2007-01-10 |
| CN1894220B CN1894220B (en) | 2012-06-06 |
Family
ID=37598211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200480037819XA Active CN1894220B (en) | 2003-12-19 | 2004-12-16 | Herbicidal pyrimidines |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN1894220B (en) |
| GT (1) | GT200400272A (en) |
| TN (1) | TNSN06184A1 (en) |
| UA (1) | UA84724C2 (en) |
| ZA (1) | ZA200604258B (en) |
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| CN102066336A (en) * | 2008-04-18 | 2011-05-18 | 陶氏益农公司 | 2-(substituted phenyl)-6-hydroxy or alkoxy-5-substituted-4-pyrimidinecarboxylates and their use as herbicides |
| CN102227162A (en) * | 2008-11-29 | 2011-10-26 | 拜尔农作物科学股份公司 | Herbicide-safener combination |
| CN102361556A (en) * | 2009-03-21 | 2012-02-22 | 拜尔农作物科学股份公司 | Pyrimindine-4-ylpropane dinitrile derivatives, method for the production thereof, and use thereof as herbicide and plant growth regulators |
| CN101784531B (en) * | 2007-08-30 | 2013-05-01 | 陶氏益农公司 | 2-(substituted phenyl)-6-amino-5-alkoxy, thioalkoxy and aminoalkyl-4-pyrimidinecarboxylates and their use as herbicides |
| CN101778829B (en) * | 2007-08-13 | 2013-07-31 | 陶氏益农公司 | 2-(2-fluoro-substituted phenyl)-6-amino-5-chloro-4-pyrimidinecarboxylates and their use as herbicides |
| CN103442570A (en) * | 2011-01-25 | 2013-12-11 | 陶氏益农公司 | Arylalkyl esters of 4-mino-6-(substituted phenyl)picolinates, arylalkyl esters of 6-amino-2-(substituted phenyl)-4-pyrimidinecarboxylates, and applications thereof as herbicides |
| CN103960281A (en) * | 2008-08-12 | 2014-08-06 | 杜邦公司 | Mixture for controlling undesired vegetation selected from prosopis and acacia |
| CN104754946A (en) * | 2012-09-04 | 2015-07-01 | 美国陶氏益农公司 | Synergistic weed control from applications of aminocyclopyrachlor and clopyralid |
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| CN105052938A (en) * | 2007-08-27 | 2015-11-18 | 陶氏益农公司 | Synergistic herbicidal composition containing certain pyridine carboxylic acids and certain cereal and rice herbicides |
| CN106187911A (en) * | 2016-07-04 | 2016-12-07 | 烟台凯博医药科技有限公司 | 2 trifluoromethyl pyrimidine 4 carboxylic acids and derivant thereof and preparation method |
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| CN108774179A (en) * | 2018-05-29 | 2018-11-09 | 青岛清原化合物有限公司 | A kind of substituted pyrimidine -4- formic acid derivates and its Herbicidal combinations and purposes |
| CN109476630A (en) * | 2016-07-25 | 2019-03-15 | 巴斯夫欧洲公司 | The pyrimidine compound of weeding |
| CN109476647A (en) * | 2016-07-26 | 2019-03-15 | 巴斯夫欧洲公司 | The pyrimidine compound of weeding |
| WO2020006869A1 (en) * | 2018-07-05 | 2020-01-09 | 青岛清原化合物有限公司 | Substituted pyrimidinyl formyl oxime derivative, preparation method therefor, herbicidal composition and use thereof |
| WO2020133403A1 (en) * | 2018-12-29 | 2020-07-02 | 青岛清原化合物有限公司 | Substituted pyrimidine aryl ester derivative, preparation method therefor, herbicidal composition and application thereof |
| CN114401956A (en) * | 2019-07-22 | 2022-04-26 | 拜耳公司 | Substituted N-phenyluracils, their salts and their use as herbicides |
| RU2777594C2 (en) * | 2018-07-05 | 2022-08-08 | Циндао Кингагрут Кемикал Компаунд Ко., Лтд. | Substituted pyrimidinylformyloxime derivative, its production method, its herbicidal composition, and use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH595061A5 (en) * | 1974-05-10 | 1978-01-31 | Ciba Geigy Ag | |
| EP0136976A3 (en) * | 1983-08-23 | 1985-05-15 | Ciba-Geigy Ag | Use of phenyl pyrimidines as plant regulators |
| DE3935277A1 (en) * | 1989-10-24 | 1991-05-02 | Hoechst Ag | SULPHONATED HETEROCYCLIC CARBOXAMIDES, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THEIR USE AS HERBICIDES OR GROWTH REGULATORS |
-
2004
- 2004-12-16 UA UAA200606999A patent/UA84724C2/en unknown
- 2004-12-16 CN CN200480037819XA patent/CN1894220B/en active Active
- 2004-12-16 ZA ZA200604258A patent/ZA200604258B/en unknown
- 2004-12-17 GT GT200400272A patent/GT200400272A/en unknown
-
2006
- 2006-06-15 TN TNP2006000184A patent/TNSN06184A1/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| TNSN06184A1 (en) | 2007-11-15 |
| CN1894220B (en) | 2012-06-06 |
| ZA200604258B (en) | 2008-07-30 |
| GT200400272A (en) | 2005-09-09 |
| UA84724C2 (en) | 2008-11-25 |
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