CN1189161A - Herbicidal ketals and spirocycles - Google Patents

Herbicidal ketals and spirocycles Download PDF

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CN1189161A
CN1189161A CN96195056A CN96195056A CN1189161A CN 1189161 A CN1189161 A CN 1189161A CN 96195056 A CN96195056 A CN 96195056A CN 96195056 A CN96195056 A CN 96195056A CN 1189161 A CN1189161 A CN 1189161A
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alkyl
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halogen
carbonyl
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曾治平
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EIDP Inc
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EI Du Pont de Nemours and Co
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Abstract

Compounds of Formula (I), and their agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein Q is (Q-1) or (Q-2); R<1> and R<2> are each independently C1-C6 alkoxy, C2-C6 haloalkoxy, C1-C6 alkylthio or C2-C6 haloalkylthio; or R<1> and R<2> are taken together to form -X<1>-(CH2)r-X<2>-, -(CH2)s-X<3>-, -(CH2)t-X<3>-CH2-, -(CH2)v-X<3>-CH2CH2- or -(CH2)w-, each group optionally substituted with at least one member selected from 1-6 halogen, 1-6 CH3 and one C1-C3 alkoxy; or R<1> and R<2> are taken together to form -O-N(C1-C3 alkyl)-CHR<12>-CH2- or -O-N=CHR<12>-CH2-, each group optionally substituted with at least one member selected from 1-2 halogen and 1-2 CH3; or R<1> and R<2> are taken together with the carbon to which they are attached to form C(=O) or C(=S); and R<3>-R<10>, X<1>-X<3>, X, Y, Z, k, m, p, q, r, s, t, v, w, and x are as defined in the disclosure. Also disclosed are compositions containing 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).

Description

The ketal and loop coil of weeding
The background of invention
The present invention relates to some ketals and loop coil, its agriculturally suitable salt and composition, and the method for not needing plant growth using their controls.
In order to obtain the high efficiency of crops, it is critically important to control unwanted plant, in useful crop such as rice, soybean, beet, corn (maize), potato, wheat, in barley, tomato and botanical garden crop, the growth that particularly can optionally control weeds is highly desirable.Weeds, which arbitrarily grow, in above-mentioned useful crop can cause the serious underproduction, therefore add the burden of consumer.Unwanted plant is controlled to be also critically important in non-crop place.Many products are commercially available for this purpose, but are still needed more effectively, and price is lower, and toxicity is smaller, and environment is safer or has the new compound of different binding modes.
EP 283,261 discloses the heterocyclic compound of the formula i as herbicide：
Figure A9619505600071
Wherein
X, X1And X2It is independently O or S；
R1It is monocyclic or fusion bicyclic heterocyclic radical, they are unsubstituted or are selected from oxygen, sulfydryl, halogen, nitro by one or more; cyano group, amino, single-or dialkyl amido, acylamino-, alkyl; alkenyl, alkynyl, cycloalkyl, haloalkyl, halogenated alkoxy; aryl, hydroxyl, alkoxy, alkoxy carbonyl group, alkyl-carbonyl; single-or double alkyl-carbamoyls, alkylthio group, alkyl sulphinyl, alkyl sulphonyl; sulfoamido, alkyl carbonyl oxy, alkyl-carbonyl-amino, or heterocyclic radical；And
Y particularly C2-4Alkylidene.
The ketal and loop coil of the present invention is not disclosed in the above documents.The general introduction of invention
The present invention relates to the compound of formula I for including all geometric isomers and stereoisomer, its agriculturally suitable salt, the agriculturally useful compositions containing them and they control the purposes of unwanted plants：Wherein：
Q is
Figure A9619505600082
R1And R2Each is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6Halogenated alkylthio；Or R1And R2Formation-X together1-(CH2)r-X2,-(CH2)s-X3,-(CH2)t-X3-CH2,-(CH2)v-X3-CH2CH2- or-(CH2)w-, each group is unsubstituted or is selected from 1-6 halogen, 1-6 CH3With a C1-C3At least one member substitution in alkoxy；Or R1And R2Formation-O-N (C together1-C3Alkyl)-CHR12-CH2- or-O-N=CHR12-CH2-, each group is unsubstituted or is selected from 1-2 halogen, 1-2 CH3In at least one member substitution；Or R1And R2The carbon atom connected with them forms C (=O) or C (=S) together；
X1And X2Each is independently O, S or N (C1-C3Alkyl)；
X3It is O or S；
Each R3It is independently H or CH3；
R4And R5Each is independently H, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl sulphinyl, C1-C6Alkylsulfinyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, halogen, cyano group, nitro；
R6It is OR11, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl sulphinyl, C1-C6Alkylsulfinyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, cyano group, cyanato-, thiocyanato or halogen；
Each R7It is independently C1-C3Alkyl, C1-C3Alkoxy, C1-C3Alkylthio group or halogen；Or as two R7When being connected on same carbon atom, described two R7Formation-OCH together2CH2O- ,-OCH2CH2CH2O- ,-SCH2CH2S- or-SCH2CH2CH2S-, each group is unsubstituted or by 1-4 CH3Substitution；
R8It is H, C1-C6Alkyl, C1-C6Haloalkyl, C2-C6Alkoxyalkyl, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, or C1-C6Halogenated alkyl sulfonyl；Or R8It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R9It is H, C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl；Or R9It is phenyl or benzyl, each of which is unsubstituted or on phenyl ring by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R10It is H, C1-C6Alkyl, C1-C6Haloalkyl, halogen, cyano group or nitro；
R11It is H, C1-C6Alkyl, C1-C6Haloalkyl, C2-C6Alkoxyalkyl, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl；Or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R12It is C1-C3Alkyl, or R12It is unsubstituted or by C1-C3The phenyl of alkyl, halogen, cyano group or nitro substitution；
X is S (O)n, O or NR13；
R13It is H, C1-C3Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, formoxyl, C2-C3Alkyl-carbonyl, C2-C3Alkoxy carbonyl or C1-C2Alkyl sulphonyl；
Y is O, S, NH, N (C1-C3Alkyl), or when q is not 0 be unsubstituted or by R7Substituted CH2；
Z is direct key, O, S (O)2, NH, N (C1-C3Alkyl), or when q is not 0 be unsubstituted or by R7Substituted CH2, its condition is when Y is O, S, NH or N (C1-C3Alkyl) when, Z is direct key or unsubstituted or by R7Substituted CH2；
K and m are independently each 0,1 or 2, and its condition is k and m and is 0,1 or 2；
N and p are independently each 0,1 or 2；
Q is 0,1,2,3 or 4；
R is 2,3 or 4；
S is 2,3,4 or 5；
T is 1,2,3 or 4；
V is 2 or 3；
W is 2,3,4,5 or 6；
X is 1 or 2；And
Z is 0,1 or 2；
Its condition is：
(i) when X is S (O)n, Q is Q-1 and R1And R2It is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6When halogenated alkylthio or the carbon atom connected with them form C (=O) together, then n is 1 or 2；And
(ii) when X is O or NR13And R1And R2It is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6When halogenated alkylthio or the carbon atom connected with them form C (=O) together, then Q is Q-2.
Term " alkyl " that is above being used alone or being used in portmanteau word such as " alkylthio group " or " haloalkyl " includes the isomers of the alkyl of straight or branched, such as methyl, ethyl, n-propyl, isopropyl or different butyl, amyl group or hexyl.Term " 1-6CH3" refer to that commutable substituent can be methyl, term " 1-4CH on 1-6 positions3" and " 1-2CH3" there is similar implication." alkenyl " includes the isomers of the alkenyl of straight or branched, such as 1- acrylic, 2- acrylic and different cyclobutenyls, pentenyl and hexenyl, and " alkenyl " also includes polyenoid such as 1,2- allene, 2,4- hexadienes." alkynyl " includes the isomers of straight or branched alkynyl, 1- propinyls, 2-propynyl and different butynyls, pentynyl and hexin base, and " alkynyl " also includes group such as 2, the 5- adipic alkynyls being made up of multiple three keys." alkoxy " includes the isomers of such as methoxyl group, ethyoxyl, positive propoxy, isopropoxy and different butoxy, amoxy and hexyloxy." alkoxyalkyl " refers to the alkyl of alkoxy substitution, and the example of " alkoxyalkyl " includes CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2And CH3CH2OCH2CH2." alkylthio group " includes the alkylthio group of straight or branched, such as methyl mercapto, ethylmercapto group, different rosickyite bases, butylthio, the isomers of penta sulfenyl and own sulfenyl." alkyl sulphinyl " includes two kinds of enantiomers of alkyl sulphinyl, and the example of alkyl sulphinyl includes CH3S (O), CH3CH2S (O), CH3CH2CH2S (O), (CH3)2The isomers of CHS (O) and different butylsulfinyls, pentylsulfinyl and hexylsulfinyl.The example of " alkyl sulphonyl " includes CH3S(O)2, CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2With different butyl sulfonyls, the isomers of pentylsulfonyl and hexyl sulfonyl.Alkyl amino and dialkyl amido etc. are defined similarly as examples detailed above.
The term " halogen " for being used alone or being used in portmanteau word such as " haloalkyl " includes fluorine, chlorine, bromine and iodine.Term " 1-6 halogens " refers to that commutable substituent can be the independent halogen selected on 1-6 positions, and term " 1-2 halogens " implication is similar.In addition when being used in portmanteau word such as " haloalkyl ", the alkyl partially or completely can be replaced by identical or different halogen atom.The example of " haloalkyl " includes F3C, ClCH2, CF3CH2And CF3CCl2.Term " halogenated alkoxy ", the implication of " halogenated alkylthio " etc. is similar in appearance to term " haloalkyl ", and the example of " halogenated alkoxy " includes CF3CO, CCl3CH2O, HCF2CH2CH2O and CF3CH2O, the example of term " halogenated alkylthio " includes CCl3S, CF3S, CCl3CH2S and ClCH2CH2CH2S, the example of term " alkylsulfinyl " includes CF3S (O), CCl3S (O), CF3CH2S (O) and CF3CF2S (O), the example of term " halogenated alkyl sulfonyl " includes CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2And CF3CF2S(O)2。
The sum of substituent carbon atom uses prefix Ci-CjRepresent, i and j therein are digital 1-7, such as C1-C3Alkyl sulphonyl is methylsulfonyl to sulfonyl propyl base, C2Alkoxyalkyl refers to CH3OCH2；C3Alkoxyalkyl refers to such as CH3CH(OCH3), CH3OCH2CH2Or CH3CH2OCH2；C4Alkoxyalkyl refers to the various isomers containing the alkyl replaced by alkoxy of 4 carbon atoms altogether, and example includes CH3CH2CH2OCH2And CH3CH2OCH2CH2.The example of alkyl-carbonyl includes C (O) CH3, C (O) CH2CH2CH3With C (O) CH (CH3)2.The example of alkoxy carbonyl group includes CH3OC (=O), CH3CH2OC (=O), CH3CH2CH2OC (=O), (CH3)2CHOC (=O) and different butoxy-or pentoxycarbonyl isomers.
When compound is with there is lower target substituent to replace, 1 can be can exceed that by representing the number of the substituent, and the substituent (when more than 1) is independently selected from defined one group of substituent.
When the substituent that group contains is hydrogen, such as R4Or R11If this substituent is hydrogen, it should think that above-mentioned group is equivalently employed without the group of substituent.
The compounds of this invention can exist with one or more stereoisomers, and various stereoisomers include enantiomer, diastereomer, atrop isomers and geometric isomer.Those skilled in the art is it should be appreciated that a kind of stereoisomer may be active higher and/or may show more preferable effect should so make it more be enriched with or be separated from other stereoisomers relative to other stereoisomers.In addition, it will be apparent to one skilled in the art that how to separate, enrichment and/or the stereoisomer is optionally prepared.Therefore the present invention includes the compound for being selected from Formulas I and its agriculturally suitable salt.The compounds of this invention individual stereoisomer or can exist with stereoisomer mixture with optical active forms.
Some compounds of the present invention can exist with one or more dynamic isomers, and those skilled in the art is it should be appreciated that such as wherein R6It is OR11And R11The Formulas I a compounds (wherein Q is Q-1 Formulas I) for being H can be with another dynamic isomer presence described as follows, those skilled in the art understand, the dynamic isomer often exists with the state balanced each other, when this dynamic isomer mutual phase in version under environment and physiological condition, they can provide identical useful biology effect, the mixture of above-mentioned dynamic isomer of the present invention including compound of formula I and individual dynamic isomer.
The salt of the compounds of this invention includes the acid-addition salts with inorganic acid or organic acid formation, and these acid are hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4- toluenesulfonic acids and valeric acid.When the compounds of this invention contains acidic-group such as enol, the salt of the compounds of this invention also includes and organic base (such as pyridine, ammonia or triethylamine) or inorganic base (such as sodium, potassium, lithium, calcium, the hydride of magnesium or barium, hydroxide, or carbonate) formed salt.
The preferred compound higher and/or be readily synthesized of activity is：
It is preferred that 1：Above-mentioned compound of formula I and its agriculturally suitable salt, wherein：Each R7It is independently C1-C3Alkyl or halogen；X is S (O)n；Y and Z are independently unsubstituted or by R7Substituted CH2；K is 0；And x is 1.
It is preferred that 2：It is preferred that the compound in 1, wherein：R1And R2Each is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6Halogenated alkylthio；Or R1And R2Formation-X together1-(CH2)r-X2-, it is unsubstituted or is selected from 1-6 halogens, 1-6CH3In at least one member substitution；Or R1And R2The carbon atom connected with them forms C (=O) together；X1And X2Both are that O or both is S；M is 1 or 2；R is 2 or 3.
It is preferred that 3：It is preferred that the compound in 2, wherein：R4And R5Each is independently H, C1-C3Alkyl or halogen；R7It is C1-C3Alkyl；R9It is H, C1-C6Alkyl or C3-C6Alkenyl；R10It is H；R11It is H, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, or C1-C6Halogenated alkyl sulfonyl；Or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；And n is 2.
It is preferred that 4：It is preferred that the compound in 3, wherein：R1And R2Each is independently methoxyl group, or R1And R2Formation-X together1-(CH2)r-X2-, or R1And R2The carbon atom connected with them forms C (=O) together；X1And X2It is O；R4And R5Each is independently H, methyl or halogen；R6It is OR11；R8It is H, C1-C2Alkyl sulphonyl, or R8It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；R11It is H, C1-C2Alkyl sulphonyl, or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；And m is 1；It is 2 with r.
It is preferred that 5：It is preferred that the compound in 4, wherein：R5It is methyl or halogen, and is connected on phenyl ring and-S (O)nOn-adjacent position.
It is preferred that 6：It is preferred that the compound in 5, wherein：Q is Q-1.
It is preferred that 7：It is preferred that the compound in 6, wherein：Q is Q-2.
Most preferably the compound in preferably 2, is selected from：2 [(2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide；(2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone S, S- dioxide；2 [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide；(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone S, S- dioxide；6- [(1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) carbonyl] -2,3- dihydro -5,8- dimethyl -4H-1- benzothiopyran derivative -4- ketone 1,1- dioxide；2 [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones；(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone.
The invention further relates to Herbicidal combinations, it contains the compounds of this invention and at least one surfactant, solid diluent or liquid diluent of herbicidally effective amount.Currently preferred composition is the composition containing above-mentioned preferred compound.
It is administered to the invention further relates to the method for controlling not needing plant, including with the compounds of this invention (such as being made into above-mentioned composition) of herbicidally effective amount at plant growth, application method preferably is to apply above-mentioned preferred compound.
Detailed description of the invention
Compound of formula I can use such as following flow 1-22 one or more methods and its method for some changes to prepare, the Q, R of compound in following formula I-XVIII1-R13, X1-X3, X, Y, Z, k, m, n, p, q, r, s, t, v, w, x and z are as defined above the definition stated in present invention general introduction, and Formulas I a-Ic compounds are included in the compound of several subgroups in compound of formula I, the definition of all substituents is identical with the definition in above-mentioned Formulas I in Formulas I a-Ic, for example, following formula Ia compounds are the compound of formula I that wherein Q is Q-1.
Figure A9619505600151
Flow I formula Ia (R1And R2The carbon not connected with them forms C (=O) and C (=S), R together6It is OR14, R14With the R described in present invention general introduction11Define it is identical, but be not H) preparation method of compound, that is by Formulas I a compounds (R1And R2The carbon not connected with them forms C (=O) and C (=S), R together6=OH) handled in the presence of a base with the reagent of Formula II, wherein X4It is chlorine, bromine, fluorine, triflate or acetic acid esters, R14It is as defined above.Coupling reaction is carried out according to conventional method well known in the art, for example, see K.Nakamura et al. WO/04054.
Flow 1Ia (R1And R2Getting along well, they connect Ia (R1And R2The carbon not connected with them forms C (=O) and+R together14X4- → carbon connect forms C (=O) and C (=S), R together6=OH) alkali C (=S), R6=OR14)                          II
The formula Ia compounds (R of flow 21And R2The carbon not connected with them forms C (=O) and C (=S), R together6=S (O)yR15；Y=1 or 2；And R15=C1-C6Alkyl or C1-C6Haloalkyl), that is make compound Ia (R1And R2The carbon not connected with them forms C (=O) and C (=S), R together6=SR15) and oxidant such as Peracetic acid, metachloroperbenzoic acid, potassium hydrogen persulfate or hydroperoxidation, (reaction can be buffered with alkali such as sodium acetate or sodium carbonate).Oxidation reaction is completed with method well known in the art, for example, see B M.Trost et al., J.OrgChem. (1988), 53,532；B.M Trost et al., Tetrahedron Lett. (1981), 21,1287；S.Patai et al. The Chemistry of Sulphonesand Sulphoxides, John Wiley ＆ Sons.
Flow 2Ia (R1And R2Getting along well, they connect oxidant Ia (R1And R2Not with they connect carbon form C (=O) together --- → the carbon connect formed together C (=O) and with C (=S), R6=SR15) C (=S), R6=S (O)yR15,
Y=1 or 2)
For Formulas I a compounds (R1And R2The carbon not connected with them forms C (=O) and C (=S), R together6=SR15, CN, SCN, OCN or OR16；R15It is as defined above；And R16It is C1-C6Alkyl, C1-C6Haloalkyl or C2-C6Alkoxyalkyl), those skilled in the art can be from Formulas I a compounds (R1And R2The carbon not connected with them forms C (=O) and C (=S) and R together6=halogen) with the nucleopilic reagent (MSR of formula III15, MCN, MSCN, MOCN or MOR16；M=Na, Cu, K or Li) handle to prepare, as shown in flow 3, i.e., with the universal method in documents below, such as S.Miyano et al., J.Chem.Soc., Perkin Trans.I (1976), 1146；P.H.Nelson. and J.T.Nelson, Synthesis (1992), 12,1287-1291；S.Miller et al., DE 4241999-A1.
Flow 3Ia (R1And R2Getting along well, they connect MSR15, or Ia (R1And R2The carbon not connected with them forms C (=O)+MOR together16Or-→ carbon connect formed together C (=O) and with C (=S), R6=halogen) MCN or C (=S), R6=SR15, CN,
MSCN or SCN, OCN or OR16) 
                     MOCN
                     III
Formulas I a compounds (R1And R2The carbon not connected with them forms C (=O) and C (=S) together, and R6=halogen) can be by making Formulas I a compounds (R1And R2The carbon not connected with them forms C (=O) and C (=S) together, and R6=OH) and halogenating agent such as oxalyl bromine or oxalyl chloride reaction prepare (flow 4), S.Muller et al., WO 94/13619 are for example shown in this conversion conventional method well known in the art completion；S.Muller et al., DE 4241999-A1.
Flow 4Ia (R1And R2Getting along well, they connect --- --- → Ia (R1And R2The carbon not connected with them forms C (=O) and halogenating agent together, and (carbon such as connect forms C (=O) and C (=S), R together6=OH) oxalyl bromine or C (=S), R6=halogen)
Oxalyl chloride)
The formula Ia compounds (R of flow 51And R2The carbon connected with them forms C (=O) preparation method together, i.e., by Formulas I a compounds (R1And R2It is independently C1-C6Alkoxy or R1And R2Formation-O- (CH together2)rO-) in 0 DEG C -100 DEG C stirring 30 minutes to three days in hydrochloric acid or hydrobromic acid aqueous solution (0.1N-12N).This conversion method well known in the art completion (or with the method slightly changed), for example, be shown in P.A.Crieco et al., J.Am.ChemSoc (1977), 99, p5773；P.A.Grieco et al., J.Org Chem. (1978), 43, p4178.
Flow 5
Ia                                 Ia(R1And R2It is independently C1-C6   HCl/H2O or (R1And R2With their alkoxies, or R1And R2Carbon formation-O- (CH together of --- --- → connection together2)r-O-)      HBr/H2O C (=O))
The formula Ia compounds (R of flow 61And R2The carbon not connected with them forms C (=O) and C (=S), and R together6=OH) preparation method, i.e., by formula IV a enol ester (R1And R2Not with they connect carbon form C (=O) and C (=S) together) and/or their formula IV b region isomer (regioisomer) in the presence of catalytic amount cyanide source (such as acetone cyanohydrin or potassium cyanide) with alkali such as triethylamine react, the rearrangement reaction is completed by the art known method, for example see W.J.Michaely, EP 0369803-A1；D.Cartwright et al., EP 0283261-B1.
Flow 6
Figure A9619505600181
Formula IV a enol ester (R1And R2Not with they connect carbon form C (=O) and C (=S) together) and/or its region isomer formula IV b can be by making the dicarbonyl compound of Formula V and the acyl chlorides (R of Formula IV1And R2The carbon not connected with them forms C (=O) and C (=S) together) in the presence of slightly excessive mole of alkali such as triethylamine, in inert organic solvents such as acetonitrile, in dichloromethane or toluene, react to prepare (flow 7) at 0-110 DEG C.Such coupling reaction completes (or method improved slightly) with conventional method well known in the art, for example, see W.J.Michaely, EP 0369803-A1；D.Cartwright et al., EP 0283261-B1.
Flow 7
Figure A9619505600191
Acyl chlorides (the R of Formula IV1And R2The carbon not connected with them forms C (=O) and C (=S) together) can be by making the acid (R of Formula VII1And R2The carbon not connected with them forms C (=O) and C (=S) together) and the dimethylformamide reaction of oxalyl chloride (or thionyl chloride) and catalytic amount prepare (flow 8).The halogenation is the EP 0369803-A1 it is known in the art that for example see W.J.Michaely.
Flow 8
Figure A9619505600192
The formula VII of flow 9 acid (R1And R2The carbon not connected with them forms C (=O) and C (=S) together；X=S (O)n, and n=1 or preparation method 2), that is make the acid (R of Formula VII1And R2The carbon not connected with them forms C (=O) and C (=S) together；) and oxidant such as peracetic acid, metachloroperbenzoic acid, potassium hydrogen persulfate or hydroperoxidation X=S.The reaction can be buffered with alkali such as sodium acetate or sodium carbonate.Above-mentioned oxidation reaction is completed (for example to see B.M.Trost et al., J.Org.Chem. (1988), 53,532 with conventional method well known in the art；B.M.Trost et al., Tetrahedron Lett. (1981), 21,1287；S.Patai et al., The Chemistry of Sulphones and Sulpoxides, John Wiley＆Sons).
Flow 9VII (R1And R2Get along well them --- → VII (R1And R2Do not form the carbon that C (=O) oxidant connects together with the carbon of their downlink connections and form C (O) and C (=S) together, and X=S) and C (=S)；X=S (O)n,
N=1 or 2)
The formula VII compounds (R of flow 101And R2The carbon not connected with them forms C (=O) and C (=S), and X=S, O or NR together13) preparation, i.e., by the pheriyl bromide (R of Formula VIII1And R2The carbon not connected with them forms C (=O) and C (=S) together, and X is S, O or NR13) handled with n-BuLi (or magnesium), by the lithium salts being formed in situ (or RMgBr) and carbon dioxide reaction, then with acid such as HCl treatment.The conversion reaction is completed with conventional method well known in the art, for example, see M.A.Ogliaruso et al. Synthesis of CarboxylicAcid, Ester and Their Derivatives, pp27-28, John Wiley＆Sons；A.J.Bridge et al., J.Org.Chem. (1990), 55 (2), 773；C.Franke et al., Angew.Chem.Int.Ed (1969), 8,68.In some cases, protection/deprotection steps are added or functional group interconversion is carried out in synthesis and will be helpful to obtain required product.It is obviously (for example to see Green.T.W for the technical staff in the field of chemical synthesis to use and select protection group；Wuts.P G.M., Protective Groups inOrganic Synthesis, 2nd ed；Wiley：New York, 1991).
Flow 10
The formula VIII of flow 11 pheriyl bromide (R1And R2It is independently C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group or C1-C6Halogenated alkylthio, or R1And R2Formed together unsubstituted or be selected from 1-8 halogen, 1-8 CH3With a C1-C3- the X of at least one member substitution in alkoxy1-(CH2)r-X2-；X1And X2Definition be same as definition in present invention general introduction, and X is S, O or NR13) preparation method, this method is that (X is S, O or NR by the ketone of Formula IX13) and alcohol, alkyl hydrosulfide or HX1-(CH2)r-X2H (can be unsubstituted or be selected from 1-8 halogen, 1-8 CH3With 1 C1-C3In alkoxy at least one substitution；X1And X2And r definition such as summary of the invention) in bronsted acid catalyst such as p-methyl benzenesulfonic acid (or lewis acid such as BF3) in the presence of, in inert organic solvents as in toluene or alcohol (if if alcohol is reaction reagent) reacted.This conversion is carried out according to conventional method well known in the art.For example see T.W.Greane et al., ProtectiveGroups in Organic Synthesis (Second Edition), pp175-221, John Wiley ＆ Sons, Inc.
Flow 11
Figure A9619505600221
The formula VIII of flow 12 pheriyl bromide (R1And R2Formation-(CH together2)s- O ,-(CH2)t-X3-CH2,-(CH2)v-X3-CH2CH2- or-(CH2)w-, each group is unsubstituted or is selected from 1-8 halogen, 1-8 CH3With a C1-C3At least one member substitution in alkoxy；X is S, O or NR13) preparation method, i.e., (X is S, O or NR to the ketone of Formula IX13) and RMgBr, cycloalkylation sulfonium (sulfonium cycloalkylide), lithium alkoxide lithium (lithium lithioalkoxide), organic palladium reagent, (sulfoniumylide) or other equivalent reagents are reacted in organic solvent in sulfonium, and some reaction intermediates of flow 12 can be modified further so as to the pheriyl bromide of the Formula VIII needed for obtaining.Above-mentioned reaction carries out (or slightly improved method) according to method well known in the art, for example, see S.Umio et al., J.Med.Chem. (1972), 15, p855；B.Mudryk et al., J.Org.Chem. (1989), 54, (24), p5657；Z.Paryzek et al., Can.J.Chem. (1987), 65 (1), p229；B.M.Trost et al., J.Am.Chem.Soc. (1972), 94, p4777；B.M.Trost et al., J.Am.Chem.Soc. (1985), 107, p1778；S.Fukuzawa et al., J.Chem.Soc.Chem.Comm. (1986), 8, p624；J.F.Gil et al., Tetrahedron (1994), 50 (11), p3437；T.J.Jenkins et al., J.Org.Chem. (1994), 59 (6), p1485；C.J.Li et al., Organometallics (1991), 10 (8), p2548；E.J.Corey et al., J.Am.Chem.Soc. (1965), 87, p1353；K.Okuma et al., J.Org.Chem. (1983), 48,5133.
Flow 12
RMgBr, cycloalkylation sulfonium, lithium alcoxyl
Change lithium (lithium lithioalkoxide), have
Machine palladium reagent, in sulfonium or other equivalent reagent IX --- --- --- (X is S, O or NR to --- --- → VIII13)                (R1And R2Formed together
                               -(CH2)s- O- ,-(CH2)t-X3-CH2-,
                               -(CH2)v-X3-CH2CH2- or
                               -(CH2)w-, each group is not take
Generation or be selected from 1-8
Halogen, 1-8 CH3With one
Individual C1-C3In alkoxy extremely
Few member substitution；X is
S, O or NR13)
The formula VIII of flow 13 pheriyl bromide (R1And R2Formation-(CH together2)s- S, it is unsubstituted or is selected from 1-8 halogen, 1-8 CH3With a C1-C3At least one member substitution in alkoxy；X is S, O or NR13) preparation method, i.e., (X is S, O or NR to the thioketones of Formula X13) with Formula X I dibromoalkane in the presence of equimolar amounts or slightly excessive Yb metals, reacted in the inert organic solvents such as mixing of benzene and HMPA, the conversion reaction is by conventional method well known in the art progress.For example see Y.Makioka et al., Chem.Lett. (1994), 611.
Flow 13
Figure A9619505600241
(k is 0 to some of Formula VIII compound；R1And R2Formation-(CH together2)s-X3- ,-(CH2)t-X3-CH2- ,-(CH2)v-X3-CH2CH2- or-(CH2)w-, its door is each unsubstituted or is selected from 1-8 halogen, 1-8 CH3With a C1-C3At least one member substitution in alkoxy) can also be by making unsaturated alkyl sulfur phenenyl bromide Formula X II and lewis acid such as SnCl4Or ACl3Or acid such as trifluoroacetic acid or polyphosphoric acid are in inert organic solvents such as CH2Cl2In, 30 minutes are reacted at 0-110 DEG C to preparing (flow 14) over 3 days.The conversion reaction is carried out by conventional method well known in the art.For example see M.J.Dawson et al., J.Med., Chem. (1984), 27 (11), p1516；H.G.Viehe et al., J.Chem.Soc., Chem.Commun (1995), (10), p993.
Flow 14
(k is 0 to some of Formula VIII compound；R1And R2Formation-(CH together2)s-X3,-(CH2)t-X3-CH2- ,-(CH2)v-X3-CH2CH2-, or-(CH2)w-；Each group is unsubstituted or is selected from 1-8 halogen, 1-8 CH3With a C1-C3At least one member substitution in alkoxy；X is S, O or NR13) also can (X is S, O or NR by making Formula X III chloro alkyl sulfur phenenyl bromide13) and Formula X IV compounds in lewis acid such as SnCl4, EtAlCl2Or ACl3In the presence of in inert organic solvents such as CH2Cl2In, prepared in reaction at 0-110 DEG C over -3 days (flow 15) within 15 minutes.The conversion reaction is carried out according to conventional method well known in the art.For example see Y.Tamura et al., Tet.Lett. (1981), p3773；H.Ishibashi et al., J.Chem.Soc.Chem.Commun. (1988), (12), p827.
Flow 15
Figure A9619505600261
(k is 0 to the formula VIII of flow 16 pheriyl bromide；R1And R2CH is formed together2CH2-, it is unsubstituted or is selected from 1-4 halogen, 1-4 CH3With a C1-C3At least one member substitution in alkoxy；Or R1And R2Formation-O-N (C together1-C3Alkyl)-CHR12-CH2- or-O-N=CHR12-CH2-, each of which is unsubstituted or is selected from 1-2 halogen and 1-2 CH3In at least one member substitution；X is S, O or NR13), i.e., (X is S, O or NR to Formula X V alkene13) and the uncommon reagent (Wittingreagent) of dimension ladder, nitrone, nitronic acid monosilane ester, itrile oxides or Simmons-Smith reagents react in inert organic solvents, and some intermediate products reacted in flow 16 can further modify the pheriyl bromide for obtaining required Formula VIII.Above-mentioned reaction can be carried out according to method well known in the art.For example see：R.Mechoulam et al., J.Am.Chem.Soc. (1958), 80, p4386；A.Hosomi et al., Chem.Lett. (1985), (7), p1049；SMzengeza et al., J.Chem.Soc.Chem.Commun. (1984), 9, p606；H.Mitsu et al., Tet.Lett. (1983), 24 (10), p1049；J.E.Baldwir et al., J.Chem.Soc.Chem.Commun. (1968)；p373；S.L.Ioffe et al., J.Gen.Chem.USSR (Engl.Transl.) (1973), 43, p1699；A.Brandi et al., Tet.Lett. (1987), 28 (33), p3845；D.P.Curran et al., J.Org.Chem (1984), 49 (19), p3474；R.J.Rawson et al., J.Org.Chem. (1970), 35 (6), p2057.
Flow 16
(X is S, O or NR to some Formula VIII compounds13) also can (X is S, O or NR by making Formula X VI substituted benzene13) and bromine react to prepare (flow 17) in inert organic solvents.The bromination reaction is carried out by conventional method well known in the art.For example see Campaigne et al., J.Heterocycl.Chem. (1969), 6, p517；H.Gilman, J.Am.Chem.Soc. (1955), 77, p6059.
Flow 17
Figure A9619505600281
Wherein：R1-R5, m and p define such as summary of the invention；
X is S, O or NR13
The ketone of Formula IX can be prepared (or slightly improved method) by conventional method well known in the art, for example, see：W.Flemming et al., Chem.Ber. (1925), 58,1612；I.W.J.Still et al., Can.J.Chem. (1976), 54,453-470；V.J.Traynelis et al., J.Org.Chem. (1961), 26,2728；I.Nasuno et al., WO 94/08988；F.Camps et al., J.Heterocycl.Chem. (1985), 22 (5), p.1421；T.S.Rao et al., Indian.J.Chem.B. (1985), 24 (11), p.1159；S.Ghosh et al., Tetrahedron (1989), 45 (5), p.1441；A.Danan et al., Synthesis-Stuttgart (1991), (10), p.879；P.Magnus et al., J.Chem.Soc.Chem.Comm. (1991), (7), p.544；A.Padwa et al., J.Org.Chem (1989), 54 (12), p.2862；S.A.Ali et al., J.Org.Chem. (1979), 44, p.4213；J.Blake et al., J.Am.Chem.Soc (1966), 88, p.4061；M.Mori et al., J.Chem.Soc.Chem.Comm. (1990), (18), p.1222；S.Kano et al., J.Chem.Soc.Perkin.Trans.l (1980), p2105；A.F.Bekhli et al., KhimGeterotsikl.Soedin (1975), p.1118；W.S.Johnson et al., J.Am.Chem.Soc (1949), 71, p.1901；J.A.Hirsch et al., J.Org.Chem. (1974), 39 (14), p.2044；F.G.Mann et al., J.Chem.Soc (1957), p.4166；A.C.Jain et al., Indian.J.Chem.B (1987), 26 (2), p.136；G.Ariamala et al., Tet.Lett. (1988), 29 (28), p.3487；B.Loubinoux et al., Tet.Lett. (1992), 33 (16), p.2145；S.Cabiddu et al., J.Organomet.Chem. (1989), 366 (1-2), p.1；R.HasenKamp et al., Chem.Ber. (1980), 113, p.1708；D.A.Pulman et al., J.Chem.Soc.Perkin.Trans.1 (1973), p.410；W.C.Lumma et al., J.Org.Chem. (1969), 34, p.1566；P.D.Clark et al., Can.J.Chem. (1982), 60 (3), p.243.
The thioketones of Formula X can be prepared according to conventional method well known in the art from the ketone of Formula IX, for example, see V.K.Lusis et al., Khim.Geterotsiklt. (1986), (5), p709；T.A.Chibisova et al., Zh.Org.Khim. (1986), 22 (9), p2019.Formula XI can be prepared (or slightly improved method) by conventional method well known in the art, see W.Adams et al., Chem.Ber. (1982), 115, p2592；M.J.Dawson et al., J.Med.Chem. (1984), 27 (11), p1516.Formula XII can prepare (or slightly improved method) according to conventional method well known in the art, see H.Ishibashi et al., J.Chem.Soc.Chem.Commun. (1988), (12), p827；L.Brandsma et al., Synthesis (1978), p577.Formula XIV can be prepared by conventional method well known in the art from the ketone of Formula IX, for example, see J.Hibino et al., Tet.Lett. (1985), 26 (45), p5579；A.S.Rao, Synthetic Commun. (1989), 19 (5-6), p931-942；R.G.Gentles et al., J.Chem.Soc.PerK.Trans.1 (1991), (6), p1423；F.A.Davis, Tet.Lett (1991), 32 (52), p7671.
Formula XVI can with the reaction described in flow 12-15 and technology by those skilled in the art from Formula IX, it is prepared by X, XII, the debrominate analog of XIII and XV compounds.The dicarbonyl compound of Formula V can either be bought or be prepared (or slightly improved method) by conventional method well known in the art.For example see：D.Cartwright et al., EP 0283261-B1；J.Dangelo et al., Tet.Lett. (1991), 32 (26), p.3063；T.Okado et al., J.Org.Chem. (1977), 42, p.1163；B.E.Maryanoff et al., J.Am.Chem.Soc. (1975), 97, p.2718；E.Er et al., Helv.Chim.Acta (1992), 75 (7), p.2265；Y.D.Vankar et al., Tet.Lett, (1987), 28 (5), p.551；C.S.Pak et al., Tet.Lett. (1991), 32 (42), p.6011；I.Nishiguchi et al., Chem.Lett. (1981), p.551；B.Eistert et al., Liebigs Ann.Chem. (1962), 659, p.64；N.K.Hamer.Tet.Lett. (1986), 27 (19), p.2167；M.Sato et al., Heterocycles (1987), 26 (10), p.2611；A.Murray et al., Tet.Lett. (1955), 36 (2), p.291；K.S.Kochhar et al., Tet.Lett. (1984), 25 (18), p.1871；M.Sato et al., Tetrahedron (1991), 47 (30), p.5689；M.Sato et al., Chem.Pharm.Bull (1990), 38 (1), p.94；T.Meal.U.S.4,931,570；T.Muel et al., U.S.5,093.503.
Compounds of general formula Ib can easily be prepared with the reaction shown in this section flow 18-21 and technology by those skilled in the art, can also be prepared with the specific process of following embodiments 2 and 4.K, m, p, R1-R5, R8-R10Definition with X is identical with summary of the invention.
Figure A9619505600301
The formula Ib compounds (R of flow 181And R2The carbon not connected with them forms C (=O) and C (=S) together, and R8=R8a, wherein R8aWith R described in summary of the invention8Definition it is identical, but be not H) preparation method.That is Formulas I b compounds (R1And R2The carbon atom not connected with them forms C (=O) and C (=S) together, and R8=H) and Formula X VII reagent react in the presence of a base, wherein X5It is chlorine, bromine, fluorine, triflate or acetic acid esters, and R8aIt is as defined above.The coupling reaction is carried out by conventional method well known in the art, for example, see K.Nakamura et al. WO 95/04054.
Flow 18Ib (R1And R2Getting along well, they connect Ib (R1And R2Not with they with carbon together with form C (=O) and+R8aX5- → carbon connect forms C (=O) C (=S), R together8=H) XVII and C (=S), and R8=R8a)
The formula Ib compounds (R of flow 191And R2The carbon not connected with them forms C (=O) and C (=S) together, and R8=H) preparation method, i.e. Formula X VIII ester (R1And R2The carbon atom not connected with them forms C (=O) and C (=S) together) and alkali such as triethylamine reacted in the presence of the cyanide source (such as acetone cyanohydrin or potassium cyanide) of catalytic amount.The rearrangement reaction is carried out by conventional method well known in the art, for example, see W.J.Michaely.EP 0369803-A1.
Flow 19
Formula Ib (the R of flow 201And R2Together with they connect carbon formation C (=O)) preparation method, i.e., by Formulas I b compounds (R1And R2It is independently C1-C6Alkoxy or R1And R2Formation-O- (CH together2)rO-) in hydrochloric acid or hydrobromic acid aqueous solution (0.1N-12N), in stirring 30 minutes to 3 days at 0 DEG C -100 DEG C.Above-mentioned conversion reaction carries out (or slightly improved method) by method well known in the art, for example, see P.A.Grieco et al., J.Am.Chem.Soc (1977), 99, p5773；P.A.Grieco et al., J.Am.Chem.Soc. (1978), 43, p4178.
Flow 20
     Ib                                 Ib(R1And R2It is independently C1-C6      HCl/H2O    (R1And R2Alkoxy, or R are connected with them1And R2Together --- --- → carbon form C (=O) together) formation-O- (CH2)r- O-) or HBr/H2O
Formula X VIII ester (R1And R2The carbon not connected with them forms C (=O) and C (=S) together) can be by making Formula X IX hydroxypyrazoles and the acyl chlorides (R of Formula IV1And R2The carbon not connected with them forms C (=O) and C (=S) together) in the presence of mole slightly excessive alkali such as triethylamine, in inert organic solvents such as acetonitrile, in dichloromethane or toluene, prepared (flow 21) in being reacted at 0 DEG C -110 DEG C.The coupling reaction of the type is carried out by method well known in the art, for example, see W.J.Michaely, EP 0369803-A1.
Flow 21
Formula Ic compounds can be from formula Ia compounds (R1And R2The carbon connected with them forms C (=O) together) or Ib compounds (R1And R2The carbon connected with them forms C (=O) together) by using P4S10Or Lawesson ' s agent treatments are prepared (flow 22).The conversion reaction carries out (or slightly improved method) by conventional method well known in the art, for example, see V.K.Lusis et al. Khim.Geterotsiklt. (1986), 5, p709；T.A.Chibisova et al., Zh.Org.Khim. (1986), 22 (9), p2019.Formula Ia (R1And R2The carbon connected with them forms C (=O) together) or formula Ib (R1And R2The carbon connected with them forms C (=O) together) protection/deprotection of some of raw material functional group is probably necessary.Using and selecting for protection group is obviously (for example to see for the technical staff of the field of chemical synthesis：T.W.Greene et al., Protective Groups in Organic Sythesis, 2nded；Wiley：New York.1991).Wherein：K, m, p, R3-R5, Q and X definition are as described in summary of the invention
Flow 22
    P4S10Or Lawesson ' s reagents Ia or Ib --- --- --- --- → Ic (R1And R2The carbon connected with them forms C (=O) together)
It can be seen that; above-mentioned some reagent and some of reaction condition and the intermediate features for preparing compound of formula I are probably incompatible; in this case, protection/deprotection steps are added in synthesis or functional group interconversion is introduced and will be helpful to obtain required product.It is obviously (for example to see Greene, T.W., Wuts, P.G.M.Protective Groups in Organic Sythesis, 2nd ed. for the technical staff of the field of chemical synthesis to use and select protection group； Wiley：New York.1991).Those skilled in the art can be seen that in some cases, after the given reagent of the addition as described in any separate processes, in order to complete the synthesis of compound of formula I, it may be necessary to the other conventional synthesis steps not being documented.Those skilled in the art is, it will be appreciated that combining and operated suitably may be needed each step described in above-mentioned flow, and do not mean that and be adopted as preparing the specific reaction sequence needed for compound of formula I.
It will be readily apparent to those skilled in the art that in order to import the substituent that substituent or modification are present, compound of formula I and described intermediate can be carried out into various electrophilic, nucleophilic, free radical, organic metal, oxidation and reduction reaction.
It need not be described in further detail, it is believed that those skilled in the art just most can sufficiently realize the present invention using described above.Therefore, set up following embodiments to be intended to be merely illustrative of the present, regardless of whether how they also do not limit the disclosure in any way.Except for chromatographic solvent mixtures and in addition to being otherwise noted, percentage is all referring to percetage by weight.Abbreviation " dec " refers to that compound is decomposed in fusing.1HNMR spectrums record the low field ppm numerical value since tetramethylsilane, and s=is unimodal, d=doublets, t=triplets, q=quartets, m=multiplets, brs=width unimodals.
The step A of embodiment 1：The preparation of 3- [(4- bromophenyls) sulphur] propionic acid
8.5g (0.211mol) sodium hydroxide is added in 45ml water, then 20.0g (0.106mol) 4- bromo thiophenols (being purchased from Aldrich Chemical Company) are added, mixture is cooled to about 0 DEG C, portioning adds 18.0g (0.116mol) 3- bromo acids (being purchased from AldrichChemical Company), and below 5 DEG C of keeping temperature, mixture is warmed to room temperature, in stirring 1 hour under blanket of nitrogen, washed with ether (3 × 100ml), aqueous phase is acidified with 1N hydrochloric acid, it is filtrated to get 27.95g solid steps A title compound, 101-103 DEG C of fusing point；1HNMR(CDCl3)：δ 2.66 (t, 2H), 3.14 (t, 2H), 7.2 (m, 2H), 7.4 (m, 2H).Step B：The preparation of bromo- 2, the 3- dihydros -4H-1- benzothiopyran derivatives -4- ketone of 6-
The 200ml concentrated sulfuric acids are added in 27.7g (0.106mol) steps A title compound, in being stirred overnight compound under blanket of nitrogen, are poured into trash ice, filter mixture, and solid is dissolved in dichloromethane, dry resulting solution (MgSO4), filtering, be evaporated to dryness, obtain 14.77g steps B title compound, be in 50 DEG C fusing solids (dec),1H NMR(CDCl3)：δ 3.0 (m, 2H), 3.2 (m, 2H), 7.16-8.2 (3H).Step C：The preparation of bromo- 2, the 3- dihydros spiral shells of 6- [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes]
14.7g (0.060mol) steps B title compound, 11ml (0.19mol) ethylene glycol (being purchased from Aldrich Chemical Company) and 0.4g (2.10mmol) p-methyl benzenesulfonic acid monohydrate (being purchased from Aldrich Chemical Company) are added in 125ml toluene, solution flows through night next time in blanket of nitrogen, washed (2 × 250ml) with 1M sodium carbonate, then washing (2 × 250ml), dries organic phase (Na2SO4) filtering, it is evaporated to dryness, obtains 13.58g steps C title compound, is grease.1H NMR(CDCl3)：δ 2.2 (m, 2H), 3.16 (m, 2H), 4.1 (m, 2H), 4.2 (m, 2H), 7.0-7.6 (3H).Step D：The preparation of 2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids
13.58g (0.047mol) steps C title compound is added in 150ml tetrahydrofurans, solution is cooled to about -65 DEG C, the n-BuLi (being purchased from Aldrich Chemical Company) being added dropwise in 23ml (0.057mol) 2.5M hexanes, and maintain the temperature at less than -55 DEG C, in stirring 1 hour under blanket of nitrogen, once add excessive drikold, the mixture was stirred overnight, it is warming to room temperature simultaneously, 100ml hexanes are added into mixture, filtering, 500ml water and 400ml dichloromethane are added into solid residue, solution is cooled to about 0 DEG C, pH1 is acidified to concentrated hydrochloric acid, extracted with dichloromethane (3 × 400ml), dry resulting solution (MgSO4), filtering is evaporated to dryness, obtains 8.58g steps D title compound, is in the solid (dec) of 186.7 DEG C of fusings.1H NMR(Me2SO-d6)：δ 2.2 (m, 2H), 3.2 (m, 2H), 4.1 (m, 4H), 7.2-8.0 (3H), 12.8 (brs, 1H).Step E：2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids 1, the preparation of 1- dioxide
8.5g (0.034mol) steps D title compound and 41.5g (0.51mol) sodium acetate is added in 160ml methanol, and suspension is cooled to about 0 DEG C, and the OXONE of the 35.2g (0.057mol) in 160ml water is added dropwise_Solution (potassium hydrogen persulfate) (is purchased from Aldrich ChemicalCompany), below 6 DEG C of keeping temperature, mixture is warmed to room temperature and in stirred overnight under nitrogen, with 100ml water diluted mixtures, it is cooled to about 0 DEG C, pH2 is acidified to concentrated hydrochloric acid, is extracted with chloroform (3 × 200ml), the organic phase (MgSO merged is dried4), filtering is evaporated to dryness, crude product hexane: ether mixtures (9: 1) grinding, is obtained 6.98g steps E title compound, is solid, 208 DEG C of fusing point (dec).1H NMR(Me2SO-D6)：δ 2.6 (m, 2H), 3.7 (m, 2H), 4.1-4.2 (m, 4H), 7.9-8.15 (3H), 13.6 (brs, 1H).Step F：3- oxo -1- cyclohexene -1- bases 2,3- dihydros spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylates 1, the preparation of 1- dioxide
2.0g (7.0mmol) steps E title compound, 1.2ml (0.014mol) oxalyl chloride (Janssen), 2 drop N, dinethylformamide is added in 50ml dichloromethane, in backflow mixture 2 hours under blanket of nitrogen, it is evaporated to dryness, 50ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 50ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 0.86g (7.7mmol) 1, 3- cyclohexanediones (are purchased from Aldrich Chemical Company), it is subsequently added 2.7ml (0.0196mol) triethylamine, the mixture was stirred overnight, warm to room temperature simultaneously, mixture is evaporated to dryness, residue is stirred and filtered in 100ml water, crude product is washed with hexane, obtain 2.19g steps F title compound, for solid, in 185-186 DEG C of fusing.1H NMR(CDCl3)：δ 2.2 (m, 2H), 2.5 (t, 2H), 2.7 (t, 4H), 3.7 (m, 2H), 4.2 (m, 2H), 4.3 (m, 2H), 6.0 (s, 1H), 8.0-8.25 (3H).Step G：The preparation of 2- [(2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide
2.1g (0.0056mol) steps F title compound, 4 drop acetone cyanohydrins (being purchased from AldrichChemical Company) and 1.36ml (0.0097mol) triethylamine are added in 50ml acetonitriles, stirred at room temperature 3 days in blanket of nitrogen, compound is evaporated to dryness, 25ml water is added into residue, gained mixture is acidified to pH1 with concentrated hydrochloric acid, and filters, crude product is dissolved in dichloromethane, dries resulting solution (MgSO4), filtering is evaporated to dryness, obtains 1.5g steps G title compound, is solid, and (dec) is melted in 131 DEG C.1H NMR(CDCl3)：δ 2.1 (m, 2H), 2.6 (m, 6H), 3.6 (m, 2H), 4.1 (m, 2H), 4.2 (m, 2H), 7.6-7.9 (3H).
The step A of embodiment 2：1- ethyl -1H- pyrazoles 5- bases 2,3- dihydros spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylates 1, the preparation of 1- dioxide
The step E of 1.38g (4.9mmol) embodiment 1 title compound, 0.85ml (0.0097mol) oxalyl chloride (Janssen), 2 drop N, dinethylformamide is added in 50ml dichloromethane, in backflow mixture 2 hours under blanket of nitrogen, it is evaporated to dryness, 50ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 50ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 0.60g (5.4mmol) 1- ethyl -1H pyrazoles -5- alcohol, it is subsequently added 1.9ml (0.0136mol) triethylamine, the mixture was stirred overnight, warm to room temperature simultaneously, mixture is evaporated to dryness, residue is stirred and filtered in 100ml water, crude product is washed with hexane, obtain 1.45g steps A title compound, for solid, in 158-160 DEG C of fusing.1H NMR(CDCl3)：δ 1.4 (t, 3H), 2.7 (m, 2H), 3.7 (m, 2H), 4.1-4.3 (m, 6H), 6.2 (s, 1H), 7.5-8.3 (4H).Step B：The preparation of (2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone S, S- dioxide
1.43g (0.0038mol) steps A title compound, 4 drop acetone cyanohydrins (being purchased from Aldrich Chemical Company) and 0.92ml (0.0066mol) triethylamine are added in 50ml acetonitriles, gained mixture is stirred at room temperature in blanket of nitrogen to stay overnight, mixture is evaporated to dryness, 25ml water is added into residue, gained mixture is acidified to pH1 with concentrated hydrochloric acid, filter crude product, crude product is washed with hexane, dichloromethane is dissolved in, resulting solution (MgSO is dried4), filtering is evaporated to dryness, obtains 0.44g steps B title compound, is grease.1H NMR(CDCl3)：δ 1.46 (t, 3H), 2.7 (m, 2H), 3.7 (m, 2H), 4.1 (q, 2H), 4.2-4.3 (m, 4H), 7.7-8.0 (4H).
The step A of embodiment 3：The preparation of 3- [2,5- (dichlorophenyl) sulphur] propionic acid
44.68g (1.12mol) sodium hydroxide is added in 240ml water, then 100g (0.56mol) 2 is added, 5- thiophenol dichlorobenzenes (are purchased from Aldrich Chemical Company), mixture is cooled to about 10 DEG C, portioning adds 93.98g (0.62mol) 3- bromo acids (being purchased from Aldrich Chemical Company), and below 25 DEG C of keeping temperature, mixture is warmed to room temperature, in stirring 2 hours under blanket of nitrogen, washed with ether (3 × 400ml), aqueous phase is acidified with 1N hydrochloric acid, filtering, residue is dissolved in 2L dichloromethane and 50ml methanol, dry resulting solution (MgSO4), filtering, evaporation is as obtaining 126.34g steps A title compound, solid melts (dec) in 99 DEG C.1H NMR(CDCl3)：δ 2.75 (t, 2H), 3.2 (t, 2H), 7.1-7.3 (3H).Step B：The preparation of 5,8- bis- chloro- 2,3- dihydros -4H-1- benzothiopyran derivative -4- ketone
63g (0.25mol) steps A title compound and 25.6ml (0.351mol) thionyl chloride is added in 225ml chloroforms, in backflow mixture 2 hours under blanket of nitrogen, concentrate mixture, gained residue is dissolved in 75ml carbon disulfide, resulting solution is added drop-wise to 46.8g (0.351mol) aluminium chloride of cooling (0 DEG C) among the solution of 200ml carbon disulfide, keeping temperature is less than 5 DEG C, in backflow mixture 1 hour under blanket of nitrogen, stirred 2 days in 35 DEG C, reactant mixture is poured into the 300g trash ices containing 150ml concentrated hydrochloric acids, gained mixture is extracted (3 × 200ml) with chloroform, the organic phase of merging is washed (2 × 150ml) with 10% sodium hydroxide, it is washed with water and washs (2 × 150ml), dry (MgSO4), filtering is evaporated to dryness, obtains 45.1 8g steps B title compound, is in the solid of 66-68 DEG C of fusing.1H NMR(CDCl3)：δ 3.0 (m, 2H), 3.3 (m, 2H), 7.1-7.35 (2H).Step C：The preparation of chloro- 2, the 3- dihydros -4H-1- benzothiopyran derivatives -4- ketone of bromo- 5, the 8- bis- of 6-
Solution of 45.18g (0.19mol) the steps B title compound in 400ml dichloromethane under room temperature under nitrogen atmosphere in being added drop-wise in mixture of 64.6g (0.48mol) aluminium chloride in 400ml dichloromethane, stirring 15 minutes, 10.5ml (0.20mol) bromine is added dropwise, mixture is flowed back 10 minutes, poured the mixture into when also warming among the 550g trash ices containing 110ml concentrated hydrochloric acids, gained mixture is extracted (2 × 500ml) with ether, dries the organic phase (Na merged2SO4), filtering is evaporated to dryness, obtains 57.37g steps C title compound, is solid, in 8990 DEG C of fusings.1HNMR(CDCl3)：δ 3.0 (m, 2H), 3.3 (m, 2H), 7.7 (s, 1H).Step D：The preparation of chloro- 2, the 3- dihydros spiral shells of bromo- 5, the 8- bis- of 6- [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes]
15g (0.048mol) steps C title compound, 150ml ethylene glycol, 100ml trimethyl orthoformates (being purchased from Aldrich Chemical Company) and 0.06g p-methyl benzenesulfonic acid monohydrates are in 80 DEG C, it is stirred overnight together under blanket of nitrogen, mixture is diluted with 250ml ether, 1N sodium hydroxides with 1: 1: saturation NaCl mixture is washed (2 × 300ml), then washed (1 × 500ml) with saturation NaCl solution, dry (Na2SO4), filtering is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: the mixture of hexane (0.5: 95) is eluted, and obtains 8.39g steps D title compound, is solid, 152-153 DEG C of fusing.1H NMR(CDCl3)：δ 2.3 (m, 2H), 3.0 (m, 2H), 4.16 (m, 2H), 4.37 (m, 2H), 7.6 (s, 1H).Step E：The preparation of 5,8- bis- chloro- 2,3- dihydros spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids
8.3g (0.023mol) steps D title compound is added in 150ml tetrahydrofurans, in solution is cooled into about -65 DEG C under blanket of nitrogen, the n-BuLi in 11.2ml (0.028mol) 2.5M hexanes is added dropwise, and maintain the temperature at less than -55 DEG C, after stirring 30 minutes, carbon dioxide is blown into mixture 1 hour, mixture is warming to room temperature, add 150ml hexanes, mixture is filtered, solid is added to the water, gained mixture is acidified to pH1 with concentrated hydrochloric acid, extracted with dichloromethane (3 × 100ml), dry the extract (MgSO merged4), filtering is evaporated to dryness, obtains 5.03g steps E title compound, is grease.1H NMR(CDCl3)：δ 2.3 (m, 2H), 3.0 (m, 2H), 4.16 (m, 2H), 4.38 (m, 2H), 7.7 and 7,8 (2s, 1H).NMR shows to have 50mol% tetrahydrofuran to remain in grease.Step F：5,8- bis- chloro- 2,3- dihydros spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids 1, the preparation of 1- dioxide
5.03g (0.0157mol) steps E title compound and 1.93g (0.024mol) sodium acetate is added in 75ml methanol, and solution is cooled to about 0 DEG C, and the OXONE of the 16.41g (0.0267mol) in 75ml water is added dropwise_Solution (oxone) (is purchased from AldrichChemical Company), below 6 DEG C of keeping temperature, mixture is warmed to room temperature and in stirred overnight under nitrogen, with 50ml water diluted mixtures, it is cooled to about 0 DEG C, pH1 is acidified to concentrated hydrochloric acid, is extracted with chloroform (3 × 150ml), the organic phase (MgSO merged is dried4), filtering is evaporated to dryness, obtains 3.59g steps F title compound, is solid, 165 DEG C of fusing point (dec).1H NMR(Me2SO-d6)：δ 2.6 (m, 2H), 3.7 (m, 2H), 4.18 (m, 2H), 4.3 (m, 2H), 8.0 (s, 1H).Step G：3- oxo -1- cyclohexene -1- bases 5, chloro- 2, the 3- dihydros spiral shells of 8- bis- [4H1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylates 1, the preparation of 1- dioxide
1.75g (4.97mmol) steps F title compound, 1.30ml (0.015mol) oxalyl chloride (Janssen), 2 drop N, dinethylformamide is added in 50ml dichloromethane, in backflow mixture 2 hours under blanket of nitrogen, it is evaporated to dryness, 50ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 50ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 0.61g (5.5mmol) 1, 3- cyclohexanediones (are purchased from Aldrich Chemical Company), it is subsequently added 2.15ml (0.0154mol) triethylamine, stir the mixture for 2 days, warm to room temperature simultaneously, mixture is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: hexane (6: 4) is eluted, obtain 0.62g steps G title compound, for solid, (decomposition) is melted in 168 DEG C.1H NMR(CDCl3)：δ 2.1 (m, 2H), 2.5 (t, 2H), 2.7 (t, 4H), 3.6 (m, 2H), 4.2 (m, 2H), 4.4 (m, 2H), 6.1 (s, 1H), 7.8 (s, 1H).Step H：The preparation of 2- [(5,8- bis- chloro- 2,3- dihydros spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide
0.60g (1.3mmol) steps G title compound, 1 drop acetone cyanohydrin (being purchased from AldrichChemical Company) and 0.33ml (2.4mmol) triethylamine are added in 50ml acetonitriles, it is stirred overnight at room temperature in blanket of nitrogen, about 0.06g potassium cyanide is added in mixture, and stir 2 hours, it is evaporated to dryness, water is added into residue, aqueous mixture is acidified to pH1 with concentrated hydrochloric acid, filtering, 0.40g steps H title compound is obtained, is solid, (dec) is melted in 140 DEG C.1H NMR(CDCl3)：δ 2.0 (m, 2H), 2.6 (m, 6H), 3.6 (m, 2H), 4.1 (m, 2H), 4.35 (m, 2H), 7.2 (1H).NMR shows to have 33mol% triethylamine to remain in solids.
The step A of embodiment 4：The preparation of 3- [2,5- (3,5-dimethylphenyl) sulphur] propionic acid
43.4g (1.086mol) sodium hydroxide is added in 230ml water, then 75.0g (0.543mol) 2 is added, 5- thiophenol dimethyl benzenes (are purchased from Aldrich Chemical Company), mixture is cooled to about 10 DEG C, portioning adds 91.30g (0.597mol) 3- bromo acids (being purchased from Aldrich Chemical Company), and below 25 DEG C of keeping temperature, mixture is warmed to room temperature, in stirring 2 hours under blanket of nitrogen, washed with ether (3 × 500ml), aqueous phase is acidified with 1N hydrochloric acid, filtering, obtain 112.79g steps A title compound, solid, in 97-98 DEG C of fusing.1H NMR(CDCl3)：δ 2.3 (s, 3H), 2.34 (s, 3H), 2.68 (t, 2H), 3.1 (t, 2H), 6.9 (d, 1H), 7.06-7.14 (2H).Step B：The preparation of 2,3- dihydro -5,8- dimethyl -4H-1- benzopyran-4-ones
The 530ml concentrated sulfuric acids are added in 24.91g (0.119mol) steps A title compound, cooled down simultaneously with acetone/ice bath, remove ice bath, stir mixture 1 hour, pour among trash ice, aqueous mixture extracts (6 × 500ml) with 1: 9 ether: hexanes mixtures, dries (MgSO4), filtering is evaporated to dryness, obtains 11.75g steps B title compound, is grease.1H NMR(CDCl3)：δ 2.3 (s, 3H), 2.6 (s, 3H), 2.97 (m, 2H), 3.2 (m, 2H), 6.9-7.1 (2H).Step C：The preparation of bromo- 2,3- dihydros -5, the 8- dimethyl -4H-1- benzothiopyran derivatives -4- ketone of 6-
Solution of 4.07g (0.021mol) the steps B title compound in 25ml dichloromethane under room temperature under nitrogen atmosphere in being added drop-wise in 7.07g (0.053mol) aluminium chloride (be purchased from AldrichChemical Company) and the mixture of 25ml dichloromethane, by suspension stir about 15 minutes, 1.14ml (0.022mol) bromine (Janssen) is added dropwise, mixture is flowed back 10 minutes, the mixture of warm is poured into the 10ml concentrated hydrochloric acids containing 75g trash ices, stirring 10 minutes, diluted with 50ml water, extracted with ether (2 × 200ml), the organic phase of merging is washed with water (2 × 200ml), dry (Na2SO4), filtering is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: hexane (5%: 95%) is eluted, and is obtained 2.62g steps C title compound, is solid, in 87-88 DEG C of fusing.1H NMR(CDCl3)：δ 2.3 (s, 3H), 2.6 (s, 3H), 3.0 (m, 2H), 3.2 (m, 2H), 7.45 (s, 1H).Step D：The preparation of bromo- 2,3- dihydros -5, the 8- dimethyl spiral shells of 6- [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes]
26.06g (0.096mol) steps C title compound, 250ml ethylene glycol, 170ml trimethyl orthoformates (being purchased from Aldrich Chemical Company) and 0.06g p-methyl benzenesulfonic acid monohydrates are in 80 DEG C, it is stirred overnight together under blanket of nitrogen, mixture is diluted with 400ml ether, 1N sodium hydroxides with 1: 1: the mixture of the saturation NaCl aqueous solution is washed (2 × 600ml), washed (1 × 600ml) with saturation NaCl solution again, dry organic phase (Na2SO4), filtering is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: the mixture of hexane (1: 9) is eluted, and obtains 24.73g steps D title compound, is solid, 97 DEG C of fusings (dec).1H NMR(CDCl3)：δ 2.2 (s, 3H), 2.3 (m, 2H), 2.4 (s, 3H), 3.0 (m, 2H), 4.15 (m, 2H), 4.3 (m, 2H), 7.3 (s, 1H).Step E：The preparation of 2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids
24.73g (0.078mol) steps D title compound is added in 150ml tetrahydrofurans, in solution is cooled into about -70 DEG C under blanket of nitrogen, the n-BuLi in 37.68ml (0.094mol) 2.5M hexanes is added dropwise, and maintain the temperature at less than -65 DEG C, after stirring 1 hour, carbon dioxide is blown into mixture 2 hours, mixture is warming to room temperature, add 300ml hexanes, filter mixture, solid is added to water: in the mixture of dichloromethane (400ml: 400ml), it is cooled to about 0 DEG C, pH1 is acidified to concentrated hydrochloric acid, it is separated, aqueous phase is extracted (2 × 300ml) with ether, dry the extract (MgSO merged4), filtering is evaporated to dryness, obtains 4.73g steps E title compound, is solid, 207-208 DEG C of fusing.1H NMR(Me2SO-d6)：δ 2.2 (m, 5H), 2.4 (s, 3H), 3.0 (m, 2H), 4.1-4.2 (m, 4H), 7.4 (s, 1H).Step F：2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylic acids 1, the preparation of 1- dioxide
4.73g (0.017mol) steps E title compound and 2.08g (0.025mol) sodium acetate is added in 85ml methanol, and solution is cooled to about 0 DEG C, and the OXONE of the 17.66g (0.029mol) in 85ml water is added dropwise_Solution (oxone) (is purchased from Aldrich ChemicalCompany), below 6 DEG C of keeping temperature, mixture is warmed to room temperature and in stirred overnight under nitrogen, with 50ml water diluted mixtures, it is cooled to about 0 DEG C, pH2 is acidified to concentrated hydrochloric acid, is extracted with chloroform (3 × 150ml), the organic phase (MgSO merged is dried4), filtering is evaporated to dryness, residue ether: hexanes trituration (1: 9), is poured out ether-hexane, is obtained 4.18g steps F title compound, is solid, 185 DEG C of fusing point (decomposition).1H NMR(Me2SO-d6)：δ 2.35 (s, 3H), 2.5 (m, 2H), 2.6 (s, 3H), 3.5 (m, 2H), 4.16 (m, 2H), 4.2 (m, 2H), 7.6 (s, 1H).Step G：1- ethyl -1H- pyrazoles -5- bases 2,3- dihydro -5,8- dimethyl spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylates 1, the preparation of 1- dioxide
1.18g (3.8mmol) steps F title compound, 0.99ml (0.011mol) oxalyl chloride (Janssen), 2 drop N, dinethylformamide is added in 50ml dichloromethane, in backflow mixture 2 hours under blanket of nitrogen, it is evaporated to dryness, 50ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 50ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 0.51g (4.5mmol) 1- ethyl -1H- pyrazoles -5- alcohol, it is subsequently added 1.63ml (0.012mol) triethylamine, the mixture was stirred overnight, warm to room temperature simultaneously, mixture is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: hexane (6: 4) is eluted, obtain 0.24g steps G title compound, for semisolid.1H NMR(CDCl3)：δ 1.4 (t, 3H), 2.5 (s, 3H), 2.6 (m, 2H), 2.8 (s, 3H), 3.5 (m, 2H), 4.1-4.4 (m, 6H), 6.25 (s, 1H), 7.5-7.7 (2H).Step H：The preparation of (2,3 dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone S, S- dioxide
0.24g (0.59mmol) steps G title compound, 0.25 drop acetone cyanohydrin (being purchased from Aldrich Chemical Company) and 0.14ml (1.0mmol) triethylamine are added in 25ml acetonitriles, stirred at room temperature 1.5 hours in blanket of nitrogen, about 0.06g potassium cyanide is added in mixture, and be stirred at room temperature overnight, it is evaporated to dryness, water is added into residue, gained mixture is acidified to pH1 with concentrated hydrochloric acid, extracted with dichloromethane (2 × 50ml), dry the organic phase (MgSO merged4), filtering is evaporated to dryness, obtains 0.17g steps H title compound, is solid, and (dec) is melted in 111 DEG C.1H NMR(CDCl3)：δ 1.46 (t, 3H), 2.3 (s, 3H), 2.6 (m, 2H), 2.8 (s, 3H), 3.5 (m, 2H), 4.1 (q, 2H), 4.2-4.3 (m, 4H), 7.3 (2H).
The step A of embodiment 5：3- oxo -1- cyclohexene -1- bases 2,3- dihydro -5,8- dimethyl spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- carboxylates 1, the preparation of 1- dioxide
The step F of 3.0g (9.6mmol) embodiment 4 title compound, 2.5ml (0.029mol) oxalyl chloride (Janssen), with 2 drop N, N dimethylformamides are added in 100ml dichloromethane, in backflow mixture 2 hours under blanket of nitrogen, it is evaporated to dryness, 100ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 100ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 1.19g (0.0106mol) 1, 3- cyclohexanediones (are purchased from Aldrich Chemical Company), it is subsequently added 4.15ml (0.030mol) triethylamine, the mixture was stirred overnight, warm to room temperature simultaneously, mixture is evaporated to dryness, crude product is purified with silica gel chromatography, with ethyl acetate: hexane (1: 1) is eluted, obtain 1.33g steps A title compound, for solid, in 109-111 DEG C of fusing.1H NMR(CDCl3)：δ 2.1 (m, 2H), 2.5 (m, 5H), 2.6 (m, 2H), 2.7 (m, 2H), 2.8 (s, 3H), 3.5 (m, 2H), 4.2 (m, 2H), 4.3 (m, 2H), 6.0 (s, 1H), 7.7 (s, 1H).Step B：The preparation of 2- [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide
1.33g (3.3mmol) steps A title compound, 1 drop acetone cyanohydrin (being purchased from AldrichChemical Company) and 0.80ml (5.7mmol) triethylamine are added in 50ml acetonitriles, stirred at room temperature 1.5 hours in blanket of nitrogen, about 0.06g potassium cyanide is added in mixture, and in room temperature and stirred overnight under nitrogen, 0.03g potassium cyanide is added into mixture, stirring 3 hours, it is evaporated to dryness, water is added into residue, aqueous mixture is acidified to pH1 with concentrated hydrochloric acid, filtering, solid residue is dissolved in dichloromethane, dry resulting solution (MgSO4), filtering is evaporated to dryness, obtains 1.09g step B of the present invention title compound, be solid, and (dec) is melted in 130 DEG C.1H NMR(CDCl3)：δ 2.0 (m, 2H), 2.2 (s, 3H), 2.6 (m, 6H), 2.7 (s, 3H), 3.5 (m, 2H), 4.14 (m, 2H), 4.26 (m, 2H), 6.9 (1H).
The step A of embodiment 6：The preparation of bromo- 2,3- dihydros -5, the 8- dimethyl spiral shells of 6- [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes]
Toward the step C title compounds (5.0g of embodiment 4,18.4mmol) in dichloromethane (50ml) solution in adding 1 under blanket of nitrogen, 2- dithioglycols (Aldrich, 2.32ml, 27.7mmol) with Eorontrifluoride etherate compound (Janssen Chimica, 3.41ml, 27.7mmol) gained mixture is stirred at room temperature overnight, 1.0N sodium hydroxides (5ml) and saturated sodium-chloride water solution (50ml) are added into above-mentioned reactant mixture, gained mixture extracted by ether 3 times, dries suitable organic phase (MgSO4), filtering is concentrated under reduced pressure into dry, gained residue is recrystallized with 1-chlorobutane, obtains step A title compound (4.0g), is solid, 141-143 DEG C of fusing.1H NMR(CDCl3)：δ 2.19 (s, 3H), 2.78 (m, 2H), 2.80 (s, 3H), 3.09 (m, 2H), 3.45-3.70 (4H), 7.29 (s, 1H).Step B：The preparation of 2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dithiolanes] -6- carboxylic acids
Toward step A title compounds (2.7g, 7.7mmol) in the solution of 20ml tetrahydrofurans, in under blanket of nitrogen and being cooled at -78 DEG C, 2.5M solution of 4.6ml (11.5mmol) n-BuLi (Aldrich) in hexane is added dropwise, and maintain the temperature at less than -60 DEG C, after stirring 2 hours, add excessive carbon dioxide (dry ice), gained mixture is warming to room temperature, left at room temperature over night, 30ml hexanes are added into above-mentioned reactant mixture, filter mixture, solid is added to water: in the mixture of dichloromethane (20ml: 20ml), it is cooled to about 0 DEG C, pH1 is acidified to concentrated hydrochloric acid, isolate organic phase, aqueous phase is extracted (2 × 25ml) with ether, dry the organic phase (MgSO merged4), filtering is concentrated under reduced pressure into about 10ml, is settled out white solid, filter out the solid, obtains 1.62g steps B title compound, is solid, 236-238 DEG C of fusing.1H NMR(Me2SO-d6)：δ 2.17 (s, 3H), 2.68 (m, 2H), 2.81 (s, 3H), 3.11 (m, 2H), 3.50-3.70 (4H), 7.33 (s, 1H), 12.78 (s, 1H).Step C：3- oxo -1- cyclohexene -1- bases 2, the preparation of 3- dihydro -5,8- dimethyl spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dithiolanes] -6- carboxylates
In dripping N toward adding 0.63ml (7.2mmol) oxalyl chloride (Janssen) and 1 in the solution in the title compound of 0.77g (2.4mmol) the steps B in 25ml dichloromethane under blanket of nitrogen, dinethylformamide, backflow gained mixture 1.5 hours, it is evaporated to dryness, 25ml dichloromethane is added in residue, gained mixture is evaporated to dryness, after 25ml dichloromethane is added in residue again, solution is cooled to about 0 DEG C, add 0.30g (2.6mmol) 1, 3- cyclohexanediones (Aldrich), it is subsequently added 1.0ml (7.2mmol) triethylamine, the mixture was stirred overnight, warm to room temperature simultaneously, saturated sodium-chloride water solution is added into reactant mixture, gained mixture is extracted 3 times with ether, dry the organic phase (MgSO merged4), filtering is concentrated under reduced pressure into dry, crude product is purified with silica gel chromatography, with hexane: ethyl acetate (3: 1) is eluted, and obtains 0.69g steps C title compound, is semi-solid.1H NMR(CDCl3)：δ 2.13 (m, 2H), 2.26 (s, 3H), 2.45 (t, 2H), 2.66 (m, 2H), 2.76 (m, 2H), 2.95 (s, 3H), 3.18 (m, 2H), 3.50-3.70 (4H), 6.00 (s, 1H), 7.50 (s, 1H).Step D：The preparation of 2- [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dithiolanes] -6- bases) carbonyl] -3- hydroxyl -2- cyclohexene -1- ketone
In past step C title compounds (0.67g under blanket of nitrogen, acetone cyanohydrin (Aldtich 1.6mmol) is added in the solution in acetonitrile (12ml), 2 drops) and triethylamine (0.40ml, 2.8mmol), mixture is stirred overnight at room temperature, about 5mg potassium cyanide is added in reactant mixture, it is stirred at room temperature 6 hours, mixture is heated 10 hours in 50-55 DEG C, mixture is cooled to room temperature, it is concentrated under reduced pressure into dry, water (20ml) is added into gained residue, aqueous mixture is acidified to pH1 with concentrated hydrochloric acid, filtering, solid is isolated from mixture, obtain the mixture 0.60g (80: 20) of step D title compounds and step B title compounds, for solid, in 217-222 DEG C of fusing.Step D title compounds1H NMR(CDCl3)：δ 2.03 (m, 2H), 2.20 (s, 3H), 2.42 (t, 2H), 2.66 (s, 3H), 2.72-2.81 (4H), 3.16 (m, 2H), 3.42-3.60 (4H), 6.71 (s, 1H).
According to the method described above and with reference to method well known in the art, it can prepare and following abbreviation is used in the compound of table 1 below -9, table：Just, p=is aligned n=, p-tolyl=4- aminomethyl phenyls, NO2=nitro.
Table 1R3a R3b  R1     R2      R4   R5  R6   n    mH    H    -OCH2CH2O-      CH3  CH3 OH    2    1H    H    -OCH2CH2O-      CH3  H    OH    2    1H    H    -OCH2CH2O-      H     H    OH    2    1H    H    -OCH2CH2O-      Cl    Cl   OH    2    1H    H    -OCH2CH2O-      Cl    H    OH    2    1H    H    -OCH2CH2O-      Cl    CH3 OH    2    1H        H         -OCH2CH2O-               NO2    H      OH    2      1 CH3     CH3     -OCH2CH2O-               CH3    CH3   OH    2      1CH3     CH3     -OCH2CH2O-               CH3    H      OH    2      1 CH3     CH3     -OCH2CH2O-               H       H      OH    2      1CH3     CH3     -OCH2CH2O-               Cl      Cl     OH    2      1CH3     CH3     -OCH2CH2O-               Cl      H      OH    2      1CH3     CH3     -OCH2CH2O-               Cl      CH3   OH    2      1CH3     H        -OCH2CH2O-               CH3    CH3   OH    2      1CH3     H        -OCH2CH2O-               CH3    H      OH    2      1CH3     H        -OCH2CH2O-               H       H      OH    2      1CH3     H        -OCH2CH2O-               Cl      Cl     OH    2      1CH3     H        -OCH2CH2O-               Cl      H      OH    2      1CH3     H        -OCH2CH2O-               Cl      CH3   OH    2      1H        H        -OCH2CH(CH3)O-           CH3    CH3   OH    2      1H        H        -OCH2CH(CH3)O-           CH3    H      OH    2      1H        H        -OCH2CH(CH3)O-           H       H      OH    2      1H        H        -OCH2CH(CH3)O-           Cl      Cl     OH    2      1H        H        -OCH2CH(CH3)O-           Cl      H      OH    2      1H        H        -OCH2CH(CH3)O-           Cl      CH3   OH    2      1CH3     CH3    -OCH2CH(CH3)O-           CH3    CH3   OH    2      1CH3     CH3    -OCH2CH(CH3)O-           CH3    H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           H       H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      Cl     OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      CH3   OH    2      1CH3     H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      1CH3     H       -OCH2CH(CH3)O-           CH3    H      OH    2      1CH3     H       -OCH2CH(CH3)O-           H       H      OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      H      OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      1H        H       -OCH2CH2CH2O-           CH3    CH3   OH    2      1H        H       -OCH2CH2CH2O-           CH3    H      OH    2      1H        H       -OCH2CH2CH2O-           H       H      OH    2      1H        H       -OCH2CH2CH2O-           Cl      Cl     OH    2      1H        H       -OCH2CH2CH2O-           Cl      H      OH    2      1H        H       -OCH2CH2CH2O-           Cl      CH3   OH    2      1CH3     CH3   -OCH2CH2CH2O-           CH3    CH3   OH    2      1CH3    CH3    -OCH2CH2CH2O-            CH3    H      OH    2      1CH3    CH3    -OCH2CH2CH2O-            H       H      OH    2      1CH3    CH3    -OCH2CH2CH2O-            Cl      Cl     OH    2      1CH3    CH3    -OCH2CH2CH2O-            Cl      H      OH    2      1CH3    CH3    -OCH2CH2CH2O-            Cl      CH3   OH    2      1CH3    H       -OCH2CH2CH2O-            CH3    CH3   OH    2      1CH3    H       -OCH2CH2CH2O-            CH3    H      OH    2      1CH3    H       -OCH2CH2CH2O-            H       H      OH    2      1CH3    H       -OCH2CH2CH2O-            Cl      Cl     OH    2      1CH3    H       -OCH2CH2CH2O-            Cl      H      OH    2      1CH3    H       -OCH2CH2CH2O-            Cl      CH3   OH    2      1H       H        CH3O   CH3O              CH3    CH3   OH    2      1H       H        CH3O   CH3O              CH3    H      OH    2      1H       H        CH3O   CH3O              H       H      OH    2      1H       H        CH3O   CH3O              Cl      Cl     OH    2      1H       H        CH3O   CH3O              Cl      H      OH    2      1H       H        CH3O   CH3O              Cl      CH3   OH    2      1CH3    CH3    CH3O   CH3O              CH3    CH3   OH    2      1CH3    CH3    CH3O   CH3O              CH3    H      OH    2      1CH3    CH3    CH3O   CH3O              H       H      OH    2      1CH3    CH3    CH3O   CH3O              Cl      Cl     OH    2      1CH3    CH3    CH3O   CH3O              Cl      H      OH    2      1CH3    CH3    CH3O   CH3O              Cl      CH3   OH    2      1CH3    H       CH3O   CH3O              CH3    CH3   OH    2      1CH3    H       CH3O   CH3O              CH3    H      OH    2      1CH3    H       CH3O   CH3O              H       H      OH    2      1CH3    H       CH3O   C2H3O            Cl      Cl     OH    2      1CH3    H       CH3O   CH3O              Cl      H      OH    2      1CH3    H       CH3O   CH3O              Cl      CH3   OH    2      1H       H        H5C2O  H5C2O          CH3   CH3   OH    2      1H       H        H5C2O  H5C2O          CH3    H      OH    2      1H       H        H5C2O  H5C2O          H       H      OH    2      1H       H        H5C2O  H5C2O          Cl      Cl     OH    2      1H       H        H5C2O  H5C2O          Cl      H      OH    2      1H       H        H5C2O  H5C2O          Cl      CH3   OH    2      1CH3    CH3    H5C2O  H5C2O          CH3    CH3   OH    2      1CH3    CH3    H5C2O  H5C2O          CH3    H      OH    2      1CH3    CH3    H5C2O  H5C2O          H       H      OH    2       1CH3    CH3    H5C2O  H5C2O             Cl      Cl     OH    2      1CH3    CH3    H5C2O  H5C2O             Cl      H      OH    2      1CH3    CH3    H5C2O  H5C2O             Cl      CH3   OH    2      1CH3    H       H5C2O  H5C2O             CH3    CH3   OH    2      1CH3    H       H5C2O  H5C2O             CH3    H      OH    2      1CH3    H       H5C2O  H5C2O             H       H      OH    2      1CH3    H       H5C2O  H5C2O             Cl      Cl     OH    2      1CH3    H       H5C2O  H5C2O             Cl      H      OH    2      1CH3    H       H5C2O  H5C2O             Cl      CH3   OH    2      1H       H       -CH2CH2CH2CH2-           CH3    CH3   OH    2      1H       H       -CH2CH2CH2CH2-           CH3    H      OH    2      1H       H       -CH2CH2CH2CH2-           H       H      OH    2      1H       H       -CH2CH2CH2CH2-           Cl      Cl     OH    2      1H       H       -CH2CH2CH2CH2-           Cl      H      OH    2      1H       H       -CH2CH2CH2CH2-           Cl      CH3   OH    2      1CH3    CH3    -CH2CH2CH2CH2-           CH3    CH3  OH    2      1CH3    CH3    -CH2CH2CH2CH2-           CH3    H      OH    2      1CH3    CH3    -CH2CH2CH2CH2-           H       H      OH    2      1CH3    CH3    -CH2CH2CH2CH2-           Cl      Cl     OH    2      1CH3    CH3    -CH2CH2CH2CH2-           Cl      H      OH    2      1CH3    CH3    -CH2CH2CH2CH2-           Cl      CH3   OH    2      1CH3    H       -CH2CH2CH2CH2-           CH3    CH3   OH    2      1CH3    H       -CH2CH2CH2CH2-           CH3    H      OH    2      1CH3    H       -CH2CH2CH2CH2-           H       H      OH    2      1CH3    H       -CH2CH2CH2CH2-           Cl      Cl     OH    2      1CH3    H       -CH2CH2CH2CH2-           Cl      H      OH    2      1CH3    H       -CH2CH2CH2CH2-           Cl      CH3   OH    2      1H       H       -CH2CH2CH2CH2CH2-       CH3    CH3   OH    2      1H       H       -CH2CH2CH2CH2CH2-       CH3    H      OH    2      1H       H       -CH2CH2CH2CH2CH2-       H       H      OH    2      1H       H       -CH2CH2CH2CH2CH2-       Cl      Cl     OH    2      1H       H       -CH2CH2CH2CH2CH2-       Cl      H      OH    2      1H       H       -CH2CH2CH2CH2CH2-       Cl      CH3   OH    2      1CH3    CH3    -CH2CH2CH2CH2CH2-       CH3    CH3  OH    2      1CH3    CH3    -CH2CH2CH2CH2CH2-       CH3    H      OH    2      1CH3    CH3    -CH2CH2CH2CH2CH2-       H       H      OH    2      1CH3    CH3    -CH2CH2CH2CH2CH2-       Cl      Cl     OH    2      1CH3    CH3    -CH2CH2CH2CH2CH2-       Cl      H      OH    2      1CH3     CH3    -CH2CH2CH2CH2CH2-     Cl     CH3   OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     CH3   CH3   OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     CH3    H      OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     H       H      OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     Cl      Cl     OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     Cl      H      OH    2      1CH3     H       -CH2CH2CH2CH2CH2-     Cl      CH3   OH    2      1H        H       -CH2CH2CH2O-            CH3    CH3   OH    2      1H        H       -CH2CH2CH2O-            CH3    H      OH    2      1H        H       -CH2CH2CH2O-            H       H      OH    2      1H        H       -CH2CH2CH2O-            Cl      Cl     OH    2      1H        H       -CH2CH2CH2O-            Cl      H      OH    2      1H        H       -CH2CH2CH2O-            Cl      CH3   OH    2      1CH3     CH3    -CH2CH2CH2O-            CH3   CH3   OH    2      1CH3     CH3    -CH2CH2CH2O-            CH3    H      OH    2      1CH3     CH3    -CH2CH2CH2O-            H       H      OH    2      1CH3     CH3    -CH2CH2CH2O-            Cl      Cl     OH    2      1CH3     CH3    -CH2CH2CH2O-            Cl      H      OH    2      1CH3     CH3    -CH2CH2CH2O-            Cl      CH3   OH    2      1CH3     H       -CH2CH2CH2O-            CH3    CH3   OH    2      1CH3     H       -CH2CH2CH2O-            CH3    H      OH    2      1CH3     H       -CH2CH2CH2O-            H       H      OH    2      1CH3     H       -CH2CH2CH2O-            Cl      Cl     OH    2      1CH3     H       -CH2CH2CH2O-            Cl      H      OH    2      1CH3     H       -CH2CH2CH2O-            Cl      CH3   OH    2      1H        H       -OCH2CH2O-               CH3    CH3   OH    2      0H        H       -OCH2CH2O-               CH3    H      OH    2      0H        H       -OCH2CH2O-               H       H      OH    2      0H        H       -OCH2CH2O-               Cl      Cl     OH    2      0H        H       -OCH2CH2O-               Cl      H      OH    2      0H        H       -OCH2CH2O-               Cl      CH3   OH    2      0CH3     CH3    -OCH2CH2O-               CH3   CH3   OH    2      0CH3     CH3    -OCH2CH2O-               CH3    H      OH    2      0CH3     CH3    -OCH2CH2O-               H       H      OH    2      0CH3     CH3    -OCH2CH2O-               Cl      Cl     OH    2      0CH3     CH3    -OCH2CH2O-               Cl      H      OH    2      0CH3     CH3    -OCH2CH2O-               Cl      CH3   OH    2      0CH3     H       -OCH2CH2O-               CH3    CH3   OH    2      0CH3    H       -OCH2CH2O-               CH3    H      OH    2      0CH3    H       -OCH2CH2O-               H       H      OH    2      0CH3    H       -OCH2CH2O-               Cl      Cl     OH    2      0CH3    H       -OCH2CH2O-               Cl      H      OH    2      0CH3    H       -OCH2CH2O-               Cl      CH3   OH    2      0H       H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      0H       H       -OCH2CH(CH3)O-           CH3    H      OH    2      0H       H       -OCH2CH(CH3)O-           H       H      OH    2      0H       H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      0H       H       -OCH2CH(CH3)O-           Cl      H      OH    2      0H       H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      0CH3    CH3    -OCH2CH(CH3)O-           CH3   CH3   OH    2      0CH3    CH3    -OCH2CH(CH3)O-           CH3    H      OH    2      0CH3    CH3    -OCH2CH(CH3)O-           H       H      OH    2      0CH3    CH3    -OCH2CH(CH3)O-           Cl      Cl     OH    2      0CH3    CH3    -OCH2CH(CH3)O-           Cl      H      OH    2      0CH3    CH3    -OCH2CH(CH3)O-           Cl      CH3   OH    2      0CH3    H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      0CH3    H       -OCH2CH(CH3)O-           CH3    H      OH    2      0CH3    H       -OCH2CH(CH3)O-           H       H      OH    2      0CH3    H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      0CH3    H       -OCH2CH(CH3)O-           Cl      H      OH    2      0CH3    H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      0H       H       -OCH2CH2CH2O-           CH3    CH3   OH    2      0H       H       -OCH2CH2CH2O-           CH3    H      OH    2      0H       H       -OCH2CH2CH2O-           H       H      OH    2      0H       H       -OCH2CH2CH2O-           Cl      Cl     OH    2      0H       H       -OCH2CH2CH2O            Cl      H      OH    2      0H       H       -OCH2CH2CH2O            Cl      CH3   OH    2      0CH3    CH3    -OCH2CH2CH2O-          CH3    CH3   OH    2      0CH3    CH3    -OCH2CH2CH2O-          CH3    H      OH    2      0CH3    CH3    -OCH2CH2CH2O-           H       H      OH    2      0CH3    CH3    -OCH2CH2CH2O-           Cl      Cl     OH    2      0CH3    CH3    -OCH2CH2CH2O-           Cl      H      OH    2      0CH3    CH3    -OCH2CH2CH2O-           Cl      CH3   OH    2      0CH3    H       -OCH2CH2CH2O-           CH3    CH3   OH    2      0CH3    H       -OCH2CH2CH2O-           CH3    H      OH    2      0CH3    H       -OCH2CH2CH2O-           H       H      OH    2      0CH3    H       -OCH2CH2CH2O-           Cl      Cl     OH    2      0CH3    H       -OCH2CH2CH2O-           Cl      H      OH    2      0CH3    H       -OCH2CH2CH2O            Cl      CH3   OH    2      0H       H       -OCH2CH2O-               CH3    CH3   OH    2      2H       H       -OCH2CH2O-               CH3    H      OH    2      2H       H       -OCH2CH2O-               H       H      OH    2      2H       H       -OCH2CH2O-               Cl      Cl     OH    2      2H       H       -OCH2CH2O-               Cl      H      OH    2      2H       H       -OCH2CH2O-               Cl      CH3   OH    2      2CH3    CH3    -OCH2CH2O-               CH3   CH3   OH    2      2CH3    CH3    -OCH2CH2O-               CH3    H      OH    2      2CH3    CH3    -OCH2CH2O-               H       H      OH    2      2CH3    CH3    -OCH2CH2O-               Cl      Cl     OH    2      2CH3    CH3    -OCH2CH2O-               Cl      H      OH    2      2CH3    CH3    -OCH2CH2O-               Cl      CH3   OH    2      2CH3    H       -OCH2CH2O-               CH3    CH3   OH    2      2CH3    H       -OCH2CH2O-               CH3    H      OH    2      2CH3    H       -OCH2CH2O-                H      H      OH    2      2CH3    H       -OCH2CH2O-               Cl      Cl     OH    2      2CH3    H       -OCH2CH2O-               Cl      H      OH    2      2CH3    H       -OCH2CH2O-               Cl      CH3   OH    2      2H       H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      2H       H       -OCH2CH(CH3)O-           CH3    H      OH    2      2H       H       -OCH2CH(CH3)O-           H       H      OH    2      2H       H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      2H       H       -OCH2CH(CH3)O-           Cl      H      OH    2      2H       H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      2CH3    CH3    -OCH2CH(CH3)O-           CH3   CH3   OH    2      2CH3    CH3    -OCH2CH(CH3)O-           CH3    H      OH    2      2CH3    CH3    -OCH2CH(CH3)O-           H       H      OH    2      2CH3    CH3    -OCH2CH(CH3)O-           Cl      Cl     OH    2      2CH3    CH3    -OCH2CH(CH3)O-           Cl      H      OH    2      2CH3    CH3    -OCH2CH(CH3)O-           Cl      CH3   OH    2      2CH3    H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      2CH3    H       -OCH2CH(CH3)O-           CH3    H      OH    2      2CH3    H       -OCH2CH(CH3)O-           H       H      OH    2      2CH3    H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      2CH3    H       -OCH2CH(CH3)O-           Cl      H      OH    2      2CH3     H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      2H        H       -OCH2CH2CH2O-           CH3    CH3   OH    2      2H        H       -OCH2CH2CH2O-           CH3    H      OH    2      2H        H       -OCH2CH2CH2O-           H       H      OH    2      2H        H       -OCH2CH2CH2O-           Cl      Cl     OH    2      2H        H       -OCH2CH2CH2O-           Cl      H      OH    2      2H        H       -OCH2CH2CH2O-           Cl      CH3   OH    2      2CH3     CH3    -OCH2CH2CH2O-           CH3    CH3  OH    2      2CH3     CH3    -OCH2CH2CH2O-           CH3    H      OH    2      2CH3     CH3    -OCH2CH2CH2O-           H       H      OH    2      2CH3     CH3    -OCH2CH2CH2O-           Cl      Cl     OH    2      2CH3     CH3    -OCH2CH2CH2O-           Cl      H      OH    2      2CH3     CH3    -OCH2CH2CH2O-           Cl      CH3   OH    2      2CH3     H       -OCH2CH2CH2O-           CH3    CH3   OH    2      2CH3     H       -OCH2CH2CH2O-           CH3    H      OH    2      2CH3     H       -OCH2CH2CH2O-           H       H      OH    2      2CH3     H       -OCH2CH2CH2O-           Cl      Cl     OH    2      2CH3     H       -OCH2CH2CH2O-           Cl      H      OH    2      2CH3     H       -OCH2CH2CH2O-           Cl      CH3   OH    2      2H        H       -SCH2CH2S-               CH3    CH3   OH    2      1H        H       -SCH2CH2S-               CH3    CH3   OH    0      1H        H       -SCH2CH2S-               CH3    H      OH    2      1H        H       -SCH2CH2S-               H       H      OH    2      1H        H       -SCH2CH2S-               Cl      Cl     OH    2      1H        H       -SCH2CH2S-               Cl      H      OH    2      1H        H       -SCH2CH2S-               Cl      CH3   OH    2      1H        H       -SCH2CH2S-               NO2    H      OH    2      1CH3     CH3    -SCH2CH2S-               CH3    CH3   OH    2      1CH3     CH3    -SCH2CH2S-               CH3    H      OH    2      1CH3     CH3    -SCH2CH2S-               H       H      OH    2      1CH3     CH3    -SCH2CH2S-               Cl      Cl     OH    2      1CH3     CH3    -SCH2CH2S-               Cl      H      OH    2      1CH3     CH3    -SCH2CH2S-               Cl      CH3   OH    2      1CH3     H       -SCH2CH2S-               CH3    CH3   OH    2      1CH3     H       -SCH2CH2S-               CH3    H      OH    2      1CH3     H       -SCH2CH2S-               H       H      OH    2      1CH3     H       -SCH2CH2S-               Cl      Cl     OH    2      1CH3     H       -SCH2CH2S-               Cl      H      OH    2      1CH3    H       -SCH2CH2S-               Cl      CH3   OH    2      1H       H       -SCH2CH2O-               CH3    CH3   OH    2      1H       H       -SCH2CH2O-               CH3    CH3   OH    0      1H       H       -SCH2CH2O-               CH3    H      OH    2      1H       H       -SCH2CH2O-               H       H      OH    2      1H       H       -SCH2CH2O-               Cl      Cl     OH    2      1H       H       -SCH2CH2O-               Cl      H      OH    2      1H       H       -SCH2CH2O-               Cl      CH3   OH    2      1H       H       -SCH2CH2O-               NO2    H      OH    2      1CH3    CH3    -SCH2CH2O-               CH3    CH3   OH    2     1CH3    CH3    -SCH2CH2O-               CH3    H      OH    2      1CH3    CH3    -SCH2CH2O-               H       H      OH    2      1CH3    CH3    -SCH2CH2O-               Cl      Cl     OH    2      1CH3    CH3    -SCH2CH2O-               Cl      H      OH    2      1CH3    CH3    -SCH2CH2O-               Cl      CH3   OH    2      1CH3    H       -SCH2CH2O-               CH3    CH3   OH    2      1CH3    H       -SCH2CH2O-               CH3    H      OH    2      1CH3    H       -SCH2CH2O-               H       H      OH    2      1CH3    H       -SCH2CH2O-               Cl      Cl     OH    2      1CH3    H       -SCH2CH2O-               Cl      H      OH    2      1CH3    H       -SCH2CH2O-               Cl      CH3   OH    2      1H       H       -SCH2CH2CH2S-           CH3    CH3   OH    2      1H       H       -SCH2CH2CH2S-           CH3    H      OH    2      1H       H       -SCH2CH2CH2S-           H       H      OH    2      1H       H       -SCH2CH2CH2S-           Cl      Cl     OH    2      1H       H       -SCH2CH2CH2S-           Cl      H      OH    2      1H       H       -SCH2CH2CH2S-           Cl      CH3   OH    2      1H       H       -SCH2CH2CH2S-           NO2    H      OH    2      1CH3    CH3    -SCH2CH2CH2S-           CH3    CH3  OH    2      1CH3    CH3    -SCH2CH2CH2S-           CH3    H      OH    2      1CH3    CH3    -SCH2CH2CH2S-           H       H      OH    2      1CH3    CH3    -SCH2CH2CH2S-           Cl      Cl     OH    2      1CH3    CH3    -SCH2CH2CH2S-           Cl      H      OH    2      1CH3    CH3    -SCH2CH2CH2S-           Cl      CH3   OH    2      1CH3    H       -SCH2CH2CH2S-           CH3    CH3   OH    2      1CH3    H       -SCH2CH2CH2S-           CH3    H      OH    2      1CH3    H       -SCH2CH2CH2S-           H       H      OH    2      1CH3    H       -SCH2CH2CH2S-           Cl      Cl     OH    2      1CH3     H       -SCH2CH2CH2S-        Cl      H      OH    2      1CH3     H       -SCH2CH2CH2S-        Cl      CH3   OH    2      1H        H       oxo                      CH3    CH3   OH    2      1H        H       oxo                      CH3    H      OH    2      1H        H       oxo                      H        H      OH    2      1H        H       oxo                      Cl       Cl     OH    2      1H        H       oxo                      Cl       H      OH    2      1H        H       oxo                      Cl       CH3   OH    2      1H        H       oxo                      NO2     H      OH    2      1CH3     CH3    oxo                      CH3    CH3   OH    2      1CH3     CH3    oxo                      CH3    H      OH    2      1CH3     CH3    oxo                      H       H      OH    2      1CH3     CH3    oxo                      Cl      Cl     OH    2      1CH3     CH3    oxo                      Cl      H      OH    2      1CH3     CH3    oxo                      Cl      CH3   OH    2      1CH3     H       oxo                      CH3    CH3   OH    2      1CH3     H       oxo                      CH3    H      OH    2      1CH3     H       oxo                      H       H      OH    2      1CH3     H       oxo                      Cl      Cl     OH    2      1CH3     H       oxo                      Cl      H      OH    2      1CH3     H       oxo                      Cl      CH3   OH    2      1H        H       oxo                      CH3    CH3   OH    1      1H        H       oxo                      CH3    H      OH    1      1H        H       oxo                      H       H      OH    1      1H        H       oxo                      Cl      Cl     OH    1      1H        H       oxo                      Cl      H      OH    1      1H        H       oxo                      Cl      CH3   OH    1      1CH3     CH3    oxo                      CH3   CH3   OH    1      1CH3     CH3    oxo                      CH3    H      OH    1      1CH3     CH3    oxo                      H       H      OH    1      1CH3     CH3    oxo                      Cl      Cl     OH    1      1CH3     CH3    oxo                      Cl      H      OH    1      1CH3     CH3    oxo                      Cl      CH3   OH    1      1CH3     H       oxo                      CH3    CH3   OH    1      1CH3     H       oxo                      CH3    H      OH    1      1CH3     H       oxo                      H        H      OH    1      1CH3     H       oxo                      Cl       Cl     OH    1      1CH3     H       oxo                      Cl       H      OH    1      1CH3    H       oxo                      Cl      CH3The tables 2 of OH 11
Figure A9619505600551
R3a    R3b     R1     R2                R4     R5    n       mH        H       -OCH2CH2O-               CH3    CH3   2       1H        H       -OCH2CH2O-               CH3    H      2       1H        H       -OCH2CH2O-               H       H      2       1H        H       -OCH2CH2O-               Cl      Cl     2       1H        H       -OCH2CH2O-               Cl      H      2       1H        H       -OCH2CH2O-               Cl      CH3   2       1H        H       -OCH2CH2O-               NO2    H      2       1CH3     CH3    -OCH2CH2O-               CH3    CH3   2      1CH3     CH3    -OCH2CH2O-               CH3    H      2       1CH3     CH3    -OCH2CH2O-               H       H      2       1CH3     CH3    -OCH2CH2O-               Cl      Cl     2       1CH3     CH3    -OCH2CH2O-               Cl      H      2       1CH3     CH3    -OCH2CH2O-               Cl      CH3   2       lCH3     H       -OCH2CH2O-               CH3    CH3   2       1CH3     H       -OCH2CH2O-               CH3    H      2       1CH3     H       -OCH2CH2O-               H       H      2       1CH3     H       -OCH2CH2O-               Cl      Cl     2       1CH3     H       -OCH2CH2O-               Cl      H      2       1CH3     H       -OCH2CH2O-               Cl      CH3   2       1H        H       -OCH2CH(CH3)O-           CH3    CH3   2       1H        H       -OCH2CH(CH3)O-           CH3    H      2       1H        H       -OCH2CH(CH3)O-           H       H      2       1H        H       -OCH2CH(CH3)O-           Cl      Cl     2       1H        H       -OCH2CH(CH3)O-           Cl      H      2       1H        H       -OCH2CH(CH3)O-           Cl      CH3   2       1CH3     CH3    -OCH2CH(CH3)O-           CH3   CH3   2       1CH3     CH3    -OCH2CH(CH3)O-           CH3    H      2       1CH3     CH3    -OCH2CH(CH3)O-           H       H      2       1CH3     CH3    -OCH2CH(CH3)O-           Cl      Cl     2       1CH3     CH3    -OCH2CH(CH3)O-           Cl      H      2       1CH3     CH3    -OCH2CH(CH3)O-           Cl      CH3   2       1CH3     H       -OCH2CH(CH3)O-           CH3    CH3   2       1CH3     H       -OCH2CH(CH3)O-           CH3    H      2       1CH3     H       -OCH2CH(CH3)O-           H       H      2       1CH3     H       -OCH2CH(CH3)O-           Cl      Cl     2       1CH3     H       -OCH2CH(CH3)O-           Cl      H      2       1CH3     H       -OCH2CH(CH3)O-           Cl      CH3   2       1H        H       -OCH2CH2CH2O-           CH3    CH3   2       1H        H       -OCH2CH2CH2O-           CH3    H      2       1H        H       -OCH2CH2CH2O-           H       H      2       1H        H       -OCH2CH2CH2O-           Cl      Cl     2       1H        H       -OCH2CH2CH2O-           Cl      H      2       1H        H       -OCH2CH2CH2O-           Cl      CH3   2       1CH3     CH3    -OCH2CH2CH2O-           CH3   CH3   2       1CH3     CH3    -OCH2CH2CH2O-           CH3    H      2       1CH3     CH3    -OCH2CH2CH2O-           H       H      2       1CH3     CH3    -OCH2CH2CH2O-           Cl      Cl     2       1CH3     CH3    -OCH2CH2CH2O-           Cl      H      2       1CH3     CH3    -OCH2CH2CH2O-           Cl      CH3   2       1CH3     H       -OCH2CH2CH2O-           CH3    CH3   2       1CH3     H       -OCH2CH2CH2O-           CH3    H      2       1CH3     H       -OCH2CH2CH2O-           H       H      2       1CH3     H       -OCH2CH2CH2O-           Cl      Cl     2       1CH3     H       -OCH2CH2CH2O-           Cl      H      2       1CH3     H       -OCH2CH2CH2O-           Cl      CH3   2       1H        H        CH3O     CH3O            CH3    CH3   2      1H        H        CH3O     CH3O            CH3    H      2       1H        H        CH3O     CH3O            Cl      Cl     2       1H        H        CH3O     CH3O            Cl      H      2       1H        H        CH3O     CH3O            Cl      CH3   2       1CH3     CH3    CH3O     CH3O            CH3    CH3   2       1CH3     CH3    CH3O     CH3O            CH3    H      2       1CH3     CH3    CH3O     CH3O            H       H      2       1CH3     CH3    CH3O     CH3O            Cl      Cl     2       1CH3     CH3    CH3O     CH3O            Cl      H      2       1CH3     CH3    CH3O     CH3O            Cl      CH3   2       1CH3    H       CH3O     CH3O            CH3    CH3   2       1CH3    H       CH3O     CH3O            CH3    H      2       1CH3    H       CH3O     CH3O            H       H      2       1CH3    H       CH3O     CH3O            Cl      Cl     2       1CH3    H       CH3O     CH3O            Cl      H      2       1CH3    H       CH3O     CH3O            Cl      CH3   2       1H       H       H5C2O    H5C2O         CH3   CH3   2       1H       H       H5C2O    H5C2O         CH3    H      2       1H       H       H5C2O    H5C2O         H       H      2       1H       H       H5C2O    H5C2O         Cl      Cl     2       1H       H       H5C2O    H5C2O         Cl      H      2       1H       H       H5C2O    H5C2O         Cl      CH3   2       1CH3    CH3    H5C2O    H5C2O         CH3   CH3   2       1CH3    CH3    H5C2O    H5C2O         CH3    H      2       1CH3    CH3    H5C2O    H5C2O         H       H      2       1CH3    CH3    H5C2O    H5C2O         Cl      Cl     2       1CH3    CH3    H5C2O    H5C2O         Cl      H      2       1CH3    CH3    H5C2O    H5C2O         Cl      CH3   2       1CH3    H       H5C2O    H5C2O         CH3    CH3   2       1CH3    H       H5C2O    H5C2O         CH3    H      2       1CH3    H       H5C2O    H5C2O         H       H      2       1CH3    H       H5C2O    H5C2O         Cl      Cl     2       1CH3    H       H5C2O    H5C2O         Cl      H      2       1CH3    H       H5C2O    H5C2O         Cl      CH3   2       1H       H       -OCH2CH2O-               CH3    CH3   0       1H       H       -OCH2CH(CH3)O-           CH3    CH3   0       1H       H       -OCH2CH2CH2O-           CH3    CH3   0       1H       H       CH3O     CH3O            CH3    CH3   0       1H       H       H5C2O    H5C2O         CH3   CH3   0       1H       H       -OCH2CH2O-               CH3    CH3   1       1H       H       -OCH2CH(CH3)O-           CH3    CH3   1       1H       H       -OCH2CH2CH2O-           CH3    CH3   1       1H       H       CH3O     CH3O            CH3    CH3   1       1H       H       H5C2O   H5C2O         CH3    CH3   1       1H       H       -OCH2CH2O-               CH3    CH3   2       2H       H       -OCH2CH(CH3)O-           CH3    CH3   2       2H       H       -OCH2CH2CH2O-           CH3    CH3   2       2H       H       CH3O     CH3O            CH3    CH3   2       2H        H             H5C2O   H5C2O            CH3           CH3   2     2     H        H             -CH2CH2CH2CH2-           CH3           CH3   2     1H        H             -CH2CH2CH2CH2-           CH3           H      2     1H        H             -CH2CH2CH2CH2-           H              H      2     1H        H             -CH2CH2CH2CH2-           Cl             Cl     2     1H        H             -CH2CH2CH2CH2-           Cl             H      2     1H        H             -CH2CH2CH2CH2-           Cl             CH3   2     1CH3     CH3          -CH2CH2CH2CH2-           CH3          CH3   2     1CH3     CH3          -CH2CH2CH2CH2-           CH3           H      2     1CH3     CH3          -CH2CH2CH2CH2-           H              H      2     1CH3     CH3          -CH2CH2CH2CH2-           Cl             Cl     2     1CH3     CH3          -CH2CH2CH2CH2-           Cl             H      2     1CH3     CH3          -CH2CH2CH2CH2-           Cl             CH3   2     1CH3     H             -CH2CH2CH2CH2-           CH3           CH3   2     1CH3     H             -CH2CH2CH2CH2-           CH3           H      2     1CH3     H             -CH2CH2CH2CH2-           H              H      2     1CH3     H             -CH2CH2CH2CH2-           Cl             Cl     2     1CH3     H             -CH2CH2CH2CH2-           Cl             H      2     1CH3     H             -CH2CH2CH2CH2-           Cl             CH3   2     1H        H             -CH2CH2CH2CH2CH2-       CH3           CH3   2     1H        H             -CH2CH2CH2CH2CH2-       CH3           H      2     1H        H             -CH2CH2CH2CH2CH2-       H              H      2     1H        H             -CH2CH2CH2CH2CH2        Cl             Cl     2     1H        H             -CH2CH2CH2CH2CH2-       Cl             H      2     1H        H             -CH2CH2CH2CH2CH2-       Cl             CH3   2     1CH3     CH3          -CH2CH2CH2CH2CH2-       CH3          CH3   2     1CH3     CH3          -CH2CH2CH2CH2CH2-       CH3           H      2     1CH3     CH3          -CH2CH2CH2CH2CH2-       H              H      2     1CH3     CH3          -CH2CH2CH2CH2CH2-       Cl             Cl     2     1CH3     CH3          -CH2CH2CH2CH2CH2-       Cl             H      2     1CH3     CH3          -CH2CH2CH2CH2CH2-       Cl             CH3   2     1CH3     H             -CH2CH2CH2CH2CH2-       CH3           CH3   2     1CH3     H             -CH2CH2CH2CH2CH2-       CH3           H      2     1CH3     H             -CH2CH2CH2CH2CH2-       H              H      2     1CH3     H             -CH2CH2CH2CH2CH2-       Cl             Cl     2     1CH3     H             -CH2CH2CH2CH2CH2-       Cl             H      2     1CH3     H             -CH2CH2CH2CH2CH2-       Cl             CH3   2     1H        H             -CH2CH2CH2O-              CH3           CH3   2     1H       H     -CH2CH2CH2O-            CH3    H     2       1H       H     -CH2CH2CH2O-            H       H     2       1H       H     -CH2CH2CH2O-            Cl      Cl    2       1H       H     -CH2CH2CH2O-            Cl      H     2       1H       H     -CH2CH2CH2O-            Cl      CH3  2       1CH3    CH3  -CH2CH2CH2O-            CH3   CH3  2       1CH3    CH3  -CH2CH2CH2O-            CH3    H     2       1CH3    CH3  -CH2CH2CH2O-            H       H     2       1CH3    CH3  -CH2CH2CH2O-            Cl      Cl    2       1CH3    CH3  -CH2CH2CH2O-            Cl      H     2       1CH3    CH3  -CH2CH2CH2O-            Cl      CH3  2       1CH3    H     -CH2CH2CH2O-            CH3    CH3  2       1CH3    H     -CH2CH2CH2O-            CH3    H     2       1CH3    H     -CH2CH2CH2O-            H       H     2       1CH3    H     -CH2CH2CH2O-            Cl      Cl    2       1CH3    H     -CH2CH2CH2O-            Cl      H     2       1CH3    H     -CH2CH2CH2O-            Cl      CH3  2       1H       H     -OCH2CH2O-               CH3    CH3  2       0H       H     -OCH2CH2O-               CH3    H     2       0H       H     -OCH2CH2O-               H       H     2       0H       H     -OCH2CH2O-               Cl      Cl    2       0H       H     -OCH2CH2O-               Cl      H     2       0H       H     -OCH2CH2O-               Cl      CH3  2       0CH3    CH3  -OCH2CH2O-               CH3   CH3  2       0CH3    CH3  -OCH2CH2O-               CH3    H     2       0CH3    CH3  -OCH2CH2O-               H       H     2       0CH3    CH3  -OCH2CH2O-               Cl      Cl    2       0CH3    CH3  -OCH2CH2O-               Cl      H     2       0CH3    CH3  -OCH2CH2O-               Cl      CH3  2       0CH3    H     -OCH2CH2O-               CH3    CH3  2       0CH3    H     -OCH2CH2O-               CH3    H     2       0CH3    H     -OCH2CH2O-               H       H     2       0CH3    H     -OCH2CH2O-               Cl      Cl    2       0CH3    H     -OCH2CH2O-               Cl      H     2       0CH3    H     -OCH2CH2O-               Cl      CH3  2       0H       H     -OCH2CH2O-               CH3    CH3  2       2H       H     -OCH2CH2O-               CH3    H     2       2H       H     -OCH2CH2O-               H       H     2       2H              H           -OCH2CH2O-               Cl      Cl            2              2H              H           -OCH2CH2O-               Cl      H             2               2H              H           -OCH2CH2O-               Cl      CH3          2               2CH3           CH3        -OCH2CH2O-               CH3    CH3         2              2CH3           CH3        -OCH2CH2O-               CH3    H             2              2CH3           CH3        -OCH2CH2O-               H       H             2              2CH3           CH3        -OCH2CH2O-               Cl      Cl            2              2CH3           CH3        -OCH2CH2O-               Cl      H             2              2CH3           CH3        -OCH2CH2O-               Cl      CH3          2              2CH3           H           -OCH2CH2O-               CH3    CH3          2              2CH3           H           -OCH2CH2O-               CH3    H             2              2CH3           H           -OCH2CH2O-               H       H             2              2CH3           H           -OCH2CH2O-               Cl      Cl            2              2CH3           H           -O-CH2CH2-O-             Cl      H             2              2CH3           H           -O-CH2CH2-O-             Cl      CH3          2              2H              H           -OCH2CH2CH2-O-          CH3   CH3          2              0H              H           -OCH2CH2CH2-O-          CH3    H             2              0H              H           -OCH2CH2CH2-O-          H       H             2              0H              H           -OCH2CH2CH2-O-          Cl      Cl            2              0H              H           -OCH2CH2CH2-O-          Cl      H             2              0H              H           -OCH2CH2CH2-O-          Cl      CH3          2              0CH3           CH3        -OCH2CH2CH2-O-          CH3    CH3         2              0CH3           CH3        -OCH2CH2CH2-O-          CH3    H             2              0CH3           CH3        -OCH2CH2CH2-O-          H       H             2              0CH3           CH3        -OCH2CH2CH2-O-          Cl      Cl            2              0CH3           CH3        -OCH2CH2CH2-O-          Cl      H             2              0CH3           CH3        -OCH2CH2CH2-O-          Cl      CH3          2              0CH3           H           -OCH2CH2CH2-O-          CH3   CH3           2              0CH3           H           -OCH2CH2CH2-O-          CH3    H             2              0CH3           H           -OCH2CH2CH2-O-          H       H             2              0CH3           H           -OCH2CH2CH2-O-          Cl      Cl            2              0CH3           H           -OCH2CH2CH2-O-          Cl      H             2              0CH3           H           -OCH2CH2CH2-O-          Cl      CH3          2              0H              H           -SCH2CH2S-               CH3    CH3          2              1H              H           -SCH2CH2S-               CH3   CH3           0              1H              H           -SCH2CH2S-               CH3    H             2              1H              H           -SCH2CH2S-               H       H             2              1H              H           -SCH2CH2S-               Cl      Cl            2              1H       H      -SCH2CH2S-                Cl     H       2        1H       H      -SCH2CH2S-                Cl     CH3    2        1H       H      -SCH2CH2S-                NO2   H       2        1CH3    CH3   -SCH2CH2S-                CH3  CH3    2        1CH3    CH3   -SCH2CH2S-                CH3   H       2        1CH3    CH3   -SCH2CH2S-                H      H       2        1CH3    CH3   -SCH2CH2S-                Cl     Cl      2        1CH3    CH3   -SCH2CH2S-                Cl     H       2        1CH3    CH3   -SCH2CH2S-                Cl     CH3    2        1CH3    H      -SCH2CH2S-                CH3  CH3     2        1CH3    H      -SCH2CH2S-                CH3   H       2        1CH3    H      -SCH2CH2S-                H      H       2        1CH3    H      -SCH2CH2S-                Cl     Cl      2        1CH3    H      -SCH2CH2S-                Cl     H       2        1CH3    H      -SCH2CH2S-                Cl     CH3    2        1H       H      -SCH2CH2O-                CH3   CH3    2        1H       H      -SCH2CH2O-                CH3   CH3    0        1H       H      -SCH2CH2O-                CH3   H       2        1H       H      -SCH2CH2O-                H      H       2        1H       H      -SCH2CH2O-                Cl     Cl      2        1H       H      -SCH2CH2O-                Cl     H       2        1H       H      -SCH2CH2O-                Cl     CH3    2        1H       H      -SCH2CH2O-                NO2   H       2        1CH3    CH3   -SCH2CH2O-                CH3  CH3    2        1CH3    CH3   -SCH2CH2O-                CH3   H       2        1CH3    CH3   -SCH2CH2O-                H      H       2        1CH3    CH3   -SCH2CH2O-                Cl     Cl      2        1CH3    CH3   -SCH2CH2O-                Cl     H       2        1CH3    CH3   -SCH2CH2O-                Cl     CH3    2        1CH3    H      -SCH2CH2O-                CH3   CH3    2        1CH3    H      -SCH2CH2O-                CH3   H       2        1CH3    H      -SCH2CH2O-                H      H       2        1CH3    H      -SCH2C-H2O-               Cl     Cl      2        1CH3    H      -SCH2CH2O-                Cl     H       2        1CH3    H      -SCH2CH2O-                Cl     CH3    2        1H      H      -SCH2CH2CH2S-            CH3   CH3    2         1H      H      -SCH2CH2CH2S-            CH3   H       2         1H      H      -SCH2CH2CH2S-            H      H        2        1H       H      -SCH2CH2CH2S-          Cl     Cl      2       1H       H      -SCH2CH2CH2S-          Cl     H       2       1H       H      -SCH2CH2CH2S-          Cl     CH3    2       1H       H      -SCH2CH2CH2S-          NO2   H       2       1CH3    CH3   -SCH2CH2CH2S-         CH3   CH3    2       1CH3    CH3   -SCH2CH2CH2S-         CH3   H       2       1CH3    CH3   -SCH2CH2CH2S-         H      H       2       1CH3    CH3   -SCH2CH2CH2S-         Cl     Cl      2       1CH3    CH3   -SCH2CH2CH2S-         Cl     H       2       1CH3    CH3   -SCH2CH2CH2S-         Cl     CH3    2       1CH3    H      -SCH2CH2CH2S-         CH3   CH3    2       1CH3    H      -SCH2CH2CH2S-         CH3   H       2       1CH3    H      -SCH2CH2CH2S-         H      H       2       1CH3    H      -SCH2CH2CH2S-         Cl     Cl      2       1CH3    H      -SCH2CH2CH2S -        Cl     H       2       1CH3    H      -SCH2CH2CH2S-         Cl     CH3    2       1H       H      oxo                       CH3   CH3    2       1H       H      oxo                       CH3   H       2       1H       H      oxo                       Cl     Cl      2       1H       H      oxo                       Cl     H       2       1H       H      oxo                       Cl     CH3    2       1H       H      oxo                       NO2   H       2       1CH3    CH3   oxo                       CH3   CH3    2       1CH3    CH3   oxo                       CH3   H       2       1CH3    CH3   oxo                       H      H       2       1CH3    CH3   oxo                       Cl     Cl      2       1CH3    CH3   oxo                       Cl     H       2       1CH3    CH3   oxo                       Cl     CH3    2       1CH3    H      oxo                       CH3   CH3    2       1CH3    H      oxo                       CH3   H       2       1CH3    H      oxo                       H      H       2       1CH3    H      oxo                       Cl     Cl      2       1CH3    H      oxo                       Cl     H       2       1CH3    H      oxo                       Cl     CH3    2       1H       H      oxo                       CH3   CH3    1       1H       H      oxo                       CH3   H       1       1H       H      oxo                       H      H       1       1H       H      oxo                       Cl     Cl      1       1      H       H       oxo                        Cl      H      1      1H       H       oxo                        Cl      CH3   1      1CH3    CH3    oxo                        CH3   CH3   1      1CH3    CH3    oxo                        CH3    H      1      1CH3    CH3    oxo                        H       H      1      1CH3    CH3    oxo                        Cl      Cl     1      1CH3    CH3    oxo                        Cl      H      1      1CH3    CH3    oxo                        Cl      CH3   1      1    CH3    H       oxo                        CH3    CH3   1      1CH3    H       oxo                        CH3    H      1      1CH3    H       oxo                        H       H      1      1CH3    H       oxo                        Cl      Cl     1      1CH3    H       oxo                        Cl      H      1      1CH3    H       oxo                        Cl      CH311 tables 3
Figure A9619505600631
R3a R3b R1     R2          R4     R5      R8                R9      R10  n    mH    H    -OCH2CH2O-         CH3    CH3     SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         CH3    CH3     SO2CH2Cl         C2H5   H     2    1H    H    -OCH2CH2O-         CH3    H        SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         H       H        SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         Cl      Cl       SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         Cl      H        SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         Cl      CH3     SO2CH3           C2H5   H     2    1H    H    -OCH2CH2O-         CH3    CH3     SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         CH3    H        SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         H       H        SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         Cl      Cl       SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         Cl      H        SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         Cl      CH3     SO2C2H5         C2H5   H     2    1H    H    -OCH2CH2O-         CH3    CH3     SO2-n-C3H7      C2H5   H     2    1H    H    -OCH2CH2O-         CH3    H        SO2-n-C3H7      C2H5   H     2    1H   H   -OCH2CH2O-         H      H       SO2-n-C3H7       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     Cl      SO2-n-C3H7       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     H       SO2-n-C3H7       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3    SO2-n-C3H7       C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3    SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         CH3   H       SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         H      H       SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     Cl      SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     H       SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3    SO2-n-C4H9       C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3    SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         CH3   H       SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         H      H       SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         Cl     Cl      SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         Cl     H       SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3    SO2-p-tolyl        C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3    SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         CH3   H       SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         H      H       SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         Cl     Cl      SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         Cl     H       SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3    SO2-p-NO2C6H4  C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3    SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         CH3   H       SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         H      H       SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         Cl     Cl      SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         Cl     H       SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3    SO2-p-ClC6H4    C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O-         CH3H C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O- H H C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O- Cl Cl C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O- Cl H C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O-         Cl     CH3C (=O) CH3         C2H5  H   2    1H   H   -OCH2CH2O-         CH3   CH3C (=O) C2H5       C2H5  H   2    1H   H   -OCH2CH2O-         CH3H C (=O) C2H5       C2H5  H   2    1H   H   -OCH2CH2O- H H C (=O) C2H5       C2H5  H   2    1H   H   -OCH2CH2O- Cl Cl C (=O) C2H5       C2H5  H   2    1H    H   -OCH2CH2O- C l H C (=O) C2H5        C2H5  H    2   1H    H   -OCH2CH2O-       Cl     CH3C (=O) C2H5       C2H5  H    2   1H    H   -OCH2CH2O-       CH3   CH3   SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       CH3   H      SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       H      H      SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       Cl     Cl     SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       Cl     H      SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       Cl     CH3   SO2CH2Cl         CH3    H    2   1H    H   -OCH2CH2O-       CH3   CH3   SO2-n-C3H7     CH3    H    2   1     H    H   -OCH2CH2O-       CH3   H      SO2-n-C3H7      CH3    H    2   1H    H   -OCH2CH2O-       H      H      SO2-n-C3H7      CH3    H    2   1H    H   -OCH2CH2O-       Cl     Cl     SO2-n-C3H7      CH3    H    2   1H    H   -OCH2CH2O-       Cl     H      SO2-n-C3H7      CH3    H    2   1H    H   -OCH2CH2O-       Cl     CH3   SO2-n-C3H7      CH3    H    2   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       CH3   H      SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       H      H      SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       Cl     Cl     SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       Cl     H      SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       Cl     CH3   SO2-p-tolyl       CH3    H    2   1H    H   -OCH2CH2O-       CH3   CH3   SO2CH3          C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2C2H5        C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2-n-C3H7     C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2-n-C4H9     C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-tolyl       C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-NO2C6H4 C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-ClC6H4   C2H5  H    0   1 H    H   -OCH2CH2O-       CH3   CH3C (=O) CH3         C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3C (=O) C2H5       C2H5  H    0   1H    H   -OCH2CH2O-       CH3   CH3   SO2CH3           C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2C2H5         C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2-n-C3H7      C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2-n-C4H9      C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-tolyl        C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-NO2C6H4  C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3   SO2-p-ClC6H4    C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3C (=O) CH3          C2H5  H    1   1H    H   -OCH2CH2O-       CH3   CH3C (=O) C2H5        C2H5  H    1   1H    H    -OCH2CH2O-        CH3    CH3    SO2CH3           C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3    SO2C2H5         C2H5   H     2    2H    H    -OCH2CH2O         CH3    CH3    SO2-n-C3H7      C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3    SO2-n-C4H9      C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3    SO2-p-toiyl        C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3    SO2-p-NO2C6H4  C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3    SO2-p-ClC6H4    C2H5   H     2    2H    H    -OCH2CH2O-        CH3    CH3C (=O) CH3         C2H5    H     2    2H    H    -OCH2CH2O-        CH3    CH3C (=O) C2H5       C2H5The tables 4 of H 22
Figure A9619505600661
R3a    R3b    R1      R2        R4     R5    n     m     R9            R10H      H      -OCH2CH2O-         CH3    CH3    2     1     CH3           HH      H      -OCH2CH2O-         CH3    H       2     1     CH3           HH      H      -OCH2CH2O-         H       H       2     1     CH3           HH      H      -OCH2CH2O-         Cl      Cl      2     1     CH3           HH      H      -OCH2CH2O-         Cl      H       2     1     CH3           HH      H      -OCH2CH2O-         Cl      CH3    2     1     CH3           HCH3   CH3   -OCH2CH2O-         CH3   CH3    2     1     CH3           HCH3   CH3   -OCH2CH2O-         CH3    H       2     1     CH3           HCH3   CH3   -OCH2CH2O-         H       H       2     1     CH3           HCH3   CH3   -OCH2CH2O-         Cl      Cl      2     l     CH3           HCH3   CH3   -OCH2CH2O-         Cl      H       2     1     CH3           HCH3   CH3   -OCH2CH2O-         Cl      CH3    2     1     CH3           HCH3   H      -OCH2CH2O-         CH3    CH3    2     1     CH3           HCH3   H      -OCH2CH2O-         CH3    H       2     1     CH3           HCH3   H      -OCH2CH2O-         H       H       2     1     CH3           HCH3   H      -OCH2CH2O-         Cl      Cl      2     1     CH3           HCH3   H      -OCH2CH2O-         Cl      H       2     1     CH3           HCH3   H      -OCH2CH2O-         Cl      CH3    2     1     CH3           HH      H      -OCH2CH2O-         CH3    CH3    2     1     CH3           CH3H      H      -OCH2CH2O-         CH3    H       2     1     CH3           CH3H        H           -OCH2CH2O-              H                H             2           1          CH3               CH3H        H           -OCH2CH2O-              Cl               Cl            2           1          CH3               CH3H        H           -OCH2CH2O-              Cl               H             2           1          CH3               CH3H        H           -OCH2CH2O-              Cl               CH3          2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              CH3            CH3          2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              CH3             H             2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              H                H             2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              Cl               Cl            2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              Cl               H             2           1          CH3               CH3CH3     CH3        -OCH2CH2O-              Cl               CH3          2           1          CH3               CH3CH3     H           -OCH2CH2O-              CH3             CH3          2           1          CH3               CH3CH3     H           -OCH2CH2O-              CH3             H             2           1          CH3               CH3CH3     H           -OCH2CH2O-              H                H             2           1          CH3              CH3CH3     H           -OCH2CH2O-              Cl               Cl            2           1          CH3               CH3CH3     H           -OCH2CH2O-              Cl               H             2           1          CH3               CH3CH3     H           -OCH2CH2O-              Cl               CH3          2           1          CH3               CH3H        H           -OCH2CH2O-              CH3             CH3          2           1          C2H5             CH3H        H           -OCH2CH2O-              CH3             H             2           1          C2H5            CH3H        H           -OCH2CH2O-              H                H             2           1          C2H5             CH3H        H           -OCH2CH2O-              Cl               Cl            2           1          C2H5             CH3H        H           -OCH2CH2O-              Cl               H             2           1          C2H5             CH3H        H           -OCH2CH2O-              Cl               CH3          2           1          C2H5             CH3CH3     CH3        -OCH2CH2O-              CH3            CH3          2           1          C2H5              CH3CH3     CH3        -OCH2CH2O-              CH3             H             2           1          C2H5             CH3CH3     CH3        -OCH2CH2O-              H                H             2           1          C2H5             CH3CH3     CH3        -OCH2CH2O-              Cl               Cl            2           1          C2H5             CH3CH3     CH3        -OCH2CH2O-              Cl               H             2           1          C2H5             CH3H        H           -OCH2CH2O-              CH3             CH3          2           1          CH3               OCH3H        H           -OCH2CH2O-              CH3             H             2           1          CH3               OCH3H        H           -OCH2CH2O-              H                H             2           1          CH3               OCH3H        H           -OCH2CH2O-              Cl               Cl            2           1          CH3               OCH3H        H           -OCH2CH2O-              Cl               H             2           1          CH3               OCH3H        H           -OCH2CH2O-              Cl               CH3          2           1          CH3               OCH3CH3     CH3        -OCH2CH2O-              CH3            CH3          2           1          CH3               OCH3CH3     CH3        -OCH2CH2O-              CH3             H             2           1          CH3               OCH3CH3     CH3        -OCH2CH2O-              H                H             2           1          CH3               OCH3CH3     CH3        -OCH2CH2O-              Cl               Cl            2           1          CH3               OCH3CH3     CH3        -OCH2CH2O-              Cl               H             2           1          CH3               OCH3CH3    CH3    -OCH2CH2O-         Cl      CH3    2    1       CH3          OCH3CH3    H       -OCH2CH2O-         CH3    CH3    2    1       CH3          OCH3CH3    H       -OCH2CH2O-         CH3    H       2    1       CH3          OCH3CH3    H       -OCH2CH2O-         H       H       2    1       CH3          OCH3CH3    H       -OCH2CH2O-         Cl      Cl      2    1       CH3          OCH3CH3    H       -OCH2CH3O-         Cl      H       2    1       CH3          OCH3CH3    H       -OCH2CH2O-         Cl      CH3    2    1       CH3          OCH3H       H       -OCH2CH2O-         CH3    CH3    2    1       C2H5        OCH3H       H       -OCH2CH2O-         CH3    H       2    1       C2H5        OCH3H       H       -OCH2CH2O-         H       H       2    1       C2H5        OCH3H       H       -OCH2CH2O-         Cl      Cl      2    1       C2H5        OCH3H       H       -OCH2CH2O-         Cl      H       2    1       C2H5        OCH3H       H       -OCH2CH2O-         Cl      CH3    2    1       C2H5        OCH3CH3    CH3    -OCH2CH2O-         CH3   CH3    2    1       C2H5        OCH3CH3    CH3    -OCH2CH2O-         CH3    H       2    1       C2H5        OCH3CH3    CH3    -OCH2CH2O-         H       H       2    1       C2H5        OCH3CH3    CH3    -OCH2CH2O-         Cl      Cl      2    1       C2H5        OCH3CH3    CH3    -OCH2CH2O-         Cl      H       2    1       C2H5        OCH3H       H       -OCH2CH2O-         CH3    CH3    2    1       CH3          CF3H       H       -OCH2CH2O-         CH3    H       2    1       CH3          CF3H       H       -OCH2CH2O-         H       H       2    1       CH3          CF3H       H       -OCH2CH2O-         Cl      Cl      2    1       CH3          CF3H       H       -OCH2CH2O-         Cl      H       2    1       CH3          CF3H       H       -OCH2CH2O-         Cl      CH3    2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         CH3   CH3    2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         CH3    H       2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         H       H       2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         Cl      Cl      2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         Cl      H       2    1       CH3          CF3CH3    CH3    -OCH2CH2O-         Cl      CH3    2    1       CH3          CF3CH3    H       -OCH2CH2O-         CH3    CH3    2    1       CH3          CF3CH3    H       -OCH2CH2O-         CH3    H       2    1       CH3          CF3CH3    H       -OCH2CH2O-         H       H       2    1       CH3          CF3CH3    H       -OCH2CH2O-         Cl      Cl      2    1       CH3          CF3CH3    H       -OCH2CH2O-         Cl      H       2    1       CH3          CF3CH3    H       -OCH2CH2O-         Cl      CH3    2    1       CH3          CF3H       H       -OCH2CH2O-         CH3    CH3    2    1       C2H5        CF3H       H       -OCH2CH2O-         CH3    H       2    1       C2H5        CF3H            H           -OCH2CH2O-                  H               H              2           1          C2H5           CF3H            H           -OCH2CH2O-                  Cl              Cl             2           1          C2H5           CF3H            H           -OCH2CH2O-                  Cl              H              2           1          C2H5           CF3H            H           -OCH2CH2O-                  Cl              CH3           2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                 CH3            CH3           2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                 CH3            H              2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                  H               H              2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                  Cl              Cl             2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                  Cl              H              2           1          C2H5           CF3CH3         CH3        -OCH2CH2O-                  Cl              CH3           2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  CH3            CH3           2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  CH3            H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  H               H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              Cl             2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              CH3           2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  CH3            CH3           2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  CH3            H              2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  Cl              Cl             2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  Cl              H              2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  Cl              CH3           2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                 CH3            CH3           2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                  CH3            H              2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                  H               H              2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                  Cl              Cl             2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                  Cl              H              2           1          CH2CH2CH3     CH3CH3         CH3        -OCH2CH2O-                  Cl              CH3           2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  CH3            CH3           2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  CH3            H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  H               H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              Cl             2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              H              2           1          CH2CH2CH3     CH3CH3         H           -OCH2CH2O-                  Cl              CH3           2           1          CH2CH2CH3     CH3H            H           -OCH2CH2O-                  CH3            CH3           2           1          CH(CH3)2       HH            H           -OCH2CH2O-                  CH3            H              2           1          CH(CH3)2       HH            H           -OCH2CH2O-                  H               H              2           1          CH(CH3)2       HH            H           -OCH2CH2O-                  Cl              Cl             2           1          CH(CH3)2       HH            H           -OCH2CH2O-                  Cl              H              2           1          CH(CH3)2       HH       H        -OCH2CH2O-        Cl      CH3   2     1    CH(CH3)2     HCH3    CH3    -OCH2CH2O-        CH3    CH3   2     1    CH(CH3)2     HCH3    CH3    -OCH2CH2O-        CH3    H      2     1    CH(CH3)2     H CH3    CH3    -OCH2CH2O-        H       H      2     1    CH(CH3)2     HCH3    CH3    -OCH2CH2O-        Cl      Cl     2     1    CH(CH3)2     HCH3    CH3    -OCH2CH2O-        Cl      H      2     1    CH(CH3)2     HCH3    CH3    -OCH2CH2O-        Cl      CH3   2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        CH3    CH3   2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        CH3    H      2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        H       H      2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        Cl      Cl     2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        Cl      H      2     1    CH(CH3)2     HCH3    H       -OCH2CH2O-        Cl      CH3   2     1    CH(CH3)2     HH       H       -OCH2CH2O-        CH3    CH3   2     1    C6H5         HH       H       -OCH2CH2O-        CH3    H      2     1    C6H5         HH       H       -OCH2CH2O-        H       H      2     1    C6H5         HH       H       -OCH2CH2O-        Cl      Cl     2     1    C6H5         HH       H       -OCH2CH2O-        Cl      H      2     1    C6H5         HH       H       -OCH2CH2O-        Cl      CH3   2     1    C6H5         HCH3    CH3    -OCH2CH2O-        CH3   CH3   2     1    C6H5         HCH3    CH3    -OCH2CH2O-        CH3    H      2     1    C6H5         HCH3    CH3    -OCH2CH2O-        H       H      2     1    C6H5         HCH3    CH3    -OCH2CH2O-        Cl      Cl     2     1    C6H5         HCH3    CH3    -OCH2CH2O-        Cl      H      2     1    C6H5         HCH3    CH3    -OCH2CH2O-        Cl      CH3   2     1    C6H5         HCH3    H       -OCH2CH2O-        CH3    CH3   2     1    C6H5         HCH3    H       -OCH2CH2O-        CH3    H      2     1    C6H5         HCH3    H       -OCH2CH2O-        H       H      2     1    C6H5         HCH3    H       -OCH2CH2O-        Cl      Cl     2     1    C6H5         HCH3    H       -OCH2CH2O-        Cl      H      2     1    C6H5         HCH3    H       -OCH2CH2O-        Cl      CH3   2     1    C6H5         HH       H       -OCH2CH2O-        CH3    CH3   2     1    C6H5         CH3H       H       -OCH2CH2O-        CH3    H      2     1    C6H5         CH3H       H       -OCH2CH2O-        H       H      2     1    C6H5         CH3H       H       -OCH2CH2O-        Cl      Cl     2     1    C6H5         CH3H       H       -OCH2CH2O-        Cl      H      2     1    C6H5         CH3H       H       -OCH2CH2O-        Cl      CH3   2     1    C6H5         CH3CH3    CH3   -OCH2CH2O-        CH3    CH3   2     1    C6H5         CH3CH3         CH3        -OCH2CH2O-               CH3    H         2            1       C6H5          CH3CH3         CH3        -OCH2CH2O-               H       H         2            1        C6H5         CH3CH3         CH3        -OCH2CH2O-               Cl      Cl        2            1        C6H5         CH3CH3         CH3        -OCH2CH2O-               Cl      H         2            1        C6H5         CH3CH3         CH3        -OCH2CH2O-               Cl      CH3      2            1        C6H5         CH3CH3         H           -OCH2CH2O-               CH3    CH3      2            1        C6H5         CH3CH3         H           -OCH2CH2O-               CH3    H         2            1        C6H5         CH3CH3         H           -OCH2CH2O-               H       H         2            1        C6H5         CH3CH3         H           -OCH2CH2O-               Cl      Cl        2            1        C6H5         CH3CH3         H           -OCH2CH2O-               Cl      H         2            1        C6H5         CH3CH3         H           -OCH2CH2O-               Cl      CH3      2            1        C6H5         CH3H            H           -CH2CH2CH2O-            CH3    CH3      2            1        CH3           HH            H           -CH2CH2CH2O-            CH3    H         2            1        CH3           HH            H           -CH2CH2CH2O-            H       H         2            1        CH3           HH            H           -CH2CH2CH2O-            Cl      Cl        2            1        CH3           HH            H           -CH2CH2CH2O-            Cl      H         2            1        CH3           HH            H           -CH2CH2CH2O-            Cl      CH3      2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            CH3   CH3      2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            CH3    H         2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            H       H         2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            Cl      Cl        2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            Cl      H         2            1        CH3           HCH3         CH3        -CH2CH2CH2O-            Cl      CH3      2            1        CH3           HCH3         H           -CH2CH2CH2O-            CH3    CH3      2            1        CH3           HCH3         H           -CH2CH2CH2O-            CH3    H         2            1        CH3           HCH3         H           -CH2CH2CH2O-            H       H         2            1        CH3           HCH3         H           -CH2CH2CH2O-            Cl      Cl        2            1        CH3           HCH3         H           -CH2CH2CH2O-            Cl      H         2            1        CH3           HCH3         H           -CH2CH2CH2O-            Cl      CH3      2            1        CH3           HH            H           -OCH2CH2CH2O-           CH3    CH3      2            1        CH3           ClH            H           -OCH2CH2CH2O-           CH3    H         2            1        CH3           ClH            H           -OCH2CH2CH2O-           H       H         2            1        CH3           ClH            H           -OCH2CH2CH2O-           Cl      Cl        2            1        CH3           ClH            H           -OCH2CH2CH2O-           Cl      H         2            1        CH3           ClH            H           -OCH2CH2CH2O-           Cl      CH3      2            1        CH3           ClCH3         CH3        -OCH2CH2CH2O-           CH3   CH3      2            1        CH3           ClCH3         CH3        -OCH2CH2CH2O-           CH3    H         2            1        CH3           ClCH3         CH3        -OCH2CH2CH2O-           H       H         2            1        CH3           ClCH3    CH3   -OCH2CH2CH2O-     Cl       Cl       2     1     CH3           ClCH3    CH3   -OCH2CH2CH2O-     Cl       H        2     1     CH3           ClCH3    CH3   -OCH2CH2CH2O-     Cl       CH3     2     1     CH3           ClCH3    H      -OCH2CH2CH2O-     CH3     CH3     2     1     CH3           ClCH3    H      -OCH2CH2CH2O-     CH3     H        2     1     CH3           ClCH3    H      -OCH2CH2CH2O-     H        H        2     1     CH3           ClCH3    H      -OCH2CH2CH2O-     Cl       Cl       2     1     CH3           ClCH3    H      -OCH2CH2CH2O      Cl       H        2     1     CH3           ClCH3    H      -OCH2CH2CH2O-     Cl       CH3     2     1     CH3           ClH       H      -OCH2CH2O-         CH3     CH3     2     1     C2H5         ClH       H      -OCH2CH2O-         CH3     H        2     1     C2H5         ClH       H      -OCH2CH2O-         H        H        2     1     C2H5         ClH       H      -OCH2CH2O-         Cl       Cl       2     1     C2H5         ClH       H      -OCH2CH2O-         Cl       H        2     1     C2H5         ClH       H      -OCH2CH2O-         Cl       CH3     2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        CH3     CH3     2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        CH3     H        2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        H        H        2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        Cl       Cl       2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        Cl       H        2     1     C2H5         ClCH3    CH3   -OCH2CH2O-        Cl       CH3     2     1     C2H5         ClCH3    H      -OCH2CH2O-         CH3    CH3     2     1     C2H5         ClCH3    H      -OCH2CH2O-         CH3     H        2     1     C2H5         ClCH3    H      -OCH2CH2O-         H        H        2     1     C2H5         ClCH3    H      -OCH2CH2O-         Cl       Cl       2     1     C2H5         ClCH3    H      -OCH2CH2CH2O-     Cl       H        2     1     C2H5         ClCH3    H      -OCH2CH2O-         Cl       CH3     2     1     C2H5         ClH       H      -OCH2CH2CH2O-     CH3     CH3     2     1     CH3           HH       H      OCH2CH2CH2O       CH3     H        2     1     CH3           HH       H      OCH2CH2CH2O       H        H        2     1     CH3           HH       H      OCH2CH2CH2O       Cl       Cl       2     1     CH3           HH       H      OCH2CH2CH2O       Cl       H        2     1     CH3           HH       H      OCH2CH2CH2O       Cl       CH3     2     1     CH3           HCH3    CH3   OCH2CH2CH2O       CH3    CH3     2     1     CH3           HCH3    CH3   OCH2CH2CH2O       CH3     H        2     1     CH3           HCH3    CH3   OCH2CH2CH2O       H        H        2     1     CH3           HCH3    CH3   OCH2CH2CH2O       Cl       Cl       2     1     CH3           HCH3    CH3   OCH2CH2CH2O       Cl       H        2     1     CH3           HCH3    CH3   OCH2CH2CH2O     Cl       CH3                  CH3          HCH3    H      OCH2CH2CH2O     CH3     CH3                  CH3          HCH3    H      OCH2CH2CH2O     CH3     H                     CH3          HCH3    H      OCH2CH2CH2O     H        H                     CH3          HCH3    H      OCH2CH2CH2O     Cl       Cl                    CH3          HCH3    H      OCH2CH2CH2O     Cl       H                     CH3          HCH3    H      OCH2CH2CH2O     Cl       CH3                  CH3          HH       H      -SCH2CH2S-       CH3     CH3                  CH3          HH       H      -SCH2CH2S-       CH3     CH3                  CH3          HH       H      -SCH2CH2S-       CH3     H                     CH3          HH       H      -SCH2CH2S-       H        H                     CH3          HH       H      -SCH2CH2S-       Cl       Cl                    CH3          HH       H      -SCH2CH2S-       Cl       H                     CH3          HH       H      -SCH2CH2S-       Cl       CH3                  CH3          HCH3    CH3   -SCH2CH2S-       CH3     CH3                 CH3          HCH3    CH3   -SCH2CH2S-       CH3     H                     CH3          HCH3    CH3   -SCH2CH2S-       H        H                     CH3          HCH3    CH3   -SCH2CH2S-       Cl       Cl                    CH3          HCH3    CH3   -SCH2CH2S-       Cl       H                     CH3          HCH3    CH3   -SCH2CH2S-       Cl       CH3                  CH3          HCH3    H      -SCH2CH2S-       CH3     CH3                  CH3          HCH3    H      -SCH2CH2S-       CH3     H                     CH3          HCH3    H      -SCH2CH2S-       H        H                     CH3          HCH3    H      -SCH2CH2S-       Cl       Cl                    CH3          HCH3    H      -SCH2CH2S-       Cl       H                     CH3          HCH3    H      -SCH2CH2S-       Cl       CH3                  CH3          HH       H      -SCH2CH2O-       CH3     CH3                  CH3          HH       H      -SCH2CH2O-       CH3     CH3                  CH3          HH       H      -SCH2CH2O-       CH3     H                     CH3          HH       H      -SCH2CH2O-       H        H                     CH3          HH       H      -SCH2CH2O-       Cl       Cl                    CH3          HH       H      -SCH2CH2O-       Cl       H                     CH3          HH       H      -SCH2CH2O-       Cl       CH3                  CH3          HCH3    CH3   -SCH2CH2O-       CH3     CH3                 CH3          HCH3    CH3   -SCH2CH2O-       CH3     H                     CH3          HCH3    CH3   -SCH2CH2O-       H        H                     CH3          HCH3    CH3   -SCH2CH2O-       Cl       Cl                    CH3          HCH3    CH3   -SCH2CH2O-       Cl       H                     CH3          HCH3    CH3   -SCH2CH2O-          Cl      CH3    2     1    CH3         HCH3    H      -SCH2CH2O-          CH3    CH3    2     1    CH3         HCH3    H      -SCH2CH2O-          CH3    H       2     1    CH3         HCH3    H      -SCH2CH2O-          H       H       2     1    CH3         HCH3    H      -SCH2CH2O-          Cl      Cl      2     1    CH3         HCH3    H      -SCH2CH2O-          Cl      H       2     1    CH3         HCH3    H      -SCH2CH2O-          Cl      CH3    2     1    CH3         HH       H      -SCH2CH2CH2S-      CH3    CH3    2     1    CH3         HH       H      -SCH2CH2CH2S-      CH3    H       2     1    CH3         HH       H      -SCH2CH2CH2S-      H       H       2     1    CH3         HH       H      -SCH2CH2CH2S-      Cl      Cl      2     1    CH3         HH       H      -SCH2CH2CH2S-      Cl      H       2     1    CH3         HH       H      -SCH2CH2CH2S-      Cl      CH3    2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      CH3   CH3    2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      CH3    H       2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      H       H       2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      Cl      Cl      2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      Cl      H       2     1    CH3         HCH3    CH3   -SCH2CH2CH2S-      Cl      CH3    2     1    CH3         HCH3    H      -SCH2CH2CH2S-      CH3    CH3    2     1    CH3         HCH3    H      -SCH2CH2CH2S-      CH3    H       2     1    CH3         HCH3    H      -SCH2CH2CH2S-      H       H       2     1    CH3         HCH3    H      -SCH2CH2CH2S-      Cl      Cl      2     1    CH3         HCH3    H      -SCH2CH2CH2S-      Cl      H       2     1    CH3         HCH3    H      -SCH2CH2CH2S-      Cl      CH3    2     1    CH3         HH       H      oxo                    CH3    CH3    2     1    CH3         HH       H      oxo                    CH3    H       2     1    CH3         HH       H      oxo                    Cl      Cl      2     1    CH3         HH       H      oxo                    Cl      H       2     1    CH3         HH       H      oxo                    Cl      CH3    2     1    CH3         HCH3    CH3   oxo                    CH3   CH3    2     1    CH3         HCH3    CH3   oxo                    CH3    H       2     1    CH3         HCH3    CH3   oxo                    H       H       2     1    CH3         HCH3    CH3   oxo                    Cl      Cl      2     1    CH3         HCH3    CH3   oxo                    Cl      H       2     1    CH3         HCH3    CH3   oxo                    Cl      CH3    2     1    CH3         HCH3    H      oxo                    CH3    CH3    2     1    CH3         HCH3    H      oxo                    CH3    H       2     1    CH3         HCH3     H       oxo                  H        H        2      1     CH3           HCH3     H       oxo                  Cl       Cl       2      1     CH3           HCH3     H       oxo                  Cl       H        2      1     CH3           HCH3     H       oxo                  Cl       CH3     2      1     CH3           HH        H       oxo                  CH3     CH3     1      1     CH3           HH        H       oxo                  CH3     H        1      1     CH3           HH        H       oxo                  H        H        1      1     CH3           HH        H       oxo                  Cl       Cl       1      1     CH3           HH        H       oxo                  Cl       H        1      1     CH3           HH        H       oxo                  Cl       CH3     1      1     CH3           HCH3     CH3   oxo                  CH3     CH3     1      1     CH3           HCH3     CH3   oxo                  CH3     H        1      1     CH3           HCH3     CH3   oxo                  H        H        1      1     CH3           HCH3     CH3   oxo                  Cl       Cl       1      1     CH3           HCH3     CH3   oxo                  Cl       H        1      1     CH3           HCH3     CH3   oxo                  Cl       CH3     1      1     CH3           HCH3     H       oxo                  CH3    CH3     1      1     CH3           HCH3     H       oxo                  CH3     H        1      1     CH3           HCH3     H       oxo                  H        H        1      1     CH3           HCH3     H       oxo                  Cl       Cl       1      1     CH3           HCH3     H       oxo                  Cl       H        1      1     CH3           HCH3     H       oxo                  Cl       CH3     1      1     CH3H tables 5R3a    R3b    R1      R2     R4     R5  R6   n    mH       H      -OCH2CH2O-     CH3    CH3  OH    2    1  H       H      -OCH2CH2O-     CH3    H     OH    2    1H       H      -OCH2CH2O-     H       H     OH    2    1H       H      -OCH2CH2O-     Cl      Cl    OH    2    1H       H      -OCH2CH2O-     Cl      H     OH    2    1H       H      -OCH2CH2O-     Cl      CH3  OH    2    1H       H      -OCH2CH2O-     NO2    H     OH    2    1CH3     CH3    -OCH2CH2O-               CH3    CH3   OH    2      1CH3     CH3    -OCH2CH2O                CH3    H      OH    2      1CH3     CH3    -OCH2CH2O-               H       H      OH    2      1 CH3     CH3    -OCH2CH2O-               Cl      Cl     OH    2      1CH3     CH3    -OCH2CH2O                Cl      H      OH    2      1CH3     CH3    -OCH2CH2O-               Cl      CH3   OH    2      1CH3     H       -OCH2CH2O-               CH3    CH3   OH    2      1CH3     H       -OCH2CH2O-               CH3    H      OH    2      1CH3     H       -OCH2CH2O-               H       H      OH    2      1CH3     H       -OCH2CH2O-               Cl      Cl     OH    2      1CH3     H       -OCH2CH2O-               Cl      H      OH    2      1CH3     H       -OCH2CH2O-               Cl      CH3   OH    2      1H        H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      1H        H       -OCH2CH(CH3)O-           CH3    H      OH    2      1H        H       -OCH2CH(CH3)O-           H       H      OH    2      1H        H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      1H        H       -OCH2CH(CH3)O-           Cl      H      OH    2      1H        H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      1CH3     CH3    -OCH2CH(CH3)O-           CH3   CH3   OH    2      1CH3     CH3    -OCH2CH(CH3)O-           CH3    H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           H       H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      Cl     OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      H      OH    2      1CH3     CH3    -OCH2CH(CH3)O-           Cl      CH3   OH    2      1CH3     H       -OCH2CH(CH3)O-           CH3    CH3   OH    2      1CH3     H       -OCH2CH(CH3)O-           CH3    H      OH    2      1CH3     H       -OCH2CH(CH3)O-           H       H      OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      Cl     OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      H      OH    2      1CH3     H       -OCH2CH(CH3)O-           Cl      CH3   OH    2      1H        H       -OCH2CH2CH2O-           CH3   CH3   OH    2      1H        H       -OCH2CH2CH2O-           CH3    H      OH    2      1H        H       -OCH2CH2CH2O-           H       H      OH    2      1H        H       -OCH2CH2CH2O-           Cl      Cl     OH    2      1H        H       -OCH2CH2CH2O-           Cl      H      OH    2      1H        H       -OCH2CH2CH2O-           Cl      CH3   OH    2      1CH3     CH3   -OCH2CH2CH2O-           CH3    CH3   OH    2      1CH3     CH3   -OCH2CH2CH2O-           CH3    H      OH    2      1CH3     CH3    -OCH2CH2CH2O-            H        H      OH    2      1CH3     CH3    -OCH2CH2CH2O-            Cl       Cl     OH    2      1CH3     CH3    -OCH2CH2CH2O-            Cl       H      OH    2      1CH3     CH3    -OCH2CH2CH2O-            Cl       CH3   OH    2      1CH3     H       -OCH2CH2CH2O-            CH3     CH3   OH    2      1CH3     H       -OCH2CH2CH2O-            CH3     H      OH    2      1CH3     H       -OCH2CH2CH2O-            H        H      OH    2      1CH3     H       -OCH2CH2CH2O-            Cl       Cl     OH    2      1CH3     H       -OCH2CH2CH2O-            Cl       H      OH    2      1CH3     H       -OCH2CH2CH2O-            Cl       CH3   OH    2      1H        H       -CH2CH2CH2O-             CH3     CH3   OH    2      1H        H       -CH2CH2CH2O-             CH3     H      OH    2      1H        H       -CH2CH2CH2O-             H        H      OH    2      1H        H       -CH2CH2CH2O-             Cl       Cl     OH    2      1H        H       -CH2CH2CH2O-             Cl       H      OH    2      1H        H       -CH2CH2CH2O-             Cl       CH3   OH    2      1CH3     CH3    -CH2CH2CH2O-             CH3     CH3  OH    2      1CH3     CH3    -CH2CH2CH2O-             CH3     H      OH    2      1CH3     CH3    -CH2CH2CH2O-             H        H      OH    2      1CH3     CH3    -CH2CH2CH2O-             Cl       Cl     OH    2      1CH3     CH3    -CH2CH2CH2O-             Cl       H      OH    2      1CH3     CH3    -CH2CH2CH2O-             Cl       CH3   OH    2      1CH3     H       -CH2CH2CH2O-             CH3     CH3   OH    2      1CH3     H       -CH2CH2CH2O-             CH3     H      OH    2      1CH3     H       -CH2CH2CH2O-             H        H      OH    2      1CH3     H       -CH2CH2CH2O-             Cl       Cl     OH    2      1CH3     H       -CH2CH2CH2O-             Cl       H      OH    2      1CH3     H       -CH2CH2CH2O-             Cl       CH3   OH    2      1H        H       -OCH2CH2O-                CH3     CH3   OH    2      0H        H       -OCH2CH2O-                CH3     H      OH    2      0H        H       -OCH2CH2O-                H        H      OH    2      0H        H       -OCH2CH2O-                Cl       Cl     OH    2      0H        H       -OCH2CH2O-                Cl       H      OH    2      0H        H       -OCH2CH2O-                Cl       CH3   OH    2      0CH3     CH3    -OCH2CH2O-               CH3     CH3   OH    2      0CH3     CH3    -OCH2CH2O-               CH3     H      OH    2      0CH3     CH3    -OCH2CH2O-               H        H      OH    2      0CH3     CH3    -OCH2CH2O-               Cl       Cl     OH    2      0CH3     CH3    -OCH2CH2O-             Cl       H      OH    2    0CH3     CH3    -OCH2CH2O-             Cl       CH3   OH    2    0CH3     H       -OCH2CH2O-             CH3     CH3   OH    2    0CH3     H       -OCH2CH2O-             CH3     H      OH    2    0CH3     H       -OCH2CH2O-             H        H      OH    2    0CH3     H       -OCH2CH2O-             Cl       Cl     OH    2    0CH3     H       -OCH2CH2O-             Cl       H      OH    2    0CH3     H       -OCH2CH2O-             Cl       CH3   OH    2    0H        H       -OCH2CH(CH3)O-         CH3     CH3   OH    2    0H        H       -OCH2CH(CH3)O-         CH3     H      OH    2    0H        H       -OCH2CH(CH3)O-         H        H      OH    2    0H        H       -OCH2CH(CH3)O-         Cl       Cl     OH    2    0H        H       -OCH2CH(CH3)O-         Cl       H      OH    2    0H        H       -OCH2CH(CH3)O-         Cl       CH3   OH    2    0CH3     CH3    -OCH2CH(CH3)O-         CH3    CH3   OH    2    0CH3     CH3    -OCH2CH(CH3)O-         CH3    H      OH    2    0CH3     CH3    -OCH2CH(CH3)O-         H        H      OH    2    0CH3     CH3    -OCH2CH(CH3)O-         Cl       Cl     OH    2    0CH3     CH3    -OCH2CH(CH3)O-         Cl       H      OH    2    0CH3     CH3    -OCH2CH(CH3)O-         Cl       CH3   OH    2    0CH3     H       -OCH2CH(CH3)O-         CH3     CH3   OH    2    0CH3     H       -OCH2CH(CH3)O-         CH3     H      OH    2    0CH3     H       -OCH2CH(CH3)O-         H        H      OH    2    0CH3     H       -OCH2CH(CH3)O-         Cl       Cl     OH    2    0CH3     H       -OCH2CH(CH3)O-         Cl       H      OH    2    0CH3     H       -OCH2CH(CH3)O-         Cl       CH3   OH    2    0H        H       -OCH2CH2CH2O-         CH3     CH3   OH    2    0H        H       -OCH2CH2CH2O-         CH3     H      OH    2    0H        H       -OCH2CH2CH2O-         H        H      OH    2    0H        H       -OCH2CH2CH2O-         Cl       Cl     OH    2    0H        H       -OCH2CH2CH2O-         Cl       H      OH    2    0H        H       -OCH2CH2CH2O-         Cl       CH3   OH    2    0CH3     CH3    -OCH2CH2CH2O-         CH3    CH3   OH    2    0CH3     CH3    -OCH2CH2CH2O-         CH3     H      OH    2    0CH3     CH3    -OCH2CH2CH2O-         H        H      OH    2    0CH3     CH3    -OCH2CH2CH2O-         Cl       Cl     OH    2    0CH3     CH3    -OCH2CH2CH2O-         Cl       H      OH    2    0CH3     CH3    -OCH2CH2CH2O-         Cl       CH3   OH    2    0CH3     H       -OCH2CH2CH2O-           CH3    CH3   OH    2      0CH3     H       -OCH2CH2CH2O-           CH3    H      OH    2      0CH3     H       -OCH2CH2CH2O-           H       H      OH    2      0CH3     H       -OCH2CH2CH2O-           Cl      Cl     OH    2      0CH3     H       -OCH2CH2CH2O-           Cl      H      OH    2      0CH3     H       -OCH2CH2CH2O-           Cl      CH3   OH    2      0H        H       -SCH2CH2S-               CH3    CH3   OH    2      0H        H       -SCH2CH2S-               CH3    CH3   OH    0      0H        H       -SCH2CH2S-               CH3    H      OH    2      0H        H       -SCH2CH2S-               H       H      OH    2      0H        H       -SCH2CH2S-               Cl      Cl     OH    2      0H        H       -SCH2CH2S-               Cl      H      OH    2      0H        H       -SCH2CH2S-               Cl      CH3   OH    2      0H        H       -SCH2CH2S-               NO2    H      OH    2      0CH3     CH3    -SCH2CH2S-               CH3   CH3   OH    2      0CH3     CH3    -SCH2CH2S-               CH3    H      OH    2      0CH3     CH3    -SCH2CH2S-               H       H      OH    2      0CH3     CH3    -SCH2CH2S-               Cl      Cl     OH    2      0CH3     CH3    -SCH2CH2S-               Cl      H      OH    2      0CH3     CH3    -SCH2CH2S-               Cl      CH3   OH    2      0CH3     H       -SCH2CH2S-               CH3    CH3   OH    2      0CH3     H       -SCH2CH2S-               CH3    H      OH    2      0CH3     H       -SCH2CH2S-               H       H      OH    2      0CH3     H       -SCH2CH2S-               Cl      Cl     OH    2      0CH3     H       -SCH2CH2S-               Cl      H      OH    2      0CH3     H       -SCH2CH2S-               Cl      CH3   OH    2      0H        H       -SCH2CH2O-               CH3    CH3   OH    2      0H        H       -SCH2CH2O-               CH3    CH3   OH    0      0H        H       oxo                         CH3    CH3   OH    2      1H        H       oxo                         CH3    H      OH    2      1H        H       oxo                         H       H      OH    2      1H        H       oxo                         Cl      Cl     OH    2      1H        H       oxo                         Cl      H      OH    2      1H        H       oxo                         Cl      CH3   OH    2      1H        H       oxo                         NO2    H      OH    2      1CH3     CH3   oxo                         CH3    CH3   OH    2      1CH3     CH3   oxo                         CH3    H      OH    2      1CH3     CH3   oxo                         H       H      OH    2      1CH3     CH3    oxo                         Cl       Cl    OH     2       1CH3     CH3    oxo                         Cl       H     OH     2       1CH3     CH3    oxo                         Cl       CH3  OH     2       1CH3     H       oxo                         CH3     CH3  OH     2       1CH3     H       oxo                         CH3     H     OH     2       1CH3     H       oxo                         H        H     OH     2       1CH3     H       oxo                         Cl       Cl    OH     2       1CH3     H       oxo                         Cl       H     OH     2       1CH3     H       oxo                         Cl       CH3  OH     2       1H        H       oxo                         CH3     CH3  OH     1       1H        H       oxo                         CH3     H     OH     1       1H        H       oxo                         H        H     OH     1       1H        H       oxo                         Cl       Cl    OH     1       1H        H       oxo                         Cl       H     OH     1       1H        H       oxo                         Cl       CH3  OH     1       1CH3     CH3   oxo                         CH3     CH3  OH     1       1CH3     CH3   oxo                         CH3     H     OH     1       1CH3     CH3   oxo                         H        H     OH     1       1CH3     CH3   oxo                         Cl       Cl    OH     1       1CH3     CH3   oxo                         Cl       H     OH     1       1CH3     CH3   oxo                         Cl       CH3  OH     1       1CH3     H      oxo                         CH3     CH3  OH     1       1CH3     H      oxo                         CH3     H     OH     1       1CH3     H      oxo                         H        H     OH     1       1CH3     H      oxo                         Cl       Cl    OH     1       1CH3     H      oxo                         Cl       H     OH     1       1CH3     H      oxo                         Cl       CH3The tables 6 of OH 11
Figure A9619505600801
R3a   R3b   R1      R2    R4          R5        n    mH      H      -OCH2CH2O-    CH3         CH3       2    1H      H      -OCH2CH2O-    CH3         H          2    1H       H      -OCH2CH2O-            H      H       2     1H       H      -OCH2CH2O-            Cl     Cl      2     1H       H      -OCH2CH2O-            Cl     H       2     1H       H      -OCH2CH2O-            Cl     CH3    2     1H       H      -OCH2CH2O-            NO2   H       2     1CH3    CH3  -OCH2CH2O-            CH3   CH3    2     1CH3    CH3  -OCH2CH2O-            CH3   H       2     1CH3    CH3  -OCH2CH2O-            H      H       2     1CH3    CH3  -OCH2CH2O-            Cl     Cl      2     1CH3    CH3  -OCH2CH2O-            Cl     H       2     1CH3    CH3  -OCH2CH2O-            Cl     CH3    2     1CH3    H     -OCH2CH2O-            CH3   CH3    2     1CH3    H     -OCH2CH2O-            CH3   H       2     1CH3    H     -OCH2CH2O-            H      H       2     1CH3    H     -OCH2CH2O-            Cl     Cl      2     1CH3    H     -OCH2CH2O-            Cl     H       2     1CH3    H     -OCH2CH2O-            Cl     CH3    2     1H       H     -OCH2CH(CH3)O-        CH3   CH3    2     1H       H     -OCH2CH(CH3)O-        CH3   H       2     1H       H     -OCH2CH(CH3)O-        H      H       2     1H       H     -OCH2CH(CH3)O-        Cl     Cl      2     1H       H     -OCH2CH(CH3)O-        Cl     H       2     1H       H     -OCH2CH(CH3)O-        Cl     CH3    2     1CH3    CH3  -OCH2CH(CH3)O-        CH3  CH3    2     1CH3    CH3  -OCH2CH(CH3)O-        CH3   H       2     1CH3    CH3  -OCH2CH(CH3)O-        H      H       2     1CH3    CH3  -OCH2CH(CH3)O-        Cl     Cl      2     1CH3    CH3  -OCH2CH(CH3)O-        Cl     H       2     1CH3    CH3  -OCH2CH(CH3)O-        Cl     CH3    2     1CH3    H     -OCH2CH(CH3)O-        CH3   CH3    2     1CH3    H     -OCH2CH(CH3)O-        CH3   H       2     1CH3    H     -OCH2CH(CH3)O-        H      H       2     1CH3    H     -OCH2CH(CH3)O-        Cl     Cl      2     1CH3    H     -OCH2CH(CH3)O-        Cl     H       2     1CH3    H     -OCH2CH(CH3)O-        Cl     CH3    2     1H       H     -OCH2CH2CH2O-        CH3   CH3    2     1H       H     -OCH2CH2CH2O-        CH3   H       2     1H       H     -OCH2CH2CH2O-        H      H       2     1H              H       -OCH2CH2CH2O-            Cl             Cl      2        1H              H       -OCH2CH2CH2O-            Cl             H       2        1H              H       -OCH2CH2CH2O-            Cl             CH3    2        1CH3           CH3    -OCH2CH2CH2O-            CH3          CH3    2        1CH3           CH3    -OCH2CH2CH2O-            CH3           H       2        1CH3           CH3    -OCH2CH2CH2O-            H              H       2        1CH3           CH3    -OCH2CH2CH2O-            Cl             Cl      2        1CH3           CH3    -OCH2CH2CH2O-            Cl             H       2        1CH3           CH3    -OCH2CH2CH2O-            Cl             CH3    2        1CH3           H       -OCH2CH2CH2O-            CH3           CH3    2        1CH3           H       -OCH2CH2CH2O-            CH3           H       2        1CH3           H       -OCH2CH2CH2O-            H              H       2        1CH3           H       -OCH2CH2CH2O-            Cl             Cl      2        1CH3           H       -OCH2CH2CH2O-            Cl             H       2        1CH3           H       -OCH2CH2CH2O-            Cl             CH3    2        1H              H       -CH2CH2CH2O-             CH3           CH3    2        1H              H       -CH2CH2CH2O-             CH3           H       2        1H              H       -CH2CH2CH2O-             H              H       2        1H              H       -CH2CH2CH2O-             Cl             Cl      2        1H              H       -CH2CH2CH2O-             Cl             H       2        1H              H       -CH2CH2CH2O-             Cl             CH3    2        1CH3           CH3    -CH2CH2CH2O-             CH3          CH3    2        1CH3           CH3    -CH2CH2CH2O-             CH3           H       2        1CH3           CH3    -CH2CH2CH2O-             H              H       2        1CH3           CH3    -CH2CH2CH2O-             Cl             Cl      2        1CH3           CH3    -CH2CH2CH2O-             Cl             H       2        1CH3           CH3    -CH2CH2CH2O-             Cl             CH3    2        1CH3           H       -CH2CH2CH2O-             CH3           CH3    2        1CH3           H       -CH2CH2CH2O-             CH3           H       2        1CH3           H       -CH2CH2CH2O-             H              H       2        1CH3           H       -CH2CH2CH2O-             Cl             Cl      2        1CH3           H       -CH2CH2CH2O-             Cl             H       2        1CH3           H       -CH2CH2CH2O-             Cl             CH3    2        1H              H       -OCH2CH2O-                CH3           CH3    2        0H              H       -OCH2CH2O-                CH3           H       2        0H              H       -OCH2CH2O-                H              H       2        0H              H       -OCH2CH2O-                Cl             Cl      2        0H              H       -OCH2CH2O-                Cl             H       2        0H       H       -OCH2CH2O-                Cl     CH3   2       0CH3    CH3   -OCH2CH2O-                CH3   CH3   2       0CH3    CH3   -OCH2CH2O-                CH3   H      2       0CH3    CH3   -OCH2CH2O-                H      H      2       0CH3    CH3   -OCH2CH2O-                Cl     Cl     2       0CH3    CH3   -OCH2CH2O-                Cl     H      2       0CH3    CH3   -OCH2CH2O-                Cl     CH3   2       0CH3    H      -OCH2CH2O-                CH3   CH3   2       0CH3    H      -OCH2CH2O-                CH3   H      2       0CH3    H      -OCH2CH2O-                H      H      2       0CH3    H      -OCH2CH2O-                Cl     Cl     2       0CH3    H      -OCH2CH2O-                Cl     H      2       0CH3    H      -OCH2CH2O-                Cl     CH3   2       0H       H       oxo                         NO2   H      2       1CH3    CH3   oxo                         CH3   CH3   2       1CH3    CH3   oxo                         CH3   H      2       1CH3    CH3   oxo                         H      H      2       1CH3    CH3   oxo                         Cl     Cl     2       1CH3    CH3   oxo                         Cl     H      2       1CH3    CH3   oxo                         Cl     CH3   2       1CH3    H      oxo                         CH3   CH3   2       1CH3    H      oxo                         CH3   H      2       1CH3    H      oxo                         H      H      2       1CH3    H      oxo                         Cl     Cl     2       1CH3    H      oxo                         Cl     H      2       1CH3    H      oxo                         Cl     CH3   2       1H       H      oxo                         CH3   CH3   1       1H       H      oxo                         CH3   H      1       1H       H      oxo                         H      H      1       1H       H      oxo                         Cl     Cl     1       1H       H      oxo                         Cl     H      1       1H       H      oxo                         Cl     CH3   1       1CH3    CH3   oxo                        CH3   CH3   1       1CH3    CH3   oxo                        CH3   H      1       1CH3    CH3   oxo                        H      H      1       1CH3    CH3   oxo                        Cl     Cl     1       1CH3    CH3   oxo                        Cl     H      1       1CH3    CH3   oxo                        Cl     CH3   1       1CH3    H      oxo       CH3   CH3    1        1CH3    H      oxo       CH3   H       1        1CH3    H      oxo       H      H       1        1CH3    H      oxo       Cl     Cl      1        1CH3    H      oxo       Cl     H       1        1CH3    H      oxo       Cl     CH311 tables 7R3a         R3b         R1      R2             R4       R5   R6           n              m           xH           H           -OCH2CH2O-              CH3      CH3  OH             2              1           NSO2CH3H           H           -OCH2CH2O-              CH3      H     OH             2              1           NSO2CH3H           H           -OCH2CH2O-              H         H     OH             2              1           NSO2CH3H           H           -OCH2CH2O-              Cl        Cl    OH             2              1           NSO2CH3H           H           -OCH2CH2O-              Cl        H     OH             2              1           NSO2CH3H           H           -OCH2CH2O-              Cl        CH3  OH             2              1           NSO2CH3H           H           -OCH2CH2O-              NO2      H     OH             2              1           NSO2CH3H           H           -OCH2CH2O-              CH3      CH3  OH             2              1           OH           H           -OCH2CH2O-              CH3      H     OH             2              1           OH           H           -OCH2CH2O-              H         H     OH             2              1           OH           H           -OCH2CH2O-              Cl        Cl    OH             2              1           OH           H           -OCH2CH2O-              Cl        H     OH             2              1           OH           H           -OCH2CH2O-              Cl        CH3  OH             2              1           OH           H           -OCH2CH2O-              CH3      CH3  OH             2              1           NHH           H           -OCH2CH2O-              CH3      H     OH             2              1           NHH           H           -OCH2CH2O-              H         H     OH             2              1           NHH           H           -OCH2CH2O-              Cl        Cl    OH             2              1           NHH           H           -OCH2CH2O-              Cl        H     OH             2              1           NHH           H           -OCH2CH2O-              Cl        CH3  OH             2              1           NHH           H           -OCH2CH(CH3)O-          CH3      CH3  OH             2              1           NSO2CH3H           H           -OCH2CH(CH3)O-          CH3      H     OH             2              1           NSO2CH3H     H     -OCH2CH(CH3)O-   H      H        OH      2      1       NSO2CH3H     H     -OCH2CH(CH3)O-   Cl     Cl       OH      2      1       NSO2CH3H     H     -OCH2CH(CH3)O-   Cl     H        OH      2      1       NSO2CH3H     H     -OCH2CH(CH3)O-   Cl     CH3     OH      2      1       NSO2CH3H     CH3  -OCH2CH(CH3)O-   CH3  CH3     OH      2      1       OH     CH3  -OCH2CH(CH3)O-   CH3   H        OH      2      1       OH     CH3  -OCH2CH(CH3)O-   H      H        OH      2      1       OH     CH3  -OCH2CH(CH3)O-   Cl     Cl       OH      2      1       OH     CH3  -OCH2CH(CH3)O-   Cl     H        OH      2      1       OH     CH3  -OCH2CH(CH3)O-   Cl     CH3     OH      2      1       OH     H     -OCH2CH(CH3)O-   CH3   CH3     OH      2      1       NHH     H     -OCH2CH(CH3)O-   CH3   H        OH      2      1       NHH     H     -OCH2CH(CH3)O-   H      H        OH      2      1       NHH     H     -OCH2CH(CH3)O-   Cl     Cl       OH      2      1       NHH     H     -OCH2CH(CH3)O-   Cl     H        OH      2      1       NHH     H     -OCH2CH(CH3)O-   Cl     CH3     OH      2      1       NHH     H     -OCH2CH2CH2O-   CH3  CH3     OH      2      1       NSO2CH3H     H     -OCH2CH2CH2O-   CH3   H        OH     2      1       NSO2CH3H     H     -OCH2CH2CH2O-   H      H        OH     2      1       NSO2CH3H     H     -OCH2CH2CH2O-   Cl     Cl       OH     2      1       NSO2CH3H     H     oxo                CH3   CH3     OH      2      1       NSO2CH3H     H     oxo                CH3   H        OH      2      1       NSO2CH3H     H     oxo                H      H        OH      2      1       NSO2CH3H     H     oxo                Cl     Cl       OH      2      1       NSO2CH3H     H     oxo                Cl     H        OH      2      1       NSO2CH3H     H     oxo                Cl     CH3     OH      2      1       NSO2CH3H     H     oxo                NO2   H        OH      2      1       NSO2CH3H     H     oxo                CH3  CH3     OH      2      1       OH     H     oxo                CH3   H        OH      2      1       OH     H     oxo                H      H        OH      2      1       OH     H     oxo                Cl     Cl       OH      2      1       OH     H     oxo                Cl     H        OH      2      1       OH     H     oxo                Cl     CH3     OH      2      1       OH     H     oxo                CH3  CH3     OH      2      1       NHH     H     oxo                CH3   H        OH      2      1       NHH     H     oxo                H      H        OH      2      1       NHH     H     oxo                Cl     Cl       OH      2      1       NHH     H     oxo                Cl     H        OH      2      1       NHH     H     oxo               Cl     CH3    OH      2       1     NHH     H     oxo               CH3   CH3    OH      1       1     NSO2C2H5H     H     oxo               CH3   H       OH      1       1     NSO2C2H5H     H     oxo               H      H       OH      1       1     NSO2C2H5H     H     oxo               Cl     Cl      OH      1       1     NSO2C2H5H     H     oxo               Cl     H       OH      1       1     NSO2C2H5H     H     oxo               Cl     CH3    OH      1       1     NSO2C2H5Table 8
Figure A9619505600861
R3a    R3b     R1      R2      R4     R5    n      m        xH      H       -OCH2CH2O-       CH3    CH3    2      1        NSO2CH3H      H       -OCH2CH2O-       CH3    H       2      1        NSO2CH3H      H       -OCH2CH2O-       H       H       2      1        NSO2CH3H      H       -OCH2CH2O-       Cl      Cl      2      1        NSO2CH3H      H       -OCH2CH2O-       Cl      H       2      1        NSO2CH3H      H       -OCH2CH2O-       Cl      CH3    2      1        NSO2CH3H      H       -OCH2CH2O-       NO2    H       2      1        NSO2CH3H      H       -OCH2CH2O-       CH3    CH3    2      1        OH      H       -OCH2CH2O-       CH3    H       2      1        OH      H       -OCH2CH2O-       H       H       2      1        OH      H       -OCH2CH2O-       Cl      Cl      2      1        OH      H       -OCH2CH2O-       Cl      H       2      1        OH      H       -OCH2CH2O-       Cl      CH3    2      1        OCH3   H       -OCH2CH2O-       CH3    CH3   2      1        NHH      H       -OCH2CH2O-       CH3    H       2      1        NHH      H       -OCH2CH2O-       H       H       2      1        NHH      H       -OCH2CH2O-       Cl      Cl      2      1        NHH      H       -OCH2CH2O-       Cl      H       2      1        NHH      H       -OCH2CH2O-       Cl      CH3    2      1        NHH      H       -OCH2CH(CH3)O-   CH3    CH3   2      1        NSO2CH3H      H       -OCH2CH(CH3)O-   CH3    H       2      1        NSO2CH3H      H       -OCH2CH(CH3)O-   H       H       2      1        NSO2CH3H   -OCH2CH(CH3)O-  Cl     Cl    2     1      NSO2CH3H   -OCH2CH(CH3)O-  Cl     H     2     1      NSO2CH3H   -OCH2CH(CH3)O-  Cl     CH3  2     1      NSO2CH3Table 9R3a    R3b    R1      R2         R4     R5     n         m     R9            R10H       H      -OCH2CH2O-         CH3    CH3     2         1     CH3           HH       H      -OCH2CH2O-         CH3    H        2         1     CH3           HH       H      -OCH2CH2O-         H       H        2         1     CH3           HH       H      -OCH2CH2O-         Cl      Cl       2         1     CH3           HH       H      -OCH2CH2O-         Cl      H        2         1     CH3           HH       H      -OCH2CH2O-         Cl      CH3     2         1     CH3           HCH3    CH3   -OCH2CH2O-         CH3   CH3     2         1     CH3           HCH3    CH3   -OCH2CH2O-         CH3    H        2         1     CH3           HCH3    CH3   -OCH2CH2O-         H       H        2         1     CH3           HCH3    CH3   -OCH2CH2O-         Cl      Cl       2         1     CH3           HCH3    CH3   -OCH2CH2O-         Cl      H        2         1     CH3           HCH3    CH3   -OCH2CH2O-         Cl      CH3     2         1     CH3           HCH3    H      -OCH2CH2O-         CH3    CH3     2         1     CH3           HCH3    H      -OCH2CH2O-         CH3    H        2         1     CH3           HCH3    H      -OCH2CH2O-         H       H        2         1     CH3           HCH3    H      -OCH2CH2O-         Cl      Cl       2         1     CH3           HCH3    H      -OCH2CH2O-         Cl      H        2         1     CH3           HCH3    H      -OCH2CH2O-         Cl      CH3     2         1     CH3           HH       H      -OCH2CH2O-         CH3    CH3     2         1     CH3           CH3H       H      -OCH2CH2O-         CH3    H        2         1     CH3           CH3H       H      -OCH2CH2O-         H       H        2         1     CH3           CH3H       H      -OCH2CH2O-         Cl      Cl       2         1     CH3           CH3H       H      -OCH2CH2O-         Cl      H        2         1     CH3           CH3H       H      -OCH2CH2O-         Cl      CH3     2         1     CH3           CH3CH3    CH3   -OCH2CH2O-         CH3   CH3     2         1     CH3           CH3CH3    CH3   -OCH2CH2O-         CH3    H       2         1     CH3           CH3CH3    CH3    -OCH2CH2O-         H       H       2      1       CH3          CH3CH3    CH3    -OCH2CH2O-         Cl      Cl      2      1       CH3          CH3CH3    CH3    -OCH2CH2O-         Cl      H       2      1       CH3          CH3CH3    CH3    -OCH2CH2O-         Cl      CH3    2      1       CH3          CH3CH3    H       -OCH2CH2O-         CH3   CH3     2      1       CH3          CH3CH3    H       -OCH2CH2O-         CH3    H       2      1       CH3          CH3CH3    H       -OCH2CH2O-         H       H       2      1       CH3          CH3CH3    H       -OCH2CH2O-         Cl      Cl      2      1       CH3          CH3CH3    H       -OCH2CH2O-         Cl      H       2      1       CH3          CH3CH3    H       -OCH2CH2O-         Cl      CH3    2      1       CH3          CH3H       H       -OCH2CH2O-         CH3    CH3    2      0       CH3          HH       H       -OCH2CH2O-         CH3    H       2      0       CH3          HH       H       -OCH2CH2O-         H       H       2      0       CH3          HH       H       -OCH2CH2O-         Cl      Cl      2      0       CH3          HH       H       -OCH2CH2O-         Cl      H       2      0       CH3          HH       H       -OCH2CH2O-         Cl      CH3    2      0       CH3          HCH3    CH3    -OCH2CH2O-         CH3   CH3    2      0       CH3          HCH3    CH3    -OCH2CH2O-         CH3    H       2      0       CH3          HCH3    CH3    -OCH2CH2O-         H       H       2      0       CH3          HCH3    CH3    -OCH2CH2O-         Cl      Cl      2      0       CH3          HCH3    CH3    -OCH2CH2O-         Cl      H       2      0       CH3          HCH3    CH3    -OCH2CH2O-         Cl      CH3    2      0       CH3          HCH3    H       -OCH2CH2O-         CH3   CH3    2      0       CH3          CH3CH3    H       -OCH2CH2O-         CH3    H       2      0       CH3          CH3CH3    H       -OCH2CH2O-         H       H       2      0       CH3          CH3CH3    H       -OCH2CH2O-         Cl      Cl      2      0       CH3          CH3CH3    H       -OCH2CH2O-         Cl      H       2      0       CH3          CH3CH3    H       -OCH2CH2O-         Cl      CH3    2      0       CH3          CH3H       H       -OCH2CH2O-         CH3   CH3    2      0       CH3          CH3H       H       -OCH2CH2O-         CH3    H       2      0       CH3          CH3H       H       -OCH2CH2O-         Cl      Cl      2      0       CH3          CH3H       H       -OCH2CH2O-         Cl      H       2      0       CH3          CH3H       H       -OCH2CH2O-         Cl      CH3    2      0       CH3          CH3CH3    CH3    -OCH2CH2O-         CH3    CH3   2      0       CH3          CH3CH3    CH3    -OCH2CH2O-         CH3    H       2      0       CH3          CH3CH3    CH3    -OCH2CH2O-         H       H       2      0       CH3          CH3CH3    CH3    -OCH2CH2O-         Cl      Cl      2      0       CH3          CH3Preparation and purposes
The compound of the present invention is used usually as preparation or composition, and the preparation or composition are added with containing at least one liquid diluent, the agriculturally suitable carrier of solid diluent or surfactant.The selection of preparation or composition composition should be with active ingredient physical property, the type of use pattern and environmental factor such as soil, humidity, and temperature are consistent.Useful preparation includes liquid such as solution (including emulsifiable concentrate), suspension, emulsion (including micro emulsion and/or suspension emulsion (suspoemulsions)) etc., and they can be arbitrarily thickened as gel.Useful preparation also includes solid such as dust, powder agent, granule, pill, tablet, film etc., and they can be can be dispersed in water (wettable) or water miscible.Active ingredient can (micro-) it is encapsulated, and can further form suspension or solid pharmaceutical preparation；In addition, the whole preparation containing active ingredient can be with encapsulated (or " coating ").It is encapsulated to control or postpone the release of active ingredient.Spray formulation can be distributed in suitable medium, and can be used with per hectare sprinkling about one to a few hectolitre volumes.The composition of high concentration is mainly used as the intermediate of further formulated.
Preparation typically contains the active ingredient effective dose in following approximate extents, diluent and surfactant, and each composition sum is 100% weight.
Percetage by weight
Active ingredient diluent surfactant water disperses and water miscible particle, 5-90 0-94 1-15 tablets and powder agent suspension, emulsion, solution 5-50 40-95 0-15 (including emulsifiable concentrate) dust agent 1-25 70-99 0-5 granules and pill 0.01-99 5-99.99 0-15 high concentration composition 90-99 0-10 0-2
Typical solid diluent is recorded in Watkins et al. Handbook of InsecticideDust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.Typical liquid diluent is recorded in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, and 1950.McCutcheon ' sDetergents and Emulsifiers Annual, Allured Publ.Corp., Ridgewood, New Jersey, and Sisely and Wood, Encyclopedia ofSurface Active Agents, Chemical Publ.Co., Inc., New York, 1964.These documents list surfactant and recommend application.All preparations may all lump containing a small amount of additive to reduce foam, corrosion, microorganism growth etc., or thickener is to increase viscosity.
Surfactant includes the alcohol of for example many ethoxylations; the alkyl phenol of many ethoxylations, the fatty acid esters of sorbitan of many ethoxylations, the dialkyl succinate of sulfonation; alkyl sodium sulfate ester; alkylbenzenesulfonate, organic silicone, N; N- dialkyltaurates; lignosulphonates, naphthalenesulfonate formaldehyde condensation compound, polycarbonate and polyoxyethylene/polyoxypropylene block copolymers.Solid diluent includes such as clay such as bentonite, covers support soil, attapulgite clay and kaolin, starch, sugar, silica, talcum, diatomite, urea element, calcium carbonate, sodium carbonate and sodium acid carbonate and sodium sulphate.Liquid diluent includes such as water, DMF, dimethyl sulfoxide, N- alkyl pyrrolidones, ethylene glycol, polypropylene glycol, hydro carbons, alkylbenzene, alkylnaphthalene, olive oil, castor oil, Linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil and coconut oil, fatty acid ester, ketone such as cyclohexanone, 2-HEPTANONE, isophorone and 4- hydroxy-4-methyl-2-pentanones, and alcohols such as methanol, cyclohexanol, decyl alcohol and tetrahydrofuran alcohol.
Solution (including emulsifiable concentrate) can be prepared by simply by each component mixing.Dust agent, powder agent is typically to grind to prepare in hammer-mill or fluid-energy mill.Suspension is general to be prepared by wet-mill method, for example, see US 3,060,084.Granule and pill are shown in Browning, " Agglomeration " by the way that active ingredient is sprayed on the particulate vector of advance comprising or prepared by agglutination technology, Chemical Engineering, December 4,1967, pp147-80, Perry ' s Chemical Engineer ' s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp8-57 and with nextpage, and WO 91/13546.Pill can be prepared according to described in U.S 4,172,714.Water dispersible and water-soluble granular formulation can be prepared according to U.S 4,144,050, U.S.3,920,442 and DE 3,246,493 teaching.Tablet can be prepared according to U.S.5,180,587, U.S.5,232,701 and U.S.5,208,030 teaching, and film can be prepared according to GB 2,095,558 and U.S.3,299,566 teaching.
It is related to other data of preparation technique, referring to U.S.3,235,361, the row of the 6th column 16 to the row of the 7th column 19 and embodiment 10-41；U.S.3,309,192, the row of the 5th column 43 to the row of the 7th column 62 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, the row of the 3rd column 66 to the row of the 5th column 17 and embodiment 1-4；Klingman, Weed Controlas a Science, John Wiley and sons, Inc., New York, Weed the Control Handbook, 8thEd. of 1961, pp81-96 and Hance et al., Blackwell Scientific Publications, Oxford, 1989.
In following examples, all percentages are all percetages by weight, and all formulations are prepared with conventional method, and compound number refers to the compound in concordance list A-C.
Example A high concentration concentrates
Compound 2 98.5%
Siliceous reinforcing agent 0.5%
Synthesize unformed thin silica 1.0%
Example B wettable powders
Compound 8 65.0%
Dodecylphenol polyglycol ether 2.0%
Sodium lignosulfonate 4.0%
Sodium silicoaluminate 60%
Cover native (calcining) 23.0% of support
Example C granules
Compound 2 100%
Attapulgite clay particle (low volatile, 90.0%
0.71/0.30mm；U.S.S.No.25-50 mesh)
Example D extrudes pill
Compound 8 25.0%
Anhydrous sodium sulfate 10.0%
Thick Lignosite 5.0%
Negel 1.0%
Calcium/magnesium bentonite 59.0%
Result of the test points out, compound of the invention be high activity bud before and post-emergence herbicide or plant growth regulator.Their many are used as before buds of wide spectrum and/or Weeds distribution after bud, and the place for needing to be controlled completely used in all plants, for example around fuel reservoir, industrial warehouse, open parking ground, theater parking lot, airport, riverbank, irrigation canal or other water channels, around billboard, highway and railway.Some compounds are used for selectively control weeds and broadleaved herb, but allow important crop growth, these crops are (but not limited to) clovers, barley, cotton, wheat, rape, beet, corn (maize), sorghum, soybean, rice, oat, peanut, vegetables, tomato, potato, perennial plantation crops include coffee, cocoa, oil palm, rubber, sugarcane, citrus, grape, fruit tree, nutwood, banana, Asiatic plantain, pineapple, golden hop, tea and forest such as eucalyptus and coniferous tree (such as torch pine), and turf (such as Kentucky bluegrass, St.Augustine grass, Kentucky fescue and Bermuda grass).It will be apparent to those skilled in that, not all compound is all same effective to all weeds, in addition, the compounds of this invention is also adjusted for plant growth.
The compounds of this invention can be used alone, and can also be used together with other Commercial herbicides, insecticide or fungicide.The compounds of this invention can also combine Commercial herbicides safener such as benoxacor, and allyl dichloride amine and furilazole are using to improve the security to some crops.The mixture of one or more following herbicides and the compounds of this invention is especially possible for controlling weeds：Acetochlor,Acifluorfen and its sodium salt,Aclonifen,Methacrylaldehyde (2- methacrylaldehyde),Alachlor,Ametryn,Amino Huang is grand,Amrol,Amcide Ammate,Anilofos,Asulam,Atrazine,azimsulfuron,Benazolin,Benazolin-ethyl,Benfluralin,Benfuresate,Benzyl ethyl methyl-methyl,Bensulide,Bentazon,Bifenox,Bromacil,Leptophos,Leptophos caprylate,Machete,Butralin,Butylate,chlomethoxyfen,Amiben,Bromax,Pyrazon,Green ethyl methyl-ethyl,Mo 9 granular,Chlortoluron,Nitrogen grass amine spirit,Chlorsulfuron,Chlorthal-dimethyl,Cinmethylin,Cinosulfuron,Clethodim,Clomazone,Chloropyridine acid,Chloropyridine acid-olamine,Bladex,cyclosulfamuron,2,4-D and its butoxy,Butyl,Iso-octyl and isopropyl esters and its Dimethyl Ammonium,Diolamine and trolamine salt,Daimuron,Dalapon,Dalapon-Na,Dazomet,2,4-DB and its Dimethyl Ammonium,Potassium and sodium salt,Desmedipham,Desmetryn,Mediben and its diethylene glycol (DEG) ammonium,Dimethyl Ammonium,Potassium and sodium salt,Dichlobenil,2,4- drop propionic acid,Diclofop-methyl-methyl,2-[4,5- dihydro -4- methyl -4- (1- Methylethyls) -5- oxygen -1H- imidazoles -2- bases] -5- methyl-Niacin Nicitinic Acid (AC263,222),difenzoquat metilsulfate,Diflufenican,Dimepiperate,dimethenamid,Cacodylic acid and its sodium salt,Dinitramine,Enide,Diquat,Dithiopyr,Diuron,DNOC,Endothall,EPTC,Esprocarb,Ethalfluralin,ethametsulfuron-methyl,Ethofumesate,α,The chloro- 5- of 2- bis- [4- (difluoromethyl) -4,5- dihydro -3- methyl -5- oxygen -1H-1,2,4- triazol-1-yls] -4- fluorobenzene ethyl propionate (F8426),Oxazole diclofop-methyl,Gao oxazole diclofop-methyl-P- ethyls,Urab,Urab-TCA,Wheat straw lies prostrate M- methyl,Wheat straw volt-M- isopropyls,Wheat straw volt-M methyl,flazasulfuron,Fluazifop-butyl,Fluazifop-P- butyl,Fluchloralin,flumetsulam,Flumiclorac- amyl groups,flumioxazin,Fluometuron,Acetic acid AKH7088-ethyl,Amine grass azoles,Fluorine determines ketone,Fluorochloridone,Fluroxypramide,Fomesafen,Creeping weed phosphorus-ammonium,Glufosinate,Glufosinate-ammonium,Glyphosate,Glyphosate-isopropyl ammonium,Glyphosate-sesquialter sodium,Glyphosate-trimesium,halosulfuron-methyl,Haloxyfop-etotyl,Haloxyfop methyl,Hexazinone,Miaow grass ester-methyl,imazamox(AC299263),Arsenal,Scepter-ammonium,Imazethapyr,Imazethapyr-ammonium,imazosulfuron,Ioxynil,Octanoate,Ioxynil-Na,Isoproturon,Yi Evil are grand,isoxaben,isoxaflutole(RPA 201772),Lactofen,Lenacil,Profit is situated between grand,Maleic acid hydrazide,MCPA and its dimethylammonium,Potassium and sodium salt,MCPA- iso-octyl,2- first -4- chloropropionic acids,2- first -4- chloropropionic acids-P,Mefenacet,Mefluidide,Go out hundred mu of-Na,Methabenz thiazuron,[[the fluoro- 5- of the chloro- 4- of 2- [(tetrahydrochysene -3- oxygen -1H,3H-[1,3,4] thiadiazoles simultaneously [3,4-a] pyridazine -1- subunits) amino] phenyl] thio acetate (KIH 9201),Methylarsonic acid and its calcium,Single ammonium,Single sodium and disodium salt,[[[1- [5- [2- chloro- 4- (trifluoromethyl) benzene oxygen] -2- nitrobenzophenones] -2- methoxies ethylidene] amino] oxygen] methyl acetate (AKH-7088),5-[[[[(4,6- dimethyl -2- pyrimidine radicals) amino] carbonyl] amino] sulfonyl] -1- (2- pyridine radicals) -1H- pyrazoles -4- carboxylate methyl esters (NC-330),metobenzuron,Isopropyl methoxalamine,metosulam,Metoxuron,Metribuzin,Metsulfuron-methyl-methyl,Hydram,Afesin,Proproanmide,Alanap,Neburea,Nicosulfuron,Monometflurazone,Oryzalin,Evil grass spirits,3-oxetanyl 2-[[[[(4,6- dimethyl -2- pyrimidine radicals) amino] carbonyl] amino] sulfonyl] benzoic ether (CGA 277476),Oxyfluorfen,Aerial gramoxone dichloride,Pebulate,Pendimethalin,Yellow grass is lied prostrate,Phenmedipham,Picloram,Picloram-potassium,Pretilachlor,Fluoropyrimidinesulfuron-methyl,Prometon,Prometryn,Propachlor,Propanil,Propaquizafop,Propazine,Chem hoe,Na Yingte,prosulfuron,pyrazolynate,Pyrazosulfuron-ethyl,Pyridate,pyrithiobac,pyrithiobac-Na,quinelorac,Quizalofop-ethyl-ethyl,Quizalofop-ethyl-P- ethyls,Quizalofop-ethyl-P-tefuryl,rimsulfuron,Sethoxydim,Tupersan,Simanex,sulcotrione(ICIA 0051),sulfometuron-methyl,TCA,TCA-Na,Terbufos benzthiazuron,Terbacil,Special Kusatsu,Terbutryn,Thenyl,thiafluamide(BAY 11390),Thiophene methyl-methyl,Benthiocarb,Tralkoxydim,tri-allate,Triasulfuron,Tribenuron-methyl-methyl,Triclopyr,Triclopyr-butotyl,Triclopyr-triethyl ammonium,Tridiphane,Trefanocide,triflusulfuron-methyl,And vernolate.
In some cases, if will be particularly advantageous for preventing and treating resistant weed growth from having similar control spectrum but thering are other herbicides of different binding modes to combine.
To better control over unwanted plant (such as relatively low consumption, widely control weeds spectrum or the security of increase crop) or be the growth of prevention resistant weed, using the compounds of this invention and the mixture selected from following herbicides is preferred：Atrazine, bladex, Imazethapyr and its salt, Imazethapyr-ammonium, nicosulfuron, Fluoropyrimidinesulfuron-methyl, pyrazoles Huang is grand-ethyl and rimsulfuron.Particularly preferred mixture is selected from (compound number refers to the compound in concordance list A-C)：Compound 1 and atrazine；Compound 1 and bladex；Compound 1 and Imazethapyr；Compound 1 and nicosulfuron；Compound 1 and Fluoropyrimidinesulfuron-methyl；Compound 1 and pyrazoles Huang it is grand-ethyl；Compound 1 and rimsulfuron；Compound 2 and atrazine；Compound 2 and bladex；Compound 2 and Imazethapyr；Compound 2 and nicosulfuron；Compound 2 and Fluoropyrimidinesulfuron-methyl；Compound 2 and the yellow grand ethyl of pyrazoles；Compound 2 and rimsulfuron；Compound 7 and atrazine；Compound 7 and bladex；Compound 7 and Imazethapyr；Compound 7 and nicosulfuron；Compound 7 and Fluoropyrimidinesulfuron-methyl；Compound 7 and pyrazoles Huang it is grand-ethyl；Compound 7 and rimsulfuron；Compound 8 and atrazine；Compound 8 and bladex；Compound 8 and Imazethapyr；Compound 8 and nicosulfuron；Compound 8 and Fluoropyrimidinesulfuron-methyl；Compound 8 and pyrazoles Huang it is grand-ethyl；Compound 8 and rimsulfuron；Compound 10 and atrazine；Compound 10 and bladex；Compound 10 and Imazethapyr；Compound 10 and nicosulfuron；Compound 10 and Fluoropyrimidinesulfuron-methyl；Compound 10 and pyrazoles Huang it is grand-ethyl；Compound 10 and rimsulfuron.
The herbicidally effective amount of the compounds of this invention is decided by many factors, and these factors include：Selected preparation, application process, the quantity and type of plant, growth conditions etc..In general, the effective quantity of the compounds of this invention weeding is 0.001-20kg/ha, preferably 0.004-1.0kg/ha.Those skilled in the art can be readily determined herbicidally effective amount necessary to degree needed for control weeds.
Tests below illustrates control effect of the compounds of this invention for specific weeds.But, the weeds of the compounds of this invention control are not limited to these kinds, and the explanation of compound is shown in concordance list AC, and abbreviation " dec " points out that compound is decomposed in fusing, abbreviation " Ex " represents embodiment, and numeral behind illustrates that compound is to prepare in this embodiment.
Concordance list A
Figure A9619505600951
Formulas I, wherein Q are Q-1, and X is S (O)n, Y and Z are CH2, 0 and x is 1Cmpd R in k3a R3b R1     R2       R4    R5   R6  n  m    m.p.(℃)1(Ex.1)     H    H    -OCH2CH2O-      H      H     OH    2  1    131(dec)2(Ex.5)     H    H    -OCH2CH2O-      CH3   CH3  OH    2  1    130(dec)3           H    H    -OCH2CH(CH3)O-  CH3   CH3  OH    2  1    159-1604(Ex.3)     H    H    -OCH2CH2O-       Cl     Cl    OH    2  1    140(dec)5           H    H    oxo                H      H      OH    2  1    168(dec)6a(Ex.6)   H    H    -SCH2CH2S-      CH3   CH3  OH    0  1    217-222aCompound contains 2,3- dihydro -5,8- dimethyl spiral shell [4H-1- benzothiopyran derivative -4,2 '-[1,3] dithiolanes] -6- carboxylic acids of about 16% weight.
Concordance list B
Figure A9619505600961
Formulas I, wherein Q are Q-2, and X is S (O)n, and k is 0Cmpd R3a R3b  R1    R2      R4   R5  R8 n    m    m.p.(℃)7(Ex.2)  H    H     -OCH2CH2O-    H     H    H    2    1    oil*8(Ex.4)  H    H     -OCH2CH2O-    CH3  CH3 H   2    1    111(dec)9        H    H     -OCH2CH2O-    Cl    Cl   H    2    1    130(dec)10       H    H     oxo             CH3  CH3 H    2    1    semi-solid*
*1H NMR datas are shown in concordance list C.
Concordance list C
Cmpd No.    1H NMR Data(CDCl3Solution, unless otherwise indicated)a
7 δ 1.46 (1,3H), 2.7 (m, 2H), 3.7 (m, 2H), 4.1 (q, 2H), 4.2-4.3 (m, 4H), 7.7-8.0
         (4H)
10 δ 1.5 (t, 3H) .2.5 (s, 3H), 2.8 (s, 3H), 3.3 (m, 2H), 3.7 (m, 2H), 4.1 (q, 2H),
         7.3-7.46(2H).
a1H NMR datas are represented with the low field ppm since tetramethylsilane.Coupling is used
(s)-unimodal, (t)-triplet, (q)-quartet, (m)-many
Point out at weight peak.
The biological test embodiment experiment A of the present invention
Barley seed (Hordeum vulgare),Barnyard grass (Echinochloa crus-galli),Bedstraw (Galium aparine),Rush (Alopecurus myosuroides),Chickweed (Stellaria media),Storehouse ear (Xanthium strumarium),Corn (Zeamays),Cotton (Gossypium hirsutum),Lady's-grass (Digitaria sanguinalis),Downy brome (Bromus tectorum),Big fox-brush (Setaria faberii),Lamb's-quarters (Chenopodium album),(Ipomoea hederacea) is spent towards face,Rape (Brassica napus),Rice (Oryza sativa),Sorghum (Sorghum bicolor),Soybean (Glycine max),Beet (Beta vulgaris),Velvetleaf (Abutilontheophrasti),Wheat (Triticum aestivum),RHIZOMA FAGOPYRI CYMOSI (Polygonumconvolvulus),The seed and the rhizome of nutgrass flatsedge (Cyperusrotundus) stem tuber of wild oat (Avena fatua),The test compound prepared in non-plant toxicity solvent mixture (wherein containing surfactant) carries out bud pre-treatment.
Simultaneously, these crops and weeds also carry out bud post processing with the test compound in kind prepared, bud post processing plant height is 2-18cm (1-4 leaf ages), the plant of processing and check plant are put in greenhouse 12-16 days, are then compared the plant of processing and tester, for being visually evaluated, the result grade classification being listed in Table A is 0-10,0 represents to no effect, and 10 represent control completely, and (-) indicates no result of the test.Table A, , , , compound, , Table A, , , compound amount 2000g/ha, , 1, 5, 7, consumption 2000g/ha, 1, 5, after 7 buds, , , , , , , barley before bud, , , , 0, 0, 0, barley, , , 0, 0, 0 barnyard grass, , , , 8, 0, 9, barnyard grass, , , 0, 0, 2 bedstraws, , , , 6, 0, 8, bedstraw, , 5, -, 2 rushes, , , , 1, 0, 0, rush, , 0, 0, 1 chickweed, , , , 9, 0, 9, chickweed, , , 7, 0, 3 storehouse ears, , , , 9, 0, 9, storehouse ear, , , 4, 0, 0 corn, , , , 0, 0, 1, corn, , , 0, 0, 0 cotton, , , , 9, 0, 9, cotton, , , 1, 0, 0 lady's-grass, , , , 8, 0, 9, lady's-grass, , , 6, 0, 7 downy bromes, , , , 0, 0, 0, downy brome, , 0, -, 2 big fox-brush, , , , 2, 0, 8, big fox-brush, , 1, 0, 3 lamb's-quarters, , , , , 9, 0, 9, lamb's-quarters, , , 9, -, 10 spend towards face, , , , 9, 0, 2, towards face flower, , 2, 0, 0 nutgrass flatsedge, , , , 1, -, 2, nutgrass flatsedge, , , 0, 0, 0 rape, , , , 9, 0, 9, rape, , , 10, -, 7 rice, , , , , 8, 0, 8, rice, , , 9, 0, 3 sorghums, , , , 2, 0, 3, sorghum, , , 0, 0, 0 soybean, , , , 9, 0, 9, soybean, , , 2, 0, 3 beets, , , , 10, 0, 10, beet, , , 9, -, 8 velvetleafs, , , , 9, 0, 9, velvetleaf, , 6, 0, 1 wheat, , , , 0, 0, 0, wheat, , , 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 7, 0, 7, RHIZOMA FAGOPYRI CYMOSI, , 0, -, 0 wild oat, , , , 0, 0, 0, wild oat, , 0, 0, 0 Table A, , , , , , , compound amount 400g/ha, , 1, 2, 3, 4, 5, 6, 7, 8, barley after 9 buds, , , , 0, 9, 9, 5, 0, 5, 0, 0, 2 barnyard grasses, , , , 2, 9, 10, 9, 0, 9, 9, 9, 9 bedstraws, , , 5, 9, 9, 9, 0, 9, 7, 9, 9 rushes, , , 0, 9, 9, 7, 0, 4, 0, 2, 3 chickweeds, , , , 8, 9, 10, 8, 0, 9, 7, 9, 7 storehouse ears, , , , 7, 9, 9, 9, 0, 9, 9, 9, 9 corns, , , , 0, 9, 5, 2, 0, 1, 1, 7, 1 cotton, , , , 7, 10, 10, 10, 0, 9, 9, 9, 9 lady's-grass, , , , 3, 10, 9, 7, 0, 6, 9, 9, 3 downy bromes, , , 0, 9, 9, 6, 0, 0, 0, 2, 2 big fox-brush, , , 1, 9, 9, 5, 0, 1, 3, 9, 6 lamb's-quarters, , , , 6, 9, 9, 9, 0, 9, 8, 9, 9 spend towards face, , , 7, 10, 10, 10, 0, 9, 2, 8, 6 nutgrass flatsedges, , , , 0, 7, 9, 2, 0, 2, 0, -, 1 rape, , , , 8, 8, 10, 10, 0, 10, 8, 10, 10 rice, , , , 7, 9, 10, 9, 0, 9, 7, 9, 9 sorghums, , , , 0, 9, 9, 9, 0, 2, 2, 9, 2 soybean, , , , 8, 10, 10, 9, 0, 9, 8, 9, 4 beets, , , , 10, 10, 10, 10, 0, 10, 10, 10, 10 velvetleafs, , , 9, 10, 10, 10, 0, 10, 9, 9, 9 wheats, , , , 0, 10, 9, 8, 0, 3, 0, 6, 2 RHIZOMA FAGOPYRI CYMOSIs, , , 2, 8, 9, 6, 0, 5, 6, 9, 6 wild oats, , , 0, 9, 9, 4, 0, 4, 0, 8, 3 Table As, , , , , , , compound amount 400g/ha, , 1, 2, , 3, 4, 5, 6, 7, 8, barley before 9 buds, , , , 0, 3, , 0, 0, 0, 0, 0, 0, 0 barnyard grass, , , , 0, 10, 9, 5, 0, 0, 0, 9, 2 bedstraws, , , -, 9, , 8, 5, 0, 4, 0, 7, 2 rushes, , , 0, 2, , 2, 2, 0, 0, 0, 0, 0 chickweed, , , , 0, 8, , 10, 4, -, 7, 0, 8, 7 storehouse ears, , , , 0, 6, , 9, 6, 0, 2, 0, 0, 3 corns, , , , 0, 0, , 0, 0, 0, 0, 0, 0, 0 cotton, , , , 0, 6, , 4, 8, 0, 2, 0, 1, 7 lady's-grass, , , , 0, 10, 10, 8, 0, 4, 1, 8, 2 downy bromes, , , 0, 6, , 1, 6, 0, 0, 0, 0, 0 big fox-brush, , , 0, 6, , 3, 2, 0, 0, 0, 6, 1 lamb's-quarters, , , , 5, 10, 10, 10, -, 9, 9, 9, 9 spend towards face, , , 0, 7, , 9, 6, -, 1, 0, 2, 0 nutgrass flatsedge, , , , -, 10, 10, 3, 0, 0, 0, 0,-rape, , , , 0, 3, , 3, 9, 0, 0, 0, 0, 0 rice, , , , 0, 9, , 10, 7, 0, 1, 0, 6, 3 sorghums, , , , 0, 6, , 3, 2, 0, 0, 0, 5, 0 soybean, , , , 0, 9, , 9, 6, 0, 0, 0, 3, 0, beet, , , , 9, 10, 10, 10, 0, 8, 0, 9, 9 velvetleafs, , , 0, 10, 10, 10, 0, 6, 0, 10, 0 wheat, , , , 0, 7, , 2, 0, 0, 0, 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , 0, 7, , 9, -, 6, 0, 0, 0, 3 wild oats, , , 0, 4, , 2, 0, 0, 0, 0, 0, 0 Table A, , , compound, , Table A, , , compound amount 200g/ha, , 6, , , consumption 200g/ha, before 6 buds, , , , , , barley after bud, , , 5, , , barley, , , 0 barnyard grass, , , 9, , , barnyard grass, , , 0 bedstraw, , , 9, , , bedstraw, , , 2 rushes, , , 3, , , rush, , , 0 chickweed, , , 9, , , chickweed, , , 4 storehouse ears, , , 9, , , storehouse ear, , , 3 corns, , , 1, , , corn, , , 0 cotton, , , 9, , , cotton, , , 0 lady's-grass, , , 5, , , lady's-grass, , , 6 downy bromes, , , 0, , , downy brome, , , 0 big fox-brush, , , 2, , , big fox-brush, , , 0 lamb's-quarters, , , , 9, , , lamb's-quarters, , , , 9 spend towards face, , , 9, , , towards face flower, , , 1 nutgrass flatsedge, , , 2, , , nutgrass flatsedge rape, , , 10, , rape, , , 0 rice, , , , 9, , , rice, , , ,-sorghum, , , 2, , , sorghum, , , 0 soybean, , , 8, , , soybean, , , 0 beet, , , 10, , beet, , , 8 velvetleafs, , , 10, , velvetleaf wheat, , , 3, , , wheat, , , 0 RHIZOMA FAGOPYRI CYMOSI, , , 5, , , RHIZOMA FAGOPYRI CYMOSI, , , 0 wild oat, , , 4, , , wild oat, , , 0 Table A, , , , , , compound amount 100g/ha, , 2, 3, 4, 6, 8, barley after 9 buds, , , , 7, 8, 4, 3, 0, 0 barnyard grass, , , , 9, 9, 8, 9, 9, 9 bedstraws, , , 9, 9, 9, 8, 9, 6 rushes, , , 5, 8, 5, 1, 0, 2 chickweeds, , , , 9, 9, 7, 9, 9, 7 storehouse ears, , , , 9, 9, 9, 9, 9, 8 corns, , , , 7, 3, 1, 0, 5, 0 cotton, , , , 10, 10, 10, 9, 9, 9 lady's-grass, , , , 9, 9, 2, 3, 9, 2 downy bromes, , , 6, 9, 5, 0, 0, 0 big fox-brush, , , 9, 9, 3, 1, 9, 4 lamb's-quarters, , , , 9, 9, 9, 9, 9, 8 spend towards face, , , 10, 10, 10, 9, 8, 1 nutgrass flatsedge, , , , 7, 6, 2, 0, 6, 0 rape, , , , 3, 7, 8, 6, 8, 8 rice, , , , 9, 10, 9, 8, 8, 6 sorghums, , , , 9, 9, 9, 2, 9, 0 soybean, , , , 10, 10, 8, 8, 8, 3 beets, , , , 10, 10, 10, 10, 10, 9 velvetleafs, , , 10, 10, 10, 10, 9, 2 wheats, , , , 8, 8, 6, 2, 2, 1 RHIZOMA FAGOPYRI CYMOSI, , , 7, 9, 6, 3, 7, 6 wild oats, , , 4, 6, 3, 2, 4, 2 Table As, , , , , compound amount 100g/ha, , 2, 3, 4, 6, 8, barley before 9 buds, , , 0, 0, 0, 0, 0, 0 barnyard grass, , , 10, 8, 1, 0, 0, 0 bedstraw, , , 8, 8, 6, 0, 3, 0 rush, , , 0, 0, 1, 0, 0, 0 chickweed, , , 8, 8, 3, 0, 6, 7 storehouse ears, , , 2, 3, 2, 0, 0, 0 corn, , , 0, 0, 0, 0, 0, 0 cotton, , , 3, 4, 3, 0, 0, 0 lady's-grass, , , 9, 9, 7, 1, 6, 0 downy brome, , , 0, 0, 0, 0, 0, 0 big fox-brush, , , 1, 2, 1, 0, 4, 0 lamb's-quarters, , , , 9, 10, 9, 8, 9, 8 spend towards face, , , 2, 2, 5, 0, 0, 0 nutgrass flatsedge, , , 0, 1, -, 0, -,-rape, , , 0, 0, 3, 0, 0, 0 rice, , , , 9, 8, 7, 0, 2, 0 sorghum, , , 3, 0, 1, 0, 0, 0 soybean, , , 8, 9, 5, 0, 0, 0 beet, , , 10, 10, 10, 0, 9, 9 velvetleafs, , , 10, 9, 9, 0, 5, 0 wheat, , , 0, 0, 0, 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , 3, 2, 2, 0, 0, 0 wild oat, , , 1, 0, 0, 0, 0, 0 Table A, , , compound, Table A, , , compound amount 5g/ha, 3, 6, consumption 5g/ha, 3, after 6 buds, , , , , barley before bud, , , 4, 1, barley, , , 0, 0 barnyard grass, , , 9, 9, barnyard grass, , , 5, 0 bedstraw, , 9, 8, bedstraw, , 2, 0 rush, , 6, 0, rush, , 0, 0 chickweed, , , 9, 9, chickweed, , , 7, 0 storehouse ear, , , 9, 9, storehouse ear, , , 3, 0 corn, , , 1, 0, corn, , , 0, 0 cotton, , , 10, 9, cotton, , , 0, 0 lady's-grass, , , 9, 3, lady's-grass, , , 8, 1 downy brome, , 7, 0, downy brome, , 0, 0 big fox-brush, , 8, 0, big fox-brush, , 2, 0 lamb's-quarters, , , 9, 9, lamb's-quarters, , , 10, 8 spend towards face, , 10, 9, towards face flower, , 0, 0 nutgrass flatsedge, , , 6, 1, nutgrass flatsedge, , , 0, 0 rape, , , 6, -, rape, , , 0, 0 rice, , , 10, 9, rice, , , 8, 0 sorghum, , , 9, 1, sorghum, , , 0, 0 soybean, , , 10, 8, soybean, , , 6, 0 beet, , , 10, 10, beet, , , 10, 0 velvetleaf, , 10, 10, velvetleaf, , 7, 0 wheat, , , 8, 2, wheat, , , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , 8, 3, RHIZOMA FAGOPYRI CYMOSI, , 0, 0 wild oat, , 6, 2, wild oat, , 0, 0 Table A, , , compound, , Table A, , , compound amount 10g/ha, 3, , , consumption 10g/ha, after 3 buds, , , , , barley before bud, , , 2, , , barley, , , 0 barnyard grass, , , 9, , , barnyard grass, , , 0 bedstraw, , 7, , , bedstraw, , 0 rush, , 3, , , rush, , 0 chickweed, , , 7, , , chickweed, , , 0 storehouse ear, , , 9, , , storehouse ear, , , 1 corn, , , 0, , , corn, , , 0 cotton, , , 10, , cotton, , , 0 lady's-grass, , , 8, , , lady's-grass, , , 2 downy bromes, , 0, , , downy brome, , 0 big fox-brush, , 2, , , big fox-brush, , 0 lamb's-quarters, , , 9, , , lamb's-quarters, , , 10 spend towards face, , 9, , , towards face flower, , 0 nutgrass flatsedge, , , 0, , , nutgrass flatsedge, , , 0 rape, , , 0, , , rape, , , 0 rice, , , 9, , , rice, , , 1 sorghum, , , 3, , , sorghum, , , 0 soybean, , , 7, , , soybean, , , 2 beets, , , 10, , beet, , , 9 velvetleafs, , 10, , velvetleaf, , 2 wheats, , , 2, , , wheat, , , 0 RHIZOMA FAGOPYRI CYMOSI, , 2, , , RHIZOMA FAGOPYRI CYMOSI, , 0 wild oat, , 1, , , wild oat, , 0 experiment B
The compound evaluated in this experiment is prepared in the non-plant toxicity solvent mixture containing surfactant, and the soil surface of (being applied before bud) before occurring for plant seedlings, (irrigate and apply) in water for irrigation soils surface, and the plant (being applied after bud) for 1-4 leaf ages.Sand fertile soil is used for before bud and post-emergence test, and mud fertile soil is used for irrigation tests.The depth of water applied for irrigating is 2.5cm, and keeps during testing this depth.
Plant variety before bud with post-emergence test is made up of following species：Barnyard grass (Echinochloacrus-galli),Barley (Hordeum vulgare),Bedstraw (Galium aparine),Rush (Alopecurus myosuroides),Chickweed (Stellaria media),Storehouse ear (Xanthium strumarium),Corn (Zea mays),Cotton (Gossypiumirsutum),Lady's-grass (Digitaria sanguinalis),Downy brome (Bromus tectorum),Big fox-brush (Setaria faberii),Johnson grass sorghum (Sorghum halpense),Lamb's-quarters (Chenopodium album),(Ipomoea hederacea) is spent towards face,Amaranthus retroflexus (Amaranthus ertroflexus),Rape (Brassica napus),Rye grass (Loliummultiflorum),Soybean (Glycine max),Veronica (Veronica persica),Beet (Beta vulgaris),Velvetleaf (Abutilon theophrasti),Wheat (Triticum aestivum),RHIZOMA FAGOPYRI CYMOSI (Polygonum convolvulus),Wild oat (Avena fatua).The various plants of compound the previous day plantation are being applied for pre-emergence test.The plantation of these kinds is adjusted, is allowed to produce the plant for having post-emergence test suitable size.The plant variety of irrigation tests includes rice (Oryaz sativa), umbrella sedge (Cyperusdifformis), Duck salad (Heteranthera limosa), barnyard grass (Echinochloacrus-galli) and the late watergrass (Echinochloaoryzicola) of experiment use for growing into 2 leaf ages.
All plants are planted with common greenhouse technology, after test compound, the damage of plant after gross evaluations processing, and it is compared with untreated tester, the result being recorded in table B is divided into 0-100 grade, 0 represents to no effect, and 100 represent control completely, and (-) indicates no result of the test.Table B, , , , compound, table B, , , compound amount 500g/ha, , , 7, , consumption 500g/ha, after 7 buds, , , , , , barley before bud, , , , -, , barley, , , 0Barnyardgr, Flood, 20, , barnyard grass, , , 30 barnyard grasses, , , , 95, , bedstraw, , , 0 bedstraw, , , , -, , rush, , , 0 rush, , , , -, , chickweed, , , 0 chickweed, , , , -, , storehouse ear, , , 0 storehouse ear, , , , 85, , corn, , , 10 corns, , , , 0, , cotton, , , 0 cotton, , , , 40, , lady's-grass, , , 95 lady's-grass, , , , 95, , downy brome, , , 0 downy brome, , , , -, , big fox-brush, , , 20Duck, salad, , , 30, , rye grass, , , 0 big fox-brush, , , , 75, , johnson grass sorghum, , 10 rye grasses, , , , -, , lamb's-quarters, , , , 95 johnson grass sorghums, , , 30, , towards face flower, , , 0 lamb's-quarters, , , , , -, , rape, , , 0 spends towards face, , , , 80, , Amaranthus retroflexus, , , 0 rape, , , , -, , soybean, , , 0 Amaranthus retroflexus, , , , 80, , Veronica, , , 10 rice, , , , , 70, , beet, , , 10 soybean, , , , 85, , yorkshire fog grass, , , 0 Veronica, , , , -, , wheat, , , 0 beet, , , , -, , RHIZOMA FAGOPYRI CYMOSI, , , 0 umbrella sedge, , , , 30, , wild oat, , , 0 yorkshire fog grass, , , , 90 watergrasses, , , , 0 wheat, , , ,-RHIZOMA FAGOPYRI CYMOSI, , , ,-wild oat, , , ,-table B, , , , , compound, table B, , , compound amount 250g/ha, , , 4, 7, consumption 250g/ha, 4, after 7 buds, , , , , , , barley before bud, , , , , 15, -, barley, , , 0, 0Barnyardgr, Flood, , 70, 10, barnyard grass, , , 95, 10 barnyard grasses, , , , , 80, 90, bedstraw, , , 80, 0 bedstraw, , , , 90, -, rush, , , 0, 0 rush, , , , 40, -, chickweed, , , 0, 0 chickweed, , , , , 65, -, storehouse ear, , , 50, 0 storehouse ear, , , , , 90, 85, corn, , , 0, 10 corns, , , , , 0, 0, cotton, , , 70, 0 cotton, , , , , 90, 30, lady's-grass, , , 100, 80 lady's-grass, , , , , 85, 90, downy brome, , , 0, 0 downy brome, , , , 25, -, big fox-brush, , , 85, 0Duck, salad, , , 45, 20, rye grass, , , 0, 0 big fox-brush, , , , 50, 50, johnson grass sorghum, , 30, 0 rye grass, , , , 0, -, lamb's-quarters, , , , 90, 95 johnson grass sorghums, , , , -, 20, towards face flower, , , 100, 0 lamb's-quarters, , , , , 95, -, rape, , , 95, 0 spends towards face, , , , 90, 80, Amaranthus retroflexus, , , -, 0 rape, , , , , 95, -, soybean, , , 90, 0 Amaranthus retroflexus, , , , 90, 80, Veronica, , , 100, 0 rice, , , , , 60, 30, beet, , , 100, 0 soybean, , , , , 90, 70, yorkshire fog grass, , , 100, 0 Veronica, , , , 100, -, wheat, , , 0, 0 beet, , , , , 100, -, RHIZOMA FAGOPYRI CYMOSI, , , 10, 0 umbrella sedge, , , , 50, 0, wild oat, , , 0, 0 yorkshire fog grass, , , , 100, 90 watergrasses, , , , 75, 0 wheat, , , , , 25,-RHIZOMA FAGOPYRI CYMOSI, , , , 65,-wild oat, , , , 0,-table B, , , , , compound, , table B, , , , compound amount 125g/ha, , 2, 4, 7, 8, consumption 125g/ha, 2, 4, 7, after 8 buds, , , , , , , , barley before bud, , , , 75, 0, -, 0, barley, , , 0, 0, 0, 0Barnyardgr, Flood, 100, 60, 10, 95, barnyard grass, , , 95, 50, 10, 100 barnyard grasses, , , , 90, 70, 90, 90, bedstraw, , , 95, 65, 0, 0 bedstraw, , , , 100, 90, -, 85, rush, , , 10, 0, 0, 0 rush, , , , 80, 30, -, 40, chickweed, , , 100, 0, 0, 95 chickweeds, , , , 95, 65, -, 100, storehouse ear, , , 70, 40, 0, 30 storehouse ears, , , , 90, 90, 85, 90, corn, , , 0, 0, 0, 20 corns, , , , 0, 0, 0, 35, cotton, , , 90, 40, 0, 20 cottons, , , , 100, 90, 30, 95, lady's-grass, , , 100, 90, 40, 100 lady's-grass, , , , 90, 75, 80, 90, downy brome, , , 10, -, 0, 0 downy brome, , , , 60, 20, -, 0, big fox-brush, , , 50, 40, 0, 100Duck, salad, , , 35, 30, 15, 35, rye grass, , , 40, 0, 0, 0 big fox-brush, , , , 90, 40, 40, 90, thatch sorghum, , , 35, 20, 0, 20 rye grasses, , , , 70, 0, -, 0, lamb's-quarters, , , , 100, 90, 90, 100 johnson grass sorghums, , , 90, -, 20, 90, towards face flower, , , 85, 75, 0, 50 lamb's-quarters, , , , , 100, 95, -, 100, rape, , , 0, 30, 0, 0 spends towards face, , , , 90, 90, 50, 90, Amaranthus retroflexus, , , 90, -, 0, 100 rapes, , , , 70, 95, -, 90, soybean, , , 90, 70, 0, 20 Amaranthus retroflexus, , , , 90, 90, 70, 95, Veronica, , , 100, 90, 0, 100 rice, , , , , 95, 40, 30, 70, beet, , , 100, 100, 0, 100 soybean, , , , 90, 80, 70, 90, yorkshire fog grass, , , 100, 100, 0, 100 Veronicas, , , , 100, 95, -, 100, wheat, , , 0, 0, 0, 0 beet, , , , 100, 100, -, 100, RHIZOMA FAGOPYRI CYMOSI, , , 10, 0, 0, 0 umbrella sedge, , , , 75, 40, 0, 85, wild oat, , , 0, 0, 0, 0 yorkshire fog grass, , , , 95, 100, 85, 100 watergrasses, , , , 95, 65, 0, 80 wheats, , , , 75, 0, -, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 70, 65, -, 70 wild oats, , , , 50, 0, -, 65 table B, , , , , , , compound amount 62g/ha, , , 2, 3, , 4, , 7, , 8, barley after 9 buds, , , , 65, 0, , 10, -, , 0, 0Barnyardgr, Flood, 95, 85, 35, 0, , 95, 0 barnyard grass, , , , 90, 90, 55, 80, 90, 70 bedstraws, , , , 80, 95, 90, -, , 80, 45 rushes, , , , 80, 55, 30, -, , 35, 0 chickweed, , , , 95, 85, 65, -, , 100, 60 storehouse ears, , , , 90, 90, 90, 70, 90, 0 corn, , , , 0, 0, , 30, 0, , 0, 10 cottons, , , , 90, 90, 100, 20, 95, 30 lady's-grass, , , , 90, 90, 75, 50, 90, 30 downy bromes, , , , 50, 10, 25, -, , 0, 0Duck, salad, , , 25, 15, 15, 0, , 35, 0 big fox-brush, , , , 90, 80, 30, 10, 90, 50 rye grasses, , , , 50, 10, 0, , -, , 0, 0 johnson grass sorghum, , , 90, -, , 55, 20, 90, 10 lamb's-quarters, , , , , 100, 100, 100, -, , 100, 95 spend towards face, , , , 90, 90, 90, 20, 90, 80 rapes, , , , 40, 65, 90, -, , 90, 60 Amaranthus retroflexus, , , , 80, 90, 90, 60, 95, 80 rice, , , , , 90, 50, 25, 25, 50, 0 soybean, , , , 90, 90, 90, 50, 85, 40 Veronicas, , , , 95, 100, 95, -, , 100, 60 beets, , , , 100, 100, 100, -, , 100, 100 umbrella sedges, , , , 65, 40, 15, 0, , 60, 0 yorkshire fog grass, , , , 95, 100, 100, 70, 100, 60 watergrasses, , , , 95, 80, 20, 0, , 65, 0 wheat, , , , 70, 50, 30, -, , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 50, 65, 45, -, , 70, 20 wild oats, , , , 40, 0, , 0, , -, , 45, 0 table B, , , , , , compound amount 62g/ha, 2, 3, 4, 7, 8, barley before 9 buds, , , 0, 0, 0, 0, 0, 0 barnyard grass, , , 85, 90, 20, 0, 70, 0 bedstraw, , 50, 70, 10, 0, 0, 0 rush, , 0, 0, 0, 0, 0, 0 chickweed, , , 100, 85, 0, 0, 75, 0 storehouse ear, , , 50, 70, 20, 0, 20, 10 corns, , , 0, 25, 0, 0, 10, 0 cotton, , , 90, 50, 30, 0, -, 0 lady's-grass, , , 100, 100, 50, 20, 40, 0 downy brome, , 0, 80, 0, 0, 0, 0 big fox-brush, , 40, 40, 20, 0, 80, 0 rye grass, , 0, 10, 0, 0, 0, 0 johnson grass sorghum, , 25, 70, 10, 0, 10,-lamb's-quarters, , , 100, 100, 95, 0, 95, 95 spend towards face, , 60, 0, 65, 0, 0, 0 rape, , , 0, 0, 0, 0, 0, 0 Amaranthus retroflexus, , 10, -, 75, 0, 70, 30 soybean, , , 80, 40, 40, 0, 0, 10 Veronicas, , 95, 100, 95, 0, 100,-beet, , , 100, 100, 100, 0, 100, 85 yorkshire fog grasses, , 100, 100, 100, 0, 60, 10 wheats, , , 0, 0, 0, 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , 0, 0, 0, 0, 0, 0 wild oat, , 0, 20, 0, 0, 0, 0 table B, , , , , , , compound amount 31g/ha, , , 2, , 3, , 4, , 8, , barley after 9 buds, , , , , 35, 0, , 10, 0, , 0Barnyardgr, Flood, 85, 85, 20, 80, 0 barnyard grass, , , , , 90, 90, 40, 90, 50 bedstraws, , , , 80, 85, 80, 80, 0 rush, , , , 40, 30, 30, 25, 0 chickweed, , , , , 80, 85, 60, 100, 50 storehouse ears, , , , , 80, 90, 90, 90, 70 corns, , , , , 0, , 0, , 0, , 0, , 0 cotton, , , , , 90, 90, 90, 95, 30 lady's-grass, , , , , 90, 90, 60, 90, 20 downy bromes, , , , 20, 0, , 10, 0, , 0Duck, salad, , , 20, 15, 0, , 0, , 0 big fox-brush, , , , 90, 50, 20, 90, 30 rye grasses, , , , 40, 10, 0, , 0, , 0 johnson grass sorghum, , , , 70, -, , 45, 85, 10 lamb's-quarters, , , , , 95, 100, 95, 100, 95 spend towards face, , , , 90, 90, 90, 90, 80 rapes, , , , , 30, 20, 90, 70, 35 Amaranthus retroflexus, , , , 70, 90, 80, 95, 60 rice, , , , , 65, 35, 25, 30, 0 soybean, , , , , 90, 90, 90, 75, 30 Veronicas, , , , 70, 95, 80, 100, 15 beets, , , , , 100, 100, 100, 100, 90 umbrella sedges, , , , 30, 25, 0, , 20, 0 yorkshire fog grass, , , , 95, 100, 95, 100, 50 watergrasses, , , , 80, 30, 0, , 25, 0 wheat, , , , , 55, 35, 25, 0, , 0 RHIZOMA FAGOPYRI CYMOSI, , , , 50, 35, 30, 50, 20 wild oats, , , , 20, 0, , 0, , 20, 0 table B, , , , , , compound amount 31g/ha, , 2, , 3, , 4, , 8, barley before 9 buds, , , 0, , 0, , 0, , 10, 0 barnyard grass, , , 50, 30, 0, , 50, 0 bedstraw, , , 0, , 20, 10, 80, 0 rush, , , 0, , 0, , 0, , 0, 0 chickweed, , , 0, , 70, 0, , 55, 0 storehouse ear, , , 40, 50, 10, 0, 10 corns, , , 0, , 0, , 0, , 0, 0 cotton, , , 10, 50, 10, 0, 0 lady's-grass, , , 100, 80, 20, 70, 0 downy brome, , , 0, , 40, 0, , 0, 0 big fox-brush, , , 20, -, , 35, 70, 0 rye grass, , , 0, , 0, , 0, , 40, 0 johnson grass sorghum, , 10, 50, 0, , 70, -, lamb's-quarters, , , , 95, 95, 95, 90, 30 spend towards face, , , 50, 0, , 20, 100, 0 rape, , , 0, , 0, , 0, , 95, 0 Amaranthus retroflexus, , , 10, -, , 20, 0, 20 soybean, , , 55, -, , 20, 40, 10 Veronicas, , , 30, 100, 95, 100, 100 beets, , , 100, 100, 100, 40, 80 yorkshire fog grasses, , , 100, 80, 30, 30, 0 wheat, , , 0, , 0, , 0, , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , 0, , 0, , 0, , 20, 0 wild oat, , , 0, , 0, , 0, , 0, 0 table B, , , , , , compound amount 16g/ha, , , 2, , 3, , 4, , 8, , barley after 9 buds, , , , 0, , 0, , 10, 0, , 0Barnyardgr, Flood, 20, 40, 0, , 65, 0 barnyard grass, , , , 90, 90, 20, 90, 20 bedstraws, , , , 70, 85, 40, 65, 0 rush, , , , 20, 15, 10, 5, , 0 chickweed, , , , 70, 85, 10, 100, 10 storehouse ears, , , , 80, 90, 90, 90, 50 corns, , , , 0, , 0, , 0, , 0, , 0 cotton, , , , 90, 90, 90, 95, 20 lady's-grass, , , , 85, 90, 40, 90, 10 downy bromes, , , , 10, 0, , 0, , 0, , 0Duck, salad, , , 0, , 0, , 0, , 0, , 0 big fox-brush, , , , 70, 40, 10, 95, 10 rye grasses, , , , 10, 10, 0, , 0, , 0 johnson grass sorghum, , , 60, -, , 35, 65, 0 lamb's-quarters, , , , , 95, 95, 90, 100, 90 spend towards face, , , , 90, 90, 90, 95, 40 rapes, , , , 20, 15, 70, 35, 20 Amaranthus retroflexus, , , , 50, 90, 60, 100, 30 rice, , , , , 30, 25, 0, , 20, 0 soybean, , , , 90, 80, 80, 75, 30 Veronicas, , , , 70, 90, 40, 100, 0 beet, , , , 100, 100, 100, 100, 80 umbrella sedges, , , , 30, 0, , 0, , 0, , 0 yorkshire fog grass, , , , 95, 100, 90, 100, 30 watergrasses, , , , 0, , 15, 0, , 15, 0 wheat, , , , 40, 0, , 0, , 0, , 0 RHIZOMA FAGOPYRI CYMOSI, , , , 30, 35, 20, 45, 10 wild oats, , , , 10, 0, , 0, , 10, 0 table B, , , , , , compound amount 16g/ha, , , 2, 3, 4, 8, barley before 9 buds, , , , 0, 0, 0, 0, 0 barnyard grass, , , , 35, 20, 0, 15, 0 bedstraw, , , , 0, 10, 0, 80, 0 rush, , , , 0, 0, 0, 0, 0 chickweed, , , , 0, 50, 0, 25, 0 storehouse ear, , , , 30, 30, 0, 0, 10 corns, , , , 0, 0, 0, 0, 0 cotton, , , , 10, 30, 0, 0, 0 lady's-grass, , , , 95, -, 0, 5, 0 downy brome, , , , 0, 0, 0, 0, 0 big fox-brush, , , , 0, 40, 0, 20, 0 rye grass, , , , 0, 0, 0, 25, 0 johnson grass sorghum, , , 10, 50, 0, 40,-lamb's-quarters, , , , , 95, 90, 95, 55, 30 spend towards face, , , , 50, 0, 0, 60, 0 rape, , , , 0, 0, 0, 50, 0 Amaranthus retroflexus, , , , 0, -, 0, 0, 0 soybean, , , , 20, -, 10, 30, 0 Veronica, , , , 30, 100, 0, 100, 100 beets, , , , 80, 100, 100, 30, 0 yorkshire fog grass, , , , 100, 50, 0, 5, 0 wheat, , , , 0, 0, 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 0, 0, 0, 20, 0 wild oat, , , , 0, 0, 0, 0, 0 table B, , , , , , compound, , table B, , , compound amount 8g/ha, , , 3, 4, 8, 9, consumption 8g/ha, 3, 4, 8, after 9 buds, , , , , , , , barley before bud, , , , 0, 10, 0, 0, barley, , 0, 0, 0, 0Barnyardgr, Flood, 25, 0, -, 0, barnyard grass, , 0, 0, 0, 0 barnyard grass, , , , 90, 15, 90, 10, bedstraw, , 0, 0, 10, 0 bedstraw, , , , 80, 20, 50, 0, rush, , 0, 0, 0, 0 rush, , , , 10, 0, 0, 0, chickweed, , 10, 0, 0, 0 chickweed, , , , 85, 0, 95, 0, storehouse ear, , 10, 0, 0, 0 storehouse ear, , , , 90, 80, 90, 35, corn, , 0, 0, 0, 0 corn, , , , 0, 0, 0, 0, cotton, , 30, 0, 0, 0 cotton, , , , 80, 80, 90, 20, lady's-grass, , 10, 0, 20, 0 lady's-grass, , , , 90, 30, 80, 0, downy brome, , 0, 0, 0, 0 downy brome, , , , 0, 0, 0, 0, big fox-brush, , 30, 0, 25,-Duck, salad, , , 0, 0, -, 0, rye grass, , 0, 0, 0, 0 big fox-brush, , , , 30, 0, 85, 0, thatch sorghum, , 40, 0, 30,-rye grass, , , , 0, 0, 0, 0, lamb's-quarters, , , 90, 80, 90, 0 johnson grass sorghum, , , -, 20, 40, 0, towards face flower, , 0, 0, 50, 0 lamb's-quarters, , , , , 95, 80, 95, 85, rape, , 0, 0, 0, 0 spends towards face, , , , 90, 90, 90, 40, Amaranthus retroflexus, , -, 0, -, 0 rape, , , , 15, 50, 0, 0, soybean, , -, 0, 0, 0 Amaranthus retroflexus, , , , 90, 20, 85, 20, Veronica, , 80, -, 100, 100 rice, , , , , 20, 0, -, 0, beet, , 85, 100, 10, 0 soybean, , , , 80, 70, 70, 20, yorkshire fog grass, , 20, 0, 20, 0 Veronica, , , , 80, 10, 80, 0, wheat, , 0, 0, 0, 0 beet, , , , 100, 100, 100, 10, RHIZOMA FAGOPYRI CYMOSI, , 0, 0, 0, 0 umbrella sedge, , , , 0, 0, -, 0, wild oat, , 0, 0, 0, 0 yorkshire fog grass, , , , 90, 90, 100, 30 watergrasses, , , , 15, 0, -, 0 wheat, , , , 0, 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 35, 0, 40, 0 wild oat, , , , 0, 0, 0, 0 table B, , , , , , compound, , table B, , , compound amount 4g/ha, , , , 4, 8, 9, consumption 4g/ha, 4, 8, after 9 buds, , , , , , , , , barley before bud, , , , , 10, 0, 0, barley, , 0, 0, 0Barnyardgr, Flood, , 0, -, 0, barnyard grass, , 0, 0, 0 barnyard grass, , , , , 0, 90, 0, bedstraw, , 0, 0, 0 bedstraw, , , , , 20, 35, 0, rush, , 0, 0, 0 rush, , , , , 0, 0, 0, chickweed, , 0, 0, 0 chickweed, , , , , 0, 80, 0, storehouse ear, , 0, 0, 0 storehouse ear, , , , , 65, 80, 10, corn, , 0, 0, 0 corn, , , , , 0, 0, 0, cotton, , 0, 0, 0 cotton, , , , , 10, 90, 0, lady's-grass, , 0, 0, 0 lady's-grass, , , , , 10, 70, 0, downy brome, , 0, 0, 0 downy brome, , , , , 0, 0, 0, big fox-brush, , 0, 0, 0Duck, salad, , , , 0, -, 0, rye grass, , 0, 0, 0 big fox-brush, , , , , 0, 60, 0, johnson grass sorghum, 0, 30,-rye grass, , , , , 0, 0, 0, lamb's-quarters, , , 0, 90, 0 johnson grass sorghum, , , , 10, 30, 0, towards face flower, , 0, 20, 0 lamb's-quarters, , , , , , 80, 80, 80, rape, , 0, 0, 0 spends towards face, , , , , 40, 80, 30, Amaranthus retroflexus, , 0, -, 0 rape, , , , , 10, 0, 0, soybean, , 0, 10, 0 Amaranthus retroflexus, , , , , 10, 70, 10, Veronica, , 0, 90, 10 rice, , , , , , 0, -, 0, beet, , 0, 0, 0 soybean, , , , , 50, 70, 10, yorkshire fog grass, , 0, 0, 0 Veronica, , , , , 0, 70, 0, wheat, , 0, 0, 0 beet, , , , , 100, 100, 10, RHIZOMA FAGOPYRI CYMOSI, , 0, 0, 0 umbrella sedge, , , , , 0, -, 0, wild oat, , 0, 0, 0 yorkshire fog grass, , , , , 90, 100, 20 watergrasses, , , , , 0, -, 0 wheat, , , , , 0, 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , , 0, 40, 0 wild oat, , , , , 0, 0, 0 table B, , , , compound, table B, , compound amount 2g/ha, , , 8, , consumption 2g/ha, after 8 buds, , , , , , , barley before bud, , , , , 0, , barley, , 0Barnyardgr, Flood, , -, , barnyard grass, , 0 barnyard grass, , , , , 90, , bedstraw, , 0 bedstraw, , , , 10, , rush, , 0 rush, , , , 0, , chickweed, , 0 chickweed, , , , , 25, , storehouse ear, , 0 storehouse ear, , , , , 80, , corn, , 0 corn, , , , , 0, , cotton, , 0 cotton, , , , , 50, , lady's-grass, , 0 lady's-grass, , , , , 40, , downy brome, , 0 downy brome, , , , 0, , big fox-brush, , 0Duck, salad, , , -, , rye grass, , 0 big fox-brush, , , , 20, , johnson grass sorghum, 0 rye grass, , , , 0, , lamb's-quarters, , , 70 johnson grass sorghums, , , , 10, , towards face flower, , 0 lamb's-quarters, , , , , 30, , rape, ,-spent towards face, , , , 80, , Amaranthus retroflexus, ,-rape, , , , , 0, , soybean, , 0 Amaranthus retroflexus, , , , -, , Veronica, , 10 rice, , , , , -, , beet, , 0 soybean, , , , , 40, , yorkshire fog grass, , 0 Veronica, , , , 10, , wheat, , 0 beet, , , , , 70, , RHIZOMA FAGOPYRI CYMOSI, , 0 umbrella sedge, , , , -, , wild oat, , 0 yorkshire fog grass, , , , 100 watergrasses, , , ,-wheat, , , , , 0 RHIZOMA FAGOPYRI CYMOSI, , , , 0 wild oat, , , , 0 table B, , , , , compound, table B, , compound amount 1g/ha, , , , 8, , consumption 1g/ha, after 8 buds, , , , , , , barley before bud, , , , , 0, , barley, , , 0Barnyardgr, Flood, , -, , barnyard grass, , , 0 barnyard grass, , , , , 80, , bedstraw, , 0 bedstraw, , , , 0, , rush, , 0 rush, , , , 0, , chickweed, , , 0 chickweed, , , , , 0, , storehouse ear, , , 0 storehouse ear, , , , , 70, , corn, , , 0 corn, , , , , 0, , cotton, , , 0 cotton, , , , , 20, , lady's-grass, , , 0 lady's-grass, , , , , 10, , downy brome, , 0 downy brome, , , , 0, , big fox-brush, , 0Duck, salad, , , -, , rye grass, , 0 big fox-brush, , , , 10, , johnson grass sorghum, , 0 rye grass, , , , 0, , lamb's-quarters, , , 40 johnson grass sorghums, , , , 0, , towards face flower, , 0 lamb's-quarters, , , , , 0, , rape, , , 0 spends towards face, , , , 40, , Amaranthus retroflexus, ,-rape, , , , , 0, , soybean, , , 0 Amaranthus retroflexus, , , , 10, , Veronica, , 0 rice, , , , , -, , beet, , , 0 soybean, , , , , 10, , yorkshire fog grass, , 0 Veronica, , , , 0, , wheat, , , 0 beet, , , , , 40, , RHIZOMA FAGOPYRI CYMOSI, , 0 umbrella sedge, , , , -, , wild oat, , 0 yorkshire fog grass, , , , 80 watergrasses, , , ,-wheat, , , , , 0 RHIZOMA FAGOPYRI CYMOSI, , , , 0 wild oat, , , , 0 experiment C
Barnyard grass (Echinochloa crus-galli),Field bindweed (Convolvulus arvensis),Black nightshade (Solanum ptycanthum dunal),Cassia (Cassia obtusifolia),Storehouse ear (Xanthium strumarium),common ragweed(Ambrosiaartemisiifolia),Corn (Zea mays),Cotton (Gossypium irsutum),Digitaria ciliaris (Digitaria spp),The foreign big fox-brush (Setaria faberii) of open country broomcorn millet (Panicum dichotomiflorum),Green fox-brush (Setaria viridis),Stramonium (Duturastramonium),Johnson grass sorghum (Sorghum halpense),Lamb's-quarters (Chenopodiumalbum),(Ipomoea spp) is spent towards face,Amaranthus retroflexus (Amaranthus ertroflexus),Chrysanthemum twists with the fingers (Sida spinosa) Brachiaria Griseb (Sorghum vulgare),signalgrass(Brachiaria platyphylla),Knotweed (Polygonum pensylvanicum),Soybean (Glycine max),Heronsbill (Helianthum annuus),Velvetleaf (Abutilontheophrasti),Wild broomcorn millet (Panicum miliaceum),Wool grass (Eriochloavillosa),The seed and the rhizome of nutgrass flatsedge (Cyperusrotundus) stem tuber of yellow fox-brush (Setaria lutescens) are planted in sand fertile soil,These crops and weeds are grown in greenhouse until growing tall to 2-18cm (1-4 leaf ages),Then it is used in the test compound prepared in the non-plant toxicity solvent mixture containing surfactant and carries out bud post processing.When carrying out bud pre-treatment, the flowerpot of this processing of above-mentioned receiving is placed in greenhouse by the planting plants immediately in the flowerpot after applying test compound, is nursed according to conventional chamber planting method.
After test compound, processing and untreated check plant is kept for 14-21 days in greenhouse, and the result of record gross evaluations plant injury, the result being recorded in table C is divided into 0-100 grade, and 0 represents to no effect, and 100 represent control completely.Table C, , , compound, table C, , , compound amount 70g/ha, , 2, , consumption 35g/ha, 2, , after 8 buds, , , , , , barnyard grass after bud, , , , 100, , barnyard grass, , , 100, 90 field bindweeds, , , 100, , japanese bearbind, , , 100, 50 black nightshades, , , , 100, , black nightshade, , , 100, 100 Cassia, , , , -, , Cassia, , , -, , 10 Siberian cockleburs, , , , 100, , Siberian cocklebur, , , 100, 90 corns, , , , 10, , corn, , , 5, , 0 cotton, , , , 100, , cotton, , , 100, 40 digitaria ciliaris, , , 100, , digitaria ciliaris, , 90, , the wild broomcorn millet in 70 oceans, , , 100, , foreign open country broomcorn millet, , 100, 90 big fox-brush, , , 90, , big fox-brush, , 40, , 90 green fox-brush, , , 90, , green fox-brush, , 80, , 90 Thorn-Apples, , , 100, , Thorn-Apple, , 100, 95 johnson grass sorghums, , , 40, , johnson grass sorghum, , 20, , 80 lamb's-quarters, , , , 100, , lamb's-quarters, , , 100, 90 spend towards face, , , 100, , towards face flower, , 100, 90 nutgrass flatsedges, , , , 90, , nutgrass flatsedge, , , 90, , 0 Amaranthus retroflexus, , , 100, , Amaranthus retroflexus, , 100, 100 burs, , , 100, , bur, , 95, , 5 artemisiifolias, , , , 100, , artemisiifolia, , , 100, 90Shattercane, , 100, , Shattercane, 100, 80 Brachiaria Grisebs, , , 100, , Brachiaria Griseb, , 100,-knotweed, , , , 100, , knotweed, , , 100, 100 soybean, , , , 100, , soybean, , , 100, 60 heronsbills, , , 100, , heronsbill, , 100, 90 yorkshire fog grasses, , , 100, , yorkshire fog grass, , 100, 95 broomcorn millets, , , , 100, , broomcorn millet, , , 100, 90 wools grass, , , 90, , wool grass, , 90, , 80 yellow fox-brush, , , 80, , yellow fox-brush, , 70, , 90 table C, , , , , compound, , table C, , , compound amount 17g/ha, , , 2, 8, , consumption 8g/ha, 2, after 8 buds, , , , , , , barnyard grass after bud, , , , 95, 90, barnyard grass, , , 95, 90 field bindweeds, , , , 90, 10, field bindweed, , 90, 0 black nightshade, , , , 100, 95, black nightshade, , , 100, 85 Cassia, , , , -, 5, , Cassia, , , -, 0 Siberian cocklebur, , , , 100, 85, Siberian cocklebur, , , 100, 70 corns, , , , 5, 0, , corn, , , 0, 0 cotton, , , , 100, 40, cotton, , , 90, 25 digitaria ciliaris, , , , 85, 70, digitaria ciliaris, , 80, the wild broomcorn millet in 10 oceans, , , , 90, 90, foreign open country broomcorn millet, , 50, 50 big fox-brush, , , , 30, 90, big fox-brush, , 5, 40 green fox-brush, , , , 50, 90, green fox-brush, , 5, 30 Thorn-Apples, , , , 100, 95, Thorn-Apple, , 100, 90 johnson grass sorghums, , , 10, 30, johnson grass sorghum, , 0, 0 lamb's-quarters, , , , , 100, 90, lamb's-quarters, , , 100, 85 spend towards face, , , , 100, 85, towards face flower, , 100, 40 nutgrass flatsedges, , , , 70, 0, , nutgrass flatsedge, , , 5, 0 Amaranthus retroflexus, , , , 90, 100, Amaranthus retroflexus, , 80, 80 burs, , , , 90, 0, , bur, , 70, 0 artemisiifolia, , , , 100, 90, artemisiifolia, , , 100, 80Shattercane, , , 80, 5, , Shattercane, 10, 0 Brachiaria Griseb, , , , 90, -, , Brachiaria Griseb, , 80,-knotweed, , , , , 100, 100, knotweed, , , 100, 80 soybean, , , , 100, 40, soybean, , , 100, 30 heronsbills, , , , 100, 70, heronsbill, , 90,-yorkshire fog grass, , , , 100, 95, yorkshire fog grass, , 100, 90 broomcorn millets, , , , , 100, 90, broomcorn millet, , , 80, 90 wools grass, , , , 80, 50, wool grass, , 30, 5 yellow fox-brush, , , , 50, 60, yellow fox-brush, , 10, 20 table C, , , , , compound, table C, , compound amount 4g/ha, , , 2, 8, consumption 2g/ha, after 8 buds, , , , , , , after bud, barnyard grass, , , , , 80, 80, barnyard grass, , , 5 field bindweeds, , , , 80, 0, japanese bearbind, , , 0 black nightshade, , , , , 100, 80, black nightshade, , , 80 Cassia, , , , , -, 0, Cassia, , , 0 Siberian cocklebur, , , , , 100, 50, Siberian cocklebur, , , 40 corns, , , , , 0, 0, corn, , , 0 cotton, , , , , 90, 20, cotton, , , 10 digitaria ciliaris, , , , 40, 5, digitaria ciliaris, , the wild broomcorn millet in 0 ocean, , , , 5, 50, foreign open country broomcorn millet, , 0 big fox-brush, , , , 0, 30, big fox-brush, , 0 green fox-brush, , , , 0, 20, green fox-brush, , 0 Thorn-Apple, , , , 100, 90, Thorn-Apple, , 90 johnson grass sorghums, , , , 0, 0, johnson grass sorghum, , 0 lamb's-quarters, , , , , 90, 80, lamb's-quarters, , , 5 spend towards face, , , , 100, 10, towards face flower, , 0 nutgrass flatsedge, , , , , 5, 0, nutgrass flatsedge, , , 0 Amaranthus retroflexus, , , , 40, 5, Amaranthus retroflexus, , 0 bur, , , , 65, 0, bur, , 0 artemisiifolia, , , , , 90, 5, artemisiifolia, , , 5Shattercane, , , 0, 0, Shattercane, 0 Brachiaria Griseb, , , , 50, -, Brachiaria Griseb, ,-knotweed, , , , , 90, 70, knotweed, , , 20 soybean, , , , , 100, 10, soybean, , , 5 heronsbills, , , , 90, 30, heronsbill, ,-yorkshire fog grass, , , , 100, 90, yorkshire fog grass, , 0 broomcorn millet, , , , , 70, 50, broomcorn millet, , , 5 wools grass, , , , 30, 5, wool grass, , 0 yellow fox-brush, , , , 0, 0, yellow fox-brush, , 0 experiment D
Compound for being evaluated in the experiment is prepared in the non-plant toxicity solvent mixture containing surfactant, (bud pre-treatment) is applied to soil surface before plant seedlings are unearthed, and it is applied to each period (bud post processing) of plant growth, sand fertile soil is used for pre-emergence test, post-processed for bud using the native mixture of 60: 40 sand fertile soil and greenhouse basin, for bud pre-treatment, test compound was applied at after planting about one day.
For post-emergence test,Crop and weeds are adjusted to appropriate height,Crop and weeds include American Black eggplant (Solanum americanum),Chrysanthemum twists with the fingers (Sida rhombifolia),Barnyard grass (Echinochloa crus-galli),Storehouse ear (Xanthium strumarium),Lamb's-quarters (Chenopodium album),Artemisiifolia (Ambrosia artemisiifolia),Corn (Zea mays),Cotton (Gossypium irsutum),The black eggplant in east (Solanumptycanthum),Foreign open country broomcorn millet (Panicum dichotomifiorum),Japanese bearbind (Convolvulusarvensis),F1 beggars (Desmodium purpureum),Big fox-brush (Setariafaberii),Bur beggar-ticks (Bidens pilosa),Pharbitis nilChoisy (Ipomoea hederacea),Johnson grass sorghum (Sorghum halpense),Knotweed (Polygonum pensylvanicum),Lady's-grass (Digitaria sanguinalis),The rhizome of nutgrass flatsedge (Cyperus rotundus),Amaranthus retroflexus (Amaranthus retroflexus),Soybean (Glycine max),Finish as (Brachiariadecumbens),Velvetleaf (Abutilon theophrasti) and big Ji (Euphorbiaheterophylla).
Processing and untreated check plant are placed in greenhouse about 14-21 days, thereafter the plant of all processing and tester are compared, with the naked eye evaluate, it is 0-100 grade to record the result grade classification in table D, 0 represents to no effect, 100 represent control completely, and (-) indicates no result of the test.Table D, , , , compound amount 140g/ha, , chrysanthemum is twisted with the fingers after 8 buds, , , 35 barnyard grasses, , , , 100 storehouse ears, , , , 95 artemisiifolias, , , , 95 corns, , , , 10 cottons, , , , 95Estrn, Blknight, 100 broomcorn millets, , , , 100 japanese bearbinds, , , , 80 beggars, , , 100 big fox-brush, , , 100 bur beggar-ticks, , , 70 pharbitis nilChoisies, , , 85 johnson grass sorghums, , , 50Ladysthumb, , 90 lamb's-quarters, , , , 100 lady's-grass, , , , 95 purple nutgrass flatsedges, , , 70 Amaranthus retroflexus, , , -, soybean, , , , 90 finish work as, , , , 85 yorkshire fog grasses, , , 100 roots of Beijing euphorbia, , , , 60 table D, , , , compound, , table D, , , , compound amount 70g/ha, , 2, 8, , consumption 70g/ha, , , 2, after 8 buds, , , , , , , chrysanthemum is twisted with the fingers before bud, , , 90, 40, , chrysanthemum is twisted with the fingers, , , , 95, 15 barnyard grasses, , , , 95, 100, barnyard grass, , , , 70, 40 storehouse ears, , , , 100, 100, Siberian cocklebur, , , , 95, 10 artemisiifolias, , , , 100, 100, artemisiifolia, , , , 95, 65 corns, , , , 10, 10, , corn, , , , 0, 0 cotton, , , , 100, 100, cotton, , , , 25, 15Estrn, Blknight, 100, 100, broomcorn millet, , , , , -, 100 broomcorn millets, , , , 95, 100, japanese bearbind, , , , 80,-japanese bearbind, , , , 90, 65, , beggar, , , , -,-beggar, , , 100, 100, big fox-brush, , , , 10, 80 big fox-brush, , , 85, 100, bur beggar-ticks, , , , 10, 25 bur beggar-ticks, , , 75, 90, , pharbitis nilChoisy, , , 0, 15 pharbitis nilChoisies, , , 100, 95, , johnson grass sorghum, , , 0, 10 johnson grass sorghums, , , 50, 80, , Ladysthumb, , , -,-Ladysthumb, , 100, 100, lamb's-quarters, , , , , 100,-lamb's-quarters, , , , 100, 100, Large, Crabgrass, 100, 25 lady's-grass, , , , 95, 95, , purple nutgrass flatsedge, , , , 50, 45 purple nutgrass flatsedges, , , 75, 75, , Amaranthus retroflexus, , , , -,-Amaranthus retroflexus, , , 100, 100, soybean, , , , -, 10 soybean, , , , 100, 100, finish and work as, , , , 70, 75 finish work as, , , , 85, 100, yorkshire fog grass, , , , 100, 100 yorkshire fog grasses, , , 100, 100, the root of Beijing euphorbia, , , , 85, 30 roots of Beijing euphorbia, , , , 100, 70 table D, , , , compound, , table D, , , , compound amount 35g/ha, , , 2, 3, 8, consumption 35g/ha, , 2, 3, after 8 buds, , , , , , , chrysanthemum is twisted with the fingers before bud, , , , 85, 80, 35, chrysanthemum is twisted with the fingers, , , 95, 10, 10 barnyard grasses, , , , 95, 90, 95, barnyard grass, , , 30, 20, 10 storehouse ears, , , , 100, 100, 100, Siberian cocklebur, , , 40, 25, 0 artemisiifolia, , , , 100, 95, 100, artemisiifolia, , , 95, 75, 50 corns, , , , 10, 0, 0, corn, , , 0, 0, 0 cotton, , , , 100, 100, 100, cotton, , , -, 0, 10Estrn, Blknight, , 100, 100, 100, broomcorn millet, , , , -, 15, 40 broomcorn millets, , , , , 85, 80, 100, japanese bearbind, , , -, 0, 0 japanese bearbind, , , , 85, 90, 65, beggar, , , -, -,-beggar, , , , 100, 100, 100, big fox-brush, , , 10, 0, 20 big fox-brush, , , , 65, 65, 95, bur beggar-ticks, , , 0, 25, 25 bur beggar-ticks, , , , 50, 45, 90, pharbitis nilChoisy, , 0, 20, 10 pharbitis nilChoisies, , , 95, 95, 85, johnson grass sorghum, , 0, 0, 0 johnson grass sorghum, , , 15, 30, 80, Ladysthumb, , -, 95, 30Ladysthumb, , , 100, 100, 95, lamb's-quarters, , , , 100, -,-lamb's-quarters, , , , , 100, 100, 100, Large, Crabgrass, 100, 35, 15 lady's-grass, , , , 90, 85, 95, purple nutgrass flatsedge, , , 35, -, 25 purple nutgrass flatsedges, , , , 50, 40, 65, Amaranthus retroflexus, , , -, 100, 65 Amaranthus retroflexus, , , , 100, 95, 100, soybean, , , -, -, 0 soybean, , , , 100, 95, 100, finish and work as, , , 45, 15, 35 finish work as, , , , 80, 75, 75, yorkshire fog grass, , , 100, 80, 85 yorkshire fog grasses, , , , 100, 100, 100, the root of Beijing euphorbia, , , 75, 25, 55 roots of Beijing euphorbia, , , , 100, 95, 45 table D, , , , compound, , table D, , , , compound amount 17g/ha, , 2, 3, 8, consumption 17g/ha, , 2, 3, after 8 buds, , , , , , , chrysanthemum is twisted with the fingers before bud, , , 80, 70, 25, chrysanthemum is twisted with the fingers, , , 50, 0, 0 barnyard grass, , , , 90, 60, 85, barnyard grass, , , 25, 0, 0 storehouse ear, , , , 100, 100, 100, Siberian cocklebur, , , 10, 0, 0 artemisiifolia, , , , 100, 80, 95, artemisiifolia, , , 85, 25, 25 corns, , , , 0, 0, 0, corn, , , 0, 0, 0 cotton, , , , 100, 95, 85, cotton, , , 10, 0, 0Estrn, Blknight, 95, 95, 100, broomcorn millet, , , , 20, 0, 25 is safe, , , , 70, -, 95, japanese bearbind, , , 25, 0, 0 japanese bearbind, , , , 70, 85, 50, beggar, , , -, -,-beggar, , , 100, 85, 100, big fox-brush, , , 0, 0, 10 big fox-brush, , , 35, 30, 95, bur beggar-ticks, , , 0, 0, 25 bur beggar-ticks, , , 30, 25, 75, pharbitis nilChoisy, , -, 0,-pharbitis nilChoisy, , , 95, 90, 80, johnson grass sorghum, , 0, 0, 0 johnson grass sorghum, , , 0, 10, 15, Ladysthumb, , -, 80,-Ladysthumb, , 85, 100, 90, lamb's-quarters, , , , 100, -,-lamb's-quarters, , , , 100, 95, 95, Large, Crabgrass, 70, 10, 0 lady's-grass, , , , 80, -, 80, purple nutgrass flatsedge, , , 25, -, 0 purple nutgrass flatsedge, , , 20, 25, 10, Amaranthus retroflexus, , , -, 100,-Amaranthus retroflexus, , , 75, 90, 95, soybean, , , -, 0, 0 soybean, , , , 100, 95, 75, finish and work as, , , 20, 0, 10 finish work as, , , , 65, 60, 70, yorkshire fog grass, , , 100, 75, 65 yorkshire fog grasses, , , 100, 100, 100, the root of Beijing euphorbia, , , 15, 85, 15 roots of Beijing euphorbia, , , , 100, -, 25 table D, , , , compound, table D, , , , compound amount 8g/ha, , 2, 3, 8, consumption 8g/ha, , , 2, 3, after 8 buds, , , , , , , chrysanthemum is twisted with the fingers before bud, , , 65, 40, 15, chrysanthemum is twisted with the fingers, , , 10, 0, 0 barnyard grass, , , , 85, 45, 75, barnyard grass, , , , 0, 0, 0 storehouse ear, , , , 100, 90, 95, Siberian cocklebur, , , , 0, 0, 0 artemisiifolia, , , , 100, 70, 85, artemisiifolia, , , , 10, 0, 0 corn, , , , 0, 0, 0, corn, , , , 0, 0, 0 cotton, , , , 95, 90, 70, cotton, , , , 0, 0, 0Estrn, Blknight, 90, 50, 75, broomcorn millet, , , , -, 0, 10 broomcorn millets, , , , 55, 25, 80, japanese bearbind, , , , -, 0,-japanese bearbind, , , , 50, 60, 40, beggar, , , -, 0, 25 beggars, , , 100, -, 95, big fox-brush, , , 0, 0, 0 big fox-brush, , , 15, 15, 55, bur beggar-ticks, , , 0, 0, 0 bur beggar-ticks, , , 25, 20, 65, pharbitis nilChoisy, , , 0, 0, 0 pharbitis nilChoisy, , , 90, 70, 65, johnson grass sorghum, , , 0, 0, 0 johnson grass sorghum, , , 0, 0, 10, Ladysthumb, , -, -, 0Ladysthumb, , 75, 95, 45, lamb's-quarters, , , , 75, 95, 0 lamb's-quarters, , , , 100, 95, 95, Large, Crabgrass, 10, 10, 0 lady's-grass, , , , 70, 60, 55, purple nutgrass flatsedge, , , 0, 0, 0 purple nutgrass flatsedge, , , 10, 10, 10, Amaranthus retroflexus, , , -, 90, -, Amaranthus retroflexus, , , 65, 80, 85, soybean, , , , -, 0, 0 soybean, , , , 100, 90, 65, finish and work as, , , , 0, 0, 0 finish work as, , , , 35, 35, 40, yorkshire fog grass, , , 35, 60, 15 yorkshire fog grasses, , , 100, 95, 95, the root of Beijing euphorbia, , , , 0, 0, 0 root of Beijing euphorbia, , , , 95, 80, 20 table D, , , , , compound, table D, , , , compound amount 4g/ha, , , 2, 3, 8, consumption 4g/ha, , 2, 3, after 8 buds, , , , , , , chrysanthemum is twisted with the fingers before bud, , , 60, 35, 10, chrysanthemum is twisted with the fingers, , , -, 0, 0 barnyard grass, , , , 70, 20, 45, barnyard grass, , , , 0, 0, 0 storehouse ear, , , , 95, 85, 85, Siberian cocklebur, , , , 0, 0, 0 artemisiifolia, , , , 95, 60, 85, artemisiifolia, , , , 0, 0, 0 corn, , , , 0, 0, 0, corn, , , , 0, 0, 0, cotton, , , , 90, 85, 15, cotton, , , , -, 0,-Estrn, Blknight, 85, 45, 70, broomcorn millet, , , , 0, 0, 0 is safe, , , , 45, 10, 80, japanese bearbind, , , , -, 0,-japanese bearbind, , , , 35, 45, 35, beggar, , , -, -,-beggar, , , 100, 25, 100, big fox-brush, , , 0, 0, 0 big fox-brush, , , 15, 10, 15, bur beggar-ticks, , , 0, 0, 0 bur beggar-ticks, , , 20, 0, 30, pharbitis nilChoisy, , , -, -, -, pharbitis nilChoisy, , , 90, 50, 55, johnson grass sorghum, , , 0, 0, 0 johnson grass sorghum, , , 0, 0, 0, Ladysthumb, , -, -, 0Ladysthumb, , 50, 45, 25, lamb's-quarters, , , , 50, -, 0 lamb's-quarters, , , , 95, 90, 75, Large, Crabgrass, 0, 0, 0 lady's-grass, , , , 55, 35, 30, purple nutgrass flatsedge, , , 0, -, 0 purple nutgrass flatsedge, , , 0, 0, 0, Amaranthus retroflexus, , , -, 0,-Amaranthus retroflexus, , , 35, 50, 80, soybean, , , , -, 0, 0 soybean, , , , 95, 85, 60, finish and work as, , , , 0, 0, 0 finish work as, , , , 20, 10, 15, yorkshire fog grass, , , 15, 20, 0 yorkshire fog grass, , , 100, 90, 75, the root of Beijing euphorbia, , , , 0, 0, 0 root of Beijing euphorbia, , , , 85, 45, 15 table D, , , , compound, table D, , , , compound amount 2g/ha, , 2, 3, 8, consumption 2g/ha, , 2, 3, after 8 buds, , , , , , before bud, chrysanthemum is twisted with the fingers, , , 20, 25, 0, chrysanthemum is twisted with the fingers, , , -, 0, 0 barnyard grass, , , 25, 15, 15, barnyard grass, , , , 0, 0, 0 storehouse ear, , , 90, 45, 45, Siberian cocklebur, , , , 0, 0, 0 artemisiifolia, , , 85, 55, 25, artemisiifolia, , , , 0, 0, 0 corn, , , 0, 0, 0, corn, , , , 0, 0, 0 cotton, , , 80, 40, 10, cotton, , , , 0, 0, 0Estrn, Blknight, 70, 35, 60, broomcorn millet, , , , -, 0, 0 broomcorn millet, , , , 20, 0, 0, japanese bearbind, , , , -, 0,-japanese bearbind, , , 25, 40, 25, beggar, , , -, -,-beggar, , , 95, 20, 10, big fox-brush, , , 0, 0, 0 big fox-brush, , , 10, 0, 0, bur beggar-ticks, , , 0, 0, 0 bur beggar-ticks, , , 10, 0, 0, pharbitis nilChoisy, , , 0, 0,-pharbitis nilChoisy, , 65, 15, 0, johnson grass sorghum, , , 0, -, 0 johnson grass sorghum, , 0, 0, 0, Ladysthumb, , -, 0, 0Ladysthumb, , 30, 30, 15, lamb's-quarters, , , , 10, 85, 0 lamb's-quarters, , , , 95, 70, 20, Large, Crabgrass, 0, 0, 0 lady's-grass, , , 30, 15, 10, purple nutgrass flatsedge, , , 0, -, 0 purple nutgrass flatsedge, , , 0, 0, 0, Amaranthus retroflexus, , , -, -,-Amaranthus retroflexus, , , 15, 40, 70, soybean, , , , 15, -, 0 soybean, , , 80, 65, 25, finish and work as, , , , 0, 0, 0 finish work as, , , 15, 0, 0, yorkshire fog grass, , , 10, 0, 0 yorkshire fog grass, , , 100, 35, 25, the root of Beijing euphorbia, , , , 0, 0, 0 root of Beijing euphorbia, , , 55, 25, 10 experiment E
Plastic tub inserts mud fertile soil, filled with water, by the seed of rice (Oryza sativa) and the rice shoot of 2 leaf ages, selected from barnyard grass (Ecghinochloa crus-galli), duck salad (Heteranthera limosa), awns barnyard grass (Ecghinochloa colonum) evening watergrass (Ecghinochloa oryzicola), red shank (Ammania species), rice nutgrass flatsedge (Cyperus iria), little Hua nutgrass flatsedges (Cyperus difformis) and the seed of moleplant seed (Leptochloa fasiculars), stem tuber or plant part are planted in soil, planting and watering to be adjusted makes these crops and weed growth to appropriate test height, the water surface is brought up into soil surface above 3cm in 2 leaf age, this height is maintained during whole experiment, the compound prepared in the non-plant toxicity solvent mixture containing surfactant is directly administered in paddy field water by suction pipe, or be administered to by the belt transmission sprinkling air compression system of demarcation on plant leaf.
Processing and untreated control thing are placed in greenhouse about 21 days, are thereafter compared the plant of all processing and tester, are with the naked eye evaluated, it is 0-100 grade to record the result grade classification in table E, 0 represents to no effect, and 100 represent control completely, and (-) indicates no result of the test.Table E, , , , , , , , , compound amount 64g/ha, , , , , , , , 8PADDY, APPL/TAMA, SOIL barnyard grasses, , , , , , , , , 30ducksalad, , , , , , , , 95 awns barnyard grasses, , , , , , , , , 70 watergrasses, , , , , , , , , 0 red shank, , , , , , , , , 75 rice nutgrass flatsedges, , , , , , , , , 100 little Hua nutgrass flatsedges, , , , , , , , 100 moleplant seeds, , , , , , , , , 1002, LF, direct, seeded, indica, type, rice, 702, LF, transp, indica, type, rice, , , 60 table E, , , , , , , , , compound amount 32g/ha, , , , , , , , 8PADDY, APPL/TAMA, SOIL barnyard grasses, , , , , , , , , 20ducksalad, , , , , , , , 90 awns barnyard grasses, , , , , , , , , 80 watergrasses, , , , , , , , , 0 red shank, , , , , , , , , 60 rice nutgrass flatsedges, , , , , , , , , 100 little Hua nutgrass flatsedges, , , , , , , , 100 moleplant seeds, , , , , , , , , 952, LF, direct, seeded, indica, type, rice, , 452, LF, transp, indica, type, rice, , , 35 table E, , , , , , , , , compound amount 16g/ha, , , , , , , , 8PADDY, APPL/TAMA, SOIL barnyard grasses, , , , , , , , , 0ducksalad, , , , , , , , 45 awns barnyard grasses, , , , , , , , , 60 watergrasses, , , , , , , , , 0 red shank, , , , , , , , , 45 rice nutgrass flatsedges, , , , , , , , , 100 little Hua nutgrass flatsedges, , , , , , , , 50 moleplant seeds, , , , , , , , , 1002, LF, direct, seeded, indica, type, rice, , 352, LF, transp, indica, type, rice, , , 30 table E, , , , , , , , , compound amount 8g/ha, , , , , , , , 8PADDY, APPL/TAMA, SOIL barnyard grasses, , , , , , , , , 0ducksalad, , , , , , , , 50 awns barnyard grasses, , , , , , , , , 30 watergrasses, , , , , , , , , 0 red shank, , , , , , , , , 20 rice nutgrass flatsedges, , , , , , , , , 00 little Hua nutgrass flatsedges, , , , , , , , 65 moleplant seeds, , , , , , , , , 802, LF, direct, seeded, indica, type, rice, 402, LF, transp, indica, type, rice, , , 20 table E, , , , , , , , , compound amount 4g/ha, , , , , , , , 8PADDY, APPL/TAMA, SOIL barnyard grasses, , , , , , , , , 0ducksalad, , , , , , , , 55 awns barnyard grasses, , , , , , , , , 0 watergrass, , , , , , , , , 10 red shanks, , , , , , , , , 0 rice nutgrass flatsedge, , , , , , , , , 90 little Hua nutgrass flatsedges, , , , , , , , 45 moleplant seeds, , , , , , , , , 502, LF, direct, seeded, indica, type, rice, , 202, LF, transp, indica, type, rice, , , 10 experiment F
By careless (Brachiaria plantaginea) Bermuda grass (Cynodondactylon) of Alexandria,Brdif Sgnlgrass(Brachiaria plantyphylla),Shame amaranth (Portulaca oleracea),Artemisiifolia (Ambrosia elatior),Hairy flowered paspalum (Paspalumdilatatum),Eleusine indica (Eleusine indica),Big broomcorn millet ocean is careless (Panicummaximum),Rottboellia exaltata (Rottboellia exaltata),Johnson grass sorghum (Sorghumhalpense),Lady's-grass (Digitaria sanguinalis),Peanut (Arachis hypogaea),(Ipomoea lacunosa) is spent towards face,purple nutsrdge(Cyperusrotundus),Triple thatches (Cenvhrus echinatus),sourgrass(Trichachneinsularis),The seed of the shore tree of heaven careless (Brachiaria decumbens),Stem tuber or plant part are planted in greenhouse flowerpot,Or it is planted in the level land containing greenhouse soil,Plant growth is in separated flowerpot or individual compartment,Test compound is prepared in the non-plant toxicity solvated compoundses containing surfactant,Plant is carried out to apply before bud or after bud,It is applied in plantation seed or plant part one day and carries out before bud,It is applied in after bud when plant grows to 2-4 leaf ages and carries out (3-20cm).
The plant of untreated check plant and processing is put in greenhouse, was with the naked eye evaluated and is damaged using 13-21 days after herbicide, the grade of plant reaction is recorded in table F, it is divided into 0-100 grade, 0 represents not damaged, and 100 represent control completely, and (-) indicates no result of the test.Table F, , , , compound, table F, , , , compound amount 125g/ha, , , 2, , consumption 125g/ha, , , after 2 buds, , , , , , Alexandria grass before bud, , , 100, , Alexandria grass, , , 35 Bermuda grasses, , , , 95, , Bermuda grass, , , , 75Brdlf, Sgnlgrass, , 98, , Brdlf, Sgnlgrass, , 20 purslanes, , , , 98, , purslane, , , , 90 artemisiifolias, , , , 90, , artemisiifolia, , , , 98 cottons, , , , 100, , cotton, , , , 60 hairy flowered paspalums, , , 90, , hairy flowered paspalum, , , 25 eleusine indicas, , , , 80, , Rottboellia exaltata, , , , 35 big broomcorn millet sheep's hays, , , 40, , johnson grass sorghum, , , 35 Rottboellia exaltatas, , , , 35, , lady's-grass, , , , 85 johnson grass sorghums, , , 80, , peanut, , , , 25 lady's-grass, , , , 90, , towards face flower, , , , 90 peanuts, , , , 60, , purple nutgrass flatsedge, , , , 0 spends towards face, , , , 100, , triple thatches, , , , 0 purple nutgrass flatsedge, , , , 65, , Sourgrass, , , 100 triple thatches, , , , 75, , shore tree of heaven grass, , , , 80Sourgrass, , , 80 shore tree of heaven grass, , , , 75 table F, , , , , compound, table F, , , compound amount 64g/ha, , , 2, , consumption 64g/ha, , after 2 buds, , , , , , , Alexandria grass before bud, , , 80, , Alexandria grass, ,-Bermuda grass, , , , 90, , Bermuda grass, , , 65Brdlf, Sgnlgrass, , 98, , Brdlf, Sgnlgrass, 20 purslanes, , , , 98, , purslane, , , 65 artemisiifolias, , , , , 85, , artemisiifolia, , , , 80 cottons, , , , , 100, , cotton, , , , 60 hairy flowered paspalums, , , , 75, , hairy flowered paspalum, , , 0 eleusine indica, , , , 75, , Rottboellia exaltata, , , 25 big broomcorn millet sheep's hays, , , , 20, , johnson grass sorghum, , , 35 Rottboellia exaltatas, , , , 15, , lady's-grass, , , , 0 johnson grass sorghum, , , , 40, , peanut, , , , 0 lady's-grass, , , , , 75, , towards face flower, , , 0 peanut, , , , , 50, , purple nutgrass flatsedge, , , 0 spends towards face, , , , 85, , triple thatches, , , 0 purple nutgrass flatsedge, , , , 65, , Sourgrass, , 100 triple thatches, , , , 40, , shore tree of heaven grass, , , 0Sourgrass, , , , 80 shore tree of heaven grass, , , , 70 experiment G
Compound for being evaluated in the experiment is prepared in the non-plant toxicity solvent mixture containing surfactant, (bud pre-treatment) is applied to soil surface before plant seedlings are unearthed, and it is applied to the 2-4 leaf age stages (bud post processing) of plant growth, sand fertile soil is used for pre-emergence test, post-processed for bud using the native mixture of 60: 40 sand fertile soil and greenhouse basin, for bud pre-treatment, test compound was applied at after planting about one day.
For post-emergence test,Crop and weeds adjustment are grown into appropriate height,All plants are cultivated in common greenhouse,Crop and weeds include annual bluegrass (Poa annua),Black nightshade (Solanum nigra),Rush (Alopecurus myosuroides),Chickweed (Stellaria media),Benbie (Lamium amplexicaule),Downy brome (Bromus tectorum),Corydalis (Viola arvensis),Pig seedling (Galiumaparine),Green fox-brush (Setaria viridis),Goatweed (Aegilops cylindrica),Summer cypress (Kochia scoparia),Lamb's-quarters (Chenopodium album),littleseedcanarygrass(Phalaris minor),Rape (Brassica napus),Amaranthus retroflexus (Amaranthus retroflexus),Rye grass (Lolium multiflorum),scentlessChamon(Matricaria inodora),Veronica (Veronica persica),Spring barley (Hordeum vulgare cv.Klages '),Spring wheat (Triticum aestivumcv ' ERA '),Beet (Beta vulgaris cv. ' USI '),Heronsbill (Helianthumannuus cv ' Russiian Giant '),RHIZOMA FAGOPYRI CYMOSI (Polygonum convolvulus),Mustard seed (Sinapis arvensis),Wild oat (Avena fatua),Windgrass (Aperaspica-venti),Winter barley (Hordeum vulgare cv ' Igri '),Winter wheat (Triticum aestivum cv ' Talent ').
Wild oat is handled in two growth phases, 1st stage was when plant has 2-3 piece leaves, the leaves or initial tillering stage of 2nd stage was when plant has 4, processing and untreated check plant are placed in greenhouse about 21-28 days, are thereafter compared the plant of all processing and tester, are with the naked eye evaluated, it is 0-100 grade to record the result grade classification in table G, 0 represents to no effect, the represent control completely of and 100, the lamb's-quarters 100 45 40 of 100 90 10 black nightshade of annual bluegrass 0-5 annual bluegrass 00 rush, 0 10 5 rush, 00 black nightshades, 10 5 65 40 35 00 summer cypress 35-0 lamb's-quarters of big fox-brush 00 big fox-brush, 10 100 0 goatweed, 00 goatweed, 505 summer cypress of chickweed 0-0 chickweed 10 10 benbie, 90 85 10 benbie, 20 0 downy brome, 10 05 downy brome, 00 corydalis, 0 80- pigs seedling, 00 pig seedlings 95 85 before bud after the buds of 489 consumption 31g/ha of and (-) indicates no result of the test. table G compound table G compound amounts 31g/ha 28
Figure A9619505601391
Grass 00
Figure A9619505601392
Grass, , , , , 0, 0, 5, Amaranthus retroflexus, , , -, 85 rapes, , , , , 30, -, 15, wild wheat straw, , , 0, 0 Amaranthus retroflexus, , , , 85, 50, 65, Scentless, Chamom, -, 0 wild wheat straw, , , , 5, 0, 0, Veronica, , , 35, 75Scentless, Chamom, , 80, 45, 70, spring barley, , , 0, 0 Veronica, , , , 30, 80, 0, wheat, (, spring, ), , , 0, 0 spring barley, , , , 10, 0, 0, wheat, (, winter, ), , , 0, 30 beets, , , , , 100, -, 100, RHIZOMA FAGOPYRI CYMOSI, , , 0, 0 heronsbill, , , , 75, -, 5, mustard seed, , , , 15, 0 wheat, (, spring, ), , , , 15, 0, 0, wild oat, (, 1, ), , , 0, 0 wheat, (, winter, ), , , , 15, 0, 0, windgrass, , , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 0, 10, 0, winter barley, , , 0, 5 mustard seeds, , , , , 100, 100, 70 wild oats, (, 1, ), , , , -, 0,-wild oat, (, 2, ), , , , 5, 5, 0 windgrass, , , , 0, 0, 5 winter barleys, , , , 5, 0, 0 table G, , , , , , compound, , table G, , , , , compound amount 16g/ha, , , , 4, 8, 9, consumption 16g/ha, , , 2, after 8 buds, , , , , , , , , annual bluegrass before bud, , , , , 0, -, 0, annual bluegrass, , , , 0, 0 rush, , , , , 0, 10, 0, rush, , , , 0, 0 black nightshade, , , , , , 30, 80, 0, black nightshade, , , , 10, 0 chickweed, , , , , , 0, 100, 0, chickweed, , , , 20, 0 benbie, , , , , 35, 90, 5, benbie, , , , 0, 0 downy brome, , , , , 0, 0, 0, downy brome, , , , 0, 0 corydalis, , , , , , 0, 80, 0, pig seedling, , , , 0, 0 pig seedling, , , , , , 10, 65, 0, big fox-brush, , , , 0, 0 big fox-brush, , , , , 5, 85, 0, goatweed, , , , 0, 0 goatweed, , , , , 0, 0, 0, summer cypress, , , , 0, 0 summer cypress, , , , , , 0, -, 0, lamb's-quarters, , , , , 85, 80 lamb's-quarters, , , , , , 30, 50, -, Grass 00Grass, , , , , 0, 0, 0, Amaranthus retroflexus, , , , 60,-rape, , , , , , 0, -, 0, wild wheat straw, , , , 0, 0 Amaranthus retroflexus, , , , , 60, 55, -, Scentless, Chamom, -, 0 wild wheat straw, , , , , 5, 0, 0, Veronica, , , , 10, 65Scentless, Chamom, , , 70, 50, 40, spring barley, , , , 0, 0 Veronica, , , , , 15, 80, 0, wheat, (, spring, ), , , , 0, 0 spring barley, , , , , 0, 0, 0, wheat, (, winter, ), , , , 0, 10 beets, , , , , , 35, -, 70, RHIZOMA FAGOPYRI CYMOSI, , , , 0, 0 heronsbill, , , , , 0, -, 0, mustard seed, , , , 15, 0 wheat, (, spring, ), , , , , 0, 0, 0, wild oat, (, 1, ), , , , 0, 0 wheat, (, winter, ), , , , , 0, 0, 0, windgrass, , , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , , 0, 10, 0, winter barley, , , , 0, 0 mustard seed, , , , , , 50, 100, 85 wild oats, (, 1, ), , , , , -, 0,-wild oat, (, 2, ), , , , , 0, 0, 0 windgrass, , , , , 0, 0, 0 winter barley, , , , , 0, 0, 0 table G, , , , , , compound, , table G, , , , compound amount 8g/ha, , , , 4, 8, 9, consumption 8g/ha, , , 2, after 8 buds, , , , , , , , before bud, , annual bluegrass, , , , 0, -, 0, annual bluegrass, , , 0, 0 rush, , , , 0, 0, 0, rush, , , 0, 0 black nightshade, , , , , 10, 75, 0, black nightshade, , , , 0, 0 chickweed, , , , , 0, 85, 0, chickweed, , , , 0, 0 benbie, , , , 0, 50, 0, benbie, , , 10, 0 downy brome, , , , 0, 0, 0, downy brome, , , 0, 0 corydalis, , , , , 0, 30, -, pig seedling, , , , 0, 0 pig seedling, , , , , 0, 20, 0, big fox-brush, , , 0, 0 big fox-brush, , , , 0, 85, 0, goatweed, , , 0, 0 goatweed, , , , 0, 0, 0, summer cypress, , , , 0, 0 summer cypress, , , , , 0, -, 0, lamb's-quarters, , , , 75, 60 lamb's-quarters, , , , , 0, 50, 30,
Figure A9619505601411
Grass 00
Figure A9619505601412
Grass, , , , 0, 0, 0, Amaranthus retroflexus, , , 10, 65 oily Lays, , , , , 5, -, -, wild wheat straw, , , 0, 0 Amaranthus retroflexus, , , , -, 45, -, Scentless, Chamom, -, 0 wild wheat straw, , , , 0, 0, 0, Veronica, , , 10, 30Scentless, Chamom, , -, 70, 0, spring barley, , , 0, 0 Veronica, , , , 0, 65, 0, wheat, (, spring, ), , , 0, 0 spring barley, , , , 0, 0, 0, wheat, (, winter, ), , , 0, 0 beet, , , , , 25, -, 70, RHIZOMA FAGOPYRI CYMOSI, , , 0, 0 heronsbill, , , , 0, -, 0, mustard seed, , , , 5, 0 wheat, (, spring, ), , , , 0, 0, 0, wild oat, (, 1, ), , , 0, 0 wheat, (, winter, ), , , , 0, 0, 0, windgrass, , , 0, 0 RHIZOMA FAGOPYRI CYMOSI, , , , 0, 0, 0, winter barley, , , 0, 0 mustard seed, , , , , 30, -, 25 wild oats, (, 1, ), , , , -, 0,-wild oat, (, 2, ), , , , 0, 0, 0 windgrass, , , , 0, 0, 0 winter barley, , , , 0, 0, 0 table G, , , , , compound, , table G, , , , compound amount 4g/ha, , , 4, 8, 9, , consumption 4g/ha, , , 2, after 8 buds, , , , , , , non-irrigated ripe standing grain before bud, , , 0, -, 0, , annual bluegrass, , , 0, 0 rush, , , 0, 0, 0, , rush, , , 0, 0 black nightshade, , , , 0, 80, 0, , black nightshade, , , , 0, 0 chickweed, , , , 0, 65, 0, , chickweed, , , , 0, 0 benbie, , , 0, 15, 0, , benbie, , , 0, 0, downy brome, , , 0, 0, 0, , downy brome, , , 0, 0 corydalis, , , , 0, 15, 0, , pig seedling, , , , 0, 0 pig seedling, , , , 0, 20, 0, , big fox-brush, , , 0, 0 big fox-brush, , , 0, 40, 0, , goatweed, , , 0, 0 goatweed, , , 0, 0, 0, , summer cypress, , , , -, 0 summer cypress, , , , 0, -, 0, , lamb's-quarters, , , , 50, 10 lamb's-quarters, , , , 0, 50, 10,
Figure A9619505601421
Grass 00
Figure A9619505601422
Grass amaranthus retroflexus 0 0 0 0 25 oil pod 0 - wild wheatgrass 0 0 amaranthus retroflexus 15-30 Scentless Chamom wild wheatgrass 0 0 0 0 lepidium apetalum 10 15 Scentless Chamom 25 spring barley 10 0 0 lepidium apetalum 0 20 wheat (spring) spring barley 0 0 0 0 0 0 wheat (winter) 0 0 0 0 beet 15 to 40 wild buckwheat sunflower 0-0 mustard (spring) 0 0 0 0 0 wheat wild oats (1) (winter) 0 0 0 0 0 wheat wind cut strands of glume 0 0 0 0 0 0 0 winter barley wild buckwheat mustard 30, 90 wild oats (1) - 0-20 wild oats (2) 0 0 0 wind cut glume 0 0 0 winter barley 0 0 0

Claims (9)

1. compound in Formulas I or its agriculturally suitable salt：
Figure A9619505600021
Wherein：
Q is
Figure A9619505600022
R1And R2Each is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6Halogenated alkylthio；Or R1And R2Formation-X together1-(CH2)r-X2- ,-(CH2)s-X3,-(CH2)t-X3-CH2,-(CH2)v-X3-CH2CH2- or-(CH2)w-, each group is unsubstituted or is selected from 1-6 halogen, 1-6 CH3With a C1-C3At least one member substitution in alkoxy；Or R1And R2Formation-O-N (C together1-C3Alkyl)-CHR12-CH2- or-O-N=CHR12-CH2-, each group is unsubstituted or is selected from 1-2 halogen, 1-2 CH3In at least one member substitution；Or R1And R2The carbon atom connected with them forms C (=O) or C (=S) together；
X1And X2Each is independently O, S or N (C1-C3Alkyl)；
X3It is O or S；
Each R3It is independently H or CH3；
R4And R5Each is independently H, C1-C6Alkyl, C1-C6Haloalkyl, C1-C6Alkoxy, C1-C6Halogenated alkoxy, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl sulphinyl, C1-C6Alkylsulfinyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, halogen, cyano group, nitro；
R6It is OR11, C1-C6Alkylthio group, C1-C6Halogenated alkylthio, C1-C6Alkyl sulphinyl, C1-C6Alkylsulfinyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl, cyano group, cyanato-, thiocyanato or halogen；
Each R7It is independently C1-C3Alkyl, C1-C3Alkoxy, C1-C3Alkylthio group or halogen；Or as two R7When being connected on same carbon atom, described two R7Formation-OCH together2CH2O- ,-OCH2CH2CH2O- ,-SCH2CH2S- or-SCH2CH2CH2S-, each group is unsubstituted or by 1-4 CH3Substitution；
R8It is H, C1-C6Alkyl, C1-C6Haloalkyl, C2-C6Alkoxyalkyl, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl；Or R8It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R9It is H, C1-C6Alkyl, C1-C6Haloalkyl, C3-C6Alkenyl, C3-C6Alkynyl；Or R9It is phenyl or benzyl, each of which is unsubstituted or on phenyl ring by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R10It is H, C1-C6Alkyl, C1-C6Haloalkyl, halogen, cyano group or nitro；
R11It is H, C1-C6Alkyl, C1-C6Haloalkyl, C2-C6Alkoxyalkyl, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl；Or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；
R12It is C1-C3Alkyl, or R12It is unsubstituted or by C1-C3The phenyl of alkyl, halogen, cyano group or nitro substitution；
X is S (O)n, O or NR13；
R13It is H, C1-C3Alkyl, C3-C4Alkenyl, C3-C4Alkynyl, formoxyl, C2-C3Alkyl-carbonyl, C2-C3Alkoxy carbonyl or C1-C2Alkyl sulphonyl；
Y is O, S, NH, N (C1-C3Alkyl), or be unsubstituted or by R when q is not 07Substituted CH2；
Z is direct key, O, S (O)2, NH, N (C1-C3Alkyl), or when q is not 0 be unsubstituted or by R7Substituted CH2, its condition is when Y is O, S, NH or N (C1-C3Alkyl) when, Z is direct key or unsubstituted or by R7Substituted CH2；
K and m are independently each 0,1 or 2, and its condition is k and m and is 0,1 or 2；
N and p are independently each 0,1 or 2；
Q is 0,1,2,3 or 4；
R is 2,3 or 4；
S is 2,3,4 or 5；
T is 1,2,3 or 4；
V is 2 or 3；
W is 2,3,4,5 or 6；
X is 1 or 2；And
Z is 0,1 or 2；
Its condition is：
(i) when X is S (O)n, Q is Q-1 and R1And R2It is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6When halogenated alkylthio or the carbon atom connected with them form C (=O) together, then n is 1 or 2；And
(ii) when X is O or NR13And R1And R2It is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6When halogenated alkylthio or the carbon atom connected with them form C (=O) together, then Q is Q-2.
2. according to the compound of claim 1, wherein：Each R7It is independently C1-C3Alkyl or halogen；X is S (O)n；Y and Z are independently unsubstituted or by R7Substituted CH2；K is 0；And x is 1.
3. according to the compound of claim 2, wherein：R1And R2Each is independently C1-C6Alkoxy, C2-C6Halogenated alkoxy, C1-C6Alkylthio group or C2-C6Halogenated alkylthio；Or R1And R2Formation-X together1-(CH2)r-X2, it is unsubstituted or is selected from 1-6 halogen, 1-6 CH3In at least one member substitution；Or R1And R2The carbon atom connected with them forms C (=O) together；X1And X2Both are that O or both is S；M is 1 or 2；R is 2 or 3.
4. according to the compound of claim 3, wherein：R4And R5Each is independently H, C1-C3Alkyl or halogen；R7It is C1-C3Alkyl；R9It is H, C1-C6Alkyl or C3-C6Alkenyl；R10It is H；R11It is H, formoxyl, C2-C6Alkyl-carbonyl, C2-C6Alkoxy carbonyl, C2-C6Alkyl amino-carbonyl, C3-C7Dialkyl amino carbonyl, C1-C6Alkyl sulphonyl, C1-C6Halogenated alkyl sulfonyl；Or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；And n is 2.
5. according to the compound of claim 4, wherein：R1And R2Each is independently methoxyl group, or R1And R2Formation-X together1-(CH2)r-X2-, or R1And R2The carbon atom connected with them forms C (=O) together；X1And X2It is O；R4And R5Each is independently H, methyl or halogen；R6It is OR11；R8It is H, C1-C2Alkyl sulphonyl, or R8It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；R11It is H, C1-C2Alkyl sulphonyl, or R11It is benzoyl or phenyl sulfonyl, each of which is unsubstituted or by C1-C3Alkyl, halogen, cyano group or nitro substitution；And m is 1；It is 2 with r.
6. according to the compound of claim 5, wherein：R5It is methyl or halogen, and is connected on phenyl ring and is adjacent to-S (O)n- position on.
7. according to the compound of claim 3, it is selected from：2 [(2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide；(2,3- dihydro spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (base of 1- ethyl -5- hydroxyl -1H- pyrazoles -4) ketone S, S- dioxide；2 [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones S, S- dioxide；(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone S, S- dioxide；6- [(1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) carbonyl] -2,3- dihydro -5,8- dimethyl -4H-1- benzothiopyran derivative -4- ketone 1,1- dioxide；2 [(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) carbonyl] -1,3- cyclohexanediones；(2,3- dihydro -5,8- dimethyl spiral shells [4H-1- benzothiopyran derivative -4,2 '-[1,3] dioxolanes] -6- bases) (1- ethyl -5- hydroxyl -1H- pyrazoles -4- bases) ketone.
8. a kind of Herbicidal combinations, it contains the compound and at least one surfactant, solid diluent or liquid diluent of the claim 1 of herbicidally effective amount.
9. control the method for undesired plant growth, including compound with the claim 1 of herbicidally effective amount and the plant or its local environment are contacted.
CN96195056A 1995-06-29 1996-06-19 Herbicidal ketals and spirocycles Pending CN1189161A (en)

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