CN1509140A - Pyridinyl fused bicyclic amide as fungicides - Google Patents
Pyridinyl fused bicyclic amide as fungicides Download PDFInfo
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- CN1509140A CN1509140A CNA028100646A CN02810064A CN1509140A CN 1509140 A CN1509140 A CN 1509140A CN A028100646 A CNA028100646 A CN A028100646A CN 02810064 A CN02810064 A CN 02810064A CN 1509140 A CN1509140 A CN 1509140A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
This invention involves a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of a compound of Formula I (including all geometric and stereoisomers), <i>N</i>-oxides, agriculturally suitable salts and compositions thereof, wherein A is taken together with N-C=C to form a substituted fused pyridinyl ring; B is a substituted phenyl or pyridinyl ring; J is an optionally substituted linking chain of 2 to 5 members including at least one carbon member, optionally including one or two carbon members as C(=O), and optionally including one member selected from nitrogen and oxygen;W is C=L or SO>n<; L is O or S;R>1< is H; or C>1<-C>6< alkyl, C>2<-C>6< alkenyl, C>2<-C>6< alkynyl or C>3<-C>6< cycloalkyl, each optionally substituted;R>3< is H; or C>1<-C>6< alkyl, C>2<-C>6< alkenyl, C>2<191-C>6< alkynyl or C>3<-C>6< cycloalkyl, C>2<-C>6< alkylcarbonyl, C>2<-C>6< alkoxycarbonyl, C>2<-C>6< alkylaminocarbonyl or C>3<-C>8< dialkylaminocarbonyl; and n is 1 or 2.This invention also includes fungicidal compositions comprising a compound of Formula I,<i> N</i>-oxides, and agriculturally suitable salts thereof. This invention also includes compounds of Formula I, <i>N</i>-oxides and agriculturally suitable salts thereof, provided that when B is a substituted phenyl ring, W is C=O or SO>2<, R>3< is H and J is a saturated chain of from 2 to 4 carbons that is either unsubstituted or substituted with one to three substituents selected from the group consisting of alkyl, alkoxy, aryl or aralkyl, then the compounds are <i>N</i>-oxides.
Description
Background technology
The present invention relates to some and have by two adjacent carbon atoms and condense suitable salt and composition on bicyclic amide in the pyridyl ring on second ring, its N-oxide, the agricultural, also relate to method that their use as bactericide.
Background technology
For realizing high crop efficient, the plant disease that control is caused by fungal plant pathogen is very important.Plant disease can cause output obviously to descend to the infringement of ornamental plants, vegetables, field crop, cereal and fruit crop, and consumer's cost is increased.For this purpose, existing many products can commercially availablely obtain, but still need new compound, and this compound is more effective, price is cheaper, toxicity is lower, safer or have different modes of action to environment.
WO 99/42447 discloses some formula I benzamide as bactericide:
R wherein
1Be H, alkyl or acyl group, R
2Be H or alkyl, and L is-(C=O)-,-SO
2-or-(C=S)-.
GB 2219797 discloses some condensed pyridine based compound of formula II:
Wherein X is NHCO or NHSO
2, Ar is the optional phenyl that replaces, R
4Be alkyl, alkoxyl, aryl or aralkyl, m is 1,2 or 3, and n is 1,2 or 3.
Effectively the bactericide of controlling plant fungi, particularly Oomycetes class fungi (for example Phytophthora spp. and Plasmopara spp.) is that the plantation people is needed always.Usually use the combination of bactericide, with the control that helps disease and postpone chemical sproof development.The mixture that phytopathogen is produced the active component of healing property, globality and preventative combination control action is used in expectation, expands activity profile thus and strengthens the effectiveness that disease is controlled.The combination of also wishing active component can provide bigger residual control, so that the spray medicine can prolong at interval.What wish especially is that the bactericide that is made up can suppress biochemical passages different in the fungal pathogens, to postpone that any one concrete plant disease control agent is produced drug resistance.
Can reduce the burst size of active agents in environment, and can guarantee that again cover crop avoids the disease that phytopathogen causes effectively simultaneously, this all is particularly advantageous under used situation.The mixture of bactericide can provide significantly better disease control, exceeds the desired value based on the activity of single composition.This synergy is described to " synergism of two compositions in the mixture; make total effect greater than or more lasting in the summation of two (perhaps more) effects when individual composition uses separately " (referring to Tames, P.M.L., Neth.J.Plant Pathology, (1964), 70,73-80).
Wish to find for realizing the particularly advantageous bactericide of one or more above-mentioned purpose.
Summary of the invention
The present invention relates to suitable salt and composition thereof on the compound (comprising all geometry and stereoisomer), N-oxide, agricultural of formula I:
Wherein:
A forms the condensed pyridine basic ring of replacement with N-C=C,
B is phenyl or the pyridyl ring that replaces,
J is the optional 2-5 person's connection chain that replaces, and comprises at least one carbon member, optional comprise one or two C (=O) the carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen,
W is C=L or SO
n,
L is O or S,
R
1Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each is all chosen wantonly and is substituted,
R
3Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl or C
3-8Dialkyl amino carbonyl, and
N is 1 or 2.
Particularly, the present invention includes the method that is used to control the plant disease that is caused by fungal plant pathogen, it comprises to described plant or its part or to plant seed or seedling uses the formula I compound (comprising that all geometry and stereoisomer, N-oxide and agricultural go up suitable salt) of sterilization effective dose or comprises described compound compositions.
The present invention comprises that also compound (comprising all geometry and stereoisomer), its N-oxide and the agricultural of formula I go up suitable salt, and condition is to work as the phenyl ring that B is replacement, and W is C=O or SO
2, R
3Be H, and J is the saturated chain of 2-4 carbon atom, this chain can be not replace or replaced by 1-3 substituting group that is selected from following group: alkyl, alkoxyl, aryl or aralkyl, then described compound is the N-oxide.
Originally return and relate to bactericidal composition, it comprises the formula I compound (comprising that all geometry and stereoisomer, its N-oxide and agricultural go up suitable salt) of (1) sterilization effective dose, and (2) (i) at least a other insecticide, bactericide, nematocide, bactericide, miticide, growth regulator, chemosterilant, semiochemical, repellant, attractant, pheromones, help food agent or other bioactive compound; And/or (ii) at least a other compositions that are selected from surfactant, solid diluent and liquid diluent.
For example, the invention provides the composition that comprises following composition: (a) compound of at least a formula I, and (b) at least a compound that is selected from following group:
(b1) two (dithiocarbamate) bactericide of alkylidene,
(b2) act on the compound of the bc1 compound of fungi mitochondrial respiratory electronics metastasis site,
(b3) cymoxanil,
(b4) act on the compound of the demethylase in the sterol biosynthesis pathway,
(b5) act on the morpholine and the piperidines of sterol biosynthesis pathway,
(b6) phenyl amide bactericide,
(b7) pyrimidone bactericide,
(b8) phthalimide, and
(b9) fosetyl.
Embodiment
As mentioned above, A is the condensed pyridine basic ring that replaces, and B is phenyl or the pyridyl ring that replaces.The term " replacement " relevant with these A or B ring is meant that these groups have at least one non-hydrogen and bactericidal activity is disappeared substituting group.Wherein A is selected from R by one or two
5Substituting group replace and B is selected from R by 1-3
6The example of the formula I that comprises described A and B ring that replaces of substituting group be included in the ring shown in the legend 1, wherein m is the integer of 1-2, p is the integer of 1-3.What note is, at (R
5)
mWith A and (R
6)
pAnd the tie point between the B is not fixed, and (R
5)
m(R
6)
pCan be connected on phenyl or the pyridyl ring on any one feasible carbon atom.
Legend 1
Be connected the R on the A
5And be connected R on the B
6Example comprise:
Each R
5And each R
6All be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl, C
3-6Trialkylsilkl; Or
Each R
5And each R
6All be benzyl ring, 5-6 unit assorted aromatic rings, benzyl rings or phenoxy group ring independently, each ring randomly is independently selected from R by 1-3
7Group replace; Each R
7Be C independently
1-4Alkyl, C
2-4Thiazolinyl, C
2-4Alkynyl, C
3-6Cycloalkyl, C
1-4Haloalkyl, C
2-4Haloalkenyl group, C
2-4Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen,
CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
3-6(alkyl) cycloalkyl amino, C
2-4Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl.
As mentioned above, R
1Can be C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each group can be optional the replacements.With these R
1The relevant term of group " the optional replacement " is meant unsubstituted or has the substituent R that at least one bactericidal activity non-hydrogen and that do not make unsubstituted analog and had disappears
1Group.The optional R that replaces
1The example of group is that those (are up to arbitrarily concrete R with one or more
1The maximum hydrogen atom sums that have on the group) be selected from the substituting group displacement hydrogen atom in following group and the group that is optionally substituted: halogen, CN, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
2-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido and C
3-6Cycloalkyl amino.Though as above listed these substituting groups, it should be noted that they might not exist, because they are substituting groups of choosing wantonly.It is also noted that R
1Group is randomly replaced by 1-5 substituting group.
The example of the N-oxide of formula I is shown I-5 to I-10 in legend 2, wherein R
1, R
3, R
5, R
6, W, m be identical with above definition with p.
Legend 2
As mentioned above, each R
5With each R
6Can be benzyl ring, 5-6 unit assorted aromatic rings, benzyl rings or phenoxy group ring, each ring randomly be independently selected from R by 1-3
7Group replace.The term relevant with these groups " the optional replacement " is meant unsubstituted or has the substituent group that at least one bactericidal activity non-hydrogen and that do not make unsubstituted analog and had disappears.Choose wantonly by 1-3 and be independently selected from R
7The example of the benzyl ring that replaces of group be as R in the legend 3
xRing shown in-56, wherein x is 5 or 6, and r is the integer of 1-3.Choose wantonly by 1-3 and be independently selected from R
75 or 6 yuan of assorted aromatic rings replacing of group comprise in the legend 3 as R
x-1 to R
xRing shown in-55, wherein x is 5 or 6, and r is the integer of 1-3.Choose wantonly by 1-3 and be independently selected from R
7The example of the benzyl rings that replaces of group be as R in the legend 3
XRing shown in-57, wherein x is 5 or 6, and r is the integer of 1-3.Choose wantonly by 1-3 and be independently selected from R
7The example of the phenoxy group ring that replaces of group be as R in the legend 3
xRing shown in-58, wherein x is 5 or 6, and r is the integer of 1-3.
Though at R
x-1 to R
x1-3 R has been shown in-58 the structure
7Group (is expressed as (R
7)
r), but it should be noted that they do not need all to exist, because they are substituting groups of choosing wantonly.Need to replace nitrogen-atoms with the valence link relation that satisfies them by H or R
7Replace.It should be noted that some R
xGroup can only be less than 3 R
7Group replaces (R for example
x-15, R
x-16, R
x-17 to R
x-20 and R
x-31 to R
x-33 can be only by 1 R
7Group replaces).Notice, as (R
7)
rAnd the tie point between the RX group is fixedly the time, (R
7)
rCan be connected R
xOn the group on any one feasible carbon atom.
Legend 3
As mentioned above, J is the optional 2-5 person's connection chain that replaces, and comprises at least one carbon member, optionally comprises one or two C (=O) carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen.The term relevant with connection chain J " the optional replacement " is meant unsubstituted or has the substituent J group that at least one bactericidal activity non-hydrogen and that do not make unsubstituted analog and had disappears.The example of the optional J group that replaces comprises the J group shown in the legend 4.J in the legend 4 is following expression: the left end of J group is connected 3 places of A ring, and the right-hand member of J group is connected and carries N (R
3) on the carbon atom of WB group.
J group in the legend 4 can randomly be substituted by the substituting group displacement hydrogen atom that is selected from following group with one or more (being up to the maximum hydrogen atom sums that have on the arbitrarily concrete J group): C
1-2Alkyl, halogen, CN, NO
2And C
1-2Alkoxyl.Though listed these substituting groups, it should be noted that they might not exist, because they are substituting groups of choosing wantonly.It is also noted that the J group is randomly replaced by 1-4 aforesaid substituting group.
Legend 4
-CH
2CH
2-?????????????????????-OCH
2-??????????????-NHCH
2-
-CH
2CH
2CH
2--OCH
2CH
2--N (C
1-2Alkyl) CH
2-
-CH
2CH
2CH
2CH
2-????????????-OCH
2CH
2CH
2-??????-NHCH
2CH
2-
-CH
2CH
2CH
2CH
2CH
2--CH
2OCH
2--N (C
1-2Alkyl) CH
2CH
2-
-C(＝O)NHC(＝O)-????????????????-CH
2OC(＝O)-????????-CH
2NHCH
2-
-C (=O) N (C
1-2Alkyl) C (=O)--CH
2CH
2OC (=O)--CH
2N (C
1-2Alkyl) CH
2-
-CH
2N (C
1-2Alkyl) C (=O)--CH
2NHC (=O)-
-CH
2CH
2N (C
1-2Alkyl) C (=O)--CH
2CH
2NHC (=O)-
In above-mentioned example, term " alkyl " all comprises the straight or branched alkyl when using separately or use in such as " alkyl sulfenyl " or compound words such as " haloalkyls ", as methyl, ethyl, n-propyl group, i-propyl group or different butyl, amyl group or hexyl isomer." thiazolinyl " comprises the straight or branched thiazolinyl, as vinyl, 1-acrylic, 2-acrylic, different cyclobutenyl, pentenyl and hexenyl isomer." thiazolinyl " also comprises polyene, for example 1, and 2-allene base and 2,4-hexadienyl." alkynyl " comprises the straight or branched alkynyl, as acetenyl, 1-propinyl, 2-propynyl, different butynyl, pentynyl and hexin base isomer." alkynyl " also includes the group of a plurality of three keys, as 2, and 5-hexadiine base." alkoxyl " for example comprises methoxyl group, ethyoxyl, n-propoxyl group, isopropoxy and different butoxy, amoxy and own oxygen base isomer." alkyl sulfenyl " comprises straight or branched alkyl sulfenyl, for example methyl mercapto, ethylmercapto group and different propyl group sulfenyl, butyl sulfenyl, amyl group sulfenyl and hexyl sulfenyl isomer." alkyl sulfinyl " comprises two enantiomers 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 sulfonyl, amyl group sulfonyl and hexyl sulfonyl isomer." alkyl amino ", " dialkyl amido " etc. are similar to above-mentioned example and define." cycloalkyl " for example comprises cyclopropyl, cyclobutyl, cyclopenta and cyclohexyl.
" halogen " that use separately or use in the compound word such as " haloalkyl " comprises fluorine, chlorine, bromine or iodine.In addition, when the compound word that is used for such as " haloalkyl ", described alkyl can partly or completely be replaced by identical or different halogen atom.The example of " haloalkyl " comprises F
3C, ClCH
2, CF
3CH
2And CF
3CCl
2Term " haloalkenyl group ", " halo alkynyl ", " halogenated alkoxy ", " haloalkyl sulfenyl " etc. all are similar to term " haloalkyl " and define.The example of " haloalkenyl group " comprises (Cl)
2C=CHCH
2And CF
3CH
2CH=CHCH
2The example of " halo alkynyl " comprises HC CCHCl, CF
3C C, CCl
3C C and FCH
2C CCH
2The example of " halogenated alkoxy " comprises CF
3O, CCl
3CH
2O, HCF
2CH
2CH
2O and CF
3CH
2O.The example of " haloalkyl sulfenyl " comprises CCl
3S, CF
3S, CCl
3CH
2S and ClCH
2CH
2CH
2S.The example of " haloalkyl sulfinyl " comprises CF
3S (O), CCl
3S (O), CF
3CH
2S (O) and CF
3CF
2The example of S (O), " halogenated alkyl sulfonyl " comprises CF
3S (O)
2, CCl
3S (O)
2, CF
3CH
2S (O)
2And CF
3CF
2S (O)
2
The example of " alkyl-carbonyl " comprises CH
3C (=O), CH
3CH
2C (=O), CH
3CH
2CH
2C (=O) and (CH
3)
2CHC (=O).The example of " alkoxy carbonyl " comprises CH
3OC (=O), CH
3CH
2OC (=O), CH
3CH
2CH
2OC (=O), (CH
3)
2CHOC (=O) and different butoxy carbonyls or pentyloxy carbonyl isomer.The example of " alkyl amino-carbonyl " comprises CH
3NHC (=O), CH
3CH
2NHC (=O), CH
3CH
2CH
2NHC (=O), (CH
3)
2CHNHC (=O) and different butyl amino carbonyls or amyl group amino carbonyl isomer.The example of " dialkyl amino carbonyl " comprises (CH
3)
2NC (=O), (CH
3CH
2)
2NC (=O), CH
3CH
2(CH
3) NC (=O), CH
3CH
2CH
2(CH
3) NC (=O), (CH
3)
2CHN (CH
3) C (=O) and different butyl amino carbonyls or amyl group amino carbonyl isomer.
" fragrance " is meant that each annular atoms is in the identical plane basically, and has the p track perpendicular to this plane of a loop, and when n was 0 or positive integer, wherein (4n+2) π electronics and loops closed to meet the Hueckel rule." mix " with the relevant term of ring and represent that at least one annular atoms is not a carbon in this ring, and can comprise that 1-4 is individual to be independently selected from the hetero atom of nitrogen, oxygen and sulphur, its condition is to comprise to be no more than 4 nitrogen, to be no more than 2 oxygen and to be no more than 2 sulphur.Term " assorted aromatic rings " comprises the heterocycle of complete fragrance.Heterocycle can connect by the hydrogen of replacing on described carbon or the nitrogen by any feasible carbon or nitrogen.Term " aryl " is meant aryl radical, comprises phenyl, tolyl and naphthyl, and they can be chosen wantonly and be substituted.Term " aralkyl " is meant the alkyl that is replaced by aromatic yl group, comprises phenylalkyl, as benzyl (it can be chosen wantonly and be substituted).
Those skilled in the art will recognize that, not all nitrogen heterocyclic ring can form the N-oxide, this is to form oxide because nitrogen need exist lone pair electrons to be used for oxidation, and one skilled in the art will recognize that those can form the nitrogen heterocyclic ring of N-oxide.One skilled in the art will recognize that quaternary amine can form the N-oxide.Be used to prepare heterocycle and quaternary amine the N-oxide synthetic method to those skilled in the art all right and wrong Changshu know, comprise with peroxy acid such as peracetic acid and metachloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl peroxide such as TBHP, sodium perborate and dioxiranes such as dimethyl dioxirane oxygenated heterocyclic and quaternary amine.These methods that prepare the N-oxide are extensively described and are repeated in the literature, for example referring to T.L.Gilchrist, and Comprehensive Organic Synthesis, the 7th volume 748-750 page or leaf, S.V.Ley edits, Pergamon Press; M.Tisler and B.Stanovnik, ComprehensiveHeterocyclic Chemistry, the 3rd volume 18-20 page or leaf, A.J.Boulton and A.McKillop edit, Pergamon Press; M.R.Grimmett and B.R.T.Keene, Advances inHeterocyclic Chemistry, the 43rd volume 149-161 page or leaf, A.R.Katritzky edits, Academic Press; M.Tisler and B.Stanovnik, Advances in HeterocyclicChemistry, the 9th volume 285-291 page or leaf, A.R.Katritzky and A.J.Boulton edit, Academic Press; And G.W.H.Cheeseman and E.S.G.Werstiuk, Advancesin Heterocyclic Chemistry, the 22nd volume 390-392 page or leaf, A.R.Katritzky and A.J.Boulton edit, Academic Press.
Total carbon atom number in substituting group prefix " C
I-j" expression, wherein i and j are the numbers of 1-8.For example, C
1-3Alkyl sulphonyl is meant that methyl sulphonyl is to sulfonyl propyl base, C
2-8Dialkyl amido is meant for example (CH
3)
2N, (CH
3CH
2)
2N, CH
3CH
2(CH
3) N, CH
3CH
2CH
2(CH
3) N or (CH
3)
2CHN (CH
3), comprise 2-8 carbon atom altogether.
Replace if compound is substituted base, and this substituent subscript represents that described substituent quantity surpasses at 1 o'clock that then described substituting group (when they surpass 1) is independently selected from defined substituting group group.In addition, represent a scope for example (R) when subscript
I-jThe time, then this substituent quantity can be selected in the integer that comprises between i and the j.
Term " optional by 1-3 substituting group replacement " etc. is meant have 1-3 position to replace on this group.When group comprises can be the substituting group of hydrogen the time, R for example
1Or R
2, then when this substituting group is hydrogen, think that it equals this group and is not substituted.
Compound involved in the present invention can one or more stereoisomer form exist.Various stereoisomers comprise enantiomer, diastereomer, atropisomerism body and geometric isomer.One skilled in the art will recognize that, when being rich in certain stereoisomer with respect to other stereoisomers, when perhaps from other stereoisomers, separating, the effect that this stereoisomer can have various active and/or can show multiple beneficial.In addition, those skilled in the art know how to separate, enrichment and/or selectivity prepare described stereoisomer.Therefore, the present invention includes the compound, its N-oxide and the agricultural that are selected from formula I and go up suitable salt.This compound can stereoisomer mixture, single stereoisomer or exist with the optically-active form.Particularly, because the R among the formula I
1With J is different, and then described formula has chiral centre at the carbon atom place of their common keyed jointings.The present invention includes the formula I ' of equal parts and formula I " racemic mixture.
Wherein A, B, J, W, R
1, R
2And R
3Identical with above definition.
In addition, the present invention includes to compare and be rich in formula I ' or formula I " compound of enantiomer and composition with racemic mixture.Included compound and composition relate to pure basically formula I ' or formula I " enantiomer.For example, the present invention includes the compound of formula I, compare the enantiomer that it is rich in formula I ' with racemic mixture.Basically pure formula I ' enantiomer is also included among the present invention.The present invention also comprises composition, and wherein component (a) is to be rich in formula I with respect to racemic mixture " component (a) enantiomer.The present invention also comprises comparing with racemic mixture is rich in formula I " the formula I compound of enantiomer.Basically " enantiomer comprises in the present invention pure formula I.The present invention also comprises composition, and wherein component (a) is to be rich in formula I with respect to racemic mixture " component (a) enantiomer.
When the enantiomer enrichment, the amount of an enantiomer is greater than the amount of other enantiomers, and enrichment degree can define with enantiomeric excess (" ee "), this enantiomeric excess is defined as 100 (2x-1), and wherein x is the molar fraction (for example 20% ee is equivalent to the enantiomer of 60:40 ratio) of main enantiomer in the mixture.Preferred active higher isomer is at least 50% enantiomeric excess, at least 75% enantiomeric excess more preferably, and at least 90% enantiomeric excess more preferably still, and most preferably be at least 94% enantiomeric excess.It should be noted that especially more highly active isomer is an enantiomer-pure.
The salt of The compounds of this invention comprises and inorganic acid or organic acid acid-addition salts, for example hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetate, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid or valeric acid.When compound of the present invention comprised acidic group such as carboxylic acid or phenol, the salt of The compounds of this invention also comprised those salt that form with organic base (for example pyridine, ammonia or triethylamine) or inorganic base (for example hydride of sodium, potassium, lithium, calcium, magnesium or barium, hydroxide, carbonate).
The invention provides the method that is used to control the plant disease that causes by fungal plant pathogen, it comprises to described plant or its part or to plant seed or seedling uses the formula I compound of sterilization effective dose, comprises that all geometry and stereoisomer, N-oxide and agricultural go up the suitable salt composition of above-mentioned composition (for example as).
Based on higher activity and/or the reason that is easy to synthesize, preferable methods is:
Preferred 1, preferable methods comprises following formula I compound, wherein:
A forms by 1 or 2 with N-C=C and is independently selected from R
5The condensed pyridine basic ring that replaces of substituting group,
B is independently selected from R by 1-3
6Substituting group replace,
J is 2-5 person's connection chain, comprises at least one carbon member, optional comprise one or two C (=O) the carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen, randomly by 1 or more a plurality of substituting group that is selected from following group replace: C
1-2Alkyl, halogen, CN, NO
2And C
1-2Alkoxyl,
R
1Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each group are all randomly replaced by one or more substituting group that is selected from following group: halogen, CN, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
2-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido and C
3-6Cycloalkyl amino,
Each R
5With each R
6Be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl, perhaps
Each R
5With each R
6Be benzyl ring, 5 or 6 yuan of assorted aromatic rings, benzyl rings or phenoxy group rings independently, each ring randomly is independently selected from R by 1-3
7Substituting group replace, and
Each R
7Be C independently
1-4Alkyl, C
2-4Thiazolinyl, C
2-4Alkynyl, C
3-6Cycloalkyl, C
1-4Haloalkyl, C
2-4Haloalkenyl group, C
2-4Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
3-6(alkyl) cycloalkyl amino, C
2-4Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl.
It should be noted that in preferred 1 the method, wherein:
Each R
5With each R
6Be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl, C
3-6Trialkylsilkl, or
Each R
5With each R
6Be phenyl, benzyl or phenoxy group independently, each group is randomly replaced by following group: C
1-4Alkyl, C
2-4Thiazolinyl, C
2-4Alkynyl, C
3-6Cycloalkyl, C
1-4Haloalkyl, C
2-4Haloalkenyl group, C
2-4Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
3-6(alkyl) cycloalkyl amino, C
2-4Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl.
In preferred 2, preferred 1 the method, W is C=O.
Preferred 3, preferred 2 method, wherein:
J is selected from-CH
2CH
2-,-CH
2CH
2CH
2-,-CH
2CH
2CH
2CH
2-,-OCH
2-,-OCH
2CH
2-,-OCH
2CH
2CH
2-,-CH
2NHCH
2-,-CH
2N (C
1-2Alkyl) CH
2-,-CONHCO-and-CON (C
1-2Alkyl) CO-, and
Each R
5With each R
6Be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl or C
3-8Dialkyl amino carbonyl.
Preferred 4, preferred 3 method, wherein each R
5Be halogen, CN, NO independently
2, C
1-2Alkyl, C
1-2Haloalkyl, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl and C
1-2Alkyl sulphonyl, C
1-2Haloalkyl sulfenyl, C
1-2Haloalkyl sulfinyl, C
1-2Halogenated alkyl sulfonyl, C
2-4Alkoxy carbonyl or C
2-4Alkyl amino-carbonyl.
It should be noted that in preferred 4 methods, wherein R
5Be CH
3, Cl, Br, I, CN, NO
2, CF
3, CO
2CH
3, CONHCH
3CH
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
Preferred 5, preferred 4 method, wherein B chooses wantonly by 1-3 to be independently selected from R
6The benzyl ring that replaces of substituting group.
Preferred 6, preferred 5 method, wherein each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
It should be noted that in preferred 6 the method, wherein each R
6The position all the ortho position in the position that is connected with W`, an optional 1-2 extra R
6, and R
6Be halogen or methyl.
Preferred 7, preferred 6 method, wherein J is-CH
2CH
2-or-CH
2CH
2CH
2-.
Preferred 8, preferred 7 method, wherein each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3
It should be noted that in preferred 8 the method, wherein R
5Be CH
3, Cl, Br, CN, NO
2, CF
3, CO
2CH
3Or CONHCH
3
Preferred 9, preferred 4 method, wherein B chooses wantonly by 1-3 to be independently selected from R
6In substituting group the 3-pyridine radicals or the 4-pyridyl ring that replace.
Preferred 10, preferred 9 method, wherein each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
Preferred 11, preferred 10 method, wherein J is-CH
2CH
2-or-CH
2CH
2CH
2-.
Preferred 12, preferred 11 method, wherein each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3
It should be noted that in preferred 12 the method, wherein R
5Be CH
3, Cl, Br, CN, NO
2, CF
3, CO
2CH
3Or CONHCH
3
Preferred 13, preferred 12 method, wherein B is the 3-pyridyl ring, one of them R
6Be 2 one Cl, the ortho position is in the position that is connected with C=O, and another R
6Be Cl or methyl, and be positioned at 4 that also the ortho position is in the position that is connected with C=O, the 3rd optional R
6Be to be in 6 methyl.
Preferred 14, preferred 2 until preferred 13 method, wherein R
1Be H, and R
3Be H.
Particularly preferred method comprises the compound that is selected from following group: 2-chloro-6-methoxyl group-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl)-4-pyridine carboxamides, 2,6-two chloro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl) benzamide and 2,3,6-three fluoro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl) benzamide.
The invention still further relates to the bactericidal composition of the formula I compound that comprises the sterilization effective dose.Preferred composition of the present invention is that those are included in the compound compositions of mentioning in above-mentioned preferred 1 to preferred 14.
The present invention also comprises the compound of formula I, comprises that all geometry and stereoisomer, its N-oxide and agricultural go up suitable salt, and condition is to work as the phenyl ring that B is replacement, and W is C=O or SO
2, R
3Be H, and J is the saturated chain of 2-4 carbon atom, this chain can be not replace or replaced by 1-3 substituting group that is selected from following group: alkyl, alkoxyl, aryl or aralkyl, then described compound is the N-oxide.Preferred compound is those those compounds of mentioning in above-mentioned preferred 1 to preferred 14, but will satisfy above-mentioned condition.
Particularly preferred compound is 2-chloro-6-methoxyl group-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl)-4-pyridine carboxamides.
The compound of formula I can and improve with one or more methods of describing in following synthetic route 1-19 and prepare.The compound of formula Ia, Ib and Ic is subordinated to formula I compound, and all substituting groups of formula Ia, Ib and Ic compound all define suc as formula I.With A, B, J, L, W, the R in the following formula 1-19 compound
1-R
6With m all as defined above.Formula 1a-e, 6a-c, 8a-f, 10a-c, 11a-c, 16a-b, 18a-d and 19a-b are subordinated to formula 1,6,8,10,11,16,18 and 19 respectively.With the J in the following formula
1-J
6Be subordinated to J.
As shown in synthetic route 1, the compound of formula Ia is prepared as follows: in atent solvent and the alkali that 2 molar equivalents are arranged (as triethylamine (Et
3N), diisopropyl ethyl amine on polymer support or potash) when existing, handle the amine or the amine salt of formula 1 with suitable acyl chlorides.Similarly, the compound of formula Ib is prepared as follows: in atent solvent and the alkali that 2 molar equivalents are arranged (as triethylamine (Et
3N), diisopropyl ethyl amine on polymer support or potash) when existing, handle the amine or the amine salt of formula 1 with suitable sulfonic acid chloride.Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, hydrocarbon such as toluene or benzene, and halogenated hydrocarbons such as carrene or chloroform.
Synthetic route 1
Perhaps, the compound of formula Ia can followingly synthesize: shown in synthetic route 2, make the amine of formula 1 or amine salt in the presence of organic dehydrating agent with suitable carboxylic acid reaction, described organic dehydrating agent for example is 1,3-dicyclohexylcarbodiimide (DCC) or 1-[3-(dimethylamino) propyl group]-3-ethyl-carbodiimide hydrochloride (EDC).Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, hydrocarbon such as toluene or benzene, and halogenated hydrocarbons such as carrene or chloroform.
Synthetic route 2
Intermediate amine 1a is that wherein A is substituent 2-pyridyl ring shown in carrying, J
1Be-(CH
2)
q-, q is 1,2,3 or 4, and R
1And R
3All be formula 1 compound of hydrogen, can be by commercially available formula 2 pyridines preparations (synthetic route 3).As shown in synthetic route 3, be connected the CH at the ortho position of formula 2 pyridine nitrogen atoms
2Can be by following sequential steps according to the method NH that is similar among the WO 00/56729
2Replace: hydrogen peroxide oxidation, acyl groupization, hydrolysis, chlorination, nitrine displacement and reduction (are for example used H
2And carry out catalytic hydrogenation as the palladium/charcoal of catalyzer), form amine 1a.
Synthetic route 3
J
1Be (CH
2)
q, and q is 1,2,3 or 4
J wherein
2Be-CH
2O-,-CH
2CH
2O-,-CH
2NH-,-CH
2CH
2NH-,-CH
2N (C
1-2Alkyl)-,-CH
2CH
2N (C
1-2Alkyl)-,-CONH-or-CH
2N (C
1-2Alkyl)-formula Ib compound can synthesize by intermolecular displacement shown in synthetic route 4, wherein uses the compound of formula 6, has highly basic such as sodium hydride, and at polar aprotic solvent such as N, in the dinethylformamide, heats in acid medium then.Reported with 2 the similar intermolecular displacement that the pyridine that the 3-dichloro replaces carries out among the WO 99/42447.J
2Each group also can be randomly replaced by one or more (mostly being existing hydrogen sum in the concrete arbitrarily J group most) substituting group, described substituting group is independently selected from following group: C
1-2Alkyl is (as CH (CH
3) O, C (CH
3)
2O or CH (CH
2CH
3) O), halogen, CN, NO
2And C
1-2Alkoxyl.
Synthetic route 4
J
2Be CH
2O, CH
2CH
2O, CH
2NH, CH
2CH
2NH, CONH, CH
2N (C
1-2Alkyl), CH
2CH
2N (C
1-2Alkyl) or CON (C
1-2Alkyl)
J
2It can be optional the replacement
Perhaps, the compound of formula 1c (wherein A and J all as defined above, and R
1Be hydrogen) can be prepared as follows: with the compound of nitrous acid isopentyl ester and alkali such as potassium tert-butoxide (t-BuOK) processing formula 7, reduce formula 8 oximes (synthetic route 5) of gained then.Reduction reaction can for example be finished with lithium aluminium hydride reduction, zinc and acetate, perhaps finish (referring to Jerry March, Advanced Organic Chemistry:Reactions, Mechanism and S tructure by catalytic hydrogenation, the 3rd edition, John Wiley ﹠amp; Sons, New York, is used to reduce the list of references of oxime by 1985, the 1105 pages).
Synthetic route 5
Perhaps, the compound of formula Ic (wherein A and J as defined above, and R
1Be hydrogen) can shown in synthetic route 6,, formula 9 compounds prepare by being carried out reductive amination.Reported the method for many reductive aminations.For some documents that at first will reference, can be referring to Jerry March, Advanced Organic Chemistry:Reactions, Mechanism and Structure, the 3rd edition, John Wiley ﹠amp; Sons, New York, 1985, the 798-800 pages or leaves.
Synthetic route 6
J wherein
2It is optional the replacement-CH
2O-or-CH
2CH
2The formula 6a compound of O-can prepare (synthetic route 7) by the ester exchange reaction at the correspondent alcohol of the N-of alkali condition following formula 9 (diphenyl methylene) glyceride and formula 10.J wherein
2It is optional the replacement-CH
2NH-,-CH
2CH
2NH-,-CH
2N (C
1-2Alkyl)-or-CH
2CH
2N (C
1-2Alkyl)-formula 6b compound can prepare by with the corresponding amine of formula 11 N-(diphenyl methylene) glyceride of formula 9 being carried out amidatioon.J wherein
2Be optional replacement the-CONH-or-CON (C
1-2Alkyl) formula 6 compounds can prepare by with the corresponding amides of formula 15 N-(diphenyl methylene) glyceride of formula 9 being carried out amidatioon.
Synthetic route 7
J
2And J
3It can be optional the replacement
R
8Be H or C
1-2Alkyl
Shown in synthetic route 8, J wherein
3It is optional the replacement-CH
2But the ortho lithiation of formula 10a compound passing type 12 compounds of OH, prepare with aldehyde or aldehyde synthon (as paraformaldehyde) or reactive ketone then.Similarly, J wherein
3It is optional the replacement-CH
2CH
2The formula 10b compound of OH can be by ortho lithiation, prepare with epoxide reaction then.Ortho lithiation can realize by handling substrate with strong lithium alkali such as LDA (LDA), and normally implement under reducing atmosphere.Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, and hydrocarbon such as hexane, heptane or ethylbenzene.
Shown in synthetic route 9, J wherein
3Be-CH
2The formula 10c compound of OH can be prepared as follows: the compound of ortho lithiation formula 12, with carbon dioxide reaction, form the compound of formula 13, and use lithium aluminium hydride reduction (LAH) in suitable solvent such as toluene, to reduce then.The isonicotinic acid of some formulas 13 can commercially availablely obtain.
Synthetic route 8
Q
1And Q
2Be H or C independently
1-2Alkyl
Shown in synthetic route 9, J wherein
3Be-CH
2The formula 10c compound of OH also can be prepared as follows: the compound of ortho lithiation formula 12, with carbon dioxide reaction, form the compound of formula 13, and use lithium aluminium hydride reduction (LAH) in suitable solvent such as toluene, to reduce then.The isonicotinic acid of some formulas 13 can commercially availablely obtain.
Synthetic route 9
The compound of formula 11a can prepare (synthetic route 10) by forming corresponding amino methyl intermediate with lithium aluminium hydride reduction (LAH) nitrile reducing in suitable solvent such as toluene by the nitrile of formula 14.The compound of formula 11a also can be by the primary amide of formula 15 (R wherein
8Be hydrogen) by in suitable solvent such as toluene, preparing with lithium aluminium hydride reduction (LAH) is also original.The compound of formula 11b can be by R wherein
8Be C
1-2Formula 15 secondary amide of alkyl are by preparing with lithium aluminium hydride reduction (LAH) is also original in suitable solvent such as toluene.The compound of formula 11b also can prepare by carrying out reductive amination with the compound PARA FORMALDEHYDE PRILLS(91,95) of formula 11a or acetaldehyde.With formaldehyde carry out reductive amination be in the presence of formic acid according to the Eschweiler-Clarke method (referring to Jerry March, Advanced OrganicChemistry:Reactions, Mechanism and Structure, the 3rd edition, John Wiley ﹠amp; Sons, New York, 1985, the 798-800 pages or leaves, and list of references wherein) finish.
Synthetic route 10
The compound of formula 15 can also prepare (synthetic route 11) by being converted into corresponding acyl chlorides subsequently by the compound of formula 13 with ammonia or primary amine reaction.The method that carboxylic acid is converted into corresponding acyl chlorides is well known in the art, and for example comprises with thionyl chloride or oxalyl chloride processing.Handle acyl chlorides with amine or amine salt in atent solvent and when having two molar equivalent alkali (as triethylamine, diisopropyl ethyl amine or potash on polymer support).Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, hydrocarbon such as toluene or benzene, and halogenated hydrocarbons such as carrene or chloroform.Perhaps, the compound of formula 15 can synthesize with the carboxylic acid reaction of formula 13 in the presence of organic dehydrating agent by making suitable amine or amine salt, described organic dehydrating agent for example is 1,3-dicyclohexylcarbodiimide (DCC) or 1-[3-(dimethylamino) propyl group]-3-ethyl-carbodiimide hydrochloride (EDC).Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, hydrocarbon such as toluene or benzene, and halogenated hydrocarbons such as carrene or chloroform.
Synthetic route 11
Perhaps, the compound of formula 11a can followingly synthesize: making wherein, LG is such as Br, Cl, methane sulfonyl (OSO
2Me) or p-toluenesulfonyl (OSO
2-p-Tol) formula 16 compounds of leaving group in protonic solvent such as methyl alcohol with ammonia react (synthetic route 12).The compound of formula 11a also can be prepared as follows: the compound of formula 16 and the reaction of the sylvite of phthalimide, react in alcoholic solvent with ethylaminoethanol or hydrazine then, and form desirable formula 11a amino methyl intermediate.
Synthetic route 12
LG be Cl, Br ,-OSO
2Me ,-OSO
2-p-Tol
Shown in synthetic route 13, wherein LG is-OSO
2Me or-OSO
2Formula 16 compounds (16a) of-p-Tol can react with corresponding sulfonic acid chloride by the compound that makes formula 10c in the presence of diisopropyl ethyl amine on alkali such as triethylamine, the polymer support or potash and prepare.Suitable solvent is selected from following group: ether such as oxolane, dimethoxy-ethane or ether, hydrocarbon such as toluene or benzene, and halogenated hydrocarbons such as carrene or chloroform.Wherein LG is that formula 16 compounds (16b) of Br or Cl can prepare by the compound of handling formula 17 with halogenating agent such as bromine, chlorine or N-halo succinimide under condition of free radical.These transform normally to activate with visible light or ultraviolet light (hv) and hydrogen peroxide and implement, and are well-known in the art.
Synthetic route 13
LG is-OSO
2Me or-OSO
2-p-Tol
LG is Cl or Br
The compound of formula 11c can be by the compound of formula 16 by with the cyanide displacement, prepare (synthetic route 14) with for example lithium aluminium hydride reduction then.
Synthetic route 14
LG be Cl, Br ,-OSO
2Me or-OSO
2-p-Tol
But the intermolecular free radical acidylate of compound passing type 18 compounds of formula 8 prepares (synthetic route 15).These acidylates can be implemented having in the presence of TBHP, sulfuric acid and the iron sulfate (mainly referring to Chem.Communications, 1969,201; And Gazz.Chim.Ital.1977,107,491).
Synthetic route 15
Wherein J is OCH
2Or NHCH
2Formula 18 compounds (being respectively 18a or 18b) can be prepared as follows: with the bromoacetaldehyde diethyl acetal compound of formula 19 is carried out alkylation, then the acetal protecting group is carried out acidolysis (synthetic route 16).Wherein J is OCH
2CH
2Or NHCH
2CH
2Formula 18 compounds (being respectively 18c or 18d) can carry out the Michael addition to acrolein by compound and prepare with formula 19.
Synthetic route 16
19a J
4Be O 18a J
5Be OCH
2
19b J
4Be NH 18b J
5Be NHCH
2
19a J
4Be O 18c J
5Be OCH
2CH
2
19b J
4Be NH 18d J
5Be NHCH
2CH
2
Wherein J is N (C
1-2Alkyl) CH
2Or N (C
1-2Alkyl) CH
2CH
2Formula 8 compounds (being respectively 8e and 8f) can be prepared as follows: usually in the presence of extra alkali such as sodium carbonate or potash, the compound of formula 8b or 8d is carried out alkylation (synthetic route 17) with alkylating agent such as alkyl halide (as iodomethane or iodoethane) or dialkyl group sulphonic acid ester such as dimethyl suflfate.
Synthetic route 17
8a J
5Be OCH
28e J
5Be N (C
1-2Alkyl) CH
2
8b J
5Be NHCH
28f J
5Be N (C
1-2Alkyl) CH
2CH
2
8c J
5Be OCH
2CH
2
8d J
5Be NHCH
2CH
2LG
1Be Cl, Br, I ,-OSO
2Me ,-OSO
2-p-Tol
J wherein
6Be CH
2NHCH
2Or CH
2N (C
1-2Alkyl) CH
2Formula 1e compound can prepare (synthetic route 18) by compound with lithium aluminium hydride reduction formula 1d.
Synthetic route 18
J
6Be CH
2NH or CH
2CH
2NH
The compound of formula Ic (wherein W is C=L, and L is the compound of S) can be synthetic according to synthetic route 19.Formula Ia acid amides shown below can be by making this acid amides contact with Lawesson reagent or phosphoric sulfide in suitable solvent to be converted into thioamides (referring to Jerry March, Advanced Organic Chemistry:Reactions, Mechanism and Structure, the 4th edition, John Wiley ﹠amp; Sons, New York, 893-4 page or leaf).
Synthetic route 19
It should be understood that above-mentioned some reagent and the reaction condition that is used for preparation I compound might not be complementary with some functional group that intermediate product exists.In these cases, introducing protection/deprotection steps or functional group transform mutually and will help to obtain desirable product in synthetic.Using and selecting technical staff for the field of chemical synthesis of protecting group is conspicuous (for example referring to Greene, T.W.; Wuts, P.G.M.Protective Groups in Organic Synthesis, the 2nd edition; Wiley:New York, 1991).Those skilled in the art also can recognize, in some cases, as certain synthetic route be shown in introduce specific reagent after, might must carry out the extra conventional synthesis step of not describing in detail, with synthesizing of perfect I compound.Those of skill in the art also will appreciate that, be the compound of preparation formula I, might need to carry out, and its order is different with concrete sequence of steps in the combination of a plurality of steps shown in the synthetic route as mentioned above.
Those of skill in the art also will appreciate that the compound of formula I and intermediate described here can carry out various parent's electricity, nucleophilic, free radical, organic metal, oxidation and reduction reaction, to add substituting group or to change the substituting group that oneself exists.
Need not further detailed description, believe after those skilled in the art state description in the use and can utilize the present invention fully.Therefore, following examples only are to be used to illustrate the present invention, and never limit the scope of the present invention.The starting material of each reactions steps might not need to prepare by concrete preparation method among this embodiment.Except that the chromatographic solvent mixture or have in addition the explanation, percentage is percetage by weight.The umber of chromatographic solvent mixture or percentage are based on volume, except as otherwise noted.
1H NMR spectrum is to be represented with the ppm downfield by tetramethylsilane, and s is unimodal, and d is a doublet, and t is a triplet, and q is a quartet, and m is a multiplet, and dd is a double doublet, and dt is two triplets, and br s is wide unimodal.
Embodiment 1
Preparation 2,6-two chloro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl) benzamide
Steps A: preparation 5,6,7,8-tetrahydrochysene-3-methylquinoline
Under 0 ℃, (20g 140mmol) is dissolved in the trifluoroacetic acid (80mL), adds palladium/charcoal (10g) of 10 weight % then with the 3-methylquinoline.The mixture H of hydrogen at room temperature, 345kPa (50psi)
2In Parr jolting machine, handled 5 hours under the pressure.The mixture of gained is by Celite_ (SiO
2Filtering agent) filters in the bed, to remove catalyzer.(2 * 20mL) wash Celite_/charcoal bed with methyl alcohol.Filtrate is carried out vacuum concentration.Residue distributes between 2N sodium hydrate aqueous solution and ether.The organic extract drying (sodium sulphate) that merges concentrates then, obtains title compound (19g).
1H?NMR(CDCl
3)δ：8.17(s，1H)，7.15(s，1H)，2.87(t，J＝6.2Hz，2H)，2.72(t，J＝6.4Hz，2H)，2.25(s，3H)，1.86(m，2H)，1.80(m，2H)。
Step B: preparation 5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl acetic acid esters
5,6,7,8-tetrahydrochysene-3-methylquinoline (39.1g, 266mmol) solution in acetate (130mL) is at room temperature handled with 30% aqueous hydrogen peroxide solution (26mL), then the reactant mixture of gained is heated to 70 ℃ totally 6 hours.Add 30% hydrogen peroxide (26mL) of a part in addition, mixture is heated to 70 ℃ then and spends the night.Reactant mixture is cooled to room temperature, then vacuum concentration.Residue is dissolved in the carrene, and uses Na
2CO
3(87g) handle.After 1 hour, filtering mixt is used washed with dichloromethane then.The filtrate vacuum concentration obtains semisolid oil.
The solution of this semisolid oil in acetic anhydride (200mL) is heated to 90 ℃ and spends the night.Reactant mixture is cooled to room temperature, and vacuum is removed acetic anhydride.Under reduced pressure distillation leftover obtains title compound (49g).
1H?NMR(CDCl
3)δ：8.34(s，1H)，7.28(s，1H)，5.93(t，J＝4.4Hz，1H)，2.8(m，2H)，2.31(s，3H)，2.10(s，3H)，2.18-1.77(m，4H).
Step C: preparation 8-chloro-5,6,7,8-tetrahydrochysene-3-methylquinoline
5,6,7, and 8-tetrahydrochysene-3-methyl-8-quinolyl acetic acid esters (49g, 195mmol) and K
2CO
3(100g) solution in methyl alcohol (250mL) stirs under room temperature and spends the night.Mixture distributes between water and carrene.The organic extract drying (sodium sulphate) that merges concentrates then.Residue obtains bright brown grease (24g) passing through the pure system of flash chromatography (using the solution of 10% to 60% ethyl acetate in hexane as the gradient elution agent) on the silica gel.
Under 0 ℃ methane sulfonyl chloride (25.6g) is being added in above-mentioned grease (24g) and the solution of triethylamine in carrene (150mL) lentamente.Reactant mixture slowly is warmed to room temperature, adds hot reflux then and spends the night.Mixture is cooled to room temperature, and between water and carrene, distributes.The organic extract drying (sodium sulphate) that merges concentrates then.Residue is passing through the pure system of flash chromatography (using the solution of 10% to 60% ethyl acetate in hexane as the gradient elution agent) on the silica gel, obtain the title compound (21.8g) of glassy yellow oily.
1H?NMR(CDCl
3)δ：8.31(s，1H)，7.24(s，1H)，5.29(t，J＝3.0Hz，1H)，2.81(m，1H)，2.37(m，1H)，2.30(s，3H)，2.19(m，2H)，1.88(m，1H)。
Step D: preparation 5,6,7,8-tetrahydrochysene-3-methyl-8-quinolinamine
With 8-chloro-5,6,7, the suspension of 8-tetrahydrochysene-3-methylquinoline (21.8g) and sodium azide (15.6g) be heated to 70 ℃ totally 4 hours.Reactant mixture is cooled to room temperature, distributes between water and ether.The organic extract drying (sodium sulphate) that merges concentrates then.Residue (17.2g) is dissolved in the methyl alcohol (170mL), adds palladium/charcoal (1.73g) of 10 weight % then.Mixture is depressed with the H2 of hydrogen at room temperature, 276kPa (40psi), handles 4 hours in Parr jolting machine.The gained mixture filters by the Celiet_ bed.(2 * 10mL) wash Celite_/charcoal bed with methyl alcohol.Filtrate is carried out vacuum concentration, obtains the title compound of (13g).
1H?NMR(CDCl
3)δ：8.32(s，1H)，7.27(s，1H)，4.69(t，J＝4.1Hz，1H)，2.75(m，2H)，2.31(s，3H)，2.01-1.78(m，4H).
Step e: preparation 2,6-two chloro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinoline
The quinoline base) benzamide
5,6,7,8-tetrahydrochysene-3-methyl-8-quinolinamine (162mg, 1mmol), 2,6-dichlorobenzoyl chloride (209.5mg, 1mmol) and be carried on diisopropyl ethyl amine on the polymer (1.0g, 3mmol/g) jolting under room temperature of the suspension in acetonitrile (5mL) is spent the night.Reactant mixture filters, and (2 * 2mL) wash solid with acetonitrile.Filtrate concentrates, and the gained residue obtains title compound carrying out pure system (using the solution of 10% to 60% ethyl acetate in hexane as the gradient elution agent) by flash chromatography on the silica gel, promptly, compound of the present invention (190mg).
1H?NMR(CDCl
3)δ：8.22(s，1H)，7.30(s，1H)，7.36-7.23(m，3H)，6.99(bs，1H)，5.03(m，1H)，2.82(m，3H)，2.29(s，3H)，1.94(m，3H).
By method described above and method known to those skilled in the art, can prepare the compound of showing 1-8.Used abbreviation has following implication in the table: " Me " represent methylidene, and " OMe " representation methoxy, " SMe " represent methylidene sulfenyl, " CN " represents cyano group, " NO
2" represent nitro, " S (O) Me " represent methylidene sulfinyl, and " S (O)
2Me " represent methylidene sulfonyl.The R that substituting group M and R equal independently at institute cursor position place
5Substituting group.The R that substituting group T, U and V equal independently at institute cursor position place
6Substituting group.
Table 1
| ??T?????U???V | ??T???U?????V | ??T?????U???V | ??T?????U?????V |
| ??Me????Me??Me ??Me????Me??F ??Me????Me??Cl ??Me????Me??Br ??Me????Me??CF 3??Me????Me??NO 2??Me????Me??OMe | ??F???Me????Me ??F???Me????F ??F???Me????Cl ??F???Me????Br ??F???Me????CF 3??F???Me????NO 2??F???Me????OMe | ??F?????F???Me ??F?????F???F ??F?????F???Cl ??F?????F???Br ??F?????F???CF 3??F?????F???NO 2??F?????F???OMe | ??CF 3???Me???Me ??CF 3???Me???F ??CF 3???Me???Cl ??CF 3???Me???Br ??CF 3???Me???CF 3??CF 3???Me???NO 2??CF 3???Me???OMe |
| T?????U???????V | T????U???????V | ?T????U???????V | ?T??????U???????V |
| Me????F???????Me Me????F???????F Me????F???????Cl Me????F???????Br Me????F???????CF 3Me????F???????NO 2Me????F???????OMe Me????Cl??????Me Me????Cl??????F Me????Cl??????Cl Me????Cl??????Br Me????Cl??????CF 3Me????Cl??????NO 2Me????Cl??????OMe Me????Br??????Me Me????Br??????F Me????Br??????Cl Me????Br??????Br Me????Br??????CF 3Me????Br??????NO 2Me????Br??????OMe Me????CF 3????Me Me????CF 3????F Me????CF 3????Cl Me????CF 3????Br Me????CF 3????CF 3Me????CF 3????NO 2Me????CF 3????OMe Me????NO 2????Me Me????NO 2????F Me????NO 2????Cl Me????NO 2????Br Me????NO 2????Cf 3Me????NO 2????NO 2Me????NO 2????OMe Me????OMe?????Me Me????OMe?????F | Cl????Me?????Me Cl????Me?????F Cl????Me?????Cl Cl????Me?????Br Cl????Me?????CF 3Cl????Me?????NO 2Cl????Me?????OMe F?????Cl?????Me F?????Cl?????F F?????Cl?????Cl F?????Cl?????Br F?????Cl?????CF 3F?????Cl?????NO 2F?????Cl?????OMe Cl????Cl?????Me Cl????Cl?????F Cl????Cl?????Cl Cl????Cl?????Br Cl????Cl?????CF 3Cl????Cl?????NO 2Cl????Cl?????OMe F?????CF 3???Me F?????CF 3???F F?????CF 3???Cl F?????CF 3???Br F?????CF 3???CF 3F?????CF 3???NO 2F?????CF 3???OMe Cl????CF 3???Me Cl????CF 3???F Cl????CF 3???Cl Cl????CF 3???Br Cl????CF 3???CF 3Cl????CF 3???NO 2Cl????CF 3???OMe F?????OMe????Me F?????OMe????F | Cl????F??????Me Cl????F??????F Cl????F??????Cl Cl????F??????Br Cl????F??????CF 3Cl????F??????NO 2Cl????F??????OMe F?????Br?????Me F?????Br?????F F?????Br?????Cl F?????Br?????Br F?????Br?????CF 3F?????Br?????NO 2F?????Br?????OMe Cl????Br?????Me Cl????Br?????F Cl????Br?????Cl Cl????Br?????Br Cl????Br?????CF 3Cl????Br?????NO 2Cl????Br?????OMe F?????NO 2???Me F?????NO 2???F F?????NO 2???Cl F?????NO 2???Br F?????NO 2???CF 3F?????NO 2???NO 2F?????NO 2???OMe Cl????NO 2???Me Cl????NO 2???F Cl????NO 2???Cl Cl????NO 2???Br Cl????NO 2???CF 3Cl????NO 2???NO 2Cl????NO 2???OM 2F?????H??????Me F?????H??????F | NO 2?????Me?????Me NO 2?????Me?????F NO 2?????Me?????Cl NO 2?????Me?????Br NO 2?????Me?????CF 3NO 2?????Me?????NO 2NO 2?????Me?????OMe CF 3?????F??????Me CF 3?????F??????F CF 3?????F??????Cl CF 3?????F??????Br CF 3?????F??????CF 3CF 3?????F??????NO 2CF 3?????F??????OMe NO 2?????F??????Me NO 2?????F??????F NO 2?????F??????Cl NO 2?????F??????Br NO 2?????F??????CF 3NO 2?????F??????NO 2NO 2?????F??????OMe CF 3?????Cl?????Me CF 3?????Cl?????F CF 3?????Cl?????Cl CF 3?????Cl?????Br CF 3?????Cl?????CF 3CF 3?????Cl?????NO 2CF 3?????Cl?????OMe NO 2?????Cl?????Me NO 2?????Cl?????F NO 2?????Cl?????Cl NO 2?????Cl?????Br NO 2?????Cl?????CF 3NO 2?????Cl?????NO 2NO 2?????Cl?????OMe CF 3?????Br?????Me CF 3?????Br?????F |
| ?T????????U????????V | T????U??????V | T?????U?????V | T??????U???????V |
| Me????????OMe??????Cl Me????????OMe??????Br Me????????OMe??????CF 3Me????????OMe??????NO 2Me????????OMe??????OMe Me????????H????????Me Me????????H????????F Me????????H????????Cl Me????????H????????Br Me????????H????????CF 3Me????????H????????NO 2Me????????H????????OMe OMe???????Me???????Me OMe???????Me???????F OMe???????Me???????Cl OMe???????Me???????Br OMe???????Me???????CF 3OMe???????Me???????NO 2OMe???????Me???????OMe OMe???????F????????Me OMe???????F????????F OMe???????F????????Cl OMe???????F????????Br OMe???????F????????CF 3OMe???????F????????NO 2OMe???????F????????OMe OMe???????Cl???????Me OMe???????Cl???????F OMe???????Cl???????Cl OMe???????Cl???????Br OMe???????Cl???????CF 3OMe???????Cl???????NO 2OMe???????Cl???????OMe OMe???????H????????Me OMe???????H????????F OMe???????H????????Cl OMe???????H????????OMe | F????OMe????Cl F????OMe????Br F????OMe????CF 3F????OMe????NO 2F????OMe????OMe Cl???OMe????Me Cl???OMe????F Cl???OMe????Cl Cl???OMe????Br Cl???OMe????CF 3Cl???OMe????NO 2Cl???OMe????OMe Br???Me?????Me Br???Me?????F Br???Me?????Cl Br???Me?????Br Br???Me?????CF 3Br???Me?????NO 2Br???Me?????OMe Br???Cl?????Me Br???Cl?????F Br???Cl?????Cl Br???Cl?????Br Br???Cl?????CF 3Br???Cl?????NO 2Br???Cl?????OMe Br???CF 3???Me Br???CF 3???F Br???CF 3???Cl Br???CF 3???Br Br???CF 3???CF 3Br???CF 3???NO 2Br???CF 3???OMe Br???OMe????Me Br???OMe????F Br???OMe????Cl Br???OMe????Br | F?????H?????Cl F?????H?????Br F?????H?????CF 3F?????H?????NO 2F?????H?????OMe Cl????H?????Me Cl????H?????F Cl????H?????Cl Cl????H?????Br Cl????H?????CF 3Cl????H?????NO 2Cl????H?????OMe Br????F?????Me Br????F?????F Br????F?????Cl Br????F?????Br Br????F?????CF 3Br????F?????NO 2Br????F?????OMe Br????Br????Me Br????Br????F Br????Br????Cl Br????Br????Br Br????Br????CF 3Br????Br????NO 2Br????Br????OMe Br????NO 2??Me Br????NO 2??F Br????NO 2??Cl Br????NO 2??Br Br????NO 2??CF 3Br????NO 2??NO 2Br????NO 2??OMe Br????H?????Me Br????H?????F Br????H?????Cl Br????H?????Br | CF 3????Br?????Cl CF 3????Br?????Br CF 3????Br?????CF 3CF 3????Br?????NO 2CF 3????Br?????OMe NO 2????Br?????Me NO 2????Br?????F NO 2????Br?????Cl NO 2????Br?????Br NO 2????Br?????CF 3NO 2????Br?????NO 2NO 2????Br?????OMe CF 3????CF 3???Me CF 3????CF 3???F CF 3????CF 3???Cl CF 3????CF 3???Br CF 3????CF 3???CF 3CF 3????CF 3???NO 2CF 3????CF 3???OMe NO 2????CF 3???Me NO 2????CF 3???F NO 2????CF 3???Cl NO 2????CF 3???Br NO 2????CF 3???CF 3NO 2????CF 3???NO 2NO 2????CF 3???OMe CF 3????NO 2???Me CF 3????NO 2???F CF 3????NO 2???Cl CF 3????NO 2???Br CF 3????NO 2???CF 3CF 3????NO 2???NO 2CF 3????NO 2???OMe NO 2????NO 2???Me NO 2????NO 2???F NO 2????NO 2???Cl NO 2????NO 2???Br |
| T???????U??????V | T??????U??????V | T????????U??????V | T??????U???????V |
| OMe?????OMe????CF 3OMe?????OMe????NO 2OMe?????OMe????OMe OMe?????Br?????Me OMe?????Br?????F OMe?????Br?????Cl OMe?????Br?????Br OMe?????Br?????CF 3OMe?????Br?????NO 2OMe?????Br?????OMe OMe?????H??????Br OMe?????H??????CF 3OMe?????H??????NO 2OMe?????OMe????Me OMe?????OMe????F OMe?????OMe????Cl OMe?????OMe????Br | Br?????OMe????CF 3Br?????OMe????NO 2Br?????OMe????OMe OMe????CF 3???Me OMe????CF 3???F OMe????CF 3???Cl OMe????CF 3???Br OMe????CF 3???CF 3OMe????CF 3???NO 2OMe????CF 3???OMe OMe????NO 2???Me OMe????NO 2???F OMe????NO 2???Cl OMe????NO 2???Br OMe????NO 2???CF 3OMe????NO 2???NO 2OMe????NO 2???OMe | Br????????H?????CF 3Br????????H?????NO 2Br????????H?????OMe CF 3??????H?????Me CF 3??????H?????F CF 3??????H?????Cl CF 3??????H?????Br CF 3??????H?????CF 3CF 3??????H?????NO 2CF 3??????H?????OMe NO 2??????H?????Me NO 2??????H?????F NO 2??????H?????Cl NO 2??????H?????Br NO 2??????H?????CF 3NO 2??????H?????NO 2NO 2??????H?????OMe | NO 2????NO 2??CF 3NO 2????NO 2??NO 2NO 2????NO 2??OMe CF 3????OMe????Me CF 3????OMe????F CF 3????OMe????Cl CF 3????OMe????Br CF 3????OMe????CF 3CF 3????OMe????NO 2CF 3????OMe????OMe NO 2????OMe????Me NO 2????OMe????F NO 2????OMe????Cl NO 2????OMe????Br NO 2????OMe????CF 3NO 2????OMe????NO 2NO 2????OMe????OMe |
Table 2
| T??????U?????V | T????U????V | T??????U?????V | T?????U?????V |
| Me?????Me????Me Me?????Me????F Me?????Me????Cl Me?????Me????Br Me?????Me????CF 3Me?????Me????NO 2Me?????Me????OMe Me?????F?????Me Me?????F?????F Me?????F?????Cl | F????Me???Me F????Me???F F????Me???Cl F????Me???Br F????Me???CF 3F????Me???NO 2F????Me???OMe Cl???Me???Me Cl???Me???F Cl???Me???Cl | F??????F?????Me F??????F?????F F??????F?????Cl F??????F?????Br F??????F?????CF 3F??????F?????NO 2F??????F?????OMe Cl?????F?????Me Cl?????F?????F Cl?????F?????Cl | CF 3???Me???Me CF 3???Me????F CF 3???Me????Cl CF 3???Me????Br CF 3???Me????CF 3CF 3???Me????NO 2CF 3???Me????OMe NO 2???Me????Me NO 2???Me????F NO 2???Me????Cl |
| T???????U???????V | T???????U??????V | T???????U??????V | T??????U???????V |
| Me??????F????????Br Me??????F????????CF 3Me??????F????????NO 2Me??????F????????OMe Me??????Cl???????Me Me??????Cl???????F Me??????Cl???????Cl Me??????Cl???????Br Me??????Cl???????CF 3Me??????Cl???????NO 2Me??????Cl???????OMe Me??????Br???????Me Me??????Br???????F Me??????Br???????Cl Me??????Br???????Br Me??????Br???????CF 3Me??????Br???????NO 2Me??????Br???????OMe Me??????CF 3?????Me Me??????CF 3?????F Me??????CF 3?????Cl Me??????CF 3?????Br Me??????CF 3?????CF 3Me??????CF 3?????NO 2Me??????CF 3?????OMe Me??????NO 2?????Me Me??????NO 2?????F Me??????NO 2?????Cl Me??????NO 2?????Br Me??????NO 2?????CF 3Me??????NO 2?????NO 2Me??????NO 2?????NOe Me??????OMe??????Me Me??????OMe??????F Me??????OMe??????Cl Me??????OMe??????Br Me??????OMe??????CF 3 | Cl??????Me?????Br Cl??????Me??????CF 3Cl??????Me??????NO 2Cl??????Me??????OMe F???????Cl??????Me F???????Cl??????F F???????Cl??????Cl F???????Cl??????Br F???????Cl??????CF 3F???????Cl??????NO 2F???????Cl??????OMe Cl??????Cl??????Me Cl??????Cl??????F Cl??????Cl??????Cl Cl??????Cl??????Br Cl??????Cl??????CF 3Cl??????Cl??????NO 2Cl??????Cl??????OMe F???????CF 3????Me F???????CF 3????F F???????CF 3????Cl F???????CF 3????Br F???????CF 3????CF 3F???????CF 3????NO 2F???????CF 3????CF 3Cl??????CF 3????Me Cl??????CF 3????F Cl??????CF 3????Cl Cl??????CF 3????Br Cl??????CF 3????CF 3Cl??????CF 3????NO 2Cl??????CF 3????OMe F???????OMe?????Me F???????OMe?????F F???????OMe?????Cl F???????OMe?????Br F???????OMe?????CF 3 | Cl??????F???????Br Cl??????F???????CF 3Cl??????F???????NO 2Cl??????F???????OMe F???????Br??????Me F???????Br??????F F???????Br??????Cl F???????Br??????Br F???????Br??????CF 3F???????Br??????NO 2F???????Br??????OMe Cl??????Br??????Me Cl??????Br??????F Cl??????Br??????Cl Cl??????Br??????Br Cl??????Br??????CF 3Cl??????Br??????NO 2Cl??????Br??????OMe F???????NO 2????Me F???????NO 2????F F???????NO 2????Cl F???????NO 2????Br F???????NO 2????CF 3F???????NO 2????NO 2F???????NO 2????OMe Cl??????NO 2????Me Cl??????NO 2????F Cl??????NO 2????Cl Cl??????NO 2????Br Cl??????NO 2????CF 3Cl??????NO 2????NO 2Cl??????NO 2????OMe F???????H???????Me F???????H???????F F???????H???????Cl F???????H???????Br F???????H???????CF 3 | NO 2????Me????Br NO 2????Me????CF 3NO 2????Me????NO 2NO 2????Me????OMe CF 3????F?????Me CF 3????F?????F CF 3????F?????Cl CF 3????F?????Br CF 3????F?????CF 3CF 3????F?????NO 2CF 3????F?????OMe NO 2????F?????Me NO 2????F?????F NO 2????F?????Cl NO 2????F?????Br NO 2????F?????CF 3NO 2????F?????NO 2NO 2????F?????OMe CF 3????Cl????Me CF 3????Cl????F CF 3????Cl????Cl CF 3????Cl????Br CF 3????Cl????CF 3CF 3????Cl????NO 2CF 3????Cl????OMe NO 2????Cl????Me NO 2????Cl????F NO 2????Cl????Cl NO 2????Cl????Br NO 2????Cl????CF 3NO 2????Cl????NO 2NO 2????Cl????OMe CF 3????Br????Me CF 3????Br????F CF 3????Br????Cl CF 3????Br????Br CF 3????Br????CF 3 |
| T??????U?????V | T??????U?????V | T???????U??????V | T??????U???????V |
| Me?????OMe???NO 2Me?????OMe???OMe Me?????H?????Me Me?????H?????F Me?????H?????Cl Me?????H?????Br Me?????H?????CF 3Me?????H?????NO 2Me?????H?????OMe OMe????Me????Me OMe????Me????F OMe????Me????Cl OMe????Me????Br OMe????Me????CF 3OMe????Me????NO 2OMe????Me????OMe OMe????F?????Me OMe????F?????F OMe????F?????Cl OMe????F?????Br OMe????F?????CF 3OMe????F?????NO 2OMe????F?????OMe OMe????Cl????Me OMe????Cl????F OMe????Cl????Cl OMe????Cl????Br OMe????Cl????CF 3OMe????Cl????NO 2OMe????Cl????OMe OMe????H?????Me OMe????H?????F OMe????H?????Cl OMe????H?????OMe OMe????OMe???CF 3 | F??????OMe???NO 2F??????OMe???OMe Cl?????OMe???Me Cl?????OMe???F Cl?????OMe???Cl Cl?????OMe???Br Cl?????OMe???CF 3Cl?????OMe???NO 2Cl?????OMe???OMe Br?????Me????Me Br?????Me????F Br?????Me????Cl Br?????Me????Br Br?????Me????CF 3Br?????Me????NO 2Br?????Me????OMO Br?????Cl????Me Br?????Cl????F Br?????Cl????Cl Br?????Cl????Br Br?????Cl????CF 3Br?????Cl????NO 2Br?????Cl????OMe Br?????CF 3??Me Br?????CF 3??F Br?????CF 3??Cl Br?????CF 3??Br Br?????CF 3??CF 3Br?????CF 3??NO 2Br?????CF 3??OMe Br?????OMe???Me Br?????OMe???F Br?????OMe???Cl Br?????OMe???Br Br?????OMe???CF 3 | F???????H??????NO 2F???????H??????Oe Cl??????H??????Me Cl??????H??????F Cl??????H??????Cl Cl??????H??????Br Cl??????H??????CF 3Cl??????H??????NO 2Cl??????H??????OMe Br??????F??????Me Br??????F??????F Br??????F??????Cl Br??????F??????Br Br??????F??????CF 3Br??????F??????NO 2Br??????F??????OMe Br??????Br?????Me Br??????Br?????F Br??????Br?????Cl Br??????Br?????Br Br??????Br?????CF 3Br??????Br?????NO 2Br??????Br?????OMe Br??????NO 2???Me Br??????NO 2???F Br??????NO 2???Cl Br??????NO 2???Br Br??????NO 2???CF 3Br??????NO 2???NO 2Br??????NO 2???OMe Br??????H??????Me Br??????H??????F Br??????H??????Cl Br??????H??????Br Br??????H??????CF3 | CF 3????Br?????NO 2CF 3????Br?????OMe NO 2????Br?????Me NO 2????Br?????F NO 2????Br?????Cl NO 2????Br?????Br NO 2????Br?????CF 3NO 2????Br?????NO 2NO 2????Br?????OMe CF 3????CF 3???Me CF 3????CF 3???F CF 3????CF 3???Cl CF 3????CF 3???Br CF 3????CF 3???CF 3CF 3????CF 3???NO 2CF 3????CF 3???OMe NO 2????CF 3???Me NO 2????CF 3???F NO 2????CF 3???Cl NO 2????CF 3???Br NO 2????CF 3???CF 3NO 2????CF 3???NO 2NO 2????CF 3???OMe CF 3????NO 2???Me CF 3????NO 2???F CF 3????NO 2???Cl CF 3????NO 2???Br CF 3????NO 2???CF 3CF 3????NO 2???NO 2CF 3????NO 2???OMe NO 2????NO 2???Me NO 2????NO 2???F NO 2????NO 2???Cl NO 2????NO 2???Br NO 2????NO 2???CF 3 |
| T???????U??????V | T???????U??????V | T???????U??????V | T?????U????????V |
| OMe?????OMe????NO 2OMe?????OMe????OMe OMe?????Br?????Me OMe?????Br?????F OMe?????Br?????Cl OMe?????Br?????Br OMe?????Br?????CF 3OMe?????Br?????NO 2OMe?????Br?????OMe OMe?????H??????Br OMe?????H??????CF 3OMe?????H??????NO 2OMe?????OMe????Me OMe?????OMe????F OMe?????OMe????Cl OMe?????OMe????Br | Br??????OMe?????NO 2Br??????OMe?????OMe OMe?????CF 3????me OMe?????CF 3????F OMe?????CF 3????Cl OMe?????CF 3????Br OMe?????CF 3????CF 3OMe?????CF 3????NO 2OMe?????CF 3????OMe OMe?????NO 2????Me OMe?????NC 2????F OMe?????NO 2????Cl CMe?????NO 2????Br OMe?????NO 2????CF 3OMe?????NO 2????NO 2OMe?????NO 2????OMe | Br???????H??????NO 2Br???????H??????OMe CF 3?????H??????Me CF 3?????H??????F CF 3?????H??????Cl CF 3?????H??????Br CF 3?????H??????CF 3CF 3?????H??????NO 2CF 3?????H??????OMe NO 2?????H??????Me NO 2?????H??????F NO 2?????H??????Cl NO 2?????H??????Br NO 2?????H??????CF 3NO 2?????H??????NO 2NO 2?????H??????OMe | NO 2??NO 2????NO 2NO 2???NO 2???OMe CF 3???OMe????Me CF 3???OMe????F CF 3???OMe????Cl CF 3???OMe????Br CF 3???OMe????CF 3CF 3???OMe????NO 2CF 3???OMe????OMe NO 2???OMe????Me NO 2???OMe????F NO 2???OM?????Cl NO 2???OMe????Br NO 2???OMe????CF 3NO 2???OMe????NO 2NO 2???OMe????OMe |
Table 3
| T??????U?????V | T?????U????V | T??????U?????V | T??????U???????V |
| Me?????Me????Me Me?????Me????F Me?????Me????Cl Me?????Me????Br Me?????Me????CF 3Me?????Me????NO 2Me?????Me????OMe Me?????F?????Me Me?????F?????F Me?????F?????Cl Me?????F?????Br Me?????F?????CF 3 | F???Me????Me F???Me????F F???Me????Cl F???Me????Br F???Me????CF 3F???Me????NO 2F???Me????OMe Cl??Me????Me Cl??Me????F Cl??Me????Cl Cl??Me????Br Cl??Me????CF 3 | F??????F?????Me F??????F?????F F??????F?????Cl F??????F?????Br F??????F?????CF 3F??????F?????NO 2F??????F?????OMe Cl?????F?????Me Cl?????F?????F Cl?????F?????Cl Cl?????F?????Br Cl?????F?????CF 3 | CF 3????Me????Me CF 3????Me????F CF 3????Me????Cl CF 3????Me????Br CF 3????Me????CF 3CF 3????Me????NO 2CF 3????Me????OMe NO 2????Me????Me NO 2????Me????F NO 2????Me????Cl NO 2????Me????Br NO 2????Me????CF 3 |
| T???????U??????V | T???????U??????V | T???????U??????V | T??????U????????V |
| Me??????F??????NO 2Me??????F??????OMe Me??????Cl?????Me Me??????Cl?????F Me??????Cl?????Cl Me??????Cl?????Br Me??????Cl?????CF 3Me??????Cl?????NO 2Me??????Cl?????OMe Me??????Br?????Me Me??????Br?????F Me??????Br?????Cl Me??????Br?????Br Me??????Br?????CF 3Me??????Br?????NO 2Me??????Br?????OMe Me??????CF 3???Me Me??????CF 3???F Me??????CF 3???Cl Me??????CF 3???Br Me??????CF 3???CF 3Me??????CF 3???NO 2Me??????Cf 3???OMe Me??????NO 2???Me Me??????NO 2???F Me??????NO 2???Cl Me??????NO 2???Br Me??????NO 2???CF 3Me??????NO 2???NO 2Me??????NO 2???OM 2Me??????OMe????Me Me??????OMe????F Me??????OMe????Cl Me??????OMe????Br Me??????OMe????CF 3Me??????OMe????NO 2Me??????OMe????OMe | Cl??????Me?????NO 2Cl??????Me?????OMe F???????Cl?????Me F???????Cl?????F F???????Cl?????Cl F???????Cl?????Br F???????Cl?????CF 3F???????Cl?????NO 2F???????Cl?????OMe Cl??????Cl?????Me Cl??????Cl?????F Cl??????Cl?????Cl Cl??????Cl?????Br Cl??????Cl?????CF 3Cl??????Cl?????NO 2Cl??????Cl?????OMe F???????CF 3???Me F???????CF 3???F F???????CF 3???Cl F???????CF 3???Br F???????CF 3???CF 3F???????CF 3???NO 2F???????CF 3???OMe Cl??????CF 3???Me Cl??????CF 3???F Cl??????CF 3???Cl Cl??????CF 3???Br Cl??????CF 3???CF 3Cl??????CF 3???NO 2Cl??????CF 3???OMe F???????OMe????Me F???????OMe????F F???????OMe????Cl F???????OMe????Br F???????OMe????CF 3F???????OMe????NO 2F???????OMe????OMe | Cl??????F??????NO 2Cl??????F??????OMe F???????Br?????Me F???????Br?????F F???????Br?????Cl F???????Br?????Br F???????Br?????CF 3F???????Br?????NO 2F???????Br?????OMe Cl??????Br?????Me Cl??????Br?????F Cl??????Br?????Cl Cl??????Br?????Br Cl??????Br?????CF 3Cl??????Br?????NO 2Cl??????Br?????OMe F???????NO 2???Me F???????NO 2???F F???????NO 2???Cl F???????NO 2???Br F???????NO 2???CF 3F???????NO 2???NO 2F???????NO 2???OMe Cl??????NO 2???Me Cl??????NO 2???F Cl??????NO 2???Cl Cl??????NO 2???Br Cl??????NO 2???CF 3Cl??????NO 2???NO 2Cl??????NO 2???OMe F???????H??????Me F???????H??????F F???????H??????Cl F???????H??????Br F???????H??????CF 3F???????H??????NO 2F???????H??????OMe | NO 2????Me?????NO 2NO 2????Me?????OMe CF 3????F??????Me CF 3????F??????F CF 3????F??????Cl CF 3????F??????Br CF 3????F??????CF 3CF 3????F??????NO 2CF 3????F??????OMe NO 2????F??????Me NO 2????F??????F NO 2????F??????Cl NO 2????F??????Br NO 2????F??????CF 3NO 2????F??????NO 2NO 2????F??????OMe CF 3????Cl?????Me CF 3????Cl?????F CF 3????Cl?????Cl CF 3????Cl?????Br CF 3????Cl?????CF 3CF 3????Cl?????NO 2CF 3????Cl?????OMe NO 2????Cl?????Me NO 2????Cl?????F NO 2????Cl?????Cl NO 2????Cl?????Br NO 2????Cl?????CF 3NO 2????Cl?????NO 2NO 2????Cl?????OMe CF 3????Br?????Me CF 3????Br?????F CF 3????Br?????Cl CF 3????Br?????Br CF 3????Br?????CF 3CF 3????Br?????NO 2CF 3????Br?????OMe |
| T??????U?????V | T???????U??????V | T??????U?????V | T??????U???????V |
| Me?????H?????Me Me?????H?????F Me?????H?????Cl Me?????H?????Br Me?????H?????CF 3Me?????H?????NO 2Me?????H?????OMe OMe????Me????Me OMe????Me????F OMe????Me????Cl OMe????Me????Br OMe????Me????CF 3OMe????Me????NO 2OMe????Me????OMe OMe????F?????Me OMe????F?????F OMe????F?????Cl OMe????F?????Br OMe????F?????CF 3OMe????F?????NO 2OMe????F?????OMe OMe????Cl????Me OMe????Cl????F OMe????Cl????Cl OMe????Cl????Br OMe????Cl????CF 3OMe????Cl????NO 2OMe????Cl????OMe OMe????H?????Me OMe????H?????F OMe????H?????Cl OMe????H?????OMe OMe????OMe???CF 3OMe????OMe???NO 2OMe????OMe???OMe OMe????Br????Me OMe????Br????F | Cl??????OMe????Me Cl??????OMe????F Cl??????OMe????Cl Cl??????OMe????Br Cl??????OMe????CF 3Cl??????OMe????NO 2Cl??????OMe????OMe Br??????Me?????Me Br??????Me?????F Br??????Me?????Cl Br??????Me?????Br Br??????Me?????CF 3Br??????Me?????NO 2Br??????Me?????OMe Br??????Cl?????Me Br??????Cl?????F Br??????Cl?????Cl Br??????Cl?????Br Br??????Cl?????CF 3Br??????Cl?????NO 2Br??????Cl?????OMe Br??????CF 3???Me Br??????CF 3???F Br??????CF 3???Cl Br??????CF 3???Br Br??????CF 3???CF 3Br??????CF 3???NO 2Br??????CF 3???OMe Br??????OMe????Me Br??????OMe????F Br??????OMe????Cl Br??????OMe????Br Br??????OMe????CF 3Br??????OMe????NO 2Br??????OMe????OMe OMe?????CF 3???Me OMe?????CF 3???F | Cl?????H?????Me Cl?????H?????F Cl?????H?????Cl Cl?????H?????Br Cl?????H?????CF 3Cl?????H?????NO 2Cl?????H?????OMe Br?????F?????Me Br?????F?????F Br?????F?????Cl Br?????F?????Br Br?????F?????CF 3Br?????F?????NO 2Br?????F?????OMe Br?????Br????Me Br?????Br????F Br?????Br????Cl Br?????Br????Br Br?????Br????CF 3Br?????Br????NO 2Br?????Br????OMe Br?????NO 2??Me Br?????NO 2??F Br?????NO 2??Cl Br?????NO 2??Br Br?????NO 2??CF 3Br?????NO 2??NO 2Br?????NO 2??OMe Br?????H?????Me Br?????H?????F Br?????H?????Cl Br?????H?????Br Br?????H?????CF 3Br?????H?????NO 2Br?????H?????OMe CF 3???H?????Me CF 3???H?????F | NO 2????Br????Me NO 2????Br?????F NO 2????Br?????Cl NO 2????Br?????Br NO 2????Br?????CF 3NO 2????Br?????NO 2NO 2????Br?????OMe CF 3????CF 3???Me CF 3????CF 3???F CF 3????CF 3???Cl CF 3????CF 3???Br CF 3????CF 3???CF 3CF 3????CF 3???NO 2CF 3????CF 3???OMe NO 2????CF 3???Me NO 2????CF 3???F NO 2????CF 3???Cl NO 2????CF 3???Br NO 2????CF 3???CF 3NO 2????CF 3???NO 2NO 2????CF 3???OMe CF 3????NO 2???Me CF 3????NO 2???F CF 3????NO 2???Cl CF 3????NO 2???Br CF 3????NO 2???CF 3CF 3????NO 2???NO 2CF 3????NO 2???OMe NO 2????NO 2???Me NO 2????NO 2???F NO 2????NO 2???Cl NO 2????NO 2???Br NO 2????NO 2???CF 3NO 2????NO 2???NO 2NO 2????NO 2???OMe CF 3????OMe???Me CF 3????OMe???F |
| T??????U?????V | T??????U??????V | T??????U??????V | T??????U???????V |
| OMe????Br????Cl OMe????Br????Br OMe????Br????CF 3OMe????Br????NO 2OMe????Br????OMe OMe????H?????Br OMe????H?????CF 3OMe????H?????NO 2OMe????OMe???Me OMe????OMe???F OMe????OMe???Cl OMe????OMe???Br | OMe????CF 3???Cl OMe????CF 3???Br OMe????CF 3???CF 3OMe????CF 3???NO 2OMe????CF 3???OMe OMe????NO 2???Me OMe????NO 2???F OMe????NO 2???Cl OMe????NO 2???Br OMe????NO 2???CF 3OMe????NO 2???NO 2OMe????NO 2???OMe | CF 3????H?????Cl CF 3????H?????Br CF 3????H?????CF 3CF 3????H?????NO 2CF 3????H?????OMe NO 2????H?????Me NO 2????H?????F NO 2????H?????Cl NO 2????H?????Br NO 2????H?????CF 3NO 2????H?????NO 2NO 2????H?????OMe | CF 3????OMe???Cl CF 3????OMe???Br CF 3????OMe???CF 3CF 3????OMe???NO 2CF 3????OMe???OMe NO 2????OMe???Me NO 2????OMe???F NO 2????OMe???Cl NO 2????OMe???Br NO 2????OMe???CF 3NO 2????OMe???NO 2NO 2????OMe???OMe |
Table 4
| T??????U?????V | T????U?????V | T??????U?????V | T?????U??????V |
| Me?????Me????Me Me?????Me????F Me?????Me????Cl Me?????Me????Br Me?????Me????CF 3Me?????Me????NO 2Me?????Me????OMe Me?????F?????Me Me?????F?????F Me?????F?????Cl Me?????F?????Br Me?????F?????CF 3Me?????F?????NO 2Me?????F?????OMe Me?????Cl????Me Me?????Cl????F | F????Me????Me F????Me????F F????Me????Dl F????Me????Br F????Me????CF 3F????Me????NO 2F????Me????OMe Cl???Me????Me Cl???Me????F Cl???Me????Cl Cl???Me????Br Cl???Me????CF 3Cl???Me????NO 2Cl???Me????OMe F????CL????Me F????Cl????F | F??????F?????Me F??????F?????F F??????F?????Cl F??????F?????Br F??????F?????CF 3F??????F?????NO 2F??????F?????OMe Cl?????F?????Me Cl?????F?????F Cl?????F?????Cl Cl?????F?????Br Cl?????F?????CF 3Cl?????F?????NO 2Cl?????F?????OMe F??????Br????Me F??????Br????F | CF 3???Me???Me CF 3???Me???F CF 3???Me???Cl CF 3???Me???Br CF 3???Me???CF 3CF 3???Me???NO 2CF 3???Me???OMe NO 2???Me???Me NO 2???Me???F NO 2???Me???Cl NO 2???Me???Br NO 2???Me???CF 3NO 2???Me???NO 2NO 2???Me???OMe CF 3???F????Me CF 3???F????F |
| T???????U?????V | T??????U??????V | T???????U?????V | T??????U??????V |
| Me?????Cl?????Cl Me?????Cl?????Br Me?????Cl?????CF 3Me?????Cl?????NO 2Me?????Cl?????OMe Me?????Br?????Me Me?????Br?????F Me?????Br?????Cl Me?????Br?????Br Me?????Br?????CF 3Me?????Br?????NO 2Me?????Br?????OMe Me?????CF 3???Me Me?????CF 3???F Me?????CF 3???Cl Me?????CF 3???Br Me?????CF 3???CF 3Me?????CF 3???NO 2Me?????CF 3???OMe Me?????NO 2???Me Me?????NO 2???F Me?????NO 2???Cl Me?????NO 2???Br Me?????NO 2???CF 3Me?????NO 2???NO 2Me?????NO 2???OMe Me?????OMe????Me Me?????OMe????F Me?????OMe????Cl Me?????OMe????Br Me?????OMe????CF 3Me?????OMe????NO 2Me?????OMe????OMe Me?????H??????Me Me?????H??????F Me?????H??????Cl Me?????H??????Br | F??????Cl?????Cl F??????Cl?????Br F??????Cl?????CF 3F??????Cl?????NO 2F??????Cl?????OMe Cl?????Cl?????Me Cl?????Cl?????F Cl?????Cl?????Cl Cl?????Cl?????Br Cl?????Cl?????CF 3Cl?????Cl?????NO 2Cl?????Cl?????OMe F??????CF 3???Me F??????CF 3???F F??????CF 3???Cl F??????CF 3???Br F??????CF 3???CF 3F??????CF 3???NO 2F??????CF 3???OMe Cl?????CF 3???Me Cl?????CF 3???F Cl?????CF 3???Cl Cl?????CF 3???Br Cl?????CF 3???CF 3Cl?????CF 3???NO 2Cl?????CF 3???OMe F??????OMe????Me F??????OMe????F F??????OMe????Cl F??????OMe????Br F??????OMe????CF 3F??????OMe????NO 2F??????OMe????OMe Cl?????OMe????Me Cl?????OMe????F Cl?????OMe????Cl Cl?????OMe????Br | F???????Br????Cl F???????Br????Br F???????Br????CF 3F???????Br????NO 2F???????Br????OMe Cl??????Br????Me Cl??????Br????F Cl??????Br????Dl Cl??????Br????Br Cl??????Br????CF 3Cl??????Br????NO 2Cl??????Br????OMe F???????NO 2??Me F???????NO 2??F F???????NO 2??Cl F???????NO 2??Br F???????NO 2??CF 3F???????NO 2??NO 2F???????NO 2??OMe Cl??????NO 2??Me Cl??????NO 2??F Cl??????NO 2??Cl Cl??????NO 2??Br Cl??????NO 2??CF 3Cl??????NO 2??NO 2Cl??????NO 2??OMe F???????H?????Me F???????H?????F F???????H?????Cl F???????H?????Br F???????H?????CF 3F???????H?????NO 2F???????H?????OMe Cl??????H?????Me Cl??????H?????F Cl??????H?????Cl Cl??????H?????Br | CF 3????F????Cl CF 3????F????Br CF 3????F????CF 3CF 3????F????NO 2CF 3????F????OMe NO 2????F????Me NO 2????F????F NO 2????F????Cl NO 2????F????Br NO 2????F????CF 3NO 2????F????NO 2NO 2????F????OMe CF 3????Cl???Me CF 3????Cl???F CF 3????Cl???Cl CF 3????Cl???Br CF 3????Cl???CF 3CF 3????Cl???NO 2CF 3????Cl???OMe NO 2????Cl???Me NO 2????Cl???F NO 2????Cl???Cl NO 2????Cl???Br NO 2????Cl???CF 3NO 2????Cl???NO 2NO 2????Cl???OMe CF 3????Br???Me CF 3????Br???F CF 3????Br???Cl CF 3????Br???Br CF 3????Br???CF 3CF 3????Br???NO 2CF 3????Br???OMe NO 2????Br???Me NO 2????Br???F NO 2????Br???Cl NO 2????Br???Br |
| T???????U???????V | T???????U?????V | ?T?????U????V | ?T?????U??????V |
| Me??????H???????CF 3Me??????H???????NO 2Me??????H???????OMe OMe?????Me??????Me OMe?????Me??????F OMe?????Me??????Cl OMe?????Me??????Br OMe?????Me??????CF 3OMe?????Me??????NO 2OMe?????Me??????OMe OMe?????F???????Me OMe?????F???????F OMe?????F???????Cl OMe?????F???????Br OMe?????F???????CF 3OMe?????F???????NO 2OMe?????F???????OMe OMe?????Cl??????Me OMe?????Cl??????F OMe?????Cl??????Dl OMe?????Cl??????Br OMe?????Cl??????CF 3OMe?????Cl??????NO 2OMe?????Cl??????OMe OMe?????H???????Me OMe?????H???????F OMe?????H???????Cl OMe?????H???????OMe OMe?????OMe?????CF 3OMe?????OMe?????NO 2OMe?????OMe?????OMe OMe?????Br??????Me OMe?????Br??????F OMe?????Br??????Cl OMe?????Br??????Br OMe?????Br??????CF 3OMe?????Br??????NO | Cl??????OMe???CF 3Cl??????OMe???NO 2Cl??????OMe???OMe Br??????Me????Me Br??????Me????F Br??????Me????Cl Br??????Me????Br Br??????Me????Me Br??????Me????NO 2Br??????Me????OMe Br??????Cl????Me Br??????Cl????F Br??????Cl????Cl Br??????Cl????Br Br??????Cl????CF 3Br??????Cl????NO 2Br??????Cl????OMe Br??????CF 3??Me Br??????CF 3??F Br??????CF 3??Cl Br??????CF 3??Br Br??????CF 3??CF 3Br??????CF 3??NO 2Br??????CF 3??OMe Br??????OMe???Me Br??????OMe???F Br??????OMe???Cl Br??????OMe???Br Br??????OMe???CF 3Br??????OMe???NO 2Br??????OMe???OMe OMe?????CF 3??Me OMe?????CF 3??F OME?????CF 3??Cl OMe?????CF 3??Br OMe?????CF 3??CF 3OMe?????CF 3??NO 2 | Cl?????H????CF 3Cl?????H????NO 2Cl?????H????OMe Br?????F????Me Br?????F????F Br?????F????Cl Br?????F????Br Br?????F????CF 3Br?????F????NO 2Br?????F????OMe Br?????Br???Me Br?????Br???F Br?????Br???Cl Br?????Br???Br Br?????Br???CF 3Br?????Br???NO 2Br?????Br???OMe Br?????NO 2?Me Br?????NO 2?F Br?????NO 2?Cl Br?????NO 2?Br Br?????NO 2?CF 3Br?????NO 2?NO 2Br?????NO 2?OMe Br?????H????Me Br?????H????F Br?????H????Cl Br?????H????Br Br?????H????CF 3Br?????H????NO 2Br?????H????OMe CF 3???H????Me CF 3???H????F CF 3???H????Cl CF 3???H????Br CF 3???H????CF 3CF 3???H????NO 2 | NO 2????Br????CF 3NO 2????Br????NO 2NO 2????Br????OMe CF 3????CF 3??Me CF 3????CF 3??F CF 3????CF 3??Cl CF 3????CF 3??Br CF 3????CF 3??CF 3CF 3????CF 3??NO 2CF 3????CF 3??OM eNO 2????CF 3??CF 3NO 2????CF 3??F NO 2????CF 3??Cl NO 2????CF 3??Br NO 2????CF 3??CF 3NO 2????CF 3??NO 2NO 2????CF 3??OMe CF 3????NO 2??Me CF 3????NO 2??F CF 3????NO 2??Cl CF 3????NO 2??Br CF 3????NO 2??CF 3CF 3????NO 2??NO 2CF 3????NO 2??OMe NO 2????NO 2??Me NO 2????NO 2??F NO 2????NO 2??Cl NO 2????NO 2??Br NO 2????NO 2??CF 3NO 2????NO 2??NO 2NO 2????NO 2??OMe CF 3????OME????Me CF 3????OMe????F CF 3????OMe????Cl CF 3????OME????Br CF 3????OMe????CF 3CF 3????OMe????NO 2 |
| T???????U?????V | T???????U???????V | T?????U???????V | T??????U??????V |
| OMe?????Br????OMe OMe?????H?????Br OMe?????H?????CF 3OMe?????H?????NO 2OMe?????OMe???Me OMe?????OMe???F OMe?????OMe???Cl OMe?????OMe???Br | OMe?????CF 3???OMe OMe?????NO 2???Me OMe?????NO 2???F OMe?????NO 2???Cl OMe?????NO 2???Br OMe?????NO 2???CF 3OMe?????NO 2???NO 2OMe?????NO 2???OMe | CF 3???H?????OMe NO 2???H?????Me NO 2???H?????F NO 2???H?????Cl NO 2???H?????Br NO 2???H?????CF 3NO 2???H?????NO 2NO 2???H?????OMe | CF 3????OMe??OMe NO 2????OMe??Me NO 2????OMe??F NO 2????OMe??Cl NO 2????OME??Br NO 2????OMe??CF 3NO 2????OMe??NO 2NO 2????OMe??OMe |
Table 5
T and V are Cl, and U is H
| ????J?????????????R?????????????M | ????J????????????R?????????????M |
| CH 2CH 2CH 2?????Cl????????????H CH 2CH 2H 2??????Br????????????H CH 2CH 2H 2??????OCF 3?????????H CH 2CH 2CH 2?????OCHF 2????????H CH 2CH 2CH 2?????OCH 2CF 3?????H CH 2CH 2CH 2?????OCF 2CF 3?????H CH 2CH 2CH 2?????OCF 2CF 2H????H CH 2CH 2CH 2?????OCHFCF 3??????H CH 2CH 2CH 2?????SCF 3?????????H CH 2CH 2CH 2?????SCHF 2????????H CH 2CH 2CH 2?????SCH 2CF 3?????H CH 2CH 2CH 2?????SCF 2CF 3?????H CH 2CH 2CH 2?????SCF 2CF 2H????H CH 2CH 2CH 2?????SCHFCF 3??????H CH 2CH 2CH 2?????SOCF 3????????H CH 2CH 2CH 2?????SOCHF 2???????H CH 2CH 2CH 2?????SOCH 2CF 3????H CH 2CH 2CH 2?????SOCF 2CF 3????H CH 2CH 2CH 2?????SOCF 2CF 2H???H | CH 2CH 2CH 2?????Cl??????????Me CH 2CH 2CH 2?????Br??????????Me CH 2CH 2CH 2?????OCF 3???????Me CH 2CH 2CH 2?????OCHF 2??????Me CH 2CH 2CH 2?????OCH 2CF 3???Me CH 2CH 2CH 2?????OCF 2CF 3???Me CH 2CH 2CH 2?????OCF 2CF 2H??Me CH 2CH 2CH 2?????OCHFCF 3????Me CH 2CH 2CH 2?????SCF 3???????Me CH 2CH 2CH 2?????SCHF 2??????Me CH 2CH 2CH 2?????SCH 2CF 3???Me CH 2CH 2CH 2?????SCF 2CF 3???Me CH 2CH 2CH 2?????SCF 2CF 2H??Me CH 2CH 2CH 2?????SCHFCF 3????Me CH 2CH 2CH 2?????SOCF 3??????Me CH 2CH 2CH 2?????SOCHF 2?????Me CH 2CH 2CH 2?????SOCF 2CF 3??Me CH 2CH 2CH 2?????SOCF 2CF 3??Me CH 2CH 2CH 2?????SOCF 2CF 2H?Me |
T and V are Cl, and U is H
| ????J???????????????R?????????????M | ????J???????????????R???????????????M |
| CH 2CH 2CH 2??SOCHFCF 3?????????H CH 2CH 2CH 2??SO 2CF 3??????????H CH 2CH 2CH 2??SO 2CHF 2?????????H CH 2CH 2CH 2??SO 2CH 2CF 3??????H CH 2CH 2CH 2??SO 2CF 2CF 3??????H CH 2CH 2CH 2??SO 2CF 2CF 2H?????H CH 2CH 2CH 2??SO 2CHFCF 3???????H CH 2CH 2CH 2??CN?????????????????H CH 2CH 2CH 2??SMe????????????????H CH 2CH 2CH 2??S(O)Me?????????????H CH 2CH 2CH 2??S(O) 2Me???????????H CH 2CH 2CH 2??NO 2???????????????H CH 2CH 2??????Cl??????????????????H CH 2CH 2??????Br??????????????????H CH 2CH 2??????OCF 3???????????????H CH 2CH 2??????OCHF 2??????????????H CH 2CH 2??????OCH 2CF 3???????????H CH 2CH 2??????OCF 2CF 3???????????H CH 2CH 2??????OCF 2CF 2H??????????H CH 2CH 2??????OCHFCF 3????????????H CH 2CH 2??????SCF 3???????????????H CH 2CH 2??????SCHF 2??????????????H CH 2CH 2??????SCH 2CF 3??????????H CH 2CH 2??????SCF 2CF 3??????????H CH 2CH 2??????SCF 2CF 2H?????????H CH 2CH 2??????SCHFCF 3????????????H CH 2CH 2??????SOCF 3??????????????H CH 2CH 2??????SOCHF 2?????????????H CH 2CH 2??????SOCH 2CF 3??????????H CH 2CH 2??????SOCF 2CF 3??????????H CH 2CH 2??????SOCF 2CF 2H?????????H CH 2CH 2??????SOCHFCF 3???????????H CH 2CH 2??????SO 2CF 3????????????H CH 2CH 2??????SO 2CHF 2???????????H CH 2CH 2??????SO 2CH 2CF 3????????H CH 2CH 2??????SO 2CF 2CF 3????????H | ??CH 2CH 2CH 2???SOCHFCF 3?????????Me ? CH 2CH 2CH 2??SO 2CF 3???????????Me ??CH 2CH 2CH 2???SO 2CHF 2?????????Me ??CH 2CH 2CH 2???SO 2CH 2CF 3??????Me ??CH 2CH 2CH 2???SO 2CF 2CF 3??????Me ??CH 2CH 2CH 2???SO 2CF 2CF 2H?????Me ??CH 2CH 2CH 2???SO 2CGFCF 3???????Me ??CH 2CH 2CH 2???CN?????????????????Me ??CH 2CH 2CH 2???SMe????????????????Me ??CH 2CH 2CH 2???S(O)Me?????????????Me ??CH 2CH 2CH 2???S(O) 2Me???????????Me ??CH 2CH 2CH 2???NO 2???????????????Me ??CH 2CH 2???????Cl??????????????????Me ??CH 2CH 2???????Br??????????????????Me ??CH 2CH 2???????OCF 3???????????????Me ??CH 2CH 2???????OCHF 2??????????????Me ??CH 2CH 2???????OCH 2CF 3???????????Me ??CH 2CH 2???????OCF 2CF 3???????????Me ??CH 2CH 2???????OCF 2CF 2H??????????Me ??CH 2CH 2???????OCHFCF 3????????????Me ??CH 2CH 2???????SCF 3???????????????Me ??CH 2CH 2???????SCHF 2??????????????Me ??CH 2CH 2???????SCH 2CF 3???????????Me ??CH 2CH 2???????SCF 2CF 3???????????Me ??CH 2CH 2???????SCF 2CF 2H??????????Me ??CH 2CH 2???????SCHFCF 3????????????Me ??CH 2CH 2???????SOCF 3??????????????Me ??CH 2CH 2???????SOCHF 2?????????????Me ??CH 2CH 2???????SOCH 2CF 3??????????Me ??CH 2CH 2???????SOCF 2CF 3??????????Me ??CH 2CH 2???????SOCF 2CF 2H?????????Me ??CH 2CH 2???????SOCHFCF 3???????????Me ??CH 2CH 2???????SO 2CF 3????????????Me ??CH 2CH 2???????SO 2CHF 2???????????Me ??CH 2CH 2???????SO 2CH 2CF 3????????Me ??CH 2CH 2???????SO 2CF 2CF 3????????Me |
T and V are Cl, and U is H
| ???J??????????R????????????????M | ??J????????????R???????????????????M |
| CH 2CH 2????SO 2CF 2CF 2H???H CH 2CH 2????SO 2CHFCF 3?????H CH 2CH 2????CN???????????????H CH 2CH 2????SMe??????????????H CH 2CH 2????S(O)Me???????????H CH 2CH 2????S(O) 2Me?????????H CH 2CH 2????NO 2?????????????H | CH 2CH 2????SO 2CF 2CF 2H?????????Me CH 2CH 2????SO 2CHFCF 3???????????Me CH 2CH 2????CN?????????????????????Me CH 2CH 2????SMe????????????????????Me CH 2CH 2????S(O)Me?????????????????Me CH 2CH 2????S(O) 2Me???????????????Me CH 2CH 2????NO 2???????????????????Me |
T and V are Cl, and U is Me
| ????J????????????R?????????????M | ????J????????????R????????????????M |
| CH 2CH 2CH 2????Cl????????????H CH 2CH 2CH 2????Br????????????H CH 2CH 2CH 2????OCF 3?????????H CH 2CH 2CH 2????OCHF 2????????H CH 2CH 2CH 2????OCH 2CF 3?????H CH 2CH 2CH 2????OCF 3CF 3?????H CH 2CH 2CH 2????OCF 2CF 2H????H CH 2CH 2CH 2????OCHFCF 3??????H CH 2CH 2CH 2????SCF 3?????????H CH 2CH 2CH 2????SCHF 2????????H CH 2CH 2CH 2????SCH 2CF 3?????H CH 2CH 2CH 2????SCF 2CF 3?????H CH 2CH 2CH 2????SCF 2CF 2H????H CH 2CH 2CH 2????SCHFCF 3??????H CH 2CH 2CH 2????SOCF 3????????H CH 2CH 2CH 2????SOCHF 2???????H CH 2CH 2CH 2????SOCH 2CF 3????H CH 2CH 2CH 2????SOCF 2CF 3????H CH 2CH 2CH 2????SOCF 2CF 2H???H CH 2CH 2CH 2????SOCHFCF 3?????H CH 2CH 2CH 2????SO 2CF 3??????H CH 2CH 2CH 2????SO 2CHF 2?????H CH 2CH 2CH 2????SO 2CH 2CF 3??H CH 2CH 2CH 2????SO 2CF 2CF 3??H CH 2CH 2CH 2????SO 2CF 2CF 2H?H CH 2CH 2CH 2????SO 2CHFCF 3???H | CH 2CH 2CH 2????Cl???????????????Me CH 2CH 2CH 2????Br???????????????Me CH 2CH 2CH 2????OCF 3????????????Me CH 2CH 2CH 2????OCHF 2???????????Me CH 2CH 2CH 2????OCH 2CF 3????????Me CH 2CH 2CH 2????OCF 2CF 3????????Me CH 2CH 2CH 2????OCF 2CF 2H???????Me CH 2CH 2CH 2????OCHFCF 3?????????Me CH 2CH 2CH 2????SCF 3????????????Me CH 2CH 2CH 2????SCHF 2???????????Me CH 2CH 2CH 2????SCH 2CF 3????????Me CH 2CH 2CH 2????SCF 2CF 3????????Me CH 2CH 2CH 2????SCF 2CF 2H???????Me CH 2CH 2CH 2????SCHFCF 3?????????Me CH 2CH 2CH 2????SOCF 3???????????Me CH 2CH 2CH 2????SOCHF 2??????????Me CH 2CH 2CH 2????SOCH 2CF 3???????Me CH 2CH 2CH 2????SOCF 2CF 3???????Me CH 2CH 2CH 2????SOCF 2CF 2H??????Me CH 2CH 2CH 2????SOCHFCF 3????????Me CH 2CH 2CH 2????SO 2CF 3?????????Me CH 2CH 2CH 2????SO 2CHF 2????????Me CH 2CH 2CH 2????SO 2CH 2CF 3?????Me CH 2CH 2CH 2????SO 2CF 2CF 3?????Me CH 2CH 2CH 2????SO 2CF 2CF 2H????Me CH 2CH 2CH 2????SO 2CHFCF 3??????Me |
| CH 2CH 2CH 2???CN?????????????H CH 2CH 2CH 2???SMe????????????H CH 2CH 2CH 2???S(O)Me?????????H CH 2CH 2CH 2???S(O) 2Me???????H CH 2CH 2CH 2???NO 2???????????H CH 2CH 2???????Cl??????????????H CH 2CH 2???????Br??????????????H CH 2CH 2???????OCF 3???????????H CH 2CH 2???????OCHF 2??????????H CH 2CH 2???????OCH 2CF 3??????H CH 2CH 2???????OCF 2CF 3??????H CH 2CH 2???????OCF 2CF 2H?????H CH 2CH 2???????OCHFCF 3???????H CH 2CH 2???????SCF 3??????????H CH 2CH 2???????SCHF 2?????????H CH 2CH 2???????SCH 2CF 3??????H CH 2CH 2???????SCF 2CF 3??????H CH 2CH 2???????SCF 2CF 2H?????H CH 2CH 2???????SCHFCF 3???????H CH 2CH 2???????SOCF 3?????????H CH 2CH 2???????SOCHF 2????????H CH 2CH 2???????SOCH 2CF 3?????H CH 2CH 2???????SOCF 2CF 3?????H CH 2CH 2???????SOCF 2CF 2H????H CH 2CH 2???????SOCHFCF 3??????H CH 2CH 2???????SO 2CF 3???????H CH 2CH 2???????SO 2CHF 2??????H CH 2CH 2???????SO 2CH 2CF 3???H CH 2CH 2???????SO 2CF 2CF 3???H CH 2CH 2???????SO 2CF 2CF 2H??H CH 2CH 2???????SO 2CHFCF 3????H CH 2CH 2???????CN??????????????H CH 2CH 2???????SMe?????????????H CH 2CH 2???????S(O)Me??????????H CH 2CH 2???????S(O) 2Me????????H CH 2CH 2???????NO 2????????????H | CH 2CH 2CH 2???CN??????????????Me CH 2CH 2CH 2???SMe?????????????Me CH 2CH 2CH 2???S(O)Me??????????Me CH 2CH 2CH 2???S(O) 2Me????????Me CH 2CH 2CH 2???NO 2????????????Me CH 2CH 2???????Cl???????????????Me CH 2CH 2???????Br???????????????Me CH 2CH 2???????OCF 3????????????Me CH 2CH 2???????OCHF 2???????????Me CH 2CH 2???????OCH 2CF 3????????Me CH 2CH 2???????OCF 2CF 3????????Me CH 2CH 2???????OCF 2CF 2H???????Me CH 2CH 2???????OCHFCF 3?????????Me CH 2CH 2???????SCF 3????????????Me CH 2CH 2???????SCHF 2???????????Me CH 2CH 2???????SCH 2CF 3????????Me CH 2CH 2???????SCF 2CF 3????????Me CH 2CH 2???????SCF 2CF 2H???????Me CH 2CH 2???????SCHFCF 3?????????Me CH 2CH 2???????SOCF 3???????????Me CH 2CH 2???????SOCHF 2??????????Me CH 2CH 2???????SOCH 2CF 3???????Me CH 2CH 2???????SOCF 2CF 3???????Me CH 2CH 2???????SOCF 2CF 2H??????Me CH 2CH 2???????SOCHFCF 3????????Me CH 2CH 2???????SO 2CF 3?????????Me CH 2CH 2???????SO 2CHF 2????????Me CH 2CH 2???????SO 2CH 2CF 3?????Me CH 2CH 2???????SO 2CF 2CF 3?????Me CH 2CH 2???????SO 2CF 2CF 2H????Me CH 2CH 2???????SO 2CHFCF 3??????Me CH 2CH 2???????CN????????????????Me CH 2CH 2???????SMe???????????????Me CH 2CH 2???????S(O)Me????????????Me CH 2CH 2???????S(0) 2Me??????????Me CH 2CH 2???????NO 2??????????????Me |
T is Cl, and V and U are Me
| ?J???????????????R?????????????????M | ????J???????????R???????????????????M |
| CH 2CH 2CH 2????Cl????????????????H CH 2CH 2CH 2????Br????????????????H CH 2CH 2CH 2????OCF 3?????????????H CH 2CH 2CH 2????OCHF 2????????????H CH 2CH 2CH 2????OCH 2CF 3?????????H CH 2CH 2CH 2????OCF 2CF 3?????????H CH 2CH 2CH 2????OCF 2CF 2H????????H CH 2CH 2CH 2????OCHFCF 3??????????H CH 2CH 2CH 2????SCF 3?????????????H CH 2CH 2CH 2????SCHF 2????????????H CH 2CH 2CH 2????SCH 2CF 3?????????H CH 2CH 2CH 2????SCF 2CF 3?????????H CH 2CH 2CH 2????SCF 2CF 2H????????H CH 2CH 2CH 2????SCHFCF 3??????????H CH 2CH 2CH 2????SOCF 3????????????H CH 2CH 2CH 2????SOCHF 2???????????H CH 2CH 2CH 2????SOCH 2CF 3????????H CH 2CH 2CH 2????SOCF 2CF 3????????H CH 2CH 2CH 2????SOCF 2CF 2H???????H CH 2CH 2CH 2????SOCHFCF 3?????????H CH 2CH 2CH 2????SO 2CF 3??????????H CH 2CH 2CH 2????SO 2CHF 2?????????H CH 2CH 2CH 2????SO 2CH 2CF 3??????H CH 2CH 2CH 2????SO 2CF 2CF 3??????H CH 2CH 2CH 2????SO 2CF 2CF 2H?????H CH 2CH 2CH 2????SO 2CHFCF 3???????H CH 2CH 2CH 2????CN?????????????????H CH 2CH 2CH 2????SMe????????????????H CH 2CH 2CH 2????S(O)Me?????????????H CH 2CH 2CH 2????S(O) 2Me???????????H CH 2CH 2CH 2????NO 2???????????????H CH 2CH 2???????Cl???????????????????H CH 2CH 2???????Br???????????????????H CH 2CH 2???????OCF 3????????????????H CH 2CH 2???????OCHF 2???????????????H CH 2CH 2???????OCH 2CF 3????????????H | CH 2CH 2CH 2????Cl??????????????????Me CH 2CH 2CH 2????Br??????????????????Me CH 2CH 2CH 2????OCF 3???????????????Me CH 2CH 2CH 2????OCHF 2??????????????Me CH 2CH 2CH 2????OCH 2CF 3???????????Me CH 2CH 2CH 2????OCF 2CF 3???????????Me CH 2CH 2CH 2????OCF 2CF 2H??????????Me CH 2CH 2CH 2????OCHFCF 3????????????Me CH 2CH 2CH 2????SCF 3???????????????Me CH 2CH 2CH 2????SCHF 2??????????????Me CH 2CH 2CH 2????SCH 2CF 3???????????Me CH 2CH 2CH 2????SCF 2CF 3???????????Me CH 2CH 2CH 2????SCF 2CF 2H??????????Me CH 2CH 2CH 2????SCHFCF 3????????????Me CH 2CH 2CH 2????SOCF 3??????????????Me CH 2CH 2CH 2????SOCHF 2?????????????Me CH 2CH 2CH 2????SOCH 2CF 3??????????Me CH 2CH 2CH 2????SOCF 2CF 3??????????Me CH 2CH 2CH 2????SOCF 2CF 2H?????????Me CH 2CH 2CH 2????SOCHFCF 3???????????Me CH 2CH 2CH 2????SO 2CF 3????????????Me CH 2CH 2CH 2????SO 2CHF 2???????????Me CH 2CH 2CH 2????SO 2CH 2CF 3????????Me CH 2CH 2CH 2????SO 2CF 2CF 3????????Me CH 2CH 2CH 2????SO 2CF 2CF 2H???????Me CH 2CH 2CH 2????SO 2CHFCF 3?????????Me CH 2CH 2CH 2????CN???????????????????Me CH 2CH 2CH 2????SMe??????????????????Me CH 2CH 2CH 2????S(O)Me???????????????Me CH 2CH 2CH 2????S(O) 2Me?????????????Me CH 2CH 2CH 2????NO 2?????????????????Me CH 2CH 2???????Cl?????????????????????Me CH 2CH 2???????Br?????????????????????Me CH 2CH 2???????OCF 3??????????????????Me CH 2CH 2???????OCHF 2?????????????????Me CH 2CH 2???????OCH 2CF 3??????????????Me |
| CH 2CH 2????OCF 2CF 3?????????H CH 2CH 2????OCF 2CF 2H????????H CH 2CH 2????OCHFCF 3??????????H CH 2CH 2????SCF 3?????????????H CH 2CH 2????SCHF 2????????????H CH 2CH 2????SCH 2CF 3?????????H CH 2CH 2????SCF 2CF 3?????????H CH 2CH 2????SCF 2CF 2H????????H CH 2CH 2????SCHFCF 3??????????H CH 2CH 2????SOCF 3????????????H CH 2CH 2????SOCHF 2???????????H CH 2CH 2????SOCH 2CF 3????????H CH 2CH 2????SOCF 2CF 3????????H CH 2CH 2????SOCF 2CF 2H???????H CH 2CH 2????SOCHFCF 3?????????H CH 2CH 2????SO 2CF 3??????????H CH 2CH 2????SO 2CHF 2?????????H CH 2CH 2????SO 2CH 2CF 3??????H CH 2CH 2????SO 2CF 2CF 3??????H CH 2CH 2????SO 2CF 2CF 2H?????H CH 2CH 2????SO 2CHFCF 3???????H CH 2CH 2????CN?????????????????H CH 2CH 2????SMe????????????????H CH 2CH 2????S(O)Me?????????????H CH 2CH 2????S(O) 2Me???????????H CH 2CH 2????NO 2???????????????H | CH 2CH 2????OCF 2CF 3??????????????Me CH 2CH 2????OCF 2CF 2H?????????????Me CH 2CH 2????OCHFCF 3???????????????Me CH 2CH 2????SCF 3??????????????????Me CH 2CH 2????SCHF 2?????????????????Me CH 2CH 2????SCH 2CF 3??????????????Me CH 2CH 2????SCF 2CF 3??????????????Me CH 2CH 2????SCF 2CF 2H?????????????Me CH 2CH 2????SCHFCF 3???????????????Me CH 2CH 2????SOCF 3?????????????????Me CH 2CH 2????SOCHF 2????????????????Me CH 2CH 2????SOCH 2CF 3?????????????Me CH 2CH 2????SOCF 2CF 3?????????????Me CH 2CH 2????SOCF 2CF 2H????????????Me CH 2CH 2????SOCHFCF 3??????????????Me CH 2CH 2????SO 2CF 3???????????????Me CH 2CH 2????SO 2CHF 2??????????????Me CH 2CH 2????SO 2CH 2CF 3???????????Me CH 2CH 2????SO 2CF 2CF 3???????????Me CH 2CH 2????SO 2CF 2CF 2H??????????Me CF 2CH 2????SO 2CHFCF 3????????????Me CH 2CH 2????CN??????????????????????Me CH 2CH 2????SMe?????????????????????Me CH 2CH 2????S(O)Me??????????????????Me CH 2CH 2????S(O) 2Me????????????????Me CH 2CH 2????NO 2????????????????????Me |
Table 8
T and V are Cl, and U is H
| ????J?????????????R????????????????M | ????J????????????R???????????????????M |
| CH 2CH 2CH 2?????Cl???????????????H CH 2CH 2CH 2?????Br???????????????H CH 2CH 2CH 2?????OCF 3????????????H CH 2CH 2CH 2?????OCHF 2???????????H CH 2CH 2CH 2?????OCH 2CF 3????????H CH 2CH 2CH 2?????OCF 2CF 3????????H CH 2CH 2CH 2?????OCF 2CF 2H???????H CH 2CH 2CH 2?????OCHFCF 3?????????H CH 2CH 2CH 2?????SCF 3????????????H CH 2CH 2CH 2?????SCHF 2???????????H CH 2CH 2CH 2?????SCH 2CF 3????????H CH 2CH 2CH 2?????SCF 2CF 3????????H CH 2CH 2CH 2?????SCF 2CF 2H???????H CH 2CH 2CH 2?????SCHFCF 3?????????H CH 2CH 2CH 2?????SOCF 3???????????H CH 2CH 2CH 2?????SOCHF 2??????????H CH 2CH 2CH 2?????SOCH 2CF 3???????H CH 2CH 2CH 2?????SOCF 2CF 3???????H CH 2CH 2CH 2?????SOCF 2CF 2H??????H CH 2CH 2CH 2?????SOCHFCF 3????????H CH 2CH 2CH 2?????SO 2CF 3?????????H CH 2CH 2CH 2?????SO 2CHF 2????????H CH 2CH 2CH 2?????SO 2CH 2CF 3?????H CH 2CH 2CH 2?????SO 2CF 2CF 3?????H CH 2CH 2CH 2?????SO 2CF 2CF 2H????H CH 2CH 2CH 2?????SO 2CHFCF 3??????H CH 2CH 2CH 2?????CN????????????????H CH 2CH 2CH 2?????SMe???????????????H CH 2CH 2CH 2?????S(O)Me????????????H | CH 2CH 2CH 2????Cl??????????????????Me CH 2CH 2CH 2????Br??????????????????Me CH 2CH 2CH 2????OCF 3???????????????Me CH 2CH 2CH 2????OCHF 2??????????????Me CH 2CH 2CH 2????OCH 2CF 3???????????Me CH 2CH 2CH 2????OCF 2CF 3???????????Me CH 2CH 2CH 2????OCF 2CF 2H??????????Me CH 2CH 2CH 2????OCHFCF 3????????????Me CH 2CH 2CH 2????SCF 3???????????????Me CH 2CH 2CH 2????SCHF 2??????????????Me CH 2CH 2CH 2????SCH 2CF 3???????????Me CH 2CH 2CH 2????SCF 2CF 3???????????Me CH 2CH 2CH 2????SCF 2CF 2H??????????Me CH 2CH 2CH 2????SCHFCF 3????????????Me CH 2CH 2CH 2????SOCF 3??????????????Me CH 2CH 2CH 2????SOCHF 2?????????????Me CH 2CH 2CH 2????SOCH 2CF 3??????????Me CH 2CH 2CH 2????SOCF 2CF 3??????????Me CH 2CH 2CH 2????SOCF 2CF 2H?????????Me CH 2CH 2CH 2????SOCHFCF 3???????????Me CH 2CH 2CH 2????SO 2CF 3????????????Me CH 2CH 2CH 2????SO 2CHF 2???????????Me CH 2CH 2CH 2????SO 2CH 2CF 3????????Me CH 2CH 2CH 2????SO 2CF 2CF 3????????Me CH 2CH 2CH 2????SO 2CF 2CF 2H???????Me CH 2CH 2CH 2????SO 2CHFCF 3?????????Me CH 2CH 2CH 2????CN???????????????????Me CH 2CH 2CH 2????SMe??????????????????Me CH 2CH 2CH 2????S(O)Me???????????????Me |
T and V are Cl, and U is H
| ????J????????????R????????????M | ????J????????????R??????????????M |
| CH 2CH 2CH 2???S(O) 2Me?????H CH 2CH 2CH 2???NO 2?????????H CH 2CH 2???????Cl????????????H CH 2CH 2???????Br????????????H CH 2CH 2???????OCF 3?????????H CH 2CH 2???????OCH 2?????????H CH 2CH 2???????OCH 2CF 3?????H CH 2CH 2???????OCF 2CF 3?????H CH 2CH 2???????OCF 2CF 2H????H CH 2CH 2???????OCHFCF 3??????H CH 2CH 2???????SCF 3?????????H CH 2CH 2???????SCHF 2????????H CH 2CH 2???????SCH 2CF 3?????H CH 2CH 2???????SCF 2CF 3?????H CH 2CH 2???????SCF 2CF 2H????H CH 2CH 2???????SCHFCF 3??????H CH 2CH 2???????SOCF 3????????H CH 2CH 2???????SOCHF 2???????H CH 2CH 2???????SOCH 2CF 3????H CH 2CH 2???????SOCF 2CF 3????H CH 2CH 2???????SOCF 2CF 2H???H CH 2CH 2???????SOCHFCF 3?????H CH 2CH 2???????SO 2CF 3??????H CH 2CH 2???????SO 2CHF 2?????H CH 2CH 2???????SO 2CH 2CF 3??H CH 2CH 2???????SO 2CF 2CF 3??H CH 2CH 2???????SO 2CF 2CF 2H?H CH 2CH 2???????SO 2CHFCF 3???H CH 2CH 2???????CN?????????????H CH 2CH 2???????SMe????????????H CH 2CH 2???????S(O)Me?????????H CH 2CH 2???????S(O) 2Me???????H CH 2CH 2???????NO 2???????????H | CH 2CH 2CH 2???S(O) 2Me???????Me CH 2CH 2CH 2???NO 2???????????Me CH 2CH 2???????Cl??????????????Me CH 2CH 2???????Br??????????????Me CH 2CH 2???????OCF 3???????????Me CH 2CH 2???????OCHF 2??????????Me CH 2CH 2???????OCH 2OF 3???????Me CH 2CH 2???????OCF 2CF 3???????Me CH 2CH 2???????OCF 2CF 2H??????Me CH 2CH 2???????OCHFCF 3????????Me CH 2CH 2???????SCF 3???????????Me CH 2CH 2???????SCHF 2??????????Me CH 2CH 2???????SCH 2CF 3???????Me CH 2CH 2???????SCF 2CF 3???????Me CH 2CH 2???????SCF 2CF 2H??????Me CH 2CH 2???????SCHFCF 3????????Me CH 2CH 2???????SOCF 3??????????Me CH 2CH 2???????SOCHF 2?????????Me CH 2CH 2???????SOCH 2CF 3??????Me CH 2CH 2???????SOCF 2CF 3??????Me CH 2CH 2???????SOCF 2CF 2H?????Me CH 2CH 2???????SOCHFCF 3???????Me CH 2CH 2???????SO 2CF 3????????Me CH 2CH 2???????SO 2CHF 2???????Me CH 2CH 2???????SO 2CH 2CF 3????Me CH 2CH 2???????SO 2CF 2CF 3????Me CH 2CH 2???????SO 2CF 2CF 2H???Me CH 2CH 2???????SO 2CHFCF 3?????Me CH 2CH 2???????CN???????????????Me CH 2CH 2???????SMe??????????????Me CH 2CH 2???????S(O)Me???????????Me CH 2CH 2???????S(O) 2Me?????????Me CH 2CH 2???????NO 2?????????????Me |
T and V are Cl, and U is Me
| ??????J?????????????R??????????????M | ??????J????????????R???????????????M |
| ??CH 2CH 2CH 2????Cl??????????????H ??CH 2CH 2CH 2????Br??????????????H ??CH 2CH 2CH 2????OCF 3???????????H ??CH 2CH 2CH 2????OCHF 2??????????H ??CH 2CH 2CH 2????OCH 2CF 3???????H ??CH 2CH 2CH 2????OCF 2CF 3???????H ??CH 2CH 2CH 2????OCF 2CF 2H??????H ??CH 2CH 2CH 2????OCHFCF 3????????H ??CH 2CH 2CH 2????SCF 3???????????H ??CH 2CH 2CH 2????SCHF 2??????????H ??CH 2CH 2CH 2????SCH 2CF 3???????H ??CH 2CH 2CH 2????SCF 2CF 3???????H ??CH 2CH 2CH 2????SCF 2CF 2H??????H ??CH 2CH 2CH 2????SCHFCF 3????????H ??CH 2CH 2CH 2????SOCF 3??????????H ??CH 2CH 2CH 2????SOCHF 2?????????H ??CH 2CH 2CH 2????SOCH 2CF 3??????H ??CH 2CH 2CH 2????SOCF 2CF 3??????H ??CH 2CH 2CH 2????SOCF 2CF 2H?????H ??CH 2CH 2CH 2????SOCHFCF 3???????H ??CH 2CH 2CH 2????SO 2CF 3????????H ??CH 2CH 2CH 2????SO 2CHF 2???????H ??CH 2CH 2CH 2????SO 2CH 2CF 3????H ??CH 2CH 2CH 2????SO 2CF 2CF 3????H ??CH 2CH 2CH 2????SO 2CF 2CF 2H???H ??CH 2CH 2CH 2????SO 2CHFCF 3?????H ??CH 2CH 2CH 2????CN???????????????H ??CH 2CH 2CH 2????SMe??????????????H ??CH 2CH 2CH 2????S(O)Me???????????H ??CH 2CH 2CH 2????S(O) 2Me?????????H ??CH 2CH 2CH 2????NO 2?????????????H ??CH 2CH 2???????Cl?????????????????H ??CH 2CH 2???????Br?????????????????H ??CH 2CH 2???????OCF 3??????????????H ??CH 2CH 2???????OCHF 2?????????????H ??CH 2CH 2???????OCF 2CF 3??????????H | ??CH 2CH 2CH 2????Cl??????????????Me ??CH 2CH 2CH 2????Br??????????????Me ??CH 2CH 2CH 2????OCF 3???????????Me ??CH 2CH 2CH 2????OCHF 2??????????Me ??CH 2CH 2CH 2????OCH 2CF 3???????Me ??CH 2CH 2CH 2????OCF 2CF 3???????Me ??CH 2CH 2CH 2????OCF 2CF 2H??????Me ??CH 2CH 2CH 2????OCHFCF 3????????Me ??CH 2CH 2CH 2????SCF 3???????????Me ??CH 2CH 2CH 2????SCHF 2??????????Me ??CH 2CH 2CH 2????SCH 2CF 3???????Me ??CH 2CH 2CH 2????SCF 2CF 3???????Me ??CH 2CH 2CH 2????SCF 2CF 2H??????Me ??CH 2CH 2CH 2????SCHFCF 3????????Me ??CH 2CH 2CH 2????SOCF 3??????????Me ??CH 2CH 2CH 2????SOCHF 2?????????Me ??CH 2CH 2CH 2????SOCH 2CF 3??????Me ??CH 2CH 2CH 2????SOCF 2CF 3??????Me ??CH 2CH 2CH 2????SOCF 2CF 2H?????Me ??CH 2CH 2CH 2????SOCHFCF 3???????Me ??CH 2CH 2CH 2????SO 2CF 3????????Me ??CH 2CH 2CH 2????SO 2CHF 2???????Me ??CH 2CH 2CH 2????SO 2CH 2CF 3????Me ??CH 2CH 2CH 2????SO 2CF 2CF 3????Me ??CH 2CH 2CH 2????SO 2CF 2CF 2H???Me ??CH 2CH 2CH 2????SO 2CHFCF 3?????Me ??CH 2CH 2CH 2????CN???????????????Me ??CH 2CH 2CH 2????SMe??????????????Me ??CH 2CH 2CH 2????S(O)Me???????????Me ??CH 2CH 2CH 2????S(O) 2Me?????????Me ??CH 2CH 2CH 2????NO 2?????????????Me ??CH 2CH 2????????Cl????????????????Me ??CH 2CH 2????????Br????????????????Me ??CH 2CH 2????????OCF 3?????????????Me ??CH 2CH 2????????OCHF 2????????????Me ??CH 2CH 2????????OCHCF 3???????????Me |
T and V are Cl, and U is Me
| ?????J??????????????R????????M | ?????J??????????????R?????????M |
| ??CH 2CH 2????OCF 2CF 3?????H ??CH 2CH 2????OCF 2CF 2H????H ??CH 2CH 2????OCHFCF 3??????H ??CH 2CH 2????SCF 3?????????H ??CH 2CH 2????SCHF 2????????H ??CH 2CH 2????SCH 2CF 3?????H ??CH 2CH 2????SCF 2CF 3?????H ??CH 2CH 2????SCF 2CF 2H????H ??CH 2CH 2????SCHFCF 3??????H ??CH 2CH 2????SOCF 3????????H ??CH 2CH 2????SOCHF 2???????H ??CH 2CH 2????SOCH 2CF 3????H ??CH 2CH 2????SOCF 2CF 3????H ??CH 2CH 2????SOCF 2CF 2H???H ??CH 2CH 2????SOCHFCF 3?????H ??CH 2CH 2????SO 2CF 3??????H ??CH 2CH 2????SO 2CHF 2?????H ??CH 2CH 2????SO 2CH 2CF 3??H ??CH 2CH 2????SO 2CF 2CF 3??H ??CH 2CH 2????SO 2CF 2CF 2H?H ??CH 2CH 2????SO 2CHFCF 3???H ??CH 2CH 2????CN?????????????H ??CH 2CH 2????SMe????????????H ??CH 2CH 2????S(O)Me?????????H ??CH 2CH 2????S(O) 2Me???????H ??CH 2CH 2????NO 2???????????H | ??CH 2CH 2????OCF 2CF 3??????Me ??CH 2CH 2????OCF 2CF 2H?????Me ??CH 2CH 2????OCHFCF 3???????Me ??CH 2CH 2????SCF 3??????????Me ??CH 2CH 2????SCHF 2?????????Me ??CH 2CH 2????SCH 2CF 3??????Me ??CH 2CH 2????SCF 2CF 3??????Me ??CH 2CH 2????SCF 2CF 2H?????Me ??CH 2CH 2????SCHFCF 3???????Me ??CH 2CH 2????SOCF 3?????????Me ??CH 2CH 2????SOCHF 2????????Me ??CH 2CH 2????SOCH 2CF 3?????Me ??CH 2CH 2????SOCF 2CF 3?????Me ??CH 2CH 2????SOCF 2CF 2H????Me ??CH 2CH 2????SOCHFCF 3??????Me ??CH 2CH 2????SO 2CF 3???????Me ??CH 2CH 2????SO 2CHF 2??????Me ??CH 2CH 2????SO 2CH 2CF 3???Me ??CH 2CH 2????SO 2CF 2CF 3???Me ??CH 2CH 2????SO 2CF 2CF 2H??Me ??CH 2CH 2????SO 2CHFCF 3????Me ??CH 2CH 2????CN??????????????Me ??CH 2CH 2????SMe?????????????Me ??CH 2CH 2????S(O)Me??????????Me ??CH 2CH 2????S(O) 2Me????????Me ??CH 2CH 2????NO 2????????????Me |
T is Cl, and V and U are Me
| ??????J???????????R???????????M | ??????J?????????????R??????????????M |
| ??CH 2CH 2CH 2???Cl??????????H ??CH 2CH 2CH 2???Br??????????H ??CH 2CH 2CH 2???OCF 3???????H ??CH 2CH 2CH 2???OCHF 2??????H ??CH 2CH 2CH 2???OCH 2CF 3???H ??CH 2CH 2CH 2???OCF 2CF 3???H ??CH 2CH 2CH 2???OCF 2CF 2H??H | ??CH 2CH 2CH 2?????Cl?????????????Me ??CH 2CH 2CH 2?????Br?????????????Me ??CH 2CH 2CH 2?????OCF 3??????????Me ??CH 2CH 2CH 2?????OCHF 2?????????Me ??CH 2CH 2CH 2?????OCH 2CF 3??????Me ??CH 2CH 2CH 2?????OCF 2CF 3??????Me ??CH 2CH 2CH 2?????OCF 2CF 2H?????Me |
T is Cl, and V and U are Me
| ??????J??????????R??????????M | ??????J???????????R???????M |
| ??CH 2CH 2CH 2????OCHFCF 3????????H ??CH 2CH 2CH 2????SCF 3???????????H ??CH 2CH 2CH 2????SCHF 2??????????H ??CH 2CH 2CH 2????SCH 2CF 3???????H ??CH 2CH 2CH 2????SCF 2CF 3???????H ??CH 2CH 2CH 2????SCF 2CF 2H??????H ??CH 2CH 2CH 2????SCHFCF 3????????H ??CH 2CH 2CH 2????SOCF 3??????????H ??CH 2CH 2CH 2????SOCHF 2?????????H ??CH 2CH 2CH 2????SOCH 2CF 3??????H ??CH 2CH 2CH 2????SOCF 2CF 3??????H ??CH 2CH 2CH 2????SOCF 2CF 2H?????H ??CH 2CH 2CH 2????SOCHFCF 3???????H ??CH 2CH 2CH 2????SO 2CF 3????????H ??CH 2CH 2CH 2????SO 2CHF 2???????H ??CH 2CH 2CH 2????SO 2CH 2CF 3????H ??CH 2CH 2CH 2????SO 2CF 2CF 3????H ??CH 2CH 2CH 2????SO 2CF 2CF 2H???H ??CH 2CH 2CH 2????SO 2CHFCF 3?????H ??CH 2CH 2CH 2????CN???????????????H ??CH 2CH 2CH 2????SMe??????????????H ??CH 2CH 2CH 2????S(O)Me???????????H ??CH 2CH 2CH 2????S(O) 2Me?????????H ??CH 2CH 2CH 2????NO 2?????????????H ??CH 2CH 2????????Cl????????????????H ??CH 2CH 2????????Br????????????????H ??CH 2CH 2????????OCF 3?????????????H ??CH 2CH 2????????OCHF 2????????????H ??CH 2CH 2????????OCH 2CF 3?????????H ??CH 2CH 2????????OCF 2CF 3?????????H ??CH 2CH 2????????OCF 2CF 2H????????H ??CH 2CH 2????????OCHFCF 3??????????H ??CH 2CH 2????????SCF 3?????????????H ??CH 2CH 2????????SCHF 2????????????H ??CH 2CH 2????????SCH 2CF 3?????????H ??CH 2CH 2????????SCF 2CF 3?????????H | ??CH 2CH 2CH 2????OCHFCF 3??????Me ??CH 2CH 2CH 2????SCF 3?????????Me ??CH 2CH 2CH 2????SCHF 2????????Me ??CH 2CH 2CH 2????SCH 2CF 3?????Me ??CH 2CH 2CH 2????SCF 2CF 3?????Me ??CH 2CH 2CH 2????SCF 2CF 2H????Me ??CH 2CH 2CH 2????SCHFCF 3??????Me ??CH 2CH 2CH 2????SOCF 3????????Me ??CH 2CH 2CH 2????SOCHF 2???????Me ??CH 2CH 2CH 2????SOCH 2CF 3????Me ??CH 2CH 2CH 2????SOCF 2CF 3????Me ??CH 2CH 2CH 2????SOCF 2CF 2H???Me ??CH 2CH 2CH 2????SOCHFCF 3?????Me ??CH 2CH 2CH 2????SO 2CF 3??????Me ??CH 2CH 2CH 2????SO 2CHF 2?????Me ??CH 2CH 2CH 2????SO 2CH 2CF 3??Me ??CH 2CH 2CH 2????SO 2CF 2CF 3??Me ??CH 2CH 2CH 2????SO 2CF 2CF 2H?Me ??CH 2CH 2CH 2????SO 2CHFCF 3???Me ??CH 2CH 2CH 2????CN?????????????Me ??CH 2CH 2CH 2????SMe????????????Me ??CH 2CH 2CH 2????S(O)Me?????????Me ??CH 2CH 2CH 2????S(O) 2Me???????Me ??CH 2CH 2CH 2????NO 2???????????Me ??CH 2CH 2???????Cl??????????????Me ??CH 2CH 2???????Br??????????????Me ??CH 2CH 2???????OCF 3???????????Me ??CH 2CH 2???????OCHF 2??????????Me ??CH 2CH 2???????OCH 2CF 3???????Me ??CH 2CH 2???????OCF 2CF 3???????Me ??CH 2CH 2???????OCF 2CF 2H??????Me ??CH 2CH 2???????OCHFCF 3????????Me ??CH 2CH 2???????SCF 3???????????Me ??CH 2CH 2???????SCHF 2??????????Me ??CH 2CH 2???????SCH 2CF 3???????Me ??CH 2CH 2???????SCF 2CF 3???????Me |
T is Cl, and V and U are Me
| ????J??????????????R??????????M | ????J??????????????R?????????????M |
| ??CH 2CH 2????SCF 2CF 2H?????H ??CH 2CH 2????SCHFCF 3???????H ??CH 2CH 2????SOCF 3?????????H ??CH 2CH 2????SOCHF 2????????H ??CH 2CH 2????SOCH 2CF 3?????H ??CH 2CH 2????SOCF 2CF 3?????H ??CH 2CH 2????SOCF 2CF 2H????H ??CH 2CH 2????SOCHFCF 3??????H ??CH 2CH 2????SO 2CF 3???????H ??CH 2CH 2????SO 2CHF 2??????H ??CH 2CH 2????SO 2CH 2CF 3???H ??CH 2CH 2????SO 2CF 2CF 3???H ??CH 2CH 2????SO 2CF 2CF 2H??H ??CH 2CH 2????SO 2CHFCF 3????H ??CH 2CH 2????CN??????????????H ??CH 2CH 2????SMe?????????????H ??CH 2CH 2????S(O)Me??????????H ??CH 2CH 2????S(O) 2Me????????H ??CH 2CH 2????NO 2????????????H | ??CH 2CH 2????SCF 2CF 2H???????Me ??CH 2CH 2????SCHFCF 3?????????Me ??CH 2CH 2????SOCF 3???????????Me ??CH 2CH 2????SOCHF 3??????????Me ??CH 2CH 2????SOCH 2CF 3???????Me ??CH 2CH 2????SOCF 2CF 3???????Me ??CH 2CH 2????SOCF 2CF 2H??????Me ??CH 2CH 2????SOCHFCF 3????????Me ??CH 2CH 2????SO 2CF 3?????????Me ??CH 2CH 2????SO 2CHF 2????????Me ??CH 2CH 2????SO 2CH 2CF 3?????Me ??CH 2CH 2????SO 2CF 2CF 3?????Me ??CH 2CH 2????SO 2CF 2CF 2H????Me ??CH 2CH 2????SO 2CHFCF 3??????Me ??CH 2CH 2????CN????????????????Me ??CH 2CH 2????SMe???????????????Me ??CH 2CH 2????S(O)Me????????????Me ??CH 2CH 2????S(O) 2Me??????????Me ??CH 2CH 2????NO 2??????????????Me |
Table 7
T and V are Cl, and U is H
| ????????J?????????????R | ???J???????R | ?????J??????????R |
| ??CH 2CH 2CH 2CH 2???Cl ??CH 2CH 2CH 2CH 2???Br ??CH 2CH 2CH 2CH 2???CF 3??CH 2CH 2CH 2CH 2???CO 2CH 3??CH 2CH 2CH 2CH 2???CONHCH 3??CH 2CH 2CH 2CH 2???I ??CH 2CH 2CH 2CH 2???CH 3 | ??OCH 2????Cl ??OCH 2????Br ??OCH 2????CF 3??OCH 2????CO 2CH 3??OCH 2????CONHCH 3??OCH 2????I ??OCH 2????CH 3 | ??OCH 2CH 2????Cl ??OCH 2CH 2????Br ??OCH 2CH 2????CF 3??OCH 2CH 2????CO 2CH 3??OCH 2CH 2????CONHCH 3??OCH 2CH 2????I ??OCH 2CH 2????CH 3 |
T and V are Cl, and U is H
| ????J?????????????????R | ??J?????????R | ?????J?????????????R |
| ??CH 2CH 2CH 2CH 2?OCF 3??CH 2CH 2CH 2CH 2?OCHF 2??CH 2CH 2CH 2CH 2?OCF 3??CH 2CH 2CH 2CH 2?SCHF 2??OCH 2CH 2CH 2????Cl ??OCH 2CH 2CH 2????Br ??OCH 2CH 2CH 2????CF 3??OCH 2CH 2CH 2????CO 2CH 3??OCH 2CH 2CH 2????CONHCH 3??OCH 2CH 2CH 2????I ??OCH 2CH 2CH 2????CH 3??OCH 2CH 2CH 2????OCF 3??OCH 2CH 2CH 2????OCHF 2??OCH 2CH 2CH 2????OCF 3??OCH 2CH 2CH 2????SCHF 2??CH 2NEtCH 2??????Cl ??CH 2NEtCH 2??????Br ??CH 2NEtCH 2??????CF 3??CH 2NEtCH 2??????CO 2CH 3??CH 2NEtCH 2??????CONHCH 3??CH 2NEtCH 2??????I ??CH 2NEtCH 2??????CH 3??CH 2NEtCH 2??????OCF 3??CH 2NEtCH 2??????OCHF 2??CH 2NEtCH 2??????OCF 3??CH 2NEtCH 2??????SCHF 2 | OCH 2??????OCF 3OCH 2??????OCHF 2OCH 2??????OCF 3OCH 2??????SCHF 2CH 2NHCH 2?Cl CH 2NHCH 2?Br CH 2NHCH 2?CF 3CH 2NHCH 2?CO 2CH 3CH 2NHCH 2?CONHCH 3CH 2NHCH 2?I CH 2NHCH 2?CH 3CH 2NHCH 2?OCF 3CH 2NHCH 2?OCHF 2CH 2NHCH 2?OCF 3CH 2NHCH 2?SCHF 2CH 2NHCH 2?Cl CONHCO??????Br CONHCO??????CF 3CONHCO??????CO 2CH 3CONHCO??????CONHCH 3CONHCO??????I CONHCO??????CH 3CONHCO??????OCF 3CONHCO??????OCHF 2CONHCO??????OCF 3CONHCO??????SCHF 2 | ??OCH 2CH 2??????OCF 3??OCH 2CH 2??????OCHF 2??OCH 2CH 2??????OCF 3??OCH 2CH 2??????SCHF 2??CH 2NMeCH 2????Cl ??CH 2NMeCH 2????Br ??CH 2NMeCH 2????CF 3??CH 2NMeCH 2????CO 2CH 3??CH 2NMeCH 2????CONHCH 3??CH 2NMeCH 2????I ??CH 2NMeCH 2????CH 3??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????OCHF 2??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????SCHF 2??CONMeCO?????????Cl ??CONMeCO?????????Br ??CONMeCO?????????CF 3??CONMeCO?????????CO 2CH 3??CONMeCO?????????CONHCH 3??CONMeCO?????????I ??CONMeCO?????????CH 3??CONMeCO?????????OCF 3??CONMeCO?????????OCHF 2??CONMeCO????????OCF 3??CONMeCO?????????SCHF 2 |
T and V are Cl, and U is Me
| ????????J??????????????R | ???J?????????R | ?????J??????????R |
| ??CH 2CH 2CH 2CH 2???Cl ??CH 2CH 2CH 2CH 2???Br ??CH 2CH 2CH 2CH 2???CF 3??CH 2CH 2CH 2CH 2???CO 2CH 3??CH 2CH 2CH 2CH 2???CONHCH 3??CH 2CH 2CH 2CH 2???I ??CH 2CH 2CH 2CH 2???CH 3 | ??OCH 2??????Cl ??OCH 2??????Br ??OCH 2??????CF 3??OCH 2??????CO 2CH 3??OCH 2??????CONHCH 3??OCH 2??????I ??OCH 2??????CH 3 | ??OCH 2CH 2????Cl ??OCH 2CH 2????Br ??OCH 2CH 2????CH 3??OCH 2CH 2????CO 2CH 3??OCH 2CH 2????CONHCH 3??OCH 2CH 2????I ??OCH 2CH 2????CH 3 |
T and V are Cl, and U is Me
| ????????J??????????????R | ????J???????????R | ????J??????????????R |
| ??CH 2CH 2CH 2CH 2???OCF 3??CH 2CH 2CH 2CH 2???OCHF 2??CH 2CH 2CH 2CH 2???OCF 3??CH 2CH 2CH 2CH 2???SCHF 2??OCH 2CH 2CH 2??????Cl ??OCH 2CH 2CH 2??????Br ??OCH 2CH 2CH 2??????CF 3??OCH 2CH 2CH 2??????CO 2CH 3??OCH 2CH 2CH 2??????CONHCH 3??OCH 2CH 2CH 2??????I ??OCH 2CH 2CH 2??????CH 3??OCH 2CH 2CH 2??????OCF 3??OCH 2CH 2CH 2??????OCHF 2??OCH 2CH 2CH 2??????OCF 3??OCH 2CH 2CH 2??????SCHF 2??CH 2NEtCH 2????????Cl ??CH 2NEtCH 2????????Br ??CH 2NEtCH 2????????CF 3??CH 2NEtCH 2????????CO 2CH 3??CH 2NEtCH 2????????CONHCH 3??CH 2NEtCH 2????????I ??CH 2NEtCH 2????????CH 3??CH 2NEtCH 2????????OCF 3??CH 2NEtCH 2????????OCHF 2??CH 2NEtCH 2????????OCF 3??CH 2NEtCH 2????????SCHF 2 | ??OCH 2????????OCF 3??OCH 2????????OCHF 2??OCH 2????????OCF 3??OCH 2????????SCHF 2??CH 2NHCH 2???Cl ??CH 2NHCH 2???Br ??CH 2NHCH 2???CF 3??CH 2NHCH 2???CO 2CH 3??CH 2NHCH 2???CONHCH 3??CH 2NHCH 2???I ??CH 2NHCH 2???CH 3??CH 2NHCH 2???OCF 3??CH 2NHCH 2???OCHF 2??CH 2NHCH 2???OCF 3??CH 2NHCH 2???SCHF 2??CONHCO????????Cl ??CONHCO????????Br ??CONHCO????????CF 3??CONHCO????????CO 2CH 3??CONHCO????????CONHCH 3??CONHCO????????I ??CONHCO????????CH 3??CONHCO????????OCF 3??CONHCO????????OCHF 2??CONHCO????????OCF 3??CONHCO????????SCHF 2 | ??OCH 2CH 2???????OCF 3??OCH 2CH 2???????OCHF 2??OCH 2CH 2???????OCF 3??OCH 2CH 2???????SCHF 2??CH 2NMeCH 2????Cl ??CH 2NMeCH 2????Br ??CH 2NMeCH 2????CF 3??CH 2NMeCH 2????CO 2CH 3??CH 2NMeCH 2????CONHCH 3??CH 2NMeCH 2????I ??CH 2NMeCH 2????CH 3??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????OCHF 2??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????SCHF 2??CONMeCO?????????Cl ??CONMeCO?????????Br ??CONMeCO?????????CF 3??CONMeCO?????????CO 2CH 3??CONMeCO?????????CONHCH 3??CONMeCO?????????I ??CONMeCO?????????CH 3??CONMeCO?????????OCF 3??CONMeCO?????????OCHF 2??CONMeCO?????????OCF 3??CONMeCO?????????SCHF 2 |
T is Cl, and V and U are Me
| ????????J?????????????R | ????J???????R | ?????J?????????R |
| ??CH 2CH 2CH 2CH 2???Cl ??CH 2CH 2CH 2CH 2???Br ??CH 2CH 2CH 2CH 2???CF 3??CH 2CH 2CH 2CH 2???CO 2CH 3??CH 2CH 2CH 2CH 2???CONHCH 3??CH 2CH 2CH 2CH 2???I ??CH 2CH 2CH 2CH 2???CH 3 | ??OCH 2????Cl ??OCE 2????Br ??OCH 2????CF 3??OCH 2????CO 2CH 3??OCH 2????CONHCH 3??OCH 2????I ??OCH 2????CH 3 | ??OCH 2CH 2????Cl ??OCH 2CH 2????Br ??OCH 2CH 2????CF 3??OCH 2CH 2????CO 2CH 3??OCH 2CH 2????CONHCH 3??OCH 2CH 2????I ??OCH 2CH 2????CH 3 |
T is Cl, and V and U are Me
| ??????J???????????????R | ????J?????????????R | ?????J????????????R |
| ??CH 2CH 2CH 2CH 2??OCF 3??CH 2CH 2CH 2CH 2??OCHF 2??CH 2CH 2CH 2CH 2??OCF 3??CH 2CH 2CH 2CH 2??SCHF 2??OCH 2CH 2CH 2?????Cl ??OCH 2CH 2CH 2?????Br ??OCH 2CH 2CH 2?????CF 3??OCH 2CH 2CH 2?????CO 2CH 3??OCH 2CH 2CH 2?????CONHCH 3??OCH 2CH 2CH 2?????I ??OCH 2CH 2CH 2?????CH 3??OCH 2CH 2CH 2?????OCF 3??OCH 2CH 2CH 2?????OCHF 2??OCH 2CH 2CH 2?????OCF 3??CCH 2CH 2CH 2?????SCHF 2??CH 2NEtCH 2???????Cl ??CH 2NEtCH 2???????Br ??CH 2NEtCH 2???????CF 3??CH 2NEtCH 2???????CO 2CH 3??CH 2NEtCH 2???????CONHCH 3??CH 2NEtCH 2???????I ??CH 2NEtCH 2???????CH 3??CH 2NEtCH 2???????OCF 3??CH 2NEtCH 2???????OCHF 2??CH 2NEtCH 2???????OCF 3??CH 2NEtCH 2???????SCHF 2 | ??OCH 2?????????OCF 3??OCH 2?????????OCHF 3??OCH 2?????????OCF 3??OCH 2?????????SCHF 2??CH 2NrHCH 2???Cl ??CH 2NHCH 2????Br ??CH 2NHCH 2????CF 3??CH 2NHCH 2????CO 2CH 3??CH 2NHCH 2????CONHCH 3??CH 2NHCH 2????I ??CH 2NHCH 2????CH 3??CH 2NHCH 2????OCF 3??CH 2NHCH 2????OCHF 2??CH 2NHCH 2????OCF 3??CH 2NHCH 2????SCHF 2??CONHCO?????????Cl ??CONHCO?????????Br ??CONHCO?????????CF 3??CONHCO?????????CO 2CH 3??CONHCO?????????CONHCH 3??CONHCO?????????I ??CONHCO?????????CH 3??CONHCO?????????OCF 3??CONHCO?????????OCHF 2??CONHCO?????????OCF 3??CONHCO?????????SCHF 2 | ??OCH 2CH 2??????OCF 3??OCH 2CH 2??????OCHF 2??OCH 2CH 2??????OCF 3??OCH 2CH 2??????SCHF 2??CH 2NMeCH 2????Cl ??CH 2NMeCH 2????Br ??CH 2NMeCH 2????CF 3??CH 2NMeCH 2????CO 2CH 3??CH 2NMeCH 2????CONHCH 3??CH 2NMeCH 2????I ??CH 2NMeCH 2????CH 3??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????OCHF 2??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????SCHF 2??CONMeCO?????????Cl ??CONMeCO?????????Br ??CONMeCO?????????CF 3??CONMeCO?????????CO 2CH 3??CONMeCO?????????CONHCH 3??CONMeCO?????????I ??CONMeCO?????????CH 3??CONMeCO?????????OCF 3??CONMeCO?????????OCHF 2??CONMeCO?????????OCF 3??CONMeCO?????????SCHF 2 |
Table 8
T and V are Cl, and U is H
| ????????J??????????????R | ???J???????????R | ?????J?????????????R |
| ??CH 2CH 2CH 2CH 2???Cl ??CH 2CH 2CH 2CH 2???Br ??CH 2CH 2CH 2CH 2???CF 3??CH 2CH 2CH 2CH 2???CO 2CH 3??CH 2CH 2CH 2CH 2???CONHCH 3??CH 2CH 2CH 2CH 2???I ??CH 2CH 2CH 2CH 2???CH 3??CH 2CH 2CH 2CH 2???OCF 3??CH 2CH 2CH 2CH 2???OCHF 2??CH 2CH 2CH 2CH 2???OCF 3??CH 2CH 2CH 2CH 2???SCHF 2??OCH 2CH 2CH 2??????Cl ??OCH 2CH 2CH 2??????Br ??OCH 2CH 2CH 2??????CF 3??OCH 2CH 2CH 2??????CO 2CH 3??OCH 2CH 2CH 2??????CONHCH 3??OCH 2CH 2CH 2??????I ??OCH 2CH 2CH 2??????CH 3??OCH 2CH 2CH 2??????OCF 3??OCH 2CH 2CH 2??????OCHF 2??OCH 2CH 2CH 2??????OCF 3??OCH 2CH 2CH 2??????SCHF 2??CH 2NEtCH 2????????Cl ??CH 2NEtCH 2????????Br ??CH 2NEtCH 2????????CF 3??CH 2NEtCH 2????????CO 2CH 3??CH 2NEtCH 2????????CONHCH 3??CH 2NEtCH 2????????I ??CH 2NEtCH 2????????CH 3 | ??OCH 2???????Cl ??OCH 2???????Br ??OCH 2???????CF 3??OCH 2???????CO 2CH 3??OCH 2???????CONHCH 3??OCH 2???????I ??OCH 2???????CH 3??OCH 2???????OCF 3??OCH 2???????OCHF 2??OCH 2???????OCF 3??OCH 2???????SCHF 2??CH 2NHCH 2??Cl ??CH 2NHCH 2??Br ??CH 2NHCH 2??CF 3??CH 2NHCH 2??CO 2CH 3??CH 2NHCH 2??CONHCH 3??CH 2NHCH 2??I ??CH 2NHCH 2??CH 3??CH 2NHCH 2??OCF 3??CH 2NHCH 2??OCHF 2??CH 2NHCH 2??OCF 3??CH 2NHCH 2??SCHF 2??CONHCO???????Cl ??CONHCO???????Br ??CONHCO???????CF 3??CONHCO???????CO 2CH 3??CONHCO???????CONHCH 3??CONHCO???????I ??CONHCO???????CH 3 | ??OCH 2CH 2???????Cl ??OCH 2CH 2???????Br ??OCH 2CH 2???????CF 3??CCH 2CH 2???????CO 2CH 3??OCH 2CH 2???????CONHCH 3??OCH 2CH 2???????I ??OCH 2CH 2???????CH 3??OCH 2CH 2???????OCF 3??OCH 2CH 2???????OCHF 2??OCH 2CH 2???????OCF 3??OCH 2CH 2???????SCHF 2??CH 2NMeCH 2?????Cl ??CH 2NMeCH 2?????Br ??CH 2NMeCH 2?????CF 3??CH 2NMeCH 2?????CO 2CH 3??CH 2NMeCH 2?????CONHCH 3??CH 2NMeCH 2?????I ??CH 2NMeCH 2?????CH 3??CH 2NMeCH 2?????OCF 3??CH 2NMeCH 2?????OCHF 2??CH 2NMeCH 2?????OCF 3??CH 2NMeCH 2?????SCHF 2??CONMeCO??????????Cl ??CONMECO??????????Br ??CONMECO??????????CF 3??CONMeCO??????????CO 2CH 3??CONMeCO??????????CONHCH 3??CONMeCO??????????I ??CONMeCO??????????CH 3 |
T and V are Cl, and U is H
| ??????J????????????R | ?????J???????R | ?????J????????R |
| ??CH 2NEtCH 2????OCF 3??CH 2NEtCH 2????OCHF 2??CH 2NEtCH 2????OCF 2??CH 2NEtCH 2????SCHF 2 | ??CONECO????OCF 3??CONHCO????OCHF 2??CONHCO????OCF 3??CONHCO????SCHF 2 | ??CONMeCO????OCF 3??CONMeCO????OCHF 2??CONMeCO????OCF 3??CONMeCO????SCHF 2 |
T and V are Cl, and U is Me
| ????J?????????????????R | ????J???????????R | ????J?????????????R |
| CH 2CH 2CH 2CH 2????Cl CH 2CH 2CH 2CH 2????Br CH 2CH 2CH 2CH 2????CF 3CH 2CH 2CH 2CH 2????CO 2CH 3CH 2CH 2CH 2CH 2????CONHCH 3CH 2CH 2CH 2CH 2????I CH 2CH 2CH 2CH 2????CH 3CH 2CH 2CH 2CH 2????OCF 3CH 2CH 2CH 2CH 2????OCHF 2CH 2CH 2CH 2CH 2????OCF 3CH 2CH 2CH 2CH 2????SCHF 2OCH 2CH 2CH 2???????Cl OCH 2CH 2CH 2???????Br CCH 2CH 2CH 2???????CF 3OCH 2CH 2CH 2???????CO 2CH 3OCH 2CH 2CH 2???????CONHCH 3OCH 2CH 2CH 2???????I OCH 2CH 2CH 2???????CH 3OCH 2CH 2CH 2???????OCF 3OCH 2CH 2CH 2???????OCHF 2OCH 2CH 2CH 2???????OCF 3OCH 2CH 2CH 2???????SCHF 2CH 2NEtCH 2??????????Cl CH 2NEtCH 2??????????Br CH 2NEtCH 2??????????CF 3CH 2NEtCH 2??????????CO 2CH 3CH 2NEtCH 2??????????CONHCH 3CH 2NEtCH 2??????????I CH 2NEtCH 2??????????CH 3 | ??OCH 2?????????Cl ??OCH 2?????????Br ??OCH 2?????????CF 3??OCH 2?????????CO 2CH 3??OCH 2?????????CONHCH 3??OCH 2?????????I ??OCH 2?????????CH 3??OCH 2?????????OCF 3??OCH 2?????????OCHF 2??OCH 2?????????OCF 3??OCH 2?????????SCHF 2??CH 2NHCH 2????Cl ??CH 2NHCH 2????Br ??CH 2NHCH 2????CF 3??CH 2NHCH 2????CO 2CH 3??CH 2NHCH 2????CONHCH 3??CH 2NHCH 2????I ??CH 2NHCH 2????CH 3??CH 2NHCH 2????OCF 3??CH 2NHCH 2????OCHF 2??CH 2NHCH 2????OCF 3??CH 2NHCH 2????SCHF 2??CONHCO?????????Cl ??CONHCO?????????Br ??CONECO?????????CF 3??CONHCO?????????CO 2CH 3??CONHCO?????????CONHCH 3??CONHCO?????????I ??CONHCO?????????CH 3 | ??OCH 2CH 2??????Cl ??OCH 2CH 2??????Br ??OCH 2CH 2??????CF 3??OCH 2CH 2??????CO 2CH 3??OCH 2CH 2??????CONHCH 3??OCH 2CH 2??????I ??OCH 2CH 2??????CH 3??OCH 2CH 2??????OCF 3??OCH 2CH 2??????OCHF 2??OCH 2CH 2??????OCF 3??OCH 2CH 2??????SCHF 2??CH 2NMeCH 2????Cl ??CH 2NMeCH 2????Br ??CH 2NMeCH 2????CF 3??CH 2NMeCH 2????CO 2CH 3??CH 2NMeCH 2????CONHCH 3??CH 2NMeCH 2????I ??CH 2NMeCH 2????CH 3??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????OCHF 2??CH 2NMeCH 2????OCF 3??CH 2NMeCH 2????SCHF 2??CONMeCO?????????Cl ??CONMeCO?????????Br ??CONMeCO?????????CF 3??CONMeCO?????????CO 2CH 3??CONMeCO?????????CONHCH 3??CONMeCO?????????I ??CONMeCO?????????CH 3 |
T and V are Cl, and U is Me
| ??????J??????????R | ????J?????????R | ?????J????????R |
| ??CH 2NEtCH 2????OCF 3??CH 2NEtCH 2????OCHF 2??CH 2NEtCH 2????OCF 3??CH 2NEtCH 2????SCHF 2 | ??CONHCO????OCF 3??CONHCO????OCHF 2??CONHCO????OCF 3??CONHCO????SCHF 2 | ??CONMeCO????OCF 3??CONMeCO????OCHF 2??CONMeCO????OCF 3??CONMeCO????SCHF 2 |
T is Cl, and V and U are Me
| ???????J??????????R | ????J????R | ?????J??????????R |
| ??CH 2CH 2CH 2CH 2????Cl ??CH 2CH 2CH 2CH 2????Br ??CH 2CH 2CH 2CH 2????CF 3??CH 2CH 2CH 2CH 2????CO 2CH 3??CH 2CH 2CH 2CH 2????CONHCH 3??CH 2CH 2CH 2CH 2????I ??CH 2CH 2CH 2CH 2????CH 3??CH 2CH 2CH 2CH 2????OCF 3??CH 2CH 2CH 2CH 2????OCHF 2??CH 2CH 2CH 2CH 2????OCF 3??CH 2CH 2CH 2CH 2????SCHF 2??OCH 2CH 2CH 2???????Cl ??OCH 2CH 2CH 2???????Br ??OCH 2CH 2CH 2???????CF 3??OCH 2CH 2CH 2???????CO 2CH 3??OCH 2CH 2CH 2???????CONHCH 3??OCH 2CH 2CH 2???????I ??OCH 2CH 2CH 2???????CH 3??OCH 2CH 2CH 2???????OCF 3??OCH 2CH 2CH 2???????OCHF 2??OCH 2CH 2CH 2???????OCF 3??OCH 2CH 2CH 2???????SCHF 2??CH 2NEtCH 2?????????Cl ??CH 2NEtCH 2?????????Br ??CH 2NEtCH 2?????????CF 3??CH 2NEtCH 2?????????CO 2CH 3??CH 2NEtCH 2?????????CONHCH 3??CH 2NEtCH 2?????????I ??CH 2NEtCH 2?????????CH 3 | ??OCH 2???????Cl ??OCH 2???????Br ??OCH 2???????CF 3??OCH 2???????CO 2CH 3??OCH 2???????CONHCH 3??OCH 2???????I ??OCH 2???????CH 3??OCH 2???????OCF 3??OCH 2???????OCHF 2??OCH 2???????OCF 3??OCH 2???????SCHF 2??CH 2NHCH 2??Cl ??CH 2NHCH 2??Br ??CH 2NHCH 2??CF 3??CH 2NHCH 2??CO 2CH 3??CH 2NHCH 2??CONHCH 3??CH 2NHCH 2??I ??CE 2NFCH 2??CH 3??CH 2NFCH 2??OCF 3??CH 2NHCH 2??OCHF 2??CH 2NHCH 2??OCF 3??CH 2NHCH 2??SCHF 2??CONHCO???????Cl ??CONHCO???????Br ??CONHCO???????CF 3??CONHCO???????CO 2CH 3??CONHCO???????CONHCH 3??CONHCO???????I ??CONHCO???????CH 3 | ??OCH 2CH 2???????Cl ??OCH 2CH 2???????Br ??OCH 2CH 2???????CF 3??OCH 2CH 2???????CO 2CH 3??OCH 2CH 2???????CONHCH 3??OCH 2CH 2???????I ??OCH 2CH 2???????CH 3??OCH 2CH 2???????OCF 3??OCH 2CH 2???????OCHF 2??OCH 2CH 2???????OCF 3??OCH 2CH 2???????SCHF 2??CH 2NMeCH 2?????Cl ??CH 2NMeCH 2?????Br ??CH 2NMeCH 2?????CF 3??CH 2NMeCH 2?????CO 2CH 3??CH 2NMeCH 2?????CONHCH 3??CH 2NMeCH 2?????I ??CH 2NMeCH 2?????CH 3??CH 2NMeCH 2?????OCF 3??CH 2NMeCH 2?????OCHF 2??CH 2NMeCH 2?????OCF 3??CH 2NMeCH 2?????SCHF 2??CONMeCO??????????Cl ??CONMeCO??????????Br ??CONMeCO??????????CF 3??CONMeCO??????????CO 2CH 3??CONMeCO??????????CONHCH 3??CONMeCO??????????I ??CONMeCO??????????CH 3 |
T is Cl, and V and U are Me
| ????J???????????R | ?????J???????R | ?????J????????R |
| ??CH 2NEtCH 2????OCF 3??CH 2NEtCH 2????OCHF 2??CH 2NEtCH 2????OCF 3??CH 2NEtCH 2????SCHF 2 | ??CONHCO????OCF 3??CONHCO????OCHF 2??CONHCO????OCF 3??CONHCO????SCHF 2 | ??CONMeCO????OCF 3??CONMeCO????OCHF 2??CONMeCO????OCF 3??CONMeCO????SCHF 2 |
Composition
Originally return and relate to bactericidal composition, it comprises the formula I compound (comprising that all geometry and stereoisomer, its N-oxide and agricultural go up suitable salt) of (1) sterilization effective dose, and (2) (i) at least a other insecticides, bactericide, nematocide, bactericide, miticide, growth regulator, chemosterilant, semiochemical, repellant, attractant, pheromones, help food agent or other bioactive compound; And/or (ii) at least a other compositions that are selected from surfactant, solid diluent and liquid diluent.
Noticeable composition comprises the compound of (a) at least a formula I, and (b) at least a compound that is selected from following group:
(b1) two (dithiocarbamate) bactericide of alkylidene,
(b2) act on the bc of fungi mitochondrial respiratory electronics metastasis site
1The compound of compound,
(b3) cymoxanil,
(b4) act on the compound of the demethylase in the sterol biosynthesis pathway,
(b5) act on the morpholine and the piperidine compounds of sterol biosynthesis pathway,
(b6) phenyl amide bactericide,
(b7) pyrimidone bactericide,
(b8) phthalimide, and
(b9) fosetyl.
The weight ratio of component (b) and component (a) is usually 100: 1-1: between 100, be preferably 30: 1-1: between 30, and more preferably 10: 1-1: between 10.Noticeable composition is that the weight ratio of component (b) and component (a) is 10: 1-1: between 1.Bc
1Compound bactericide (component (b2))
Oneself know imines bacterium bactericide such as nitrile Fluoxastrobin, imines bacterium, fork phenalgin acid amides (metominostrobin/fenominostrobin) (SSF-126), the bactericidal action pattern of picoxystrobin, pyraclostrobin and trifloxystrobin can suppress the bc in the mitochondrial respiratory chain
1Compound (Angew.Chem.Int.Ed.，1999，38，1328-1349)。At BiochemicalSociety Transactions 1993,22, among the 68S, (E)-and 2-[[6-(2-cyano-benzene oxygen)-4-pyrimidine radicals] the oxygen base]-α-(methoxyimino) methyl phenylacetate (being also referred to as the nitrile Fluoxastrobin) is described to bc
1The inhibitor of compound.At Biochemical Society Transactions 1993,22, among the 64S, (E)-and α-(methoxyimino)-2-[(2-methylphenoxy) methyl] methyl phenylacetate (being also referred to as imines bacterium (kresoxim-methyl)) is described to bc
1The inhibition of compound is neat.At Biochemistry and Cell Biology 1995,85 (3), among the 306-311, (E)-2-[(2,5-dimethyl phenoxy) methyl]-α-(methoxyimino)-N-methylbenzene acetamide is described to bc
1The inhibitor of compound.Suppress the bc in the mitochondrial respiratory chain
1Other compounds Bao Kuo azolactone bacterium and the fenamidone of compound.
Bc
1Compound also is known as other title sometimes in biochemical document, comprise the composite I II and the ubihydroquinones (ubihydroquinope) of electron transfer chain: the cytochrome c oxidoreductase.The Enzyme Commission is with its called after EC1.10.2.2 uniquely.For example at J.Biol.Chem.1989,264,14543-38; Methods Enzymol.1986,126, in 253-71 and the document wherein quoted bc has been described all
1Compound.
Sterol biosynthesis inhibitor bactericide (component (h4) or (b5))
Sterol biosynthesis inhibitor class material comprises DMI and non-DMI compound, and they control fungi by the enzyme that suppresses in the sterol biosynthesis path.The DMI bactericide has identical site of action in the sterol biosynthesis path of fungi; That is to say, suppress the demethylation at lanosterol or 14 places of 24-methylene lanosterol, and these two kinds of precursors that material is a sterol in the fungi.The compound that acts on this position is commonly referred to demethylase inhibitor, DMI bactericide or DMIs.In biochemical document, this demethylase also is known as other title sometimes, comprises cytochrome P-450 (14DM).For example at J.Biol.Chetn.1992,267, in 13175-79 and the document wherein quoted this demethylase has been described.The DMI bactericide has several classifications: pyroles (comprising triazole and imidazoles), miazines, piperazines and pyridines.Triazole bactericidal agent comprises bromuconazole, cyproconazole, Difenoconazole, alkene azoles alcohol, oxole bacterium, RH-7592, Fluquinconazole, Flusilazole, Flutriafol, own azoles alcohol, cycltebuconazole, ring penta azoles bacterium, penconazole, ring third azoles, Tebuconazole, fluorine azoles ether, triazolone, triadimenol, fork penta azoles bacterium and uniconazole P.The imidazoles bactericide comprises clotrimazole, econazole, IMAZALIL, isoconazole, miconazole and Prochloraz.The miazines bactericide comprises fenarimol, nuarimol and triarimol.The piperazines bactericide comprises triforine.The pyridines bactericide comprises buthiobate and pyrifenox.As people such as K.H.Kuck, Modern SelectiveFungicides-Properties, Applications and Mechanisms of Action, Lyr, H. edits; Gustav Fischer Verlag:New York, 1995, described in the 205-258, Biochemical Research shows that all above-mentioned bactericide all are the DMI bactericide.
The DMI bactericide has been referred to as one group, with sterol biosynthesis inhibitor such as morpholine and the piperidines bactericide that is different from other.Morpholine and piperidines also are the sterol biosynthesis inhibitors, but have shown it is step after suppressing to lean in the sterol biosynthesis path.The morpholine series bactericidal agent comprises aldimorph, dodemorfe, butadiene morpholine, tridemorph and trimorphamide.The piperidines bactericide comprises fenpropidin.
As people such as K.H.Kuck, Modern Selective Fungicides-Properties, Applications and Mechanisms of Action, Lyr, H. edits; Gustav Fischer Verlag:New York, 1995, described in the 185-204, Biochemical Research shows that all above-mentioned morpholines and piperidines bactericide all are sterol biosynthesis inhibitor bactericide.
Pyrimidone kills basic microbial inoculum (component (b7))
The pyrimidone bactericide comprises the compound of formula II:
Wherein:
G is fused phenyl, thiophene or pyridine ring,
R
1Be C
1-6Alkyl;
R
2Be C
1-6Alkyl or C
1-6Alkoxyl,
R
3Be halogen, and
R
4It is hydrogen or halogen.
The pyrimidone bactericide has been described: International Patent Application WO 94/26722, United States Patent (USP) 6,066,638, United States Patent (USP) 6,245,770, United States Patent (USP) 6,262,058 and United States Patent (USP) 6,277,858 in following document.
Noticeable pyrimidone bactericide is selected from following group:
6-bromo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone,
6,8-two iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone,
6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone,
6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone,
6-bromo-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone,
7-bromo-2-propoxyl group-3-propyl group thieno [3,2-d] pyrimidines-4 (3H)-ketone,
6-bromo-2-propoxyl group-3-propyl group pyrido [2,3-d] pyrimidines-4 (3H)-ketone,
6,7-two bromo-2-propoxyl group-3-propyl group thieno [3,2-d] pyrimidines-4 (3H)-ketone, and
3-(cyclopropyl methyl)-6-iodo-2-(rosickyite base) pyrido [2,3-d] pyrimidines-4 (3H)-ketone.
Table 9
The example of component (b)
(b1) alkylidene two (two Thiocarbamates) is as mancozeb, maneb, propineb and zineb
(b3) cymoxanil
(b6) phenyl amide such as metalaxyl, M 9834 He the spirit of Evil frost
(b8) phthalimide such as folpet or captan
(b9) fosetyl
Can or make up other bactericide that are included in the present composition with component (a) and component (b) with the combination of formula I compound is: acibenzolar, M 9834, benomyl, blasticidin-S, bordeaux mixture (basic copper sulfate), carpropamide, difoltan, captan, carbendazim, chloroneb, tpn, Cupravit, mantoquita such as copper sulphate and Kocide SD, cyazofamid, cymoxanil, encircle third pyrimidine, (S)-3,5-two chloro-N-(3-chloro-1-ethyl-1-methyl-2-oxo-propyl group)-4-methyl benzamide (RH 7281), diclocymet (S-3900), diclomezine, botran, dimethomorph, alkene azoles alcohol, dodemorfe, dodine, Hinosan, fencaramid (SZX0722), fenpiclonil, potato temperature tin, fentin hydroxide, fluazinam Fu Evil bacterium, fluorine biphenyl bacterium (RPA 403397), flutolanil, folpet, fosetyl, Furalaxyl, furan pyrazoles spirit (S-82658), iprobenfos, different third is fixed, kitazine, iprovalicarb, kasugarnycin, mancozeb, maneb, mefenoxam, third oxygen embroidery amine that goes out, metalaxyl, Carbatene, nitrile bacterium azoles, the spirit of Neo-Asozin (methylarsonic acid iron) Evil frost, Pencycuron, Prochloraz, the sterilization profit, the clever propineb of hundred dimensions, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen Luo Evil amylamine, sulphur, thifluzamide, thiophanate methyl, tmtd, triazolone, tricyclazole, valida, vinclozolin, zineb and zoxamid.
The description of above commercial compound can reference: The Pesticide Manual, the 12nd edition, C.D.S.Tomlin edits, British Crop Protection Council, 2000.
It should be noted that the combination of the bactericide (for example mitochondrial respiratory suppresses, synthesizes to come the Profilin synthetic or to suppress 'beta '-tubulin synthetic by what disturb rRNA) of formula I compound and different biochemical action patterns, this is for preventing that drug resistance from being particularly advantageous.The example of these combinations comprises the combination of formula I compound (as compound 1) and following bactericide: imines mushroom medicine such as nitrile Fluoxastrobin, imines bacterium, pyraclostrobin and trifloxystrobin; Carbendazim, mitochondrial respiratory inhibitor such as azolactone bacterium and fenamidone; Benomyl, cymoxanil; Dimethomorph; Folpet; Fosetyl; Metalaxyl; Mancozeb and maneb.These combinations are for preventing that drug resistance from being particularly advantageous, especially during the identical or similar disease of the bactericide control of combination.
Noticeable combination is formula I compound and is used to control the grape disease (as Plasmoparaviticola, Botrytis cinerea and Uncinula necatur) the combination of bactericide, comprise that alkylidene two (two Thiocarbamates) is as mancozeb, maneb, propineb and zineb, phthalimide such as folpet, mantoquita such as copper sulphate and Kocide SD, imines bacterium such as nitrile Fluoxastrobin, pyraclostrobin and trifloxystrobin, mitochondrial respiratory inhibitor such as azolactone bacterium and fenamidone, phenyl amide such as metalaxyl, phosphonate ester such as fosetyl, dimethomorph, pyrimidone bactericide such as 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone and 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidine-4 (3H)-ketone, and other bactericide such as cymoxanil.
Noticeable combination is a formula I compound and the combination of the bactericide that is used to control potato disease (for example Phytophthora infestans, Altemaria solani and Rhizoctonia solani), comprises that alkylidene two (two Thiocarbamates) is as mancozeb, maneb, propineb and zineb; Mantoquita such as copper sulphate and Kocide SD; Imines mushroom medicine such as pyraclostrobin and trifloxystrobin; Mitochondrial respiratory inhibitor such as azolactone bacterium and fenamidone; Phenyl amide such as metalaxyl; Carbamates is as hundred dimension spirits; Phenylpyridyl amine such as fluazinam, and other bactericide such as tpn, cyazofamid, cymoxanil, dimethomorph, zoxamid and iprovalicarb.
Noticeable combination is, wherein component (b) comprises at least a two the not compounds on the same group that are selected from respectively, and described different group then is selected from (b1), (b2), (b3), (b4), (b5), (b6), (b7), (b8) and (b9).The weight ratio of second group compound during first group compound in this two components (b) group is organized with these components (b) normally 100: 1-1: 100, that more common is 30:1-1: 30, and most typical be 10: 1-1: 10.
Noticeable composition is, wherein component (b) comprises the compound of at least a being selected from (b1), mancozeb for example, and at least a compound that is selected from second component (b) group, described second component (b) group for example is selected from (b2), (b3), (b6), (b7), (b8) or (b9).It should be noted that following composition especially, wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b1) and component (a) is 10: 1-1: 1.The example of these compositions comprises the composition that contains following mixture: component (a) (compound among preferred index table A, B or the C) and mancozeb and be selected from compound: azolactone bacterium, fenamidone, nitrile Fluoxastrobin, imines bacterium, pyraclostrobin, trifloxystrobin, cymoxanil, metalaxyl, the spirit of M 9834, Evil frost, 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone, 6-chloro-2 propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H) ketone, folpet, captan and fosetyl in following group.
Also noticeable composition is, wherein component (b) comprises the compound Li such as the azolactone bacterium of at least a being selected from (b2), and at least a compound that is selected from second component (b) group, described second component (b) group is selected from (b1), (b3), (b6), (b7), (b8) or (b9).Noticeable especially composition is that wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b2) and component (a) is 10: 1-1: 1.The example of these compositions comprises the composition that contains following mixture: (the compound) among preferred index table A, B or the C is Yu azolactone bacterium and be selected from compound in following group: mancozeb, maneb, propineb, zineb, cymoxanil, metalaxyl, the spirit of M 9834, Evil frost, 6-iodo-3-propyl group-2-propyl group oxygen base 4 (3H)-quinazolinones, 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone, folpet, captan and fosetyl for component (a).
Also noticeable composition is, wherein component (b) comprises the compound of (b3), promptly, cymoxanil, and at least a compound that is selected from second component (b) group, described second component (b) group for example is selected from (b1), (b2), (b6), (b7), (b8) or (b9).Noticeable especially composition is that wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b3) and component (a) is 10: 1-1: 1.The example of these compositions comprises the composition that contains following mixture: component (a) (preferred index table A, compound among B or the C) with cymoxanil and be selected from compound: azolactone bacterium in following group, fenamidone, the nitrile Fluoxastrobin, the imines bacterium, pyraclostrobin, trifloxystrobin, mancozeb, maneb, propineb, zineb, metalaxyl, the spirit of M 9834 Evil frost, 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone, 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone, folpet, captan and fosetyl.
Also noticeable composition is, wherein component (b) comprises the compound of at least a being selected from (b6), metalaxyl for example, and at least a compound that is selected from second component (b) group, described second component (b) group for example is selected from (b1), (b2), (b3), (b7), (b8) or (b9).Noticeable especially composition is that wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b6) and component (a) is 10: 1-1: 3.The example of these compositions comprises the composition that contains following mixture: component (a) (preferred index table A, compound among B or the C) with metalaxyl Huo Evil frost spirit and be selected from compound: azolactone bacterium in following group, fenamidone, the nitrile Fluoxastrobin, the imines bacterium, pyraclostrobin, trifloxystrobin, cymoxanil, mancozeb, maneb, propineb, zineb, 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone, 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone, folpet, captan and fosetyl.
Also noticeable composition is, wherein component (b) comprises the compound of at least a being selected from (b7), for example 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone or 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidine-4 (3H)-ketone, and at least a compound that is selected from second component (b) group, described second component (b) group is selected from (b1), (b2), (b3), (b6), (b8) or (b9).Noticeable especially composition is that wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b7) and component (a) is 1: 1-1: 20.Wherein component (b6) is 1 with the weight ratio of component (a): 4.5-1: in 9 composition is also included within.The example of these compositions comprises the composition that contains following mixture: component (a) (preferred index table A, compound among B or the C) with 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone or 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone and be selected from compound: azolactone bacterium in following group, fenamidone, the nitrile Fluoxastrobin, the imines bacterium, pyraclostrobin, trifloxystrobin, cymoxanil, mancozeb, maneb, propineb, zineb, metalaxyl, the spirit of M 9834 Evil frost, folpet, captan and fosetyl.
Also noticeable composition is, wherein component (b) comprises the compound of (b9), promptly, fosetyl, and at least a compound that is selected from second component (b) group, described second component (b) group for example is selected from (b1), (b2), (b3), (b6) or (b7).Noticeable especially composition is that wherein component (b) is 30 with the gross weight ratio of component (a): 1-1: 30, and also the weight ratio of component (b9) and component (a) is 10: 1-1: 3.The example of these compositions comprises the composition that contains following mixture: component (a) (preferred index table A, compound among B or the C) with fosetyl and be selected from compound: azolactone bacterium in following group, fenamidone, the nitrile Fluoxastrobin, the imines bacterium, pyraclostrobin, trifloxystrobin, mancozeb, maneb, propineb, zineb, metalaxyl, the spirit of M 9834 Evil frost, 6-iodo-3-propyl group-2-propyl group oxygen base-4 (3H)-quinazolinone, 6-chloro-2-propoxyl group-3-propyl group thieno [2,3-d] pyrimidines-4 (3H)-ketone, folpet, captan and cymoxanil.
Noticeable combination is formula I compound and has the more combination of the bactericide of wide spectrum agricultural protection effect, comprises imines mushroom medicine such as nitrile Fluoxastrobin, imines bacterium, pyraclostrobin and trifloxystrobin; Morpholine series bactericidal agent such as the fixed and butadiene morpholine of benzene rust; Triazole bactericidal agent such as bromuconazole, cyproconazole, Difenoconazole, oxole bacterium, Flusilazole, cycltebuconazole, ring penta azoles bacterium, ring third azoles, Tebuconazole and pitch penta azoles bacterium; The pyrimidone bactericide, benomyl; Carbendazim; Tpn; Dimethomorph; Folpet; Mancozeb; Maneb; Quinoxyfen; Valida and vinclozolin.
It should be noted that with other to have the more combination of the bactericide of wide spectrum agricultural protection effect, comprise that nitrile Fluoxastrobin, imines bacterium, pyrclostrobin, trifloxystrobin, benomyl, carbendazim, tpn, dimethomorph, folpet, mancozeb, maneb, quinoxyfen, valida, vinclozolin, benzene rust are fixed, butadiene morpholine, bromuconazole, cyproconazole, Difenoconazole, oxole bacterium, Flusilazole, cycltebuconazole, ring penta azoles bacterium, ring third azoles, Tebuconazole and pitch penta azoles bacterium.
It should be noted that and other combinations that this is for preventing that drug resistance from being particularly advantageous with bactericide (for example mitochondrial respiratory suppresses, synthesizes to come the Profilin synthetic or to suppress 'beta '-tubulin synthetic by what disturb rRNA) of different binding modes.Its example comprises the combination of compound (for example compd A l) Yu the following material of formula I: nitrile Fluoxastrobin, imines bacterium, pyrclostrobin, trifloxystrobin, carbendazim, azolactone bacterium, fenamidone, benomyl, cymoxanil, dimethomorph, folpet, fosetyl, metalaxyl, mancozeb, maneb.These combinations are for preventing that drug resistance from being particularly advantageous, especially during the identical or similar disease of the bactericide control of combination.
It should be noted that and be used to control the combination of other bactericide of grape disease, comprise dithiocarbamate such as mancozeb, maneb, propineb and zineb, phthalimide such as folpet, mantoquita such as copper sulphate and Kocide SD, imines mushroom medicine such as nitrile Fluoxastrobin, pyrclostrobin and trifloxystrobin, phenyl amide such as metalaxyl, phosphonate ester such as fosetyl, morpholine series bactericidal agent such as dimethomorph, and other bactericide such as cymoxanil, azolactone bacterium and fenamidone.
It should be noted that and be used to control the combination of other bactericide of potato, comprise dithiocarbamate such as mancozeb, maneb, propineb and zineb, mantoquita such as copper sulphate and Kocide SD, imines mushroom medicine such as pyrclostrobin and trifloxystrobin, phenyl amide such as metalaxyl, carbamate is as hundred dimension spirits, phenylpyridyl amine such as fluazinam, morpholine series bactericidal agent such as dimethomorph, and other bactericide such as tpn, cyazofamid, cymoxanil azolactone bacterium, fenamidone, zoxamid and iprovalicarb.
It should be noted that the combination of compd A l and nitrile Fluoxastrobin especially, the combination of compd A l and imines bacterium, the combination of compd A l and pyrclostrobin, the combination of compound l and trifloxystrobin, the combination of compound 1 and carbendazim, the combination of compd A l and tpn, the combination of compd A l and dimethomorph, the combination of compd A l and folpet, the combination of compd A l and mancozeb, the combination of compd A l and maneb, the combination of compd A l and quinoxyfen, the combination of compd A l and valida, the combination of compd A l and vinclozolin, compd A l and benzene rust are fixed, compd A l and butadiene morpholine, compd A l and bromuconazole, compd A l and cyproconazole, compd A l is Yu Difenoconazole, compd A l and oxole bacterium, compd A l and Flusilazole, compd A l and cycltebuconazole, compd A l and ring penta azoles bacterium, compd A l and ring third azoles, compd A l and Tebuconazole, compd A l and fork penta azoles bacterium, compd A l is Yu the azolactone bacterium, compd A l and fenamidone, compd A l and benomyl, compd A l and cymoxanil, compd A l and dimethomorph, compd A l and folpet, compd A l and fosetyl, compd A l and metalaxyl, compd A l and compd A l and propineb, compd A l and zineb, compd A l and copper sulphate, compd A l and Kocide SD, compd A l and hundred dimension etherealize compound Al and cyazofamid, compd A l and zoxamid, and the combination of compd A l and iprovalicarb.Compound number can be referring to the compound among the index table A-D.
Component (a) compound preferred 15, that preferred compositions comprises mixes with cymoxanil.
Preferred 16, preferred compositions comprises the compound and the compound that is selected from (b1) of component (a).More preferably, wherein the compound of (b1) is the composition of mancozeb.
Preferred 17, preferred compositions comprises the compound and the compound that is selected from (b2) of component (a).The composition of the compound of (b2) Wei azolactone bacterium more preferably wherein.
Preferred compositions comprises that the compound of component (a) and two are selected from two not compound on the same group, and described two is not to be selected from (b1), (b2), (b3), (b4), (b5), (b6), (b7), (b8) and (b9) on the same group.
Preferred compositions is that wherein component (a) is the formula I compound compositions that shows among the above-mentioned preferred 1-14.
Compound of the present invention also can be with one or more insecticides, bactericide, nematocide, bactericide, miticide, growth regulator, chemosterilant, semiochemical, repellant, attractant, pheromones, help food agent or other bioactive compound to mix; form multi-component insecticide, produce the more agricultural protection effect of wide spectrum.The agricultural protection agent that can prepare with composition of the present invention is: insecticide such as Olivomitecidin, orthen, gusathion m, bifenthrin, Buprofezin, furadan, fluorine azoles worm is clear, poison barnyard grass with poison, methyl is poisoned barnyard grass with poison, cyfloxylate, the beta-cyfloxylate, cyhalothrin, the lambda-cyhalothrin, decis, it is grand to kill mite sulphur, basudin, TH-6040, Rogor, esfenvalerate, ABG-6215, fenpropathrin, kill the chrysanthemum ester, sharp strength spy, flucythrinate, taufluvalinate, fonophos, the pyrrole worm is made a din, propylamine phosphorus, marathon, mite ox enemy, acephatemet, methidathion, methomyl, Entocon ZR 515, methoxychlor, 7-chloro-2,5-dihydro-2-[[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy) phenyl] amino] carbonyl] indeno [1,2-e] [1,3,4]-oxadiazines-4a (3H)-carboxylate methyl ester (oxadiazole worm), nuvacron, methomyl, one six 0 five, methyl 1, ammonia chrysanthemum ester, phorate, zolone, phosmet, phosphamidon, Aphox, Profenofos, rotenone, the second Toyodan, RH-5992, tefluthrin, Terbufos, Ravap, UC-51762, tralomethrin, chlorophos and desinsection are grand; Bactericide such as streptomycin; Miticide such as amitraz, worm mite are violent, chlorobenzilate, plictran, kelthane, Hooker HRS 16, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, azoles mite ester, Hexythiazox, propargite, pyridaben and tebufenpyrad; Nematocide such as sulfone go out prestige and Nemacur and biological agent such as Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculoviral and entomopathogenic bacterium, virus and fungi.The weight ratio of these various blending ingredients and the present invention's formula I compound is usually 100: 1-1: between 100, preferably 30: 1-1: between 30, more preferably 10: 1-1: between 10, and most preferably 4: 1-1: between 4.
The description of aforesaid commercial compound can referring to: The Pesticide Manual, the 12nd edition, C.D.S.Tomlin edits, British Crop Protection Council, 2000.
Preparation
Suitable carriers is with the form use of preparation or composition on agricultural usually for compound of the present invention, and this carrier comprises in liquid diluent, solid diluent or the surfactant at least a.The selection of preparation or composition components should be consistent with physical property, method of application and environmental factor such as soil types, humidity and the temperature of active component.Useful preparation comprises liquid such as solution (comprising emulsible concentrate), suspension, emulsion (comprising microemulsion and/or suspension emulsion) etc., and they can choose thickening wantonly is gel.Useful preparation also comprises solid, for example can disperse (wettable) or water miscible pulvis, powder, particle, pill, tablet, film etc. in water.Active component can (little) encapsulate, and can further be shaped to supensoid agent or solid pharmaceutical preparation; Perhaps, the whole preparation of active component is all by encapsulate (perhaps whole encapsulate (overcoated)).Encapsulate controlled or delayed release of active elements.Sprayable preparation can extend in the suitable medium, and uses with the sprayed volume of the hundreds of liters of per hectare 1-.High concentration composition mainly is as the intermediate of further preparing usefulness.
Preparation comprises active component and thinner in following approximate range and/or the surfactant of effective dose (for example 0.01-99.99 weight %) usually, and they add to 100 weight % mutually.
| Percetage by weight | |||
| Active component | Thinner | Surfactant | |
| Water dispersible and water miscible particle, tablet and powder | ????5-90 | ????0-94 | ??1-15 |
| Suspension, emulsion, solution (comprising emulsible concentrate) | ????5-50 | ????40-95 | ??0-25 |
| Pulvis | ????1-25 | ????70-99 | ??0-5 |
| Particle and pill | ????0.01-99 | ????5-99.99 | ??0-15 |
| High concentration composition | ????90-99 | ????0-10 | ??0-2 |
The typical solid thinner is described in the following document: people such as Watkins, Handbook ofInsecticide Dust Diluents and Cartiers, the 2nd edition, Dorland Books, Caldwell, New Jersey.Typical liquid diluent is described in the following document: Marsden, SolventsGuide, the 2nd edition, Interscience, New York, 1950.McCutcheon ' s Detergents andEmulsifiers Annual, Allured Publ.Corp., Ridgewood, New Jersey and Siselyand Wood, Encyclopedia of Surface Active Agents, Chemical Publ.Co., Inc., New York, 1964, listed the application of surfactant and recommendation.All preparations all comprise minor amounts of additives, to reduce foam, caking, burn into growth of microorganism etc., perhaps comprise thickener to increase viscosity.
Surfactant for example comprises polyethoxylated alcohols, polyethoxylated alkyl phenol, polyethoxylated fatty acid esters of sorbitan, dialkyl sulfosuccinate succinate, alkyl sulfate, benzene sulfonamide acid esters, organo-silicon compound, N, N-dialkyl group taurine ester, lignosulphonic acid ester, naphthalene sulfonic acid-formaldehyde condensation product, polycarboxylate and polyoxyethylene/polyoxypropylene block copolymers.Solid diluent for example comprises clay, as bentonite, imvite, aminanthine and kaolin, and starch, sugar, silica, talcum, diatomite, urea, calcium carbonate, sodium carbonate and sodium bicarbonate and sodium sulphate.Liquid diluent for example comprises water, N, dinethylformamide, dimethyl sulfoxide (DMSO), N-alkyl pyrrolidone, ethylene glycol, polypropylene glycol, paraffin, alkylbenzene, Fluhyzon, olive oil, castor oil, Linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soya-bean oil, rapeseed oil and cocoa butter, fatty acid ester, ketone such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2 pentanone, and alcohol is as methyl alcohol, cyclohexanol, decyl alcohol and tetrahydrofurfuryl alcohol.
Solution comprises emulsible concentrating, and can prepare by mixing each component simply.Pulvis and powder can prepare by mixing up and grinding in hammer-mill or fluid energy grinding machine usually.Suspension normally prepares by wet grinding, for example referring to U.S.3, and 060,084.Preferred suspension concentrates is those concentrates that also comprise 5-20% non-ionic surface active agent (for example polyethoxylated fatty alcohol) and optional combination 59-65% liquid diluent and maximum 5% anion surfactants except that active component.Particle and pill can prepare by active substance is sprayed on the particulate vector or by agglomeration technique.Referring to: Browning, " Agglomeration ", and ChemicalEngineering, December 4,1967, the 147-48 page or leaf; Perry ' s Chemical Engineer ' sHandbook, the 4th edition, McGraw-Hill, New York, 1963, the 8-57 and page or leaf subsequently; With WO 91/13546.Pill can be prepared described in 172,714 as U.S.4.Can in water, disperse and water miscible particle can be prepared according to the method for instructing in the following document: U.S.4,144,050, U.S.3,920,442 and DE 3,246,493.Tablet can be prepared according to the method for instructing in the following document: U.S.5,180,587, U.S.5,232,701 and U.S.5,208,030.Film can be prepared according to the method for instructing in the following document: GB 2,095, and 558 and U.S.3,299,566.
The further information of relevant preparation can be with reference to T.S.Woods, " The Formulator ' sToolbox-Product Forms for Modem Agriculture " in Pesticide Chemistry andBioscience, The Food-Environment Challenge, T.Brooks and T.R.Roberts edit, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, the 120-133 pages or leaves.Also can be with reference to U.S.3, the 235,361, the 6th hurdle the 16th walks to the 7th hurdle the 19th row and embodiment 10-41; U.S.3, the 309,192, the 5th hurdle the 43rd walks to the 7th hurdle the 62nd row and embodiment 8,12,15,39,41,52,53,58,132,138-140,162-164,166,167 and 169-182; U.S.2, the 891,855, the 3rd hurdle the 66th walks to the 5th hurdle the 17th row and embodiment 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, the 81-96 pages or leaves; And people such as Hance, Weed Control Handbook, the 8th edition, Blackwell Scientific Publications, Oxford, 1989.
In following examples, all percentage all is percentage by weight, and all preparations all prepare according to conventional method.But the compound among compound number benchmark index Table A-D.
Embodiment A
Wettable powder
| Compd A 1 | 65.0％ |
| The dodecylphenol polyglycol ether | 2.0％ |
| Sodium lignosulfonate | 4.0％ |
| Sodium silicoaluminate | 6.0％ |
| Imvite (through sintering) | 23.0％ |
Embodiment B
Particle
| Compd A 1 | 10.0％ |
| Aminanthine particle (low volatility materials, 0.71/0.30mm, U.S.S.25-50 number sieve) | 90.0％ |
Embodiment C
Extrude ball
| Compd A 1 | 25.0％ |
| Anhydrous sodium sulfate | 10.0％ |
| Thick Lignosite | 5.0％ |
| Negel | 1.0％ |
| Calcium magnesium bentonite | 59.0％ |
Embodiment D
Emulsible concentrate
| Compd A 1 | 20.0％ |
| Oil-soluble sulfonic acid ester and APEO mix up thing | 10.0％ |
| Isophorone | 70.0％ |
Embodiment E
| Compd A 1 | 20.0％ |
| Polyethoxylated fatty alcohol-non-ionic surface active agent | 15.0％ |
| The ester derivant of montan wax | 3.0％ |
| Lignosite-anion surfactant | 2.0％ |
| Polyethoxylated/poly-propoxylation polyethyleneglycol block copolymer surfactant | 1.0％ |
| Propane diols-thinner | 6.4％ |
| Poly-(dimethyl siloxane)-defoamer | 0.6％ |
| Bactericide | 0.1％ |
| Water-thinner | 51.9％ |
The preparation composition is mixed into syrupy shape, adds compd A l, then homogenizing mixture in blender.The gained slurries carry out wet grinding, form suspending concentrate.
Practicality
The compound of formula I and composition can be used as plant disease control agent and use.Therefore, the present invention includes the method that is used to control the plant disease that is caused by fungal plant pathogen, it comprises to described plant or its part or to plant seed or seedling uses the The compounds of this invention of sterilization effective dose or comprises described compound compositions.
Preferred using method relates to above preferred compound or composition.
The disease that the compound of formula I and composition controlled are caused by Basidiomycete, Ascomycete, Oomycete and Deuteromycete class broad spectrum fungus phytopathogen.They are effectively for the plant disease of control wide spectrum, particularly the leaf portion pathogene of ornamental plants, vegetables, field crop, cereal and fruit.These pathogene comprise Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonosporacubensis, Pythium aphanidermatum, Alternaria brassicae, Septorianodorum, Septoria tritici, Cercosporidium personatum, Cercosporaarach idicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicota, Pyricularia oryzae, Podosphaeraleucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Pucciniastriiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae, Pythium aphanidermatum, Phytophthora megasperma, Sclerotinia sclerotiorum, Sclerotium rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomyces graminis, Rynchosporium secalis, Fusarium roseum, kind and genus that Bremia lactucae and other these pathogene are closely related.Composition of the present invention is effective especially for Plasmopara viticola and the Phytophthora infestans on potato and the tomato on the control grape.
The control of plant disease is normally by on the part such as root, stem, leaf, fruit, seed, stem tuber or bulb of plant to be protected; perhaps on the medium that plant grew to be protected (soil and sand), before infecting or the formula I compound of using effective dose after infecting realize.Compound of the present invention also can be applied on the seed with protection seed and seedling.
The rate of application of The compounds of this invention can be subjected to many such environmental effects, and should determine according to the service condition of reality.When rate of application is lower than the 1g/ha-5000g/ha active component, can protect leaf portion usually.When the per kilogram seed digests the compound processing with 0.1-10, can protect seed and seedling usually.
Below the suitable special pathogene that is used for according to the present invention is renderd a service in the control of test confirmation The compounds of this invention.But the pathogene control protective effect that these compounds provided is not limited to these kinds.These tests can be used for also confirming that the present composition renders a service special control of pathogens.Spraying comprises the test suspension of single active component, renders a service with the independent control that confirms active component.Control during for the confirmation combination is renderd a service, (a) active component can suitable amount be combined in the single test suspension, (b) can prepare single active component raw material solution, mix with suitable ratio then and be diluted to final desirable concentration, form the test suspension, perhaps (c) the test suspension of sequentially spraying and comprising single active component according to the ratio of hope.
Synergy is described to " the effect of helping each other between two components of mixture (for example component (a) and component (b)); it is longer (referring to Tames; P.M.L.; Neth.J.Plant Pathology; 1964; 70,73-80) to make that total effect is higher than two (perhaps more a plurality of) summation or action time when component is used separately.Between two active components, exist synergy to determine (referring to Colby by means of the Colby equation, S.R.In Calculating Synergistic and AntagonisticResponses of Herbicide Combinations, Weeds, 1967,15,20-22):
p＝A+B-[A×B/100]
When using the method for Colby, the active p of mixture that the activity when at first using separately based on two components is calculated prediction determines whether there is cooperative interaction thus between two active components.If p is lower than the effect of measuring, then act synergistically.In above-mentioned equation, A is the bactericidal activity of percentage control when using a component with the x rate of application separately.B is the bactericidal activity of percentage control when using second component with the y rate of application separately.The p value of this equation estimation is that rate of application is the bactericidal activity of the mixture of the A of x and the B that rate of application is y, if the strict addition of their effect and not interacting.
Referring to being used for describing the index table A-D that is fit to the compound that the present invention uses.It is methyl that the abbreviation of using in the index table has following connotation: Me, and Et is an ethyl, and Ph is a phenyl, and OMe is a methoxyl group, and OEt is an ethyoxyl.Embodiment is represented in abbreviation " Ex. ", and numeral thereafter prepares embodiment number of this compound.
Index table A
| Compound number | ????(R 6) p | |
| ????A1(Ex.l) | ????2，6-Cl 2 | ????* |
| ????A2 | ????4-Br | ????* |
| ????A3 | ????2-CF 3 | ????* |
| ????A4 | ????2，6-F 2 | ????* |
| ????A5 | ????2-Cl | ????* |
| ????A6 | ????2，4，6-Cl 3 | ????* |
| ????A7 | ????2-Me | ????* |
| ????A8 | ????2，3，6-F 3 | ????* |
| ????A9 | ????2-Cl，6-F | ????* |
| ????A10 | ????2，6-(OMe) 2 | ????* |
*See among the index table D
1H NMR spectroscopic data
Index table B
| Compound number | ????(R 6) p | |
| ????B1 | ????2-NH(3-CF 3-Ph) | ????* |
| ????B2 | ????2-SPh | ????* |
| ????B3 | ????2-SMe | ????* |
| ????B4 | ????6-Cl | ????* |
| ????B5 | ????2-OPh | ????* |
| ????B6 | ????2-OEt | ????* |
| ????B7 | ????2，4-Cl 2 | ????* |
| ????B8 | ????2-OH | ????* |
*See among the index table D
1H NMR spectroscopic data
Index table C
| Compound number | ????(R 6) p | |
| ????Cl | ????2-Cl | ??* |
| ????C2 | ????2-Cl-6-OMe | ??* |
*See among the index table D
1H NMR spectroscopic data
Compound number
1H NMR Data (300mHz, CDCl
3Solution, except as otherwise noted)
A1??δ8.22(s，1H)，7.30(s，1H)，7.36-7.23(m，3H)，6.99(bs，1H)，5.03(m，1H)，2.82(m，3H)，2.29(s，3H)，1.94(m，3H)
A2??δ8.24(S，1H)，7.71(d，J＝8.7Hz，2H)，7.58(d，J＝8.6Hz，2H)，7.33(bs，1H)，7.27(s，1H)，4.97(m，1H)，2.82(m，3H)，2.31(s，3H)，1.95(m，2H)，1.69(m，1H)
A3??δ8.20(s，1H)，7.68(m，2H)，7.55(m，2H)，7.25(s，1H)，6.87(bs，1H)，5.02(m，1H)，2.81(t，J＝6.4Hz，2H)，2.70(m，1H)，2.29(s，3H)，1.94(m，2H)，1.79(m，1H)
A4??δ8.23(s，1H)，7.35(m，1H)，7.26(s，1H)，7.08(bs，1H)，6.69(d，J＝8.1Hz，1H)，6.91(d，J＝8.3Hz，1H)，5.02(m，1H)，2.81(m，2H)，2.74(m，1H)，2.29(s，3H)，1.95(m，2H)，1.82(m，1H)
A5??δ8.24(s，1H)，7.74(m，1H)，7.34(m，3H)，7.26(s，1H)，7.15(bs，1H)，5.10(m，1H)，2.82(m，2H)，2.70(m，1H)，2.29(s，3H)，195(m，3H)
A6??δ8.21(s，1H)，7.35(s，2H)，7.24(s，1H)，6.98(bs，1H)，4.98(m，1H)，2.80(m，3H)，2.29(s，3H)，1.95(m，2H)，1.83(m，1H)
A7??δ8.22(s，1H)，7.48(d，J＝7.7Hz，1H)，7.22(m，4H)，6.82(bs，1H)，5.03(m，1H)，2.81(t，J＝6.41Hz，2H)，2.71(m，1H)，2.52(s，3H)，2.29(s，3H)，1.94(m，2H)，1.78(m，1H)
A8??δ8.22(s，1H)，7.26(s，1H)，7.19(m，1H)，7.13(bs，1H)，6.87(m，1H)，5.02(m，1H)，2.82(t，J＝6.4Hz，2H)，2.76(m，1H)，2.30(s，3H)，1.95(m，2H)，1.78(m，1H)
A9??δ8.22(s，1H)，7.25(m，3H)，7.04(tJ＝8.4Hz，1H)，7.00(bs，1H)，5.02(m，1H)，2.82(m，3H)，2.27(s，3H)，1.95(m，2H)，1.82(m，1H)
A10??δ8.23(s，1H)，7.24(m，2H)，6.79(bs，1H)，6.55(m，2H)，5.03(m，1H)，3.82(s，6H)，2.79(m，2H)，2.71(m，1H)，2.28(s，3H)，1.92(m，3H)
B1??δ10.8(s，1H)，8.35(m，1H)，8.25(s，1H)，8.07(s，1H)，7.86(m，2H)，7.41(m，2H)，7.29(m，1H)，6.77(m，1H)，4.98(m，1H)，2.85(m，2H)，2.72(m，1H)，2.32(s，3H)，1.98(m，2H)，1.72(m，1H)
B2??δ8.37(m，1H)，8.24(s，1H)，7.91(m，1H)，7.52(m，2H)，7.37(m，4H)，7.27(s，1H)，7.07(m，1H)，5.07(m，1H)，2.82(m，3H)，2.31(s，3H)，1.98(m，2H)，1.80(m，1H)
B3??δ9.07(bs，1H)，8.51(m，1H)，8.24(s，1H)，7.90(m，1H)，7.28(s，1H)，7.05(m，1H)，5.03(m，1H)，2.83(m，2H)，2.72(m，1H)，2.55(s，3H)，2.30(s，3H)，1.97(m，2H)，1.86(m，1M：)
B4??δ8.81(d，J＝2.6Hz，1H)，8.24(s，1H)，8.12(dd，J＝2.6，8.3Hz，1H)，7.56(bs，1H)，7.37(d，J＝8.3Hz，1H)，7.32(s，1H)，5.02(m，1H)，2.85(m，2H)，2.72?(m，1H)，2.33(s，3H)，1.97(m，2H)，1.78(m，1H)
B5??δ9.36(bs，1H)，8.67(dd，J＝1.9，7.5Hz，1H)，8.21(m，1H)，8.15(s，1H)，7.44?(m，1H)，7.23(m，6H)，5.12(m，1H)，2.80(m，3H)，2.25(s，3H)，1.95(m，2H)，1.74(m，1H)
B6??δ9.03(bs，1H)，8.58(dd，J＝2.1，7.5Hz，1H)，8.29(s，1H)，8.23(dd，J＝2.1，4.9Hz，1H)，7.28(s，1H)，7.03(dd，J＝4.9，7.5Hz，1H)，5.10(m，1H)，4.51(m，2H)，2.83(m，12H)，2.70(m，1H)，2.32(s，3H)，1.95(m，2H)，1.78(m，1H)，1.39(t，J＝7.1Hz，3H)
B7??δ8.29(d，J＝5.4Hz，1H)，8.21(s，1H)，7.31(d，J＝5.4Hz，1H)，7.26(s，1H)，7.12(bs，1H)，5.02(m，1H)，2.82(m，3H)，2.29(s，3H)，1.97(m，2H)，1.84(m，1H)
C1??δ8.50(d，J＝5.0Hz，1H)，8.24(s，1H)，7.73(s，1H)，7.61(dd，J＝1.5，5.0Hz，1H)，7.50(bs，1H)，7.29(s，1H)，4.95(m，1H)，2.83(t，J＝6.5Hz，2H)，2.75(m，1H)，2.32(s，3H)，1.97(m，2H)，1.69(m，1H)
C2??δ8.24(s，1H)，7.37(bs，1H)，7.29(m，2H)，7.05(s，1H)，4.91(m，1H)，3.96(s，3H)，2.82(t，J＝6.4Hz，2H)，2.73(m，1H)，2.32(s，3H)，1.95(m，2H)，1.65(m，1H)
(d)-and doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-double doublet, (dt)-two triplets, (br s's)-wide is unimodal
Biology embodiment of the present invention
The global schema of preparation test suspension: test compounds at first is dissolved in the acetone, the final volume that its amount equals 3% is suspended in acetone with desirable concentration (ppm) then and comprises in the pure water (50/50 mix) of 250ppm surfactant Trem_014 (polyol ester).Gained test suspension is used for following test.The test suspension of 200ppm is sprayed at the point of run-off of test plants with the same amount of 500g/ha.
Test A
The test suspension is sprayed at wheat seedling until the loss point.Subsequently one day with this seedling with Erysiphe graminis f.sp.tritici conidial powder (pathogene of wheat powdery mildew) inoculation, then in the growth room in 20 ℃ of following incubations 7 days, assess ill rank afterwards.
Test b
The test suspension is sprayed at wheat seedling until the loss point.This seedling of subsequently a space-based with Puccinia recondita spore suspension (pathogene of wheat leaf rust) inoculation, then under 20 ℃ in saturated atmosphere incubation 24 hours, then moved in 20 ℃ the growth room totally 6 days, assess ill rank afterwards.
Test C
The test suspension is sprayed at the tomato seedling until the loss point.In the inoculation of subsequently one day suspension (pathogene of potato and tomato late blight) with Phytophthora infestans, then under 20 ℃ in saturated atmosphere incubation 24 hours, then moved in 20 ℃ the growth room totally 5 days, assess ill rank afterwards.
Test D
The test suspension is sprayed at grape seedling until the loss point.One day this seedling subsequently inoculates with the spore suspension (pathogene of grape) of Plasmopara viticola, then under 20 ℃ in saturated atmosphere incubation 24 hours, then moved in 20 ℃ the growth room totally 6 days, continuation under 20 ℃ in saturated atmosphere incubation 24 hours, assess ill rank afterwards.
Test A-D the results are shown among the following table A.In this table, 100 rank is represented the control of 100% disease, and 0 rank represents not have disease control (with respect to contrast).Cross break number (one) expression does not have test result.ND represents because phytotoxicity is not measured disease control.
Table A
| Compound | Test A | Test b | Test C | Test D |
| ????A1 | ????0 | ????84 | ????100 | ????- |
| ????A2 | ????0 | ????18 | ????5 | ????- |
| ????A3 | ????0 | ????41 | ????47 | ????- |
| ????A4 | ????0 | ????0 | ????90 | ????- |
| ????A5 | ????0 | ????55 | ????46 | ????- |
| ????A6 | ????0 | ????9 | ????82 | ????- |
| ????A7 | ????0 | ????45 | ????75 | ????- |
| ????A8 | ????0 | ????55 | ????100 | ????- |
| ????A9 | ????0 | ????38 | ????97 | ????- |
| ????A10 | ????- | ????- | ????- | ????- |
| ????B1 | ????0 | ????19 | ????16 | ????- |
| ????B2 | ????- | ????- | ????- | ????- |
| ????B3 | ????0 | ????23 | ????56 | ????- |
| ????B4 | ????0 | ????9 | ????32 | ????- |
| ????B5 | ????- | ????- | ????- | ????- |
| ????B6 | ????- | ????- | ????- | ????- |
| ????B7 | ????- | ????- | ????- | ????- |
| ????B8 | ????0 | ????19 | ????47 | ????- |
| ????C1 | ????0 | ????55 | ????84 | ????- |
| ????C2 | ????95 | ????28 | ????18 | ????- |
Claims (18)
1, a kind of method that is used to control the plant disease that causes by fungal plant pathogen, it comprises to described plant or its part or to plant seed or seedling uses salt suitable on the formula I compound, its N-oxide, agricultural of sterilization effective dose and comprises described compound compositions:
Wherein:
A forms the condensed pyridine basic ring of replacement with N-C=C,
B is phenyl or the pyridyl ring that replaces,
J is the optional 2-5 person's connection chain that replaces, and comprises at least one carbon member, optional comprise one or two C (=O) the carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen,
W is C=L or SO
n,
L is O or S,
R
1Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each is all chosen wantonly and is substituted,
R
3Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl or C
3-8Dialkyl amino carbonyl, and
N is 1 or 2.
2, the method for claim 1, wherein
A forms by 1 or 2 with N-C=C and is independently selected from R
5The condensed pyridine basic ring that replaces of substituting group,
B is independently selected from R by 1-3
6Substituting group replace,
J is 2-5 person's connection chain, comprises at least one carbon member, optional comprise one or two C (=O) the carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen, randomly by 1 or more a plurality of substituting group that is selected from following group replace: C
1-2Alkyl, halogen, CN, NO
2And C
1-2Alkoxyl,
R
1Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each group are all randomly replaced by one or more substituting group that is selected from following group: halogen, CN, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
2-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido and C
3-6Cycloalkyl amino,
Each R
5With each R
6Be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl, perhaps
Each R
5With each R
6Be benzyl ring, 5 or 6 yuan of assorted aromatic rings, benzyl rings or phenoxy group rings independently, each ring randomly is selected from R by 1-3
7Substituting group replace, and
Each R
7Be C independently
1-4Alkyl, C
2-4Thiazolinyl, C
2-4Alkynyl, C
3-6Cycloalkyl, C
1-4Haloalkyl, C
2-4Haloalkenyl group, C
2-4Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
3-6(alkyl) cycloalkyl amino, C
2-4Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl.
3, method as claimed in claim 2, wherein,
W is C=O,
J is selected from-CH
2CH
2-,-CH
2CH
2CH
2-,-CH
2CH
2CH
2CH
2-,-OCH
2-,-OCH
2CH
2-,-OCH
2CH
2CH
2-,-CH
2NHCH
2-,-CH
2N (C
1-2Alkyl) CH
2-,-CONHCO-and-CON (C
1-2Alkyl) CO-, and
Each R
5With each R
6All be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl or C
3-8Dialkyl amino carbonyl.
4, method as claimed in claim 3, wherein,
B chooses wantonly by 1-3 to be independently selected from R
6The benzyl ring that replaces of substituting group,
J is-CH
2CH
2-or-CH
2CH
2CH
2-,
Each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3, and
Each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
5, method as claimed in claim 3, wherein,
B chooses wantonly by 1-3 to be independently selected from R
6In substituting group the 3-pyridine radicals or the 4-pyridyl ring that replace,
J is-CH
2CH
2-or-CH
2CH
2CH
2-,
Each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3, and
Each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
6, method as claimed in claim 5, wherein, B is the 3-pyridyl ring, one of them R
6Be 2 one Cl, the ortho position is in the position that is connected with C=O, and another R
6Be Cl or methyl, and be positioned at 4 that also the ortho position is in the position that is connected with C=O, the 3rd optional R
6Be to be in 6 methyl.
7, as the described method of one of claim 1-6, wherein, R
1Be H, and R
3Be H.
8, the method for claim 1, wherein said compound are selected from following group:
2-chloro-6-methoxyl group-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl)-4-pyridine carboxamides,
2,6-two chloro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl) benzamide, and
2,3,6-three fluoro-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl) benzamide.
9, formula I compound as claimed in claim 1, its N-oxide and agricultural go up suitable salt, and condition is to work as the phenyl ring that B is replacement, and W is C=O or SO
2, R
3Be H, and J is the saturated chain of 2-4 carbon atom, this chain can be not replace or replaced by 1-3 substituting group that is selected from following group: alkyl, alkoxyl, aryl or aralkyl, then described compound is the N-oxide.
10, compound as claimed in claim 9, wherein,
A forms by 1 or 2 with N-C=C and is independently selected from R
5The condensed pyridine basic ring that replaces of substituting group,
B is independently selected from R by 1-3
6Substituting group replace,
J is 2-5 person's connection chain, comprises at least one carbon member, optional comprise one or two C (=O) the carbon member of form, and optionally comprise a member who is selected from nitrogen and oxygen, randomly by 1 or more a plurality of substituting group that is selected from following group replace: C
1-2Alkyl, halogen, CN, NO
2And C
1-2Alkoxyl,
R
1Be H, or C
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl or C
3-6Cycloalkyl, each group are all randomly replaced by one or more substituting group that is selected from following group: halogen, CN, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
2-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido and C
3-6Cycloalkyl amino,
Each R
5With each R
6Be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, CO
2H, CONH
2, NO
2, hydroxyl, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl, perhaps
Each R
5With each R
6Be benzyl ring, 5 or 6 yuan of assorted aromatic rings, benzyl rings or phenoxy group rings independently, each ring randomly is selected from R by 1-3
7Substituting group replace, and
Each R
7Be C independently
1-4Alkyl, C
2-4Thiazolinyl, C
2-4Alkynyl, C
3-6Cycloalkyl, C
1-4Haloalkyl, C
2-4Haloalkenyl group, C
2-4Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl C
1-4Alkoxy carbonyl, C
1-4Alkyl amino, C
2-8Dialkyl amido, C
3-6Cycloalkyl amino, C
3-6(alkyl) cycloalkyl amino, C
2-4Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl, C
3-8Dialkyl amino carbonyl or C
3-6Trialkylsilkl.
11, compound as claimed in claim 10, wherein,
W is C=O,
J is selected from-CH
2CH
2-,-CH
2CH
2CH
2-,-CH
2CH
2CH
2CH
2-,-OCH
2-,-OCH
2CH
2-,-OCH
2CH
2CH
2-,-CH
2NHCH
2-,-CH
2N (C
1-2Alkyl) CH
2-,-CONHCO-and-CON (C
1-2Alkyl) CO-, and
Each R
5With each R
6All be C independently
1-6Alkyl, C
2-6Thiazolinyl, C
2-6Alkynyl, C
3-6Cycloalkyl, C
1-6Haloalkyl, C
2-6Haloalkenyl group, C
2-6Halo alkynyl, C
3-6Halogenated cycloalkyl, halogen, CN, NO
2, C
1-4Alkoxyl, C
1-4Halogenated alkoxy, C
1-4Alkyl sulfenyl, C
1-4Alkyl sulfinyl, C
1-4Alkyl sulphonyl, C
1-4Haloalkyl sulfenyl, C
1-4Haloalkyl sulfinyl, C
1-4Halogenated alkyl sulfonyl, C
1-4Alkoxy carbonyl, C
2-6Alkyl-carbonyl, C
2-6Alkoxy carbonyl, C
2-6Alkyl amino-carbonyl or C
3-8Dialkyl amino carbonyl.
12, compound as claimed in claim 11, wherein,
B chooses wantonly by 1-3 to be independently selected from R
6The benzyl ring that replaces of substituting group,
J is-CH
2CH
2-or-CH
2CH
2CH
2-,
Each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3, and
Each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
13, compound as claimed in claim 11, wherein,
B chooses wantonly by 1-3 to be independently selected from R
6In substituting group the 3-pyridine radicals or the 4-pyridyl ring that replace,
J is-CH
2CH
2-or-CH
2CH
2CH
2-,
Each R
5Be CH independently
3, Cl, Br, I, CN, NO
2, CF
3, OCF
3, OCHF
2, SCF
3, SCHF
2, CO
2CH
3Or CONHCH
3, and
Each R
6Be C independently
1-2Alkyl, C
1-2Haloalkyl, halogen, CN, C
1-2Alkoxyl, C
1-2Halogenated alkoxy, C
1-2Alkyl sulfenyl, C
1-2Alkyl sulfinyl or C
1-2Alkyl sulphonyl, and at least one R
6The ortho position, position in the link position of W.
14, compound as claimed in claim 13, wherein, B is the 3-pyridyl ring, one of them R
6Be 2 one Cl, the ortho position is in the position that is connected with C=O, and another R
6Be Cl or methyl, and be positioned at 4 that also the ortho position is in the position that is connected with C=O, the 3rd optional R
6Be to be in 6 methyl.
15, as the described method of one of claim 9-14, wherein, R
1Be H, and R
3Be H.
16, method as claimed in claim 9, it is 2-chloro-6-methoxyl group-N-(5,6,7,8-tetrahydrochysene-3-methyl-8-quinolyl)-4-pyridine carboxamides.
17, a kind of composition, it comprises (a) at least a formula I compound as claimed in claim 1, and (b) at least a compound that is selected from following group:
(b1) two (dithiocarbamate) bactericide of alkylidene,
(b2) act on the compound of the bc1 compound of fungi mitochondrial respiratory electronics metastasis site,
(b3) cymoxanil,
(b4) act on the compound of the demethylase in the sterol biosynthesis pathway,
(b5) act on the morpholine and the piperidine compounds of sterol biosynthesis pathway,
(b6) phenyl amide bactericide,
(b7) pyrimidone bactericide,
(b8) phthalimide, and
(b9) fosetyl.
18, composition as claimed in claim 17, wherein, component (b) comprises at least a by two compounds of selecting on the same group each group not, and described two different groups are selected from (b1), (b2), (b3), (b4), (b5), (b6), (b7), (b8) and (b9).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29088401P | 2001-05-15 | 2001-05-15 | |
| US60/290,884 | 2001-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1509140A true CN1509140A (en) | 2004-06-30 |
Family
ID=23117917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA028100646A Pending CN1509140A (en) | 2001-05-15 | 2002-05-14 | Pyridinyl fused bicyclic amide as fungicides |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1387612A1 (en) |
| JP (1) | JP2004529943A (en) |
| CN (1) | CN1509140A (en) |
| AR (1) | AR033893A1 (en) |
| BR (1) | BR0209687A (en) |
| IL (1) | IL158009A0 (en) |
| MX (1) | MXPA03010436A (en) |
| PL (1) | PL367200A1 (en) |
| RU (1) | RU2003136089A (en) |
| WO (1) | WO2002091830A1 (en) |
| ZA (1) | ZA200307375B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR045875A1 (en) * | 2003-10-27 | 2005-11-16 | Merck & Co Inc | PROCEDURE FOR THE PREPARATION OF ANTAGONIST CCR-2 |
| JP5034293B2 (en) * | 2005-07-14 | 2012-09-26 | 住友化学株式会社 | Carboxamide compound and plant disease control agent containing the same |
| US8044043B2 (en) * | 2008-04-11 | 2011-10-25 | Bristol-Myers Squibb Company | CGRP receptor antagonists |
| MX2011012712A (en) | 2009-05-29 | 2012-01-30 | Raqualia Pharma Inc | Aryl substituted carboxamide derivatives as calcium or sodium channel blockers. |
| MY187540A (en) | 2014-08-01 | 2021-09-28 | Nuevolution As | Compounds active towards bromodomains |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| US11753413B2 (en) | 2020-06-19 | 2023-09-12 | Incyte Corporation | Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors |
| JP2023533724A (en) | 2020-07-02 | 2023-08-04 | インサイト・コーポレイション | Tricyclic urea compounds as JAK2 V617F inhibitors |
| US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
| WO2022046989A1 (en) | 2020-08-27 | 2022-03-03 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| WO2022140231A1 (en) | 2020-12-21 | 2022-06-30 | Incyte Corporation | Deazaguaine compounds as jak2 v617f inhibitors |
| US11958861B2 (en) | 2021-02-25 | 2024-04-16 | Incyte Corporation | Spirocyclic lactams as JAK2 V617F inhibitors |
| WO2023178285A1 (en) | 2022-03-17 | 2023-09-21 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69026395T2 (en) * | 1989-01-11 | 1997-03-06 | Agrevo Uk Ltd | Acrylate fungicides |
| WO1996037473A1 (en) * | 1995-05-23 | 1996-11-28 | Hoechst Schering Agrevo Gmbh | Substituted 2,3-cycloalkenopyridines, process for preparing the same, agents containing the same and their use as pesticides and fungicides |
| TW575562B (en) * | 1998-02-19 | 2004-02-11 | Agrevo Uk Ltd | Fungicides |
-
2002
- 2002-05-14 CN CNA028100646A patent/CN1509140A/en active Pending
- 2002-05-14 EP EP02744275A patent/EP1387612A1/en not_active Withdrawn
- 2002-05-14 JP JP2002588757A patent/JP2004529943A/en not_active Withdrawn
- 2002-05-14 BR BR0209687-0A patent/BR0209687A/en not_active IP Right Cessation
- 2002-05-14 WO PCT/US2002/018394 patent/WO2002091830A1/en not_active Application Discontinuation
- 2002-05-14 IL IL15800902A patent/IL158009A0/en unknown
- 2002-05-14 MX MXPA03010436A patent/MXPA03010436A/en unknown
- 2002-05-14 RU RU2003136089/04A patent/RU2003136089A/en not_active Application Discontinuation
- 2002-05-14 PL PL02367200A patent/PL367200A1/en not_active Application Discontinuation
- 2002-05-15 AR ARP020101792A patent/AR033893A1/en not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2002091830A1 (en) | 2002-11-21 |
| PL367200A1 (en) | 2005-02-21 |
| JP2004529943A (en) | 2004-09-30 |
| EP1387612A1 (en) | 2004-02-11 |
| BR0209687A (en) | 2004-09-14 |
| IL158009A0 (en) | 2004-03-28 |
| AR033893A1 (en) | 2004-01-07 |
| MXPA03010436A (en) | 2004-03-09 |
| RU2003136089A (en) | 2005-04-20 |
| ZA200307375B (en) | 2004-09-22 |
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