CN1688546A - Pyridinyl amides and imides for use as fungicides - Google Patents
Pyridinyl amides and imides for use as fungicides Download PDFInfo
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- CN1688546A CN1688546A CN 01815519 CN01815519A CN1688546A CN 1688546 A CN1688546 A CN 1688546A CN 01815519 CN01815519 CN 01815519 CN 01815519 A CN01815519 A CN 01815519A CN 1688546 A CN1688546 A CN 1688546A
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Abstract
Compounds of Formula (I), their N-oxides and agriculturally suitable salts are disclosed which are useful as fungicides formula (I), (II) wherein A is a substituted pyridinyl ring; B is a substituted pyridinyl ring; W is C=L or SOn is O or S; R<1> and R<2> are each independently H; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl, each optionally substituted; R<3> is H; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; R<4> is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl, each optionally substituted; X is O or S; and n is 1 or 2; provided that when W is C=O and R<1>, R<2> and R<3> are H; then B is other than 4-trifluoromethyl-3-pyridinyl, 2-chloro-4-pyridinyl and 2,6-dihalo-4-pyridinyl. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling plant diseases caused by fungal plant pathogens that involves applying an effective amount of a compound of Formula (I).
Description
Background of invention
The present invention relates to some picolinamide and pyridine imide, their N-oxide compound, suitable agricultural salt and composition, and as the usage of mycocide.
It is extremely important that being controlled at of the Plant diseases that is caused by the fungi plant pathogenic agent obtains in the high cereal harvest.Plant diseases can cause the obvious underproduction to damaging ornamental plant, vegetables, farmland, cereal and fruit crop, thereby causes human consumer's expense to increase.Have many commodity to can be used as this purposes, but still need more effective, cost is low, toxicity is little, more environmental protection or the different novel cpd of binding mode.
WO 99/42447 discloses the benzamide as some general formula i of mycocide.
R especially wherein
1Be H, alkyl or acyl group; R
2Be H or alkyl; With L be-(C=O)-,-SO
2-or-(C=S)-.
The present invention's general introduction
The present invention relates to comprise all how much with spatial isomer, N-oxide compound, and general formula I of their suitable agricultural salts or general formula I I compound:
Wherein
The pyridyl ring of A for replacing;
The pyridyl ring of B for replacing;
W is C=L or SO
n
L is O or S;
R
1And R
2Independently be H separately; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, each all nonessential being substituted;
R
3Be H; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl or C
3-C
8The dialkylamino carbonyl;
R
4Be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, each all nonessential being substituted;
X is O or S; With
N is 1 or 2; Condition be when W be C=O and R
1, R
2And R
3During for H; Then B is for removing 4-trifluoromethyl-3-pyridyl, 2-chloro-4-pyridyl and 2, other pyridyl ring that 6-dihalo--4-pyridyl is outer.
The invention still further relates to the The compounds of this invention that comprises the fungicidal effective dose and be selected from least a other compositions of tensio-active agent, solid diluent or liquid diluent, and/or have the fungicide composition of at least a other sterilant of different binding modes.
The invention still further relates to the control method of the Plant diseases that causes by the fungi plant pathogenic agent, comprise that the The compounds of this invention (composition for example described herein) with effective fungicidal amount is applied on plant or its part, or use on plant seed or the rice shoot.
Detailed Description Of The Invention
As mentioned above, A and B independently are the pyridyl ring that replaces separately.The term " replacement " relevant with the B group with these A refers to have and can not weaken active at least one the non-hydrogen substituent group of mycocide.Mix wherein A by 1-4 R
5Replacement, b are by 1-4 R
6The general formula I of the described pyridyl ring that replaces and the example of general formula I I are included in the ring of describing among the following Exhibit 1, and wherein m and p independently are the integers of 1-4.Note (R
5)
mAnd between the A, and (R
6)
pAnd the tie point between the B is described as moving point, and (R
5)
m(R
6)
pCan be connected on any suitable carbon atom of pyridyl ring.
Exhibit?1
R when being connected with A
5R when being connected with B
6Example comprise:
R
5And R
6Independently be C separately
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl or C
3-C
6Trialkylsilanyl.
Other R
5And R
6Group is obviously for those of ordinary skills.Each R for example
5And/or R
6Can be NH
2, NHCO (C
1-C
4Alkyl) or NHCO (C
1-C
4Alkylhalide group); Or each R
5And/or R
6Can be phenyl, benzyl or phenoxy group, each personal C
5-C
8The trialkylsilanyl alkynyl substituted.
It should be noted that the compound of general formula I, wherein
R
5And R
6Independently be C separately
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
5-C
8Trialkylsilanyl alkynyl or C
3-C
6Trialkylsilanyl.
As mentioned above, R
1And R
2Independently be H separately; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, nonessential separately being substituted; R
4Be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, nonessential separately being substituted.With these R
1, R
2And R
4The term " nonessential being substituted " that group is relevant refers to unsubstituted group, or has and can not weaken at least one the non-hydrogen substituted radical that has fungicidal activity by unsubstituted analogue.Nonessential substituted R
1, R
2And R
4Examples of groups is nonessential by one or more halogen, CN, NO of being selected from
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
2-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino and C
3-C
6Those that the substituting group of naphthene amino replaces.Although listed these substituting groups in above-mentioned example, obviously they are not to exist, because they are nonessential substituting groups.
The example of the N-oxide compound of general formula I and general formula I I respectively with the I-10 among the Exhibit 2 to I-16, and II-10 describes to II-16, wherein R
1, R
2, R
3, R
4, R
5, R
6, W, X, m and p definition as mentioned above.
Exhibit?2
In above statement, use separately or be used for the compound title and comprise the straight or branched alkyl as the term " alkyl " of " alkyl thio-base " or " alkylhalide group ", as methyl, ethyl, n-propyl, sec.-propyl, or different butyl, amyl group or hexyl isomer.Term " 1-2 alkyl " refers to that one or two correct position can be the independent alkyl of selecting." alkenyl " comprises straight or branched alkene, as vinyl, 1-propenyl, 2-propenyl, with different butenyl, pentenyl and hexenyl isomer." alkenyl " also comprises polyenoid as 1,2-propadiene base and 2,4-hexadienyl." alkynyl " comprises straight or branched alkynes such as ethynyl, 1-proyl, 2-propynyl and different butynyl, pentynyl and hexin base isomer." alkynyl " can comprise that also by such as 2,5-hexadiyne base etc. contains the group of a plurality of three keys." alkoxyl group " comprises for example methoxyl group, oxyethyl group, positive propoxy, isopropoxy and different butoxy, pentyloxy and hexyloxy isomer." alkoxyalkyl " refers to the alkoxyl group that replaces on alkyl.The example of " alkoxyalkyl " comprises CH
3OCH
2, CH
3OCH
2CH
2, CH
3CH
2OCH
2, CH
3CH
2CH
2CH
2OCH
2And CH
3CH
2OCH
2CH
2" alkoxyl group alkoxyl group " refers to the alkoxyl group that replaces on alkoxyl group.Term " alkenyl oxy " comprises the alkenyl oxy of straight or branched.The example of " alkenyl oxy " comprises H
2C=CHCH
2O, (CH
3)
2C=CHCH
2O, (CH
3) CH=CHCH
2O, (CH
3) CH=C (CH
3) CH
2O and CH
2=CHCH
2CH
2O." alkynyloxy base " comprises straight or branched alkynyloxy base.The example of " alkynyloxy base " comprises HC ≡ CCH
2O, CH
3C ≡ CCH
2O and CH
3C ≡ CCH
2CH
2O." alkyl thio-base " comprises that branched-chain or straight-chain alkyl thio group part is as methyl thio group, ethylenebis dithiocarbamate base, with different propyl dithiocarbamate base, butyl thio group, amyl group thio group and hexyl thio group isomer." alkyl-thio-alkyl " refers to the alkyl thio-base that replaces on alkyl.The example of " alkyl-thio-alkyl " comprises CH
3SCH
2, CH
3SCH
2CH
2, CH
3CH
2SCH
2, CH
3CH
2CH
2CH
2SCH
2And CH
3CH
2SCH
2CH
2" alkylthio alkoxyl group " refers to the alkyl thio-base that replaces on alkoxyl group." alkyl sulfinyl " comprises two kinds of enantiomorphs of alkyl sulfinyl.The example of " alkyl sulfinyl " comprises CH
3S (O), CH
3CH
2S (O), CH
3CH
2CH
2S (O), (CH
3)
2CHS (O) and different butyl sulfinyl, amyl group sulfinyl and hexyl sulfinyl isomer.The example of " alkyl sulphonyl " comprises CH
3S (O)
2, CH
3CH
2S (O)
2, CH
3CH
2CH
2S (O)
2, (CH
3)
2CHS (O)
2With different butyl alkylsulfonyl, amyl group alkylsulfonyl and hexyl alkylsulfonyl isomer." Qing Wanji " refers to the alkyl with a cyano group replacement.The example of " Qing Wanji " comprises NCCH
2, NCCH
2CH
2And CHCH (CN) CH
2" alkylamino ", " dialkylamino ", " alkenyl thio group ", " alkenyl sulfinyl ", " alkenyl alkylsulfonyl ", " alkynyl thio group ", " alkynyl sulfinyl ", " alkynyl alkylsulfonyl " etc. are similar with the definition of above-mentioned example." cycloalkyl " comprises for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.Term " cycloalkyloxy " comprises the identical group that connects by a Sauerstoffatom, as cyclopentyloxy and cyclohexyloxy.
Use separately or the compound title as " alkylhalide group " in the term " halogen " of use comprise fluorine, chlorine, bromine or iodine.Term " 1-2 halogen " refers to that substituent one or two correct position can be those of the independent halogen of selecting.In addition, when being used for the compound title as " alkylhalide group ", described alkyl can partly or entirely be replaced by identical or different halogen atom.The example of " alkylhalide group " comprises F
3C, ClCH
2, CF
3CH
2And CF
3CCl
2Term " halogen alkenyl ", " alkynyl halide ", " halogen alkoxyl group ", " alkylhalide group thio group " etc. are similar with the definition of term " alkylhalide group ".The example of " halogen alkenyl " comprises (Cl)
2C=CHCH
2And CF
3CH
2CH=CHCH
2The example of " alkynyl halide " comprises HC ≡ CCHCl, CF
3C ≡ C, CCl
3C ≡ C and FCH
2C ≡ CCH
2The example of " halogen alkoxyl group " comprises CF
3O, CCl
3CH
2O, HCF
2CH
2CH
2O and CF
3CH
2O.The example of " alkylhalide group thio group " comprises CCl
3S, CF
3S, CCl
3CH
2S and ClCH
2CH
2CH
2S.The example of " alkylhalide group sulfinyl " comprises CF
3S (O), CCl
3S (O), CF
3CH
2S (O) and CF
3CF
2S (O).The example of " alkylhalide group alkylsulfonyl " comprises CF
3S (O)
2, CCl
3S (O)
2, CF
3CH
2S (O)
2And CF
3CF
2S (O)
2The example of " halogen alkoxyl group alkoxyl group " comprises CF
3OCH
2O, ClCH
2CH
2OCH
2CH
2O, Cl
3CCH
2OCH
2O, and branched-chain alkyl derivative.The example of " alkyl carbonyl " comprises C (O) CH
3, C (O) CH
2CH
2CH
3And C (O) CH (CH
3)
2The example of " alkoxy carbonyl " comprises CH
3OC (=O), CH
3CH
2OC (=O), CH
3CH
2CH
2OC (=O), (CH
3)
2CHOC (=O), with different butoxy carbonyl or pentyloxy carbonyl isomer.
One of ordinary skill in the art will appreciate that not all nitrogen heterocyclic ring can both form the N-oxide compound,, form oxide compound with oxidation because nitrogen requires suitable lone electron pair.Those of ordinary skills can know the nitrogen heterocyclic ring that can form the N-oxide compound, can know that also tertiary amine can form the N-oxide compound.The synthetic method of the N-oxide compound of preparation heterocycle and tertiary amine is known to a person of ordinary skill in the art, comprises heterocycle and tertiary amine and such as peracetic acid and m-chlorine peroxybenzoic acid peroxy acids such as (MCPBA), hydrogen peroxide, such as alkyl hydroperoxides such as tert-butyl hydroperoxide, Sodium peroxoborate with such as the oxidation of diepoxide for example such as dimethyl ethylene oxide.These preparation methods of N-oxide compound extensively describe in the literature and comment, and referring to for example: T.L.Gilchrist is at Comprehensive Organic Synthesis, the 7th volume, and the 748-75O page or leaf, S.V.Ley compiles, and describes among the Pergamon Press; M.Tisler and B.Stanovnik are at Comprehensive Heterocyclic Chemistry, and the 3rd rolls up, the 18-20 page or leaf, and A.J.Boulton and A.Mckillop compile, and describe among the Pergamon Press; M.R.Grimmett and B.R.T.Keene are at Advances in HeterocyclicChemistry, and the 43rd rolls up, the 149-161 page or leaf, and A.R.Katritzky compiles, and describes among the AcademicPress; M.Tisler and B.Stanovnik are at Advances inHeterocyclic Chemistry, and the 9th rolls up, the 285-291 page or leaf, and A.R.Katritzky and A.J.Boulton compile, and describe among the Academic Press; And G.W.H.Cheeseman and E.S.G.Werstiuk be at Advances in Heterocyclic Chemistry, the 22nd, the 390-392 page or leaf, and A.R.Kartitzky and A.J.Boulton compile, and describe among the Academic Press.
The total number of carbon atoms in the substituting group " C
i-C
j" prefix designates, wherein i and j are the number of 1-8.C for example
1-C
3The alkyl sulfonyl basis representation from methyl sulphonyl to the sulfonyl propyl base; C
2Alkoxyalkyl is represented CH
3OCH
2C
3Alkoxyalkyl is represented for example CH
3CH (OCH
3), CH
3OCH
2CH
2Or CH
3CH
2OCH
2And C
4Alkoxyalkyl is represented for example to comprise CH with containing the various isomer of the alkyl of the alkoxyl group replacement of 4 carbon atoms altogether
3CH
2CH
2OCH
2And CH
3CH
2OCH
2CH
2
When a kind of compound when having the following target substituting group that can surpass 1 the described substituting group quantity of indication, described substituting group (when they surpass 1) independently is selected from the substituting group of definition.In addition, when scope of subscript indication as (R)
I-jThe time, substituent quantity can be selected from the integer that (comprises i and j) between i and the j.
When a group comprises can be the substituting group of hydrogen the time, as R
1Or R
2The time, when this substituting group is hydrogen, can think to be equal to not substituted radical so.
Compound of the present invention can exist by one or more steric isomers.Different steric isomers comprise enantiomorph, diastereomer, atropisomer and geometrical isomer.One of ordinary skill in the art will appreciate that other steric isomer content are higher relatively when a kind of steric isomer, or when it separates with other steric isomers, activity can more be arranged and/or can show useful effect.In addition, the skilled manpower know how to separate, enrichment and/or prepare described steric isomer selectively.Therefore, the present invention includes the compound, its N-oxide compound and its agricultural that are selected from general formula I and go up suitable salt.Compound of the present invention can stereoisomer mixture, independent steric isomer or exist with the photolytic activity form.Especially the R that works as general formula I and general formula I I
1And R
2Not simultaneously, described general formula does not have chiral centre with carbon atom place that it is connected jointly.The present invention includes racemic mixture.In addition, the present invention includes the higher compound of more a kind of enantiomorph content of racemic mixture in the enantiomorph with following general formula
Comprise in fact purified general formula I ' and the enantiomorph of general formula I I '.The present invention also comprises the higher compound of more a kind of enantiomorph content of racemic mixture in the enantiomorph with following general formula
Comprise in fact purified general formula I " and general formula I I " enantiomorph.
When the enantiomorph enrichment, a kind of enantiomorph can be more than the amount of other enantiomorphs, and the degree of enrichment can define with the expression (" ee ") of enantiomeric excess, promptly be defined as 100 (2x-1), wherein x is the molecular fraction (enantiomorph of 60: 40 ratio of ee correspondence as 20%) of main enantiomorph in the mixture.
With respect to R
1, R
2The more activated enantiomorph of relative position, A and other molecules that are connected by nitrogen are corresponding to 2,4-two chloro-N-[(1R)-1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-configuration of the enantiomorph of 3-pyridine carboxamide, when its at CDCl
3In the time of in the solution, (+) or dextrorotation direction Plane of rotation polarized light (being the main enantiomorph of the compound 31 of concordance list B).
The present composition preferably has the more enantiomeric excess of active isomer at least 50%; More preferably at least 75% enantiomeric excess; Preferred especially at least 90% enantiomeric excess; At least 94% enantiomeric excess most preferably.
The compound of general formula I I for the C=N key in this structure also can be (E)-or (Z)-isomer, or (E)-exist with (Z)-mixture of isomers.The present invention includes the mixture and the individual isomer of geometrical isomer.
The salt of The compounds of this invention comprises the acid salt with mineral acid or organic acid such as Hydrogen bromide, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetate, butyric acid, fumaric acid, lactic acid, toxilic acid, propanedioic acid, oxalic acid, propionic acid, Whitfield's ointment, tartrate, 4-toluenesulphonic acids or valeric acid.When The compounds of this invention contained such as the carboxylic acid of acidic groups or phenol, the salt of The compounds of this invention also comprised the salt that forms with organic bases (as pyridine, ammonia or triethylamine) or mineral alkali (as hydride, oxyhydroxide or the carbonate of sodium, potassium, lithium, calcium, magnesium or barium).
With regard to activity better and/or was easily synthesized, preferred compound was:
Preferred 1: the compound of general formula I and general formula I I preferably, wherein
A is 1-4 R
5The pyridyl ring that replaces;
B is 1-4 R
6The pyridyl ring that replaces;
R
1And R
2Independently be H separately; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, one or more halogen, CN, the NO of being selected from of nonessential separately usefulness
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
2-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino and C
3-C
6The substituting group of naphthene amino replaces;
R
4Be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, one or more halogen, CN, the NO of being selected from of nonessential separately usefulness
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
2-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino and C
3-C
6The substituting group of naphthene amino replaces; With
R
5And R
6Independently be C separately
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl or C
3-C
6Trialkylsilanyl.
It should be noted that such Preferred 1 compound, wherein
Each R
5Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Condition is when A is the 2-pyridyl, R
5Be to remove C
1-C
6Other bases that alkylhalide group is outer; With
Each R
6Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl or C
3-C
6Trialkylsilanyl replaces.
Preferred 2: wherein W is Preferred 1 compound of the general formula I of C=O.
It should be noted that wherein A is Preferred 2 compounds of the 3-pyridyl ring of replacement.It should be noted such Preferred 2 compounds equally, wherein
Each R
5Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Condition is when A is the 2-pyridyl, R
5Be to remove C
1-C
6Other bases that alkylhalide group is outer.
Preferred 3:Preferred 2 compounds, wherein
A is for using 1-4 R
5The 2-pyridyl ring that replaces; With
1-4 R of B
6Replace, but at least one R
6Be connected with the W ortho position.
It should be noted following Preferred 3 compounds, wherein R
5Be Cl, Br, CH
3, OCF
3, OCHF
2, OCH
2CF
3, OCF
2CF
3, OCF
2CF
2H, OCHFCF
3, SCF
3, SCHF
2, SCH
2CF
3, SCF
2CF
3, SCF
2CF
2H, SCHFCF
3, SOCF
3, SOCHF
2, SOCH
2CF
3, SOCF
2CF
3, SOCF
2CF
2H, SOCHFCF
3, SO
2CF
3, SO
2CHF
2, SO
2CH
2CF
3, SO
2CF
2CF
3, SO
2CF
2CF
2H or SO
2CHFCF
3It should be noted such Preferred 3 compounds equally, wherein B is an one R
6Be connected with W ortho position key in each position (with nonessential 1-2 other R
6) 3-pyridyl or 4-pyridyl ring.
The compound of Preferred 4:Preferred 3, wherein B is an one R
6Be connected and nonessential 1-2 other R with the W ortho position in each position
6And R
63-pyridyl or 4-pyridyl ring for halogen or methyl.
Preferred 5: wherein B is Preferred 4 compounds of 3-pyridyl ring, one of them R
6For Cl and be positioned on the 2-position that is connected with the W ortho position another R
6Be selected from Cl or methyl and be positioned at and be connected on the 4-position the 3rd nonessential R with the W ortho position
6Be the locational methyl of 6-.
Preferred 6: wherein A is 3-chloro-5-CF
3Preferred 5 compounds of-2-pyridyl.
Preferred 7: R wherein
1Be H and R
2Be CH
3Preferred 3 compounds, but Preferred 4 compounds especially.
Preferred 8: Preferred 1 compound of general formula I I, wherein
A is for using 1-4 R
5The 2-pyridyl ring that replaces; With
1-4 R of B
6Replace, but at least one R
6Be connected with the carbon atom ortho position key that is connected to X and B jointly.
Preferred 9: wherein X is Preferred 5 compounds of S.
Preferred compound of the present invention comprises wherein R
1Be H or CH
3, R
2Be H and (in general formula I) R
3Arrive the compound of Preferred 9 for the Preferred 1 of H.
Particularly preferably be and be selected from following compound
2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-3-pyridine carboxamide, 2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-3-pyridine carboxamide, 2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-6-methyl-3-pyridine carboxamide, with 2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-6-methyl-3-pyridine carboxamide.
Particularly preferably be equally and be selected from following compound
2,4-two chloro-N-[(3,5-two chloro-2-pyridyl) methyl]-the 3-pyridine carboxamide, 2,4-two chloro-N-[1-(3,5-two chloro-2-pyridyl) ethyl]-the 3-pyridine carboxamide, 2,4-two chloro-N-[(3,5-two chloro-2-pyridyl) methyl]-6-methyl-3-pyridine carboxamide, 2,4-two chloro-N-[1-(3,5-two chloro-2-pyridyl) ethyl]-6-methyl-3-pyridine carboxamide, N-[(5-bromo-3-chloro-2-pyridyl) methyl]-2,4-two chloro-3-pyridine carboxamides, N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2,4-two chloro-3-pyridine carboxamides, N-[(5-bromo-3-chloro-2-pyridyl) methyl]-2,4-two chloro-6-methyl-3-pyridine carboxamides, and N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2,4-two chloro-6-methyl-3-pyridine carboxamides.
The invention still further relates to The compounds of this invention that contains effective fungicidal amount and the fungicide composition that is selected from least a other compositions of tensio-active agent, solid diluent or liquid diluent.Preferred compositions of the present invention is those compositions that comprise above-mentioned preferred compound.
The invention still further relates to the control method of the Plant diseases that causes by the fungi plant pathogenic agent, comprise that the The compounds of this invention (composition for example described herein) with effective fungicidal amount is applied on plant or its part, or be administered on plant seed or the rice shoot.Preferred using method relates to the method for above-mentioned preferred compound.
The compound of general formula I and general formula I I can be by the variation preparation of describing among one or more following methods and the scheme 1-6.A, B in the compound of following general formula 1-4, L, W, R1 are to the definition of R6, X and n as mentioned above.The compound of general formula 1a, 1b and 1c is the subsystem of general formula 1.The compound of general formula I a, Ib and Ic is the subsystem of the compound of general formula I, and all substituting groups of general formula I a, Ib and Ic are identical with the above definition of general formula I.The compound of general formula I Ia is the subsystem of the compound of general formula I I, and all substituting groups of general formula I Ia are identical with the above definition of general formula I I.
The compound of general formula I can prepare with the method for describing among the following scheme 1-5.The compound of general formula I c and IIa can prepare with the method for describing in the following scheme 6.
The compound of general formula I a is by in the presence of the alkali (as triethylamine or salt of wormwood) of 2 molar equivalents, and the ammonium salt with suitable acyl chlorides processing general formula I in inert solvent prepares.Suitable solvent is selected from such as ethers such as tetrahydrofuran (THF), glycol dimethyl ether or diethyl ether; Such as hydro carbons such as toluene or dimethylbenzene; With such as halocarbon classes such as methylene dichloride or chloroforms.
Scheme 1
As selection, the compound of general formula I a can be by such as 1,3-dicyclohexyl carbodiimide (DCC) or 1-[3-(dimethylamino) propyl group]-organic dewatering agent existence such as 3-ethyl-carbodiimide hydrochloride (EDC) are down, the ammonium salt of general formula I and suitable carboxylic acid reaction are synthesized, as describing in the scheme 2.Suitable solvent is selected from such as ethers such as tetrahydrofuran (THF), glycol dimethyl ether or diethyl ether; Such as hydro carbons such as toluene or dimethylbenzene; With such as halocarbon classes such as methylene dichloride or chloroforms.
Scheme 2
Wherein A has pointed substituent 2-pyridyl, and R
1, R
2And R
3For the intermediate product salt 1a of hydrogen can use with WO99/42447 in similar method, by in the presence of highly basic, such as N, in the polarity of dinethylformamide, the aprotonic solvent, will be purchased imines ester 5 and R shown in the scheme 3 such as sodium hydride
52 of replacement, 3-dichloropyridine (general formula 4) reacts, and heats then to prepare in acidic medium.The compound of general formula 1b can be by similar method preparation, and before wherein heating in acidic medium, the middle negatively charged ion that step 1 is obtained is used such as the alkylating agent of methyl iodide and handled earlier.Should note wherein R
5Be CF
3Compound.
Scheme 3
Have an aminomethyl the compound (the wherein pyridyl ring of A) of general formula 1c for replacing can obtain corresponding aminomethyl intermediate product and synthesize (scheme 4) by in toluene, reduce the nitrile (wherein A is the pyridyl ring of replacement) of general formula 2 with lithium aluminum hydride.
Scheme 4
The pyridyl ring of A for replacing
As selection, (wherein A as above defines and R the compound of general formula 1c
1And R
2Compound for hydrogen) can be by in such as protonic solvents such as methyl alcohol, the compound and the ammonia react of general formula 3 synthesized.The compound of general formula 1c also can be by reacting the compound of general formula 3 and the sylvite of phthalic imidine, then in alcoholic solvent with monoethanolamine or hydrazine reaction, so that the sylvite that requires imines reaction to be provided, then in alcoholic solvent with monoethanolamine or hydrazine reaction, so that the amino methyl intermediate product of requirement to be provided, general formula 1c prepares (scheme 5).
Scheme 5
LG is Cl, Br ,-OSO
2Me ,-OSO
2-p-Tol
The compound of general formula I Ia (R wherein
1, R
2, A is identical with above-mentioned definition with B and X is S) can synthesize like that as scheme 6 general introduction.Below shown in the acid amides (R wherein of general formula I b
3Compound for the general formula I of H) can by the reagent of acid amides and Lawessond ' s or thiophosphoric anhydride are contacted in suitable solvent be converted into general formula I c thioamides (referring to March; J.Advanced Organic Chemistry, the 4th edition, pp893-4).Available then suitable alkylating agent is in the presence of the alkali such as salt of wormwood, sodium hydride or potassium hydroxide, with the thioamides alkylation.Suitable solvent can include, but is not limited to such as ethers such as tetrahydrofuran (THF), glycol dimethyl ether or diethyl ether; Such as hydro carbons such as toluene or dimethylbenzene; With such as halocarbon classes such as methylene dichloride or chloroforms.
Scheme 6
Know: some reagent of the compound of above-mentioned preparation general formula I and reaction conditions can be not with intermediate product in some functionality of existing compatible.In these examples, in synthetic, insert and protect/go protection order or functional group's change to help the product that obtains to require.Use and select blocking group for the those of ordinary skill of the field of chemical synthesis be clearly (referring to for example Greene, T.W.; Wuts, P.G.M.Protective Groups in OrganicSynthesis, second edition; Wiley: New York, 1991).Those of ordinary skills know: in some cases, introduce the given reagent of describing in any single scheme after, other synthesis paths of perhaps will not describing in detail, synthetic with the compound of finishing general formula I.Those of ordinary skills also know: perhaps will be with other orders the particular order that proposes in such scheme with the several steps combination, with the compound of preparation general formula I.
Those of ordinary skills also know: the compound of general formula I and intermediate product described herein can carry out various electrophilic reactions, nucleophilic reaction, radical reaction, organometallic reaction, oxidizing reaction and reduction reaction, to increase the existing substituting group of substituting group or modification.
Needn't carry out other work, can think that those of ordinary skills can utilize the present invention to reach its whole purposes with aforesaid method.Therefore following examples only are used to illustrate, and do not limit the present invention in any way.Except that the chromatographic solvent mixture or have in addition the explanation, per-cent all is weight percentage.Unless otherwise indicated, the umber of chromatographic solvent mixture and percentage ratio are the volume number.
1H NMR spectrum provides with ppm from the downfield of tetramethylsilane; S is that unimodal, d is that bimodal, t is that three peaks, q are that four peaks, m are that multimodal, dd are that double doublet, dt are that three bimodal, br is wide unimodal.
Embodiment 1
2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]
-6-methyl-3-pyridine carboxamide
The preparation of (compound 8 of key B)
Steps A: 2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-the 6-methyl
The preparation of-3-pyridine carboxamide
Compound 8 usefulness 2-amino methyls-3-chloro-5-5-flumethiazine hydrochloride preparation (pressing the method preparation that WO99/42447 describes).With 2 in the 2mL methylene dichloride, 4-two chloro-6-methyl-3-pyridine formyl chloride (0.65g) at room temperature adds in the 2-amino methyl-3-chloro-5-5-flumethiazine hydrochloride (0.79g) and triethylamine (0.68g) solution in the 10mL methylene dichloride.One night of stirred reaction mixture under the room temperature.Then reaction mixture is poured into 1 inch silica gel pipe close top, with 30mL methylene dichloride wash-out, the rotary evaporation eluent obtains 0.69g compound acid amides of the present invention (compound 8).
1H?NMR(CDCl
3；300MHz)δ2.57(s，3H)、4.96(m，2H)、7.22(s，1H)、7.48(bs，1H)、8.00(s，1H)、8.71(s，1H)。
Embodiment 2
2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]
The preparation of-3-pyridine carboxamide
Steps A: 2, the preparation of 4-dichloropyridine
With 6.7g 4-nitropyridine N-oxide compound at POCl
3In solution refluxed cool to room temperature then 3 hours.Remove under the vacuum and desolvate, remaining oily resistates.The careful saturated sodium bicarbonate solution (200mL) that adds uses methylene dichloride (2X) to extract subsequently.Under vacuum, remove methylene dichloride then, filter by the silica gel pipe close and obtain grease, and with 20% eluent ethyl acetate in the hexane.Remove under the vacuum and desolvate, obtain the 1.6g grease.
1H NMR (CDCl
3300MHz) (dd, 1H, J are 1.7 to δ 7.25,5.4Hz), 7.38 (d, 1H, J are 1.7Hz), 8.31 (d, 1H, J are 5.4Hz).
Step B:2, the preparation of 4-two chloro-3-pyridylaldehydes
Under nitrogen,, in the 6mL diisopropylaminoethyl lithium among the 25mL THF that the solution adding of 4-dichloropyridine in 5mL dry tetrahydrofuran (THF) is-70 ℃, under this temperature, stirred 3 hours subsequently 1.6g 2.Add 1mL exsiccant N down at-70 ℃ then, dinethylformamide stirred 1 hour under this temperature subsequently.Add the 25mL saturated ammonium chloride solution then, and at room temperature stirred reaction mixture spends the night.With 25mL water diluted reaction mixture, and extract with ethyl acetate (2X).The organic phase that distillation merges under vacuum obtains solid and is dissolved in the 5mL methylene dichloride, and uses filtered through silica gel, the methylene dichloride wash-out with 100%.Remove under the vacuum and desolvate, obtain the solid intermediate product shown in the title.
1H NMR (CDCl
3300MHz) δ 7.41 (d, 1H, J are 5.3Hz), 8.42 (d, 1H, J are 5.2Hz), 10.5 (s, 1H).
Step C:2, the preparation of 4-dichloro-nicotinic acid
To be dissolved among the 6mL THF from the solution of the 0.40g aldehyde of step B, add 0.27g Textone and the solution of 0.29g thionamic acid in 6mL water then.At room temperature stirred reaction mixture spends the night.With 1N sodium hydroxide (10mL) diluted reaction mixture, and extract with diethyl ether (1X).Use concentrated hydrochloric acid acidifying water layer then, extract with methylene dichloride (2X), and the dichloromethane extract that merges with dried over mgso.Remove methylene dichloride under the vacuum, obtain the 0.22g solid.
1H NMR (CDCl
3300MHz) δ 7.38 (d, 1H, J are 5.4Hz), 8.40 (d, 1H, J are 5.5Hz), 8.60 (bs, 1H).
Step D:2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-the 3-pyridine
The preparation of methane amide
To in thionyl chloride, reflux 1 hour from the solution of the 0.22g acid of step C, remove to desolvate down with final vacuum and obtain grease.This grease is dissolved in the 1mL methylene dichloride, and at room temperature adds 2-aminomethyl-3-chloro-5-5-flumethiazine hydrochloride (0.25g) and the solution of three second ammoniums (0.20g) in the 9mL methylene dichloride.At room temperature stirred reaction mixture spends the night.Then by the filtered through silica gel reaction mixture, and with 100% methylene dichloride wash-out.Remove under the vacuum and desolvate, obtain the solid title compound, fusing point is 122-124 ℃.
Embodiment 3
2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]
The preparation of-3-pyridine carboxamide
Steps A: the preparation of 3-chloro-Alpha-Methyl-5-(trifluoromethyl)-2-pyridyl-methanamine
At room temperature N-(phenylbenzene methylene radical) glycine ethyl ester (2.25g) is joined sodium hydride at the dry N of 20mL, in the suspension in the N-dimethylformamide (the oily dispersion of 0.74g 60%), produce violent gaseous emission.Stir under the room temperature after 5 minutes, add 2g 2,3-two chloro-5-5-flumethiazines at room temperature stirred 1 hour subsequently.Add the 0.80mL methyl-iodide then, at room temperature stir a night subsequently.Reaction mixture is poured in the frozen water, extracted, and distillation stays oily matter except that desolvating under vacuum with diethyl ether (2X).Then this grease is refluxed in 6N HCl and spend the night.With the reaction mixture cool to room temperature, make it become alkalescence with solid sodium carbonate, and extract with diethyl ether (2X).With the extract that dried over mgso merges, distillation removes and desolvates under the vacuum, stays the 1.5g grease.
1H NMR (CDCl
3300MHz) δ 1.4 (d, 3H, J are 6.6Hz), 4.6 (bs, 1H), 7.88 (m, 1H), 8.75 (bs, 1H).
Step B:2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-the 3-pyrrole
The preparation of pyridine methane amide
With prepare among the embodiment 1 step C 2,4-two chloronicotinoyl chlorides (0.40g) at room temperature join in the amine intermediate product (0.66g) and the solution of triethylamine (0.70g) in the 30mL methylene dichloride that steps A obtains, and stir a night subsequently.The distillation reaction mixture desolvates to remove under the vacuum, also obtains grease with 100% methylene dichloride as eluent by filtered through silica gel.Under vacuum, remove then and desolvate, obtain reddish oil smectic title compound, compound promptly of the present invention.
1HNMR (CDCl
3300MHz) δ 1.62 (d, 3H, J are 6.7Hz), 5.48 (m, 1H), 7.35 (d, 1H, J are 5.2Hz), 7.40 (d, 1H, J are 6.9), 7.99 (d, 1H, J are 1.8Hz), 8.34 (d, 1H, J are 5.2), 8.70 (s, 1H).
Embodiment 4
(+)-2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]
The preparation of-3-pyridine carboxamide
Steps A: the fractionation of 3-chloro-Alpha-Methyl-5-(trifluoromethyl)-2-pyridyl-methanamine
(-)-chloroformic acid menthyl ester (0.92g) is at room temperature joined in the Alpha-Methyl amine (1g) and the solution of triethylamine (1.2mL) in 25mL THF of embodiment 3 steps A preparation, at room temperature stirred subsequently 30 minutes.Solvent removed in vacuo then obtains comprising the grease by the isolating two kinds of carboxylamine menthyl ester diastereomers of column chromatography (with the hexane solution of 5% diethyl ether as eluent), obtains more polar diastereomer grease of 0.20g.Reflux in the 5mL trifluoroacetic acid then this grease 4 hours is with the carboxylamine menthyl ester of splitting.With the reaction mixture cool to room temperature, and water (30mL) dilution, make it become alkalescence with solid sodium carbonate, and use dichloromethane extraction.By the dried over mgso organic layer, vacuum distilling obtains the amine intermediate product of 60mg grease-like enantiomorph enrichment.
1H NMR (CDCl
3300MHz) δ 1.41 (d, 3H, J are 6.7Hz), 1.9 (bs, 2H), 4.60 (m, 1H), 7.88 (m, 1H), 8.74 (s, 1H).
Step B:(+)-2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] second
Base]-preparation of 3-pyridine carboxamide
With prepare among the embodiment 1 step C 2,4-two chloronicotinoyl chlorides (0.56g) at room temperature join in the amine (60mg) and the solution of triethylamine (54mg) in the 10mL methylene dichloride of the enantiomorph enrichment that steps A obtains, and stir a night subsequently.Then by the filtered through silica gel reaction mixture and with 100% methylene dichloride as eluent.Remove under vacuum and desolvate, obtain the solid chemical compound of this title, compound promptly of the present invention, fusing point are 110-111 ℃.About this title compound of 2mg is at 1mL CDCl
3In the polarimeter of solution measure and to show that plane polarized light is in (+) or dextrorotation direction.
3-chloro-Alpha-Methyl-5-(trifluoromethyl)-2-pyridyl-methanamine with enrichment in the opposite enantiomorph that in embodiment 4 steps A, has obtained, the enantiomorph (-)-2 for preparing embodiment 4 in a similar manner, 4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-the 3-pyridine carboxamide.
Embodiment 5
N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2, the preparation of 4-two chloro-3-pyridine carboxamides
Steps A: the preparation of 5-bromo-3-chloro-2 (1H)-pyridones
The 100mL aqueous solution of 6.2g Potcrate is joined in the dense HCl solution of 100mL of the 25g 5-bromo-2-pyridone that is preheated to 50-60 ℃, stir and formed dense throw out in 5 minutes.Add 60mL water then and stir helping, and one night of stirring at room mixture.Filter reaction mixture, water (2X) is smashed to pieces, and the vacuum-drying throw out obtains the solid intermediate that 17.7g requires.NMR (CDCl
3300MHz): δ 7.53 (d, 1H, J are 2.6Hz), 7.75 (d, 1H, J are 2.5Hz).
Step B:5-bromo-2, the preparation of 3-dichloropyridine
Product (17.7g) and 10g PCl with steps A
5With 100mL POCl
3Mixed, washing backflow mixture 4 hours.The concentrating under reduced pressure reaction mixture is to remove most of POCl
3, carefully to pour in the warm water, cool to room temperature uses methylene dichloride (2X) to extract then.Extract by dried over mgso merges concentrates and obtains grease, and carries out column chromatography (8: 2/ hexanes: EtOAc) obtain the grease-like intermediate product that 4.2g requires.NMR (CDCl
3300MHz): δ 7.94 (d, 1H, J are 2.2Hz), 8.37 (d, 1H, J are 2.3Hz).
The preparation of step C:5-bromo-3-chloro-alpha-methyl-2-pyridyl-methanamine hydrochloride
Title compound with 4.1g step B under nitrogen joins sodium hydride at the dried N of 30mL, in the suspension in the dinethylformamide (60% oily suspension), is cooled to 0 ℃.Need not add N-(phenylbenzene methylene radical) glycine ethyl ester (4.6g) under the condition of exogenous thermal source, stirring at room mixture 3 hours in batches.Add the 3.4mL methyl-iodides to be lower than 30 ℃ then, one night of stirring at room reaction mixture.The dilute with water reaction mixture also uses diethyl ether (2X) to extract.With the mixed extracting solution of saturated brine flushing, be condensed into grease in a vacuum, in 50mL 12N HCl, refluxed 4 hours then.The vacuum concentration reaction mixture becomes grease, cooling and with one night of diethyl ether slurrying.Outwell ether then, dried residue in vacuum oven obtains the solid intermediate that 1.3g requires.NMR (CDCl
3300MHz): 1.40 and 1.46 (2 is bimodal, and 3H, J are 7.0Hz), 4.7 (m, 1H), 8.48 (d, 1H, J are 1.8), 8.6 (bs, 3H), 8.79 (d, 1H, J are 1.9Hz).
Step D:N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2,4-two chloro-3-pyridine carboxamides
Preparation
With product (0.80g), 1.21mL triethylamine and the 0.62g 2 of step C, 4-two chloronicotinoyl chlorides are being blended into below 20 ℃ in the 25mL methylene dichloride in order, one night of stirring at room mixture.The vacuum concentration reaction mixture prepares the solid chemical compound of this title, compound promptly of the present invention.NMR (CDCl
3300MHz): δ 1.59 (d, 3H, J are 6.6Hz), 5.75 (m, 1H), 7.3 (bs, 1H), 7.34 (d, 1H, J are 5.2Hz), 7.91 (d, 1H, J are 1.9Hz), 8.33 (d, 1H, J are 5.4Hz), 8.49 (d, 1H, J are 1.9Hz).
Embodiment 6
2,4-two chloro-N-[1-(3,5-two chloro-2-pyridyl) ethyl]-preparation of 3-pyridine carboxamide
The preparation method of embodiment 6 is similar to Example 5, and with 2-bromo-3, the 5-dichloropyridine is made raw material, step C (preparation 3 with embodiment 5,5-two chloro-alpha-methyl-2-pyridyl-methanamines) and the conditions of similarity of describing among the D handle this raw material, obtain this title compound of solid, i.e. The compounds of this invention.NMR (CDCl
3300MHz): δ 1.58 (d, 3H, J are 6.6Hz), 5.7-5.8 (m, 1H), 7.4 (m, 2H), 7.77 (m, 1H), 8.35 (m, 1H), 8.40 (m, 1H).
With approach well known, can prepare the compound of following table 1-9 by method described herein.Below write a Chinese character in simplified form and be used for following table: t for uncle, s for secondary, n for just, i be different, c for encircle, Me is that methyl, Et are that ethyl, Pr are that propyl group, i-Pr are that sec.-propyl, Bu are that butyl, Ph are that phenyl, OMe are that methoxyl group, OEt are that oxyethyl group, SMe are that methyl thio group, SEt are that ethylenebis dithiocarbamate base, CN are cyano group, NO
2For nitro, TMS are that TMS, S (O) Me are methyl sulfinyl and S (O)
2Me is a methyl sulphonyl.The independent R of substituting group M, Q and R and specified location
5Substituting group is equal to.The independent R of substituting group T, U and V and specified location
6Substituting group is equal to.
Table 1
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3 | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3 |
| ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me | ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br | ??Br ??Br ??Br ??Br | ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br |
| ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3 | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3 |
| ??Cl ??Cl | ??Br ??Br | ??NO 2??OMe | ??NO 2??NO 2 | ??Br ??Br | ??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3 | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br |
| ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me | ??H ??H ??H | ??Me ??F ??Cl | ??Br ??Br ??Br | ??H ??H ??H | ??Me ??F ??Cl |
| ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br |
| ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Cl ??Cl ??Cl ??H ??H ??H ??H ??OMe ??OMe ??OMe | ??CF 3??NO 2??OMe ??Me ??F ??Cl ??OMe ??CF 3??NO 2??OMe | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??NO 2??NO 2??NO 2??H ??H ??H ??OMe ??OMe ??OMe ??OMe | ??CF 3??NO 2??OMe ??Br ??CF 3??NO 2??Me ??F ??Cl ??Br |
Table 2
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br |
| ??Cl ??Cl ??Cl | ??Me ??Me ??Me | ??CF 3??NO 2??OMe | ??NO 2??NO 2??NO 2 | ??Me ??Me ??Me | ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl |
| ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me | ??CF 3??CF 3 | ??Me ??F | ??Br ??Br | ??CF 3??CF 3 | ??Me ??F |
| ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2 | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl |
| ??Cl ??Cl ??Cl ??Cl | ??NO 2??NO 2??NO 2??NO 2 | ??Br ??CF 3??NO 2??OMe | ??NO 2??NO 2??NO 2??NO 2 | ??NO 2??NO 2??NO 2??NO 2 | ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F | ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F |
| ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Br ??CF 3??NO 2 |
| ??OMe ??OMe ??OMe ??OMe | ??H ??OMe ??OMe ??OMe | ??OMe ??CF 3??NO 2??OMe | ??OMe ??OMe ??OMe ??OMe | ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br |
Table 3
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me | ??F ??F ??F | ??Me ??F ??Cl | ??Br ??Br ??Br | ??F ??F ??F | ??Me ??F ??Cl |
| ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F ??F | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br |
| ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl | ??CF 2??NO 2??OMe | ??NO 2??NO 2??NO 2 | ??Cl ??Cl ??Cl | ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??Me ??F ??Cl ??Br ??CF 2??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3 | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl |
| ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3 | ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me | ??OMe ??OMe | ??Me ??F | ??Br ??Br | ??OMe ??OMe | ??Me ??F |
| ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe | ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2 | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl |
| ??Cl ??Cl ??Cl ??Cl | ??H ??H ??H ??H | ??Br ??CF 3??NO 2??OMe | ??NO 2??NO 2??NO 2??NO 2 | ??H ??H ??H ??H | ??Br ??CF 3??NO 2??OMe |
| ??T | ??U | ??V | ??T | ??U | ??V |
| ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??F ??F ??F ??F ??F ??F ??F ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??H ??H ??H ??H ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??OMe ??CF 3??NO 2??OMe | ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe ??OMe | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??CF 3??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??NO 2??H ??H ??H ??OMe ??OMe ??OMe ??OMe | ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Me ??F ??Cl ??Br ??CF 3??NO 2??OMe ??Br ??CF 3??NO 2??Me ??F ??Cl ??Br |
Table 4
T and V are Cl, and U is H
| ??Q | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H | ??Br ??Br ??Br ??Br ??Br ??Br | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me |
T is Cl, and V and U are Me
| ??O | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
Table 5
T and V are Cl, and U is H
| ??Q | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3 | ??H ??H ??H | ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3 | ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??O | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF2CF3 ??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
T is Cl, and V and U are Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3 | ??H ??H ??H | ??Cl ??Cl ??Cl | ??Cl ??Br ??OCF 3 | ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
Table 6
T and V are Cl, and U is H
| ??Q | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 2H ??SCF 3??SCHF 2??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 2H ??SCF 3??SCHF 2??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H | ??SO 2CHFCF 3??CN | ??Cl ??Cl | ??Me ??Me | ??SO 2CHFCF 3??CN | ??Cl ??Cl |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2 |
| ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T is Cl, and V and U are Me
| ??Q | ??R | ??S | ??O | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3 | ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
Table 7
T and V are Cl, and U is H
| ??O | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3 | ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3 | ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 2H ??SCF 3??SCHF 2??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3 | ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 2H ??SCF 3??SCHF 2??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me | ??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T is Cl, and V and U are Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
Table 8
T and V are Cl, and U is H
| ??Q | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl | ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl | ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H | ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T is Cl, and V and U are Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H |
| ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2 | ??SCF 3??SCHF 2??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2 | ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
Table 9
T and V are Cl, and U is H
| ??Q | ??R | ??M | ??Q | ??R | ??M |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHGFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H | ??CN | ??Cl | ??Me | ??CN | ??Cl |
T and V are Cl, and U is Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 |
| ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3 | ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
T is Cl, and V and U are Me
| ??Q | ??R | ??S | ??Q | ??R | ??S |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2 | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Br ??CF 3??OCF 3??OCHF 2??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH2CF 3??SCF2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2 | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??H ??H ??H ??H ??H | ??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??H ??H ??H ??H ??H ??H ??H ??H ??H ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2 | ??H ??H ??H ??H ??H ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??Cl ??Cl ??Cl ??Cl ??Cl | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Br ??Me ??Me ??Me ??Me ??Me | ??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN ??Cl ??Br ??CF 3??OCF 3??OCHF 2 | ??Me ??Me ??Me ??Me ??Me ??Cl ??Br ??CF3 ??OCF3 ??OCHF2 ??OCH2CF3 ??OCF2CF2H ??SCF3 ??SCHF2 ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Cl ??Cl ??Cl ??Cl ??Cl |
| ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??OCH 2CF 3??OCF 2CF 3??OCF 2CF 2H ??OCHFCF 3??SCF 3??SCHF 2??SCH 2CF 3??SCF 2CF 3??SCF 2CF 2H ??SCHFCF 3??SOCF 3??SOCHF 2??SOCH 2CF 3??SOCF 2CF 3??SOCF 2CF 2H ??SOCHFCF 3??SO 2CF 3??SO 2CHF 2??SO 2CH 2CF 3??SO 2CF 2CF 3??SO 2CF 2CF 2H ??SO 2CHFCF 3??CN | ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl ??Cl |
Table 10
| ??R | ??R 2 | ??U | ??R | ??R 2 | ??U |
| ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H | ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
Table 11
| ??Q | ??R 2 | ??U | ??Q | ??R 2 | ??U |
| ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H | ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
Table 12
| ??Q | ??R 2 | ??U | ??Q | ??R 2 | ??U |
| ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??H ??H ??H ??H ??H ??H ??H | ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN | ??H ??H ??H ??H ??H ??H ??H | ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
| ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H | ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si ??I ??OCHF 2??OCH 2F ??OCF 2Cl ??OCH 2CF 3??Et ??CN ??NH 2??NHCOMe ??NHCOCF 3??SCF 3??SCHF 2??SCH 2F ??Ph ??Me 3Si | ??H ??H ??H ??H ??H ??H ??H ??H ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me | ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me ??Me |
Preparation/practicality
The compounds of this invention can be used as preparation or the composition with the agriculture carrier that comprises at least a liquid diluent, solid diluent or tensio-active agent usually.The selection of prescription or composition components and physicals, the application model and consistent of activeconstituents such as environmental factorss such as soil type, moisture and temperature.Useful preparation comprises that they can nonessential thickening become gel such as solution (comprising emulsifiable concentrate), suspension, emulsion liquid such as (comprising microemulsion and/or suspension emulsion (suspoemulsions)).Useful prescription comprises that also they can be dispersed in (" wettable ") or water soluble in the water such as solids such as pulvis, powder, particle, ball, sheet, films.Activeconstituents can be sealed by (little), can further form suspension or solid preparation; As selection, the whole preparation of activeconstituents can coated (or " bag be coated with ").Coated can control or the time-delay release of active ingredients.Sprays may extend in the suitable media, and uses to the amount of several hectolitres with per hectare about 100.The high strength composition mainly is used as the intermediate product of further preparation.
Said preparation can typically contain the activeconstituents of significant quantity (as 0.01-99.99wt%) and thinner and/or the tensio-active agent in the following approximate extents, and is added to the amount of 100wt%.
| Weight percentage | |||
| Activeconstituents | Thinner | Tensio-active agent | |
| Water dispersible and water miscible particle, tablet and powder | ??5-90 | ??0-94 | ??1-15 |
| Suspension, emulsion, solution (comprising emulsible concentrated solution and concentrated suspension liquid) | ??5-50 | ??40-95 | ??0-25 |
| Pulvis | ??1-25 | ??70-99 | ??0-5 |
| Particle and small-particle | ??0.01-99 | ??5-99.99 | ??0-l5 |
| The high strength composition | ??90-99 | ??0-10 | ??0-2 |
The typical solid thinner is described in the Handbook ofInsecticide Dust Diluents and Carriers of Watkins etc., second edition, and Dorland Books, Caldwell is in the New Jersey.Typical liquid diluent is described in the SolventsGuide of Marsden, second edition, and Interscience, New York is in 1950.McCutcheon ' sDetergents and Emulsifiers Annual, Allured Publ.Corp., Ridgewood, the New Jersey, and the Encyclopedia of SurfaceActive Agents of Sisely and Wood, Chemical Publ.Co., Inc., New York has been listed tensio-active agent in 1964 and has been recommended and adopted.All prescriptions all can contain a small amount of additive, with minimizing foaming, caking, burn into microorganism growth etc., or contain thickening material to increase viscosity.
Tensio-active agent comprises for example alcohol, the alkylphenol of polyethoxylated, the fatty acid esters of sorbitan of polyethoxylated, dialkyl sulfosuccinate, alkyl-sulphate, benzene sulfonamide acid esters, organo-siloxane, the N of polyethoxylated; N-dialkyl group taurate, Sulfite lignin, naphthalenesulfonate formaldehyde condensation compound, polycarboxylate, and polyoxyethylene/polyoxypropylene block copolymers.Solid diluent comprises for example clay such as wilkinite, montmorillonite, attapulgite and kaolin; Starch, sugar, silicon-dioxide, talcum, diatomite, urea, lime carbonate, yellow soda ash and sodium bicarbonate, and sodium sulfate.Liquid diluent comprises for example water, N, dinethylformamide, methyl-sulphoxide, N-alkyl pyrrolidone, ethylene glycol, polypropylene glycol, paraffin, alkylbenzene, alkylnaphthalene; Sweet oil, Viscotrol C, Toenol 1140, tung oil, sesame oil, Semen Maydis oil, peanut oil, Oleum Gossypii semen, soybean oil, rape oil and theobroma oil; Fatty acid ester; Ketone such as pimelinketone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2 pentanone; And alcohol is as methyl alcohol, hexalin, decyl alcohol and tetrahydrofurfuryl alcohol.
The solution that comprises emulsible concentrate can be by simple mixed these composition preparations.Fine powder or powder can be by blendings and are normally ground at hammer mill or hydrodynamic force barreling and prepare.Suspension generally grinds by wet type and is equipped with; Referring to for example US 3060084.Preferred suspension concentrate comprises except that containing activeconstituents, also contain 5-20% nonionogenic tenside (for example Fatty Alcohol(C12-C14 and C12-C18) of polyethoxylated), and nonessential and 50-65% liquid diluent and up to 5% anion surfactant bonded those.Particle and small-particle can prepare by active material is sprayed on the preformed particulate vector or by coalescence technology.Referring to " Agglomeration " of Browning, Chemical Engineering, on December 4th, 1967,147-48 page or leaf; Perry ' s Chemical Engineer ' s Handbook, the 4th edition, McGraw-Hill, New York, 1963, below the 8-57 page or leaf reaches, and WO 91/13546.Small-particle can be as the preparation of describing among the US 4172714.Water dispersible and water-soluble granular can be as the method preparations of instruction among US5180587, US 5232701 and the US 5208030.Film can be as the method preparation of instruction among GB2095558 and the US 3299566.
Other prescriptions of consideration Recipe are seen-7 section 19 row of 6 section 16 row and the embodiment 10-41 of US 3235361;-7 section 62 row of 5 section 43 row of US 3309192 and embodiment 8,12,15,39,41,52,53,58,132,138-140,162-164,166,167 and 169-182;-5 section 17 row of 3 section 66 row and the embodiment 1-4 of US 2891855; Klingman, Weed Control as a Science, John Wiley andSons, Inc., New York, 1961, pp81-96; With the Weed ControlHandbook of Hance etc., the 8th edition, Blackwell Scientific Publications, Oxford, 1989.
In following examples, all percentage number averages refer to weight, and all preparations prepare with common method.The compound number refers to the compound among the Index Tables A-D.
Embodiment A
Wettable powder
Compound 8 65.0%
The dodecyl phenol polyglycol ether2.0%
Sodium lignosulfonate 4.0%
Sodium silicoaluminate 6.0%
Montmorillonite (incinerating) 23.0%
Embodiment B
Particle
Compound 8 10.0%
Attapulgite particle (low volatility materials, 0.71/0.30mm;
The U.S.S.No.25-50 sieve) 90.0%
Embodiment C
The extruding particle
Compound 8 25.0%
Anhydrous sodium sulphate 10.0%
Calcium lignosulfonate coarse fodder 5.0%
Sodium alkyl naphthalene sulfonate 1.0%
Calcium/magnesium wilkinite 59.0%
Embodiment D
Emulsible concentrate
Compound 8 20.0%
The mixture 10.0% of oil-soluble sulfonic acid ester and Soxylat A 25-7
Isophorone 70.0%
It should be noted that the suspension concentrate that comprises 15-25% activeconstituents, 10-20% nonionogenic tenside, 0-5% anion surfactant, 0-10% organic thinner and 45-60% water.
Embodiment E
Compound 2 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 2 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment F
Compound 5 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 5 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment G
Compound 8 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 8 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment H
Compound 28 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 28 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Example I
Compound 29 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 29 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment J
Compound 30 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 30 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment K
Compound 31 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 31 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment L
Compound 35 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 35 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment M
Compound 36 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 36 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Embodiment N
Compound 37 20.0%
The fatty alcohol nonionic surfactant 15.0% of polyethoxylated
The ester derivative 3.0% of montanin wax
Calcium lignosulfonate anion surfactant 2.0%
Polyethoxylated/poly-propenoxylated
Polyethyleneglycol block copolymer tensio-active agent 1.0%
Propylene glycol thinner 6.4%
Poly-(dimethyl siloxane) defoamer 0.6%
Disinfectant 0.1%
Diluent water 51.9%
The composition of said preparation is blended into pulpous state together, adds compound 37 and be somebody's turn to do in the blending machine mixture was homogenized.Then the wet-milling of gained slurry is formed the suspension concentrate.
Compound of the present invention can be used as plant disease-controlling agent.Therefore the present invention also comprises the method for control by the Plant diseases of fungal plant pathogen generation; comprise plant or its part, or on the plant seed of need protection or rice shoot, bestow the The compounds of this invention of significant quantity or contain the fungicide composition of described compound to need protections.Compound of the present invention and composition provide the control to the disease that is produced by the broad spectrum fungus phytopathogen in basidiomycetes, ascomycetes, oomycetes and the deuteromycetes.They are effective on the laminated pathogenic agent of control broad-spectrum plant disease, especially ornamental plant, vegetables, field, cereal and fruit crop.These pathogenic agent comprise the living single shaft bacterium (Plasmopara viticola) of grape, phytophthora infestan (Phytophthorainfestans), Peronospora tabacina (Peronospora tabacina), the false white bacterium (Pseudoperonospora cubensis) of Cuba, melon and fruit corruption mould (Pythiumaphanidermatum), black spot of cabbage alternaric bacteria (Alternaria brassicae), grain husk withered septoria musiva (Septoria nodorum), wheat septoria (Septoria tritici), Cercosporidium personatum, turn grey tail spore bacterium (Cercospora arachidicola), wheat class eye spot bacterium (Pseudocercosporella herpotrichoides) Chard dish is given birth to tail spore (Cercospora beticola), gray botrytis (Botrytis cinerea), fruit gives birth to chain sclerotinia sclerotiorum (Monilinia fructicola), piricularia oryzae (Pyriculariaoryzae), apple mildew handle coccus (Podosphaera leucotricha), venturia inaequalis (Venturia inaequalis), standing grain powdery mildew (Erysiphe graminis), naked smut (Uncinula necartur), Puccinia recondita (Puccinia recondita), puccinia graminis (Puccinia graminis), coffee rest fungus (Hemileia vastatrix) in the spore, Puccinia striiformis var. dactylis (Puccinia striiformis), Semen arachidis hypogaeae handle rest fungus (Pucciniaarachidis), dry thread Pyrenomycetes (Rhizoctonia solani), Siberian cocklebur monofilament shell bacterium (Sphaerotheca fuliginea), point sickle spore (Fusarium oxysporum), Garden Dahlia wheel branch spore (Verticillium dahliae), melon and fruit corruption mould (Pythiumaphanidermatum), big male epidemic disease mould (Phytophthora megasperma), sclerotinite (Sclerotinia sclerotiorum), Sclerotium rolfsii (Sclerotium rolfsii), erysiphe polygoni (Erysiphe polygoni), circle nuclear cavity bacteria (Pyrenophora teres), gaeumannomyce (Gaeumannomvces graminis), Rynchosporium secalis, pink sickle spore (Fusarium roseum), the lettuce dish obstructs mould (Bremia lactucae), and plants pathogenic agent with other genus that these pathogenic agent are closely related.
Compound of the present invention also can be with one or more other sterilants, mycocide, nematocides, bactericide, miticide, growth regulator, chemostefilant, semiochemicals, repellent, attractive substance, pheromone, help food agent or other biological active compound to mix, and formation provides the more multicomponent agricultural chemicals of the crop protection of wide spectrum.The example of this crop protection agent that can prepare with compound of the present invention is:sterilant such as Avrmectin, acephate, azinphos-methyl, bifenthrin, Buprofezin, carbofuran, chlorfenapyr, Chlorpyrifos 94, Chlorpyrifos 94-methyl, cyfloxylate, betacyfluthrin, cyhalothrin, lambda-cyhalothrin, Deltamethrin, the butyl ether urea, diazinon, diflubenzuron, Rogor, the S-fenvalerate, fenoxycarb, Fenvalerate, fenvalerate, fluorine worm nitrile, flucythrinate, taufluvalinate, N-2790, Provado, isofenphos, the Malathion, the methaldehyde, acephatemet, methidathion, methomyl, methoprene, methoxychlor, methyl 7-chloro-2,5-dihydro-2-[[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy) phenyl] amino] carbonyl] indeno [1,2-e] [1,3,4] oxadiazine-4 α (3H)-manthanoate (indoxacarb), monocrotophos, oxamyl, thiophos, thiophos-methyl, permethrin, phorate, Phosalone, R-1504, phosphamidon, Aphox, Profenofos, tubatoxin, sulprofos, the worm hydrazides, tefluthrin, Terbufos, tetrachlorvinphos, the two prestige of sulphur, tralomethrin, Trichlorphon and kill the bell urea; Fungicide such as thiadiazoles element; Fluoxastrobin; Benomyl; Blasticidin-S; Bordeaux mixture (three alkali copper sulphate); Bromuconazole; Carpropamid (KTU 3616); Difoltan; Captan; Carbendazim; Chloroanisole; Bravo; Copper oxychloride; Mantoquita such as copper sulphate and Kocide SD; Cyazofamid; Frost urea cyanogen; Cyproconazole; Cyprodinil (CGA219417); (S)-3,5-two chloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyls)-4-methyl benzo acid amides (RH 7281); Diclocymet (S-2900); Diclomezin; Botran; Difenoconazole; Dimethomorph; Alkene azoles alcohol; Alkene azoles alcohol-M; Dodine; Edifenphos; Epoxiconazole (BAS 480F); Yi Ling; Fenamidone; Fenarimol; RH-7592; Fencaramid (SZX0722); Fenpiclonil; Fenpropidin; Butadiene morpholine; Fentin acetate; Triphenyl tin hydroxide; Fluazinam; Fludioxonil; Flumetover (RPA 403397); Fluquinconazole; Flusilazole; Flutolanil; Flutriafol; Folpet; Phosethyl-Al; Furalaxyl; Furametapyr (S-82658); Own azoles alcohol; Plant the bacterium azoles; IBP; Iprodione; Isoprothiolane; Iprovalicarb; Kasugarnycin; Kresoxim-methyl; Mancozeb; Maneb; Mefenoxam; Mebenil; Metalaxyl; Metonazole; Metominostrobin/fenominostrobin (SSF-126); Nitrile bacterium azoles; Neo-asozin (methane arsenic acid iron); The spirit of Evil frost; Penconazole; Pencycuron; Probenazole; Prochloraz; Propamocarb; Propiconazole; Propineb; Pyrclostrobin; Pyrifenox; Phonetic mould amine; Pyroquilon; Quinoxyfen; Spiroxamine; Sulphur; Tebuconazole; Tetraconazole; Probenazole; Thifluzamide; Thiophanate-methyl; Thiram; Triazolone; Triadimenol; Tricyclazole; Trifloxystrobin; Triticonazole; Valida; Vinclozolin; Zineb and zoxamid; Nematocides such as aldoxycarb and fenamiphos; Bactericide such as Streptomycin sulphate; Acarus-killing such as amitraz, chinomethionate, G-23922, cyhexatin, kelthane, dienochlor, Te Ben oxazole, fenazaquin, fenbutatin oxide, Fenvalerate, azoles mite ester, hexythiazox, alkynes mite spy, pyridaben and tebufenpyrad; And biological reagent such as bacillus thuringiensis, bacillus thuringiensis delta-endotoxin, baculovirus (baculovirus), and entomiasis indigenous bacteria, virus and fungi.The weight ratio of these different blended and component and compound of the present invention is typically 100:1-1:100, preferred 30:1-1:30, more preferably 10:1-1:10, most preferably 4:1-1:4.
It should be noted that and the combining of other mycocides that the crop protection of wide spectrum more can be provided that described sterilant comprises Azoxystrobin, kresoxim-methyl, pyrclostrobin, trifloxystrobin, F-1991, derosal, m-tetrachlorophthalodinitrile, dimethomorph, Phaltan, zinc manganese ethylenebisdithiocarbamate, maneb, quinoxyfen, validamycin, Vinclozoline, fenpropidin, fenpropimorph, bromuconazole, SN-108266, difenoconazole, fluorine ring azoles (epoxyconazole), fluzilazol, kind bacterium azoles, metconazole, Wocosin 50TK, tebuconazole and triticonazole.
It should be noted that the combination of different with binding mode (synthesizing to come the arrestin matter synthetic as the mitochondrial respiration inhibition, by what disturb the synthetic of ribosome-RNA(rRNA) or suppress 'beta '-tubulin) other mycocides, management is especially useful to resistibility.Example comprises the compound (as compound 8) of general formula I and/or general formula I I and the mixture of Azoxystrobin, kresoxim-methyl, pyrclostrobin, trifloxystrobin, derosal, Yi Ling, fenamidone, F-1991, white urea cyanogen, dimethomorph, Phaltan, fosetylaluminium, metaxanin, zinc manganese ethylenebisdithiocarbamate, maneb.Management is especially useful to these mixtures to resistibility, particularly when the mycocide of this mixture is controlled same or analogous disease.
It should be noted that and the combining of the mycocide of other control grape diseases that described mycocide comprises dithiocarbamate such as zinc manganese ethylenebisdithiocarbamate, maneb, zinc 1,2-propylene bisdithiocarbamate and zineb; Phthalimids such as Phaltan, mantoquita such as copper sulfate and copper hydroxide; Strobilurins such as Azoxystrobin, pyrclostrobin and trifloxystrobin; Benzamide such as metaxanin; Sulfonate such as fosetylaluminium; Morpholine class such as dimethomorph, and other sterilant such as white urea cyanogen, Yi Ling and fenamidone.
It should be noted that and the combining of the mycocide of other control potato diseases that described mycocide comprises dithiocarbamate such as zinc manganese ethylenebisdithiocarbamate, maneb, zinc 1,2-propylene bisdithiocarbamate and zineb; Mantoquita such as copper sulfate and copper hydroxide; Strobilurins such as pyrclostrobin and trifloxystrobin; Benzamide such as metaxanin; Carbamate such as Propamocarb; Doxylamine (phenylpyriylamine) is as fluazinam; Morpholine class such as dimethomorph, and other mycocides such as m-tetrachlorophthalodinitrile, cyazofamid, white urea cyanogen, Yi Ling, fenamidone, zoxamid and iprovalicarb.
Especially it should be noted that the mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Azoxystrobin; The mixture of compound 2, compound 5, compound 8, compound 28, chemical combination compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and kresoxim-methyl; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and pyrclostrobin; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and trifloxystrobin; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and derosal; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and m-tetrachlorophthalodinitrile; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and dimethomorph; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Phaltan; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and zinc manganese ethylenebisdithiocarbamate; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and maneb; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and quinoxyfen; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and validamycin; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Vinclozoline; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fenpropidin; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fenpropimorph; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and bromuconazole; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and SN-108266; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and difenoconazole; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fluorine ring azoles; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fluzilazol; Compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and the mixture of planting the bacterium azoles; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and metconazole; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Wocosin 50TK; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and tebuconazole; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and triticonazole; Compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and easily clever mixture; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fenamidone; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and F-1991; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and white urea cyanogen; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and dimethomorph; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Phaltan; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and fosetylaluminium; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and metaxanin; Compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 with _ _ mixture; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and zinc 1,2-propylene bisdithiocarbamate; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and zineb; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and copper sulfate; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and copper hydroxide; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and Propamocarb; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and cyazofamid; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and zoxamid; The mixture of compound 2, compound 5, compound 8, compound 28, compound 29, compound 30, compound 31, compound 35, compound 36 or compound 37 and iprovalicarb.
Plant diseases control is general by before infection or after infecting; the The compounds of this invention of significant quantity is administered to certain part of the plant that needs protection as on root, stem, leaf, fruit, seed, stem tuber or the napiform root, maybe on the substratum of the plant-growth that need protect (soil or sand).This compound also can be administered on the seed, with protection seed and rice shoot.
The rate of application of these compounds can be subjected to many such environmental effects, is determined by actual service conditions.When to be lower than the 1g/ hectare when 5000g/ hectare absorption of active ingredient is handled, can protect leaf usually.Handle kind of a period of the day from 11 p.m. to 1 a.m when amount, can protect seed and rice shoot usually with per kilogram seed 0.1-10g.
The control effect of following test shows The compounds of this invention on concrete pathogenic agent.Yet the pathogenic agent that this compound provides control protection is not limited to these kinds.See the description of Index Tables A-E to compound.The following abbreviation that is used for Index Tables is as follows: Me is that methyl, Et are that ethyl, Ph are that phenyl, OMe are that methoxyl group, OBt are oxyethyl group.When referring to the compound fusing, abbreviation " dec " can decompose.Abbreviation " Ex. " expression " embodiment ", numeral subsequently refers to that compound prepares in this embodiment.
INDEX?TABLE?A
| Compound number | ??(R 5) m | ??(R 6) p | ??m.p.(℃.) |
| ??1 ??2 ??3 | ??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3 | ??3-Cl ??3-Cl-5-Me ??3-O-H | ??108-109 |
INDEX?TABLE?B
| Compound number | ??R 1 | ??R 2 | ??(R 5) m | ??(R 6) p | ??m.p.(℃.) |
| 45678 (Ex.1) 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 (Ex.2) 29 30 (Ex.3) racemics, 31 (Ex.4) (+)-enantiomer 36 (Ex.6) racemic 37 (Ex.5) racemics, 38 (-)-enantiomer | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ? ??H ? ??H ? ??H ? ??H | ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??H ??CH 3? ??CH 3? ??CH 3? ??CH 3? ??CH 3 | ??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3??3-Cl-5-CF 3? ??3-Cl-5-CF 3? ??3，5-Cl 2? ??3-Cl-5-Br ? ??3-Cl-5-CF 3 | ??2，6-Cl 2??2-Cl ??6-Cl ??5，6-Cl 2??2，4-Cl 2-6-Me ??2-NH 2??5-Br ??2-OH ??2-OMe ??2-OEt ??2-Cl-6-Me ??2-OPh ??2-SPh ??5-C≡C-Ph ??2-Br-6-CF 3??2-OH-6-Me ??2-Me-6-CF 3??2-Me-6-CF 2CF 3??2-OMe-6-CF 3??2-CH 2OMe-6-CF 3??2-Ph-6-CF 3??2-Me-6-Cl ??6-CF 3??2-NH-C 6H 4(3-CF 3) ??2，4-Cl 2??2，4-Cl 2-5-Me ??2，4-Cl 2? ??2，4-Cl 2? ??2，4-Cl 2? ??2，4-Cl 2? ??2，4-Cl 2 | ??110-111 ??* ? ??* ??* ? ? ? ? ? ? ? ? ? ??* ??* ??* ??* ??* ??* ??* ??* ??* ??* ??122-124 ??* ??* ? ??110-111 ? ??* ? ??* ? ??* |
* 1H NMR data are referring to Index Table E
INDEX?TABLE?C
| Compound number | ??(R 5) m | ??(R 6) p | ??m.p.(℃.) |
| ??32 ??33 | ??6-Cl ??6-OC 6H 4(3-CF 3) | ??2-Me ??2-Me | ??105-106 ??90-91 |
INDEX?TABLE?D
| Compound number | ??(R 5) m | ??(R 6) p | ??m.p.(℃.) |
| ??34 ??35 | ??3-Cl-5-CF 3??3-Cl-5-CF 3 | ??2-Cl-6-OMe ??3，5-Cl 2 | ??* ??* |
* 1H NMR data are referring to Index Table E
INDEX?TABLE?E
| Compound number | ? 1H NMR data (300mHz; CDCl 3Solution, other have explanation except) a |
| ??5 ??7 ??8 ??18 ??19 ? ??20 ??21 ??22 ??23 ? ??24 ??25 | ??δ4.95(m，2H)，7.44(m，1H)，8.0(s，1H)，8.2-8.3(m，2H)，8.5(m，1H)，8.8(m，1H) ??(DMSO-d 6)δ4.8(m，2H)，8.54(s，1H)，8.55(s，1H)，8.84(s，1H)，8.9(s，1H)，9.5(bs，1H) ??δ2.57(s，3H)，4.96(m，2H)，7.22(s，1H)，7.48(bs，1H)，8.00(s，1H)，8.71(s，1H) ??δ4.95(m，2H)，7.76(m，1H)，7.94(bs，1H)，8.00(s，1H)，8.16(m，1H)，8.74(s，1H) ??(DMSO-d 6)δ2.30(s，3H)，4.8(m，2H)，6.3(m，1H)，8.2(m，1H)，8.47(s，1H)，8.93(s，1H)，10.4 ??(m，1H)，12.4(bs，1H) ??δ2.80(s，3H)，4.94(m，2H)，7.4(bs，1H)，7.6(m，1H)，8.0(m，2H)，8.73(s，1H) ??δ2.80(s，3H)，4.95(m，2H)，7.4(bs，1H)，7.6(m，1H)，8.0(m，2H)，8.72(s，1H) ??δ4.97(m，2H)，7.44(m，1H)，7.99(s，1H)，8.71(m，1H)，8.80(s，1H)，9.42(bs，1H) ??δ3.50(s，3H)，4.87，(s，2H)，4.98(m，2H)，7.79(m，1H)，7.98(s，1H)，8.38(m，1H)，8.74(s，1H)， ??8.88(bs，1H) ??δ4.70(m，2H)，7.0(bs，1H)，7.3-4(m，3H)，7.7-7.8(m，3H)，7.9(s，1H)，8.25(m，1H)，8.4(s，1H) ??δ2.73(s，3H)，4.91(m，2H)，7.25(m，1H)，7.4(bs，1H)，7.8(m，1H)，8.00(s，1H)，8.73(s，1H) |
| ??26 ??27 ? ??30 ? ??34 ??35 ??36 ??37 ? ??38 | ??δ4.94(m，2H)，7.80(m，1H)，7.9(bs，1H)，8.0(s，1H)，8.40(m，1H)，8.77(s，1H)，9.22(s，1H) ??(DMSO-d 6)δ4.8(m，2H)，7.0(m，1H)，7.3(m，1H)，7.3(m，1H)，7.5(m，1H)，7.8(m，1H)，8.3 ??(m，2H)，8.4(m，1H)，8.5(s，1H)，8.9(s，1H)，9.5(m，1H) ??δ1.62(d，3H，J?is?6.7Hz)，5.84(m，1H)，7.35(d，1H，J?is?5.2Hz)，7.40(d，1H，J?is?6.9Hz)，7.99 ??(d，1H，J?is?1.8Hz)，8.34(d，1H，J?is?5.2Hz)，8.70(s，1H) ??δ4.00(s，3H)，4.88，(m，2H)，7.09(s，1H)，7.33(m，1H)，7.80(bs，1H)，8.00(s，1H)，8.78(s，1H) ??δ4.98(d，2H，J?is?3.8)，7.5(bs，1H)，8.00(s，1H)，8.58(s，2H)，8.71(s，1H). ??δ1.58(d，3H，J?is?6.6Hz)，5.7-5.8(m，1H)，7.4(m，2H)，7.77(m，1H)，8.35(m，1H)，8.40(m，1H). ??δ1.59(d，3H，J?is?6.6Hz)，5.75(m，1H)，7.3(bs，1H)，7.34(d，1H，J?is?5.2Hz)，7.91(d，1H，J?is?1.9Hz)， ??8.33(d，1H，J?is?5.4Hz)，8.49(d，1H，J?is?1.9Hz). ??δ1.62(d，3H，J?is?6.7Hz)，5.48(m，1H)，7.35(d，1H，J?is?5.2Hz)，7.40(d，1H，J?is?6.9)，7.99(d，1H，J ??is?1.8Hz)，8.34(d，1H，J?is?5.2)，8.70(s，1H). |
a
1H NMR data are the low field data of ppm from tetramethylsilane.Coupling is by (s)-unimodal, (d)-bimodal, (t)-three peak, (q)-four peak, (m)-multimodal, (dd)-double doublet, (dt)-Shuan Sanfeng, (brs)-wide unimodal expression.
Biological Examples of the present invention
The general method of preparation test suspension liquid: earlier test compounds is dissolved in the acetone into final volume 3% amount, is suspended in the concentration (with ppm) that requires then and contains 250ppm tensio-active agent Trem
_In the acetone of 014 (polyol ester) and the pure water (50/50 mixing ratio).Then gained test suspension liquid is used for following test.Be sprayed on the test plants until trickling with the equivalent of 500g/ hectare test suspension liquid 200ppm.
Test A
Test suspension liquid is sprayed on the wheat rice shoot to trickling.Next day, use Erysiphegraminis f.sp.tritici, spore dust (the pathogenic agent of wheat-flour powder mildew) cultivate rice shoot, and in 20 ℃ growth room, cultivated 7 days, make the disease classification then.
Test b
Test suspension liquid is sprayed on the wheat rice shoot to trickling.Next day, cultivate rice shoot with the spore suspension (the pathogenic agent of wheat tikka) of Pucciniarecondita, and in 20 ℃ saturated atmosphere, cultivated 24 hours, transfer in 20 ℃ the growth room 6 days, make the disease classification then.
Test C
Test suspension liquid is sprayed on the paddy rice shoot to trickling.Next day, cultivate rice shoot with the spore suspension (the pathogenic agent of rice blast) of Pyriculariaoryzae, and in 27 ℃ saturated atmosphere, cultivated 24 hours, transfer in 30 ℃ the growth room 5 days, make the disease classification then.
Test D
Test suspension liquid is sprayed on the tomato sprout to trickling.Next day, cultivate rice shoot with the spore suspension (the pathogenic agent of potato and tomato late blight) of Phytophthorainfestans, and in 20 ℃ saturated atmosphere, cultivated 24 hours, transfer in 20 ℃ the growth room 5 days, make the disease classification then.
Test E
Test suspension liquid is sprayed on the grape rice shoot to trickling.Next day, cultivate rice shoot with the spore suspension (the pathogenic agent of downy mildew of garpe) of Plasmoparaviticola, and in 20 ℃ saturated atmosphere, cultivated 24 hours, transfer in 20 ℃ the growth room 6 days, in 20 ℃ saturated atmosphere, cultivated 24 hours then, make the disease classification subsequently.
Test F
Spore suspension (the pathogenic agent of potato and tomato late blight) with Phytophthora infestans is cultivated tomato (or potato) rice shoot, and cultivates 24 hours in 20 ℃ saturated atmosphere.Spray test suspension liquid in second day to trickling, the plant after handling is moved in 20 ℃ of growth rooms 5 days, make the disease classification subsequently.
Test G
Spore suspension (the pathogenic agent of downy mildew of garpe) with Plasmopara viticola is cultivated the grape rice shoot, and cultivates 24 hours in 20 ℃ saturated atmosphere.Spray test suspension liquid in second day to trickling, the plant after handling is moved in 20 ℃ the growth room 6 days, in 20 ℃ saturated atmosphere, cultivated 24 hours then, make the disease classification subsequently.
Test the Table A that the results are shown in of A-E.In this table, 100 grades refer to 100% disease control, and 0 grade refers to disease-free control (for control).Whippletree (-) refers to not have test result.ND refers to disease control because phytotoxicity and uncertain.Except that test shown in following, compound of the present invention (as compound 2,5,8,28,29,30,31,35,36 and 37) is considered to particularly have significant curative effect for downy mildew of garpe.
Table A
Compound number
Test A
Test b
Test C
Test D
Test E
Test F
Test G
1?????????????0????????0???????0????????90???????29
2?????????????0????????ND??????-????????100??????-???????????????????99
3?????????21???????28???????0????????7?????????8
4?????????-????????-????????-????????99????????-
5?????????-????????19???????-????????-?????????98?????????????99
6?????????0????????0????????-????????19????????-
7?????????0????????0????????-????????-?????????-
8?????????0????????8????????-????????100???????100????????????96
9?????????0????????28???????0????????7?????????0
10????????0????????9????????74???????16????????0
11????????0????????9????????0????????7?????????8
12????????0????????19???????0????????7?????????24
13????????0????????9????????0????????3?????????23
14????????0????????19???????90???????100???????98
15????????0????????38???????30???????7?????????8
16????????0????????9????????100??????34????????8
17????????13???????0????????0????????25????????0
18????????0????????9????????80???????32????????0
19????????0????????9????????0????????7?????????8
20????????0????????28???????87???????25????????8
21????????69???????68???????88???????16????????8
22????????0????????0????????0????????7?????????0
23????????72???????9????????7????????32????????8
24????????0????????0????????7????????25????????8
25????????0????????9????????13???????79????????16
26????????0????????32???????0????????25????????0
27????????0????????0????????0????????32????????16
28????????-????????-????????0????????100???????100????97#?????37
*
29????????-????????-????????0????????100???????100????????????100
*
30????????-????????-????????0????????100???????100????????????100
*
31????????-????????-????????0????????100???????100????????????100
**
32????????0????????0????????0????????32????????-
33????????91???????-????????-????????71????????-
34????????0????????44???????-????????31????????-
35????????0????????30???????-????????100???????100????????????100
*
36????????0????????38???????0????????100???????100????????????100
37????????0????????19???????0????????100???????100????????????100
38????????-????????-????????-????????-?????????69
*???????????0
**
#100ppm is on the potato rice shoot
*100ppm.
*20ppm.
Claims (20)
1. be selected from the compound of the compound of general formula I and general formula I I, their N-oxide compound and suitable agricultural salt,
Wherein:
The pyridyl ring of A for replacing;
The pyridyl ring of B for replacing;
W is C=L or SO
n
L is O or S;
R
1And R
2Independently be H separately; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, each all nonessential being substituted;
R
3Be H; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl or C
3-C
8The dialkylamino carbonyl;
R
4Be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, each all nonessential being substituted;
X is O or S; With
N is 1 or 2; Condition be when W be C=O and R
1, R
2And R
3During for H; B is for removing 4-trifluoromethyl-3-pyridyl, 2-chloro-4-pyridyl and 2, other pyridyl ring that 6-dihalo--4-pyridyl is outer.
2. the compound of claim 1, wherein
A is 1-4 R
5The pyridyl ring that replaces;
B is 1-4 R
6The pyridyl ring that replaces;
R
1And R
2Independently be H separately; Or C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, one or more halogen, CN, the NO of being selected from of nonessential separately usefulness
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
2-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino and C
3-C
6The substituting group of naphthene amino replaces;
R
4Be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl or C
3-C
6Cycloalkyl, one or more halogen, CN, the NO of being selected from of nonessential separately usefulness
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
2-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino and C
3-C
6The substituting group of naphthene amino replaces;
R
5And R
6Independently be C separately
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl or C
3-C
6Trialkylsilanyl.
3. the compound of the claim 2 of general formula I, wherein W is C=O.
4. the compound of claim 3, wherein the 3-pyridyl ring of A for replacing.
5. the compound of claim 3, wherein A is for 1-4 R
5The 2-pyridyl ring that replaces; B is by 1-4 R
6Replace, and at least one R
6Be positioned at the ortho position that is connected with W.
6. the compound of claim 5, B or be the 3-pyridyl ring wherein, or for W ortho position link position on a R is respectively arranged
6With 1-2 nonessential other R
6The 4-pyridyl ring.
7. the compound of claim 6, wherein each R
6Or be halogen or for methyl.
8. the compound of claim 7, wherein B is the 3-pyridyl ring, one of them R
6For Cl and be positioned on the 2-position that is connected with the W ortho position another R
6Be selected from Cl or methyl and be positioned on the 4-position that is connected with the W ortho position the 3rd nonessential R
6Be the locational methyl of 6-.
9. the compound of claim 8, wherein A is 3-chloro-5-CF
3-2-pyridyl.
10. the compound of claim 5 or claim 7, wherein R
1Be H and R
2Be CH
3
11. be selected from 2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-3-pyridine carboxamide, 2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-3-pyridine carboxamide, 2,4-two chloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridyl] methyl]-6-methyl-3-pyridine carboxamide, with 2,4-two chloro-N-[1-[3-chloro-5-(trifluoromethyl)-2-pyridyl] ethyl]-compound of the claim 2 of 6-methyl-3-pyridine carboxamide.
12. the compound of the claim 2 of general formula I I, wherein:
A is 1-4 R
5The 2-pyridyl ring that replaces; With
1-4 R of B
6Replace, and at least one R
6Be positioned on the carbon ortho position link position that is connected jointly with X and B.
13. wherein X is the compound of the claim 12 of S.
14. the compound of the claim 2 of general formula I, wherein:
Each R
5Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Condition is when A is the 2-pyridyl, R
5Be to remove C
1-C
6Other bases that alkylhalide group is outer; With
Each R
6Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Or
R
5And R
6Independently be phenyl, benzyl or phenoxy group separately, not necessarily use C separately
1-C
4Alkyl, C
2-C
4Alkenyl, C
2-C
4Alkynyl, C
3-C
6Cycloalkyl, C
1-C
4Alkylhalide group, C
2-C
4Halogen alkenyl, C
2-C
4Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, NO
2, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
3-C
6(alkyl) naphthene amino, C
2-C
4Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl or C
3-C
6Trialkylsilanyl replaces.
15. the compound of claim 14, wherein:
W is C=O;
Each R
5Independently be C
1-C
6Alkyl, C
2-C
6Alkenyl, C
2-C
6Alkynyl, C
3-C
6Cycloalkyl, C
1-C
6Alkylhalide group, C
2-C
6Halogen alkenyl, C
2-C
6Alkynyl halide, C
3-C
6Halogen cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-C
4Alkoxyl group, C
1-C
4Halogen alkoxyl group, C
1-C
4Alkyl thio-base, C
1-C
4Alkyl sulfinyl, C
1-C
4Alkyl sulphonyl, C
1-C
4Alkylhalide group thio group, C
1-C
4Alkylhalide group sulfinyl, C
1-C
4Alkylhalide group alkylsulfonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkylamino, C
2-C
8Dialkylamino, C
3-C
6Naphthene amino, C
2-C
6Alkyl carbonyl, C
2-C
6Alkoxy carbonyl, C
2-C
6Alkyl amino-carbonyl, C
3-C
8Dialkylamino carbonyl, C
3-C
6Trialkylsilanyl; Condition is when A is the 2-pyridyl, R
5Be to remove C
1-C
6Other bases that alkylhalide group is outer.
16. the compound of claim 15, wherein R
5Be Cl, Br, CH
3, OCF
3, OCHF
2, OCH
2CF
3, OCF
2CF
3, OCF
2CF
2H, OCHFCF
3, SCF
3, SCHF
2, SCH
2CF
3, SCF
2CF
3, SCF
2CF
2H, SCHFCF
3, SOCF
3, SOCHF
2, SOCH
2CF
3, SOCF
2CF
3, SOCF
2CF
2H, SOCHFCF
3, SO
2CF
3, SO
2CHF
2, SO
2CH
2CF
3, SO
2CF
2CF
3, SO
2CF
2CF
2H or SO
2CHFCF
3
17. be selected from 2,4-two chloro-N-[(3,5-two chloro-2-pyridyl) methyl]-the 3-pyridine carboxamide, 2,4-two chloro-N-[1-(3,5-two chloro-2-pyridyl) ethyl]-the 3-pyridine carboxamide, 2,4-two chloro-N-[(3,5-two chloro-2-pyridyl) methyl]-6-methyl-3-pyridine carboxamide, 2,4-two chloro-N-[1-(3,5-two chloro-2-pyridyl) ethyl]-6-methyl-3-pyridine carboxamide, N-[(5-bromo-3-chloro-2-pyridyl) methyl]-2,4-two chloro-3-pyridine carboxamides, N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2,4-two chloro-3-pyridine carboxamides, N-[(5-bromo-3-chloro-2-pyridyl) methyl]-2,4-two chloro-6-methyl-3-pyridine carboxamides, and N-[1-(5-bromo-3-chloro-2-pyridyl) ethyl]-2, the compound of the claim 16 of 4-two chloro-6-methyl-3-pyridine carboxamides.
18. comprise the compound and the Bactericide composition that is selected from least a other compositions of tensio-active agent, solid diluent or liquid diluent of the claim 1 of effective fungicidal amount.
19. comprise the fungicide composition of the mixture of the compound of claim 1 at least a other mycocides different with binding mode.
20. the control method of the Plant diseases that is caused by the fungi plant pathogenic agent comprises compound administration with the claim 1 of effective fungicidal amount on plant or its part, or uses on plant seed or the rice shoot.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23337400P | 2000-09-18 | 2000-09-18 | |
| US60/233,374 | 2000-09-18 | ||
| US60/277,199 | 2001-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1688546A true CN1688546A (en) | 2005-10-26 |
Family
ID=32849359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01815519 Pending CN1688546A (en) | 2000-09-18 | 2001-09-17 | Pyridinyl amides and imides for use as fungicides |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1688546A (en) |
| ZA (1) | ZA200300643B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103249721A (en) * | 2010-10-18 | 2013-08-14 | 拉夸里亚创药株式会社 | Arylamide derivatives as TTX-S blockers |
| CN103965187A (en) * | 2008-01-25 | 2014-08-06 | 杜邦公司 | Fungicidal Hetercyclic Compounds |
| CN106316931A (en) * | 2015-07-10 | 2017-01-11 | 沈阳中化农药化工研发有限公司 | 2-phenyl nicotinic acid derivative with insecticidal/acaricidal activity |
| CN108516955A (en) * | 2018-07-09 | 2018-09-11 | 上海凯爱网络科技有限公司 | A kind of 5- trifluoromethyls -2- pyridine amides and the preparation method and application thereof |
| CN111454202A (en) * | 2019-01-18 | 2020-07-28 | 山东省联合农药工业有限公司 | Heteroaryl formanilide compound containing pentafluorothio and preparation method and application thereof |
| CN117143013A (en) * | 2023-11-01 | 2023-12-01 | 苏州开元民生科技股份有限公司 | Synthesis method of 2-chloronicotinic acid |
-
2001
- 2001-09-17 CN CN 01815519 patent/CN1688546A/en active Pending
-
2003
- 2003-01-23 ZA ZA200300643A patent/ZA200300643B/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965187A (en) * | 2008-01-25 | 2014-08-06 | 杜邦公司 | Fungicidal Hetercyclic Compounds |
| CN103249721A (en) * | 2010-10-18 | 2013-08-14 | 拉夸里亚创药株式会社 | Arylamide derivatives as TTX-S blockers |
| CN103249721B (en) * | 2010-10-18 | 2016-10-12 | 拉夸里亚创药株式会社 | Aryl amine derivatives as TTX-S blocker |
| CN106316931A (en) * | 2015-07-10 | 2017-01-11 | 沈阳中化农药化工研发有限公司 | 2-phenyl nicotinic acid derivative with insecticidal/acaricidal activity |
| CN106316931B (en) * | 2015-07-10 | 2020-05-05 | 沈阳中化农药化工研发有限公司 | 2-phenylnicotinic acid derivatives with insecticidal and acaricidal activity |
| CN108516955A (en) * | 2018-07-09 | 2018-09-11 | 上海凯爱网络科技有限公司 | A kind of 5- trifluoromethyls -2- pyridine amides and the preparation method and application thereof |
| CN111454202A (en) * | 2019-01-18 | 2020-07-28 | 山东省联合农药工业有限公司 | Heteroaryl formanilide compound containing pentafluorothio and preparation method and application thereof |
| CN111454202B (en) * | 2019-01-18 | 2021-10-01 | 山东省联合农药工业有限公司 | Heteroaryl formanilide compound containing pentafluorothio and preparation method and application thereof |
| CN117143013A (en) * | 2023-11-01 | 2023-12-01 | 苏州开元民生科技股份有限公司 | Synthesis method of 2-chloronicotinic acid |
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| Publication number | Publication date |
|---|---|
| ZA200300643B (en) | 2004-02-19 |
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