MXPA01006486A - Substituted pyridine herbicides - Google Patents
Substituted pyridine herbicidesInfo
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- MXPA01006486A MXPA01006486A MXPA/A/2001/006486A MXPA01006486A MXPA01006486A MX PA01006486 A MXPA01006486 A MX PA01006486A MX PA01006486 A MXPA01006486 A MX PA01006486A MX PA01006486 A MXPA01006486 A MX PA01006486A
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Abstract
Compounds of formula (I), in which the substituents are as defined in claim 1 and the agrochemically tolerated salts M+ and all stereoisomers and tautomers of the compounds of formula (I) are suitable for use as herbicides.
Description
SUBSTITUTE PIRIDINE HERBICIDES
DESCRIPTION OF THE INVENTION The present invention relates to novel herbicidally active pyridin ketones, to their preparation, to compositions comprising these compounds, and to their use to control herbs, especially in crops of useful plants, or to inhibit the growth of plants. The herbicidally active pyridin ketones are described, for example, in International Publication No. WO 97/46530. Now we have found novel pyridin ketones that have herbicidal and growth inhibitory properties. Accordingly, the present invention relates to compounds of the formula I:
wherein: p is 0 or 1;
Ref: 130439
R £ is haloalkyl of 1 to 6 carbon atoms; R: is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, vinyl which is substituted by alkoxy of 1 to
2 carbon atoms - carbonyl or phenyl, or is alkinyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, ethinyl which is substituted by trimethylsilyl, hydroxyl, alkoxy of 1 to 2 carbon atoms
carbon, alkoxy of 1 to 2 carbon atoms-carbonyl,
0 phenyl, or is alenyl of 3 to 6 carbon atoms, cycloalkyl of 3 to ß carbon atoms, cycloalkyl of
3 to 6 carbon atoms which is substituted by halogen, or is alkoxy of 1 to 6 carbon atoms, l- "1 alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, haloalkenyloxy of 3 to 6 carbon atoms, cyanoalkoxy of 1 to 4 carbon atoms, alkoxyc of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms, alkyl of
1 to 4 carbon atoms-sulfinylalkoxyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms- sulfonyl alkoxyl of 1 to 4 carbon atoms, alkoxyl of 1 to 4 carbonylalkyl atoms of 1 to 4 atoms from
carbon, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms 'carbon-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms carbon-sulfinyl, alkoxy of 1 to 4 carbon atoms-carbonyl-alkyl of 1 to 4 carbon atoms-sulfonyl, benzyl-S (O) nl-, alkyl of 1 to 6 carbon-amino atoms, dialkyl of 2 to 6 carbon atoms - to n, alkyl of 1 to 6 carbon atoms - aminosul fonyl, di- (alkyl of 1 to 6 carbon atoms - "'amino) sulfonyl, benzyloxy, benzyl, phenyl, phenoxy, thiophene A, phenylsul finyl, or phenylsulfonyl, it being possible that the groups containing phenyl in turn, are substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or Rg is 0S (C) n; -R;?, N ( R_) -S (O)
cyano, carbamoyl, alkoxy of 1 to 4 carbon atoms-carbonyl, formyl, halogen, thiocyanate, amino, hydroxyalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of
1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-S (O) n < -alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, benzoyl-oxyalkyl of 1 to 4 carbon atoms, oxiranyl of 2 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms- aminoalkyl of 1 to 4 carbon atoms, di- (alkyl of 1 to 4 carbon atoms) aminoalkyl of 1 to
4 carbon atoms, thioalkyl of 1 to 12 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, or formylalkyl of 1 to 4 carbon atoms, or R; is a monocyclic or bicyclic fused ring system of
to 10 members which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being linked to the pyridine ring by of an alkylene group of 1 to 4 carbon atoms, -CH = CH-r -C = C-, -CH_0-, -CH: N (alkyl of 1 to 4 carbon atoms) -, -CH2SO-, or - CH2SO2, and not being possible
each ring system contains more than 2 oxygen atoms and not more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, - ' haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 'carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 atoms of carbon, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms,;) thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon atoms carbon-thioalkyl, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms carbon-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosu fonilo, alkyl of 1 to 2 carbon atoms- to inosulfonyl, di- (alkyl of 1 to 2 carbon atoms Aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms)
carbon) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, carbon, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and the substituents on the nitrogen of the heterocyclic ring being different from halogen; Ra is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms carbon-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkyl of 1 to 6 carbon-amino atoms, dialkyl of 2 to 6 carbon atoms-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, dialkyl of 2 to 6 carbon atoms-aminosulfonyl,
phenyl, thiophenyl, phenylsulfinyl, phenylsulfonyl, or phenoxy ,. it is possible that phenyl, in turn, is substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or R3 is -N (Rg3) -S (0) r-R2;, cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms-S (0) n-alkyl of 1 to 4 carbon atoms; Ri is hydrogen, alkyl of 1 to 6 carbon atoms, hydroxyl, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, haloalkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxy, alkyl of 1 to 4 carbon atoms-sulfonyloxy, tosyloxy, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms carbon-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkoxy of 1 to 4 carbon atoms-carbonyl, haloalkyl of 1 to 4 carbon atoms, formyl, cyano, halogen, phenyl, or phenoxy, it being possible that phenyl, in turn, is substituted by
alkyl is 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro; or -1 R4 is a 5 to 10 membered monocyclic or bicyclic ring system condensed with R3, which may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being , unless this 1 condensed, linked to the pyridine ring directly or by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, -C = C-, -CONJO-, -CHA (alkyl) of 1 to 4 carbon atoms) -, -CAS-, -CHgSO-, or -CHAO, -, and it is not possible for the ring system: i to contain more than 2 carbon atoms of oxygen, and not more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, 0 haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy from 1 to 6 carbon atoms, alkenyloxy from 3 to 6 carbon atoms, alkynyloxy from 3 to 6: 'carbon atoms, thioalkyl from 1 to 6 carbon atoms
carbon, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-thioalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, cyanothioalkyl of 1 to 4 carbon atoms , alkyl of 1 to 5 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosul fonyl, alkyl of 1 to 2 carbon atoms-aminosul fonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenz :. It is possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkylation ilo of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and the substituents being on nitrogeium of the heterocyclic ring different from halogen D;
R2? is alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R22 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or di- (alkyl of 1 to 4 carbon atoms) amino; R23, R24, R25, independently of one another, are hydrogen or alkyl of 1 to 4 carbon atoms; n, ni, n2, n3 and n, independently of each other are 0, 1 or 2; Q is Q:
wherein: R,;, R ^, Rs, and RQ, independently of one another, are hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-S (O) n? 7, alkyl of 1
to 6 carbon atoms-NHS (0):, alkyl of 1 to 6 carbon atoms-amino, di- (alkyl of 1 to 6 carbon atoms) amino, hydroxyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms - sulfonyloxy-alkyl of 1 to 6 carbon atoms, tosyloxyalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-S (0) alkyl of 1 to 6 carbon atoms, cyanoalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkoxy of 1 to 6 carbon atoms, benzyloxyalkyl of 1 to 6 carbon atoms, alkoxyl of 1 to 6 carbon atoms-carbonylalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonyloxyalkyl of 1 to 6 carbon atoms, thiocyanatoalkyl of 1 to 6 carbon atoms, oxiranyl, alkyl of 1 to 6 carbon atoms-aminoalkyl of 1 to 6 carbon atoms, di- (alkyl of 1 to 6 carbon atoms] aminoalkyl of 1 to 6 carbon atoms, formylalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-maximum, halogen, cyano, nitro, phenyl, or phenyl which is substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms
carbon, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms - carbonyl, alkoxy of 1 to 4 carbon atoms - carbonyl, amino, alkyl of 1 to 4 atoms carbon-amino, dialkyl of 1 to 4 carbon-amino atoms, alkyl of 1 to 4 carbon atoms-S (0) n? &, alkyl of 1 to 4 carbon atoms-S (0) 0, haloalkyl from 1 to 4 carbon atoms-S (0) n5, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0) 2 NH, alkyl of 1 to 4 atoms carbon-S (0) mo-N (alkyl of 1 to 4 carbon atoms) 2, halogen, nitro, COOH or cyano; or Rb and R-- adjacent, or R3 and Rg are together - (CHJ rr -, C (0) 0 (CH) n2: - or -S (0) r? 1 (CH2) n 2-; n ^, n27, nlH, n2 ?, yni, independently of each other 0, 1 or 2, n2o is 2 or 3, n_ is 2, 3 or 4, m is 2, 3, 4, 5 or 6, W is oxygen, S (0) r.¿, -CRnR?, -CResRejCRes ee
R 3, RÓ, R Rf, and oe, independently of one another, are hydrogen or alkyl of 1 to 6 carbon atoms, or R (, E together with R ^ or R9 forms a direct bond, n6 is 0.1, or 2;
Rii is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl from 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 atoms carbon-sulphonyloxyalkyl of 1 to 4 carbon atoms, tosyloxyalkyl of 1 to 4 carbon atoms, di- (alkoxy of 1 to 3 carbon atoms-alkyl) methyl, di- (alkyl of 1 to 3 carbon atoms-thioalkyl) L1) methyl, (alkoxy of 1 to 3 carbon atoms-alkyl) - (alkyl of 1 to 3 carbon atoms-thioalkyl) methyl, oxacycloalkyl of 3 to 5 carbon atoms. tiacycloalkyl of 3 to 5 carbon atoms, dioxacycloalkyl of 3 to 4 carbon atoms, dithiacycloalkyl of 3 to 4 carbon atoms, oxatiac Lcloalkyl of 3 to 4 carbon atoms, formyl, alkoxy of 1 to 4 carbon atoms - carbonyl, carbamoyl, alkyl of 1 to 4 carbon atoms-aminoca trbonyl, di- (alkyl of 1 to 4 carbon atoms) aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl, or phenyl which, in turn, can be substituted by alkyl of 1 to 4 atoms carbon
haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, amino, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-S (0) n2 ?, alkyl of 1 to 4 carbon atoms-S (0) 2o, haloalkyl of 1 to 4 carbon atoms-S (0) nt, haloalkyl of 1 to 4 carbon atoms-S (0) 0, alkyl of 1 to 4 carbon atoms-S (0) NH, alkyl of 1 to 4 carbon atoms-S (0) n 0 N (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH or cyano; n7, n_n and n21, independently of each other, are 0, 1 or 2; or R? , together with R "or RQ, is a group - (CH2) C-; or is 1, 2, 3, 4 or 5; R22 is hydrogen, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms; or R12 together with RL1 is a group - (CH.) m?;
Rio is hydroxyl, 0"MJ halogen, cyano, SCN,
OCN, alkoxy of 1 to 12 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 12 carbon atoms, alkyl of 1 to 12 carbon atoms-sulfinyl, alkyl
from 1 to 12 carbon-sulfonyl, halotyl-1alkyl-1 to 12-carbon atoms, haloalkyl-1 to 12 carbon-sulfinyl, haloalkyl-1 to 12 carbon-sulfonyl, alkoxy to 1-6 carbon atoms -tioalk.Llo of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms-sulfinyl, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms- sulfonyl, thioalkenyl of 2 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms-sulfinyl, alkenyl of 1 to 12 carbon atoms-sulfonyl, thioalkynyl of 2 to 12 carbon atoms, alkynyl of 2 to 12 carbon atoms- sulfini Lo, alkynyl of 2 to 12 carbon atoms-sulfonyl Lo, halotioalkenyl of 2 to 12 carbon atoms, haloalkenyl of 2 to 12 carbon atoms-sulfinyl, haloalkyl of 2 to 12 carbon atoms-sulfonyl, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms-sulfinyl, alkoxy of 1 to 4 carbon atoms-carbonyl Lalkyl of 1 to 4 carbon-sulfonyl atoms, (C 1 -C 4 -alkoxy) 2P (O) O, C 1-4 -alkyl (C 1 -C 4 -alkoxy) P (O) O, H (alkoxy) from 1 to 4 carbon atoms) P (O) O, R14R15N, R14R1NNH, R16R17NC (O) O-,
R16Ri7NC (O) NH-, alkyl of 1 to 12 carbon atoms-S (0) 2NR: e, haloalkyl of 1 to 4 carbon atoms-S (0) N RIQ, alkyl of 1 to 12 carbon atoms-S (0) 20, haloalkyl of 1 to 4 carbon atoms -S (0) 20, alkyl of 1 to 18 carbon atoms -carbonyloxy, it being possible that the alkyl group is substituted by halogen, alkoxy of 1 to 6 carbon atoms , thioalkyl of 1 to 6 carbon atoms, or cyano, or is alkenyl of 2 to 18 carbon atoms-carbonyloxy, alkynyl of 2 to 18 carbon atoms-carbonyloxy, cycloalkyl of 3 to 6 carbon atoms-carbonyloxy, alkoxy of 1 to 12 carbon atoms-carbonyloxy, thioalkyl of 1 to 12 carbon atoms-carbonyloxy, thioalkyde of 1 to 12 carbon atoms-carbamoyl, alkyl of 1 to 6 carbon atoms-NH (CS) (alkyl of 1) at 6 carbon atoms) -NH-, dialkyl of 1 to 6 carbon atoms-N (CS) N (alkyl of 1 to 6 carbon atoms) -NH-, benzyloxy, thiobenzyl, benzylsulfinyl, benzylsulfonyl, phenoxy it, thiophenyl, phenylsulfinyl, phenylsuperionyl, phenylsulphonylamino, phenylsulphonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by alkyl of 1 to 4 carbon atoms. haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-
carboni.lo, alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, alkyl of 1 to 4 carbon atoms-S (0) 0, halotioalkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 atoms of carbon-sulfinyl, haloalkyl of 1 to
4 carbon-sulfonyl atoms, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0) NH, alkyl of 1 to 4 carbon atoms- 5 (0) N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano; or Rio is an Ary-thio group, Ar2-sul finyl, Ar3-sulfonyl, -0C0-Ar, or NH-Ar5, where Ari, Ar, Ar,
Arj, and Ar5, independently of each other, are a monocyclic or bicyclic fused ring system,
to 10 members, which may be aromatic or may be partially saturated, and may contain from 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen, and sulfur, with each ring system possibly containing no more of 2 oxygen atoms, and not more than 2 sulfur atoms, and it being possible for the ring system itself to be mono-, di-, 6 tri-s substituted by alkyl of 1 to 6 carbon atoms,
haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms , thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carotenoids Dono-thioalkyl , alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosul fonilo, alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3
carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen of the heterocyclic ring are different from halogen; R: Ris, Rie, R17, and Ris / independently of each other, are hydrogen or alkyl of 1 to 6 carbon atoms; n, na, nm, nn, ni2, nx3 and n? < , independently of each other, are 0, 1 or 2; Ru is hydrogen, alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-carbonyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinylcarbonyl of 1 to 4 carbon atoms, alkyl from 1 to 4 carbon atoms-sulfonylcarbonyl
1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carbonyl, alkyl of 1 to 4 carbon atoms Lo, phenylcarbonyl, or is phenyl which in turn may be substituted by alkyl of 1 to 4 carbon atoms. carbon, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to
4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-amino, di-alkyl of 1 to 4 carbon atoms-amino , alkyl from 1 to
4 carbon atoms-S (O) - n-5-alkyl of 1 to 4 carbon atoms - S (0) 20, haloalkyl of 1 to 4 carbon atoms - S (0) -, i6, haloalkyl of 1 to 4 atoms carbon-S (O) 0, alkyl of 1 to 4 carbon atoms-S (0) NH, alkyl of 1 to 4 carbon atoms-S (0) 2N (alkyl of 1 to 4 carbon atoms), halogen , nitro, or cyano, and n25 and ni6, independently of each other, are 0, 1 or 2, and the agrochemically tolerated salts M ~ and all the stereoisomers and tautomers of the compounds of the formula I. The alkyl groups in the definitions of the substituents may be straight or branched chain, and are, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, secondary butyl, isobutyl, tertiary butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl , undecyl, and dodecyl, and their branched isomers The alkoxy, alkenyl, and alkyne radicals are derived from the aforementioned alkyl radicals. Alkynyl can be mono- or poly-unsaturated. An alkylene groups, for example, - (CH) m-,
- (CH2) rn: - or - (CH) L- can be substituted by one or more methyl groups; preferably, these alkylene groups are in each case unsubstituted. It also applies what
same to the group -C (0) 0 (CH) 2; and -S (0) r.:? (CH2) n2 -, and to all groups containing cycloalkyl of 3 to 6 carbon atoms, oxacycloalkyl of 3 to 5 carbon atom, cycloalkyl of 3 to 5 carbon atoms, dioxacycloalkyl of 3 to 4 carbon atoms, dithiacycloalkyl of 3 to 4 carbon atoms, oxatiac Lcloalkyl of 3 to 4 carbon atoms. Halogen is, as a rule, fluorine, chlorine, bromine, or iodine. This is also applied in a manner analogous to halogen in conjunction with other meanings, such as haloalkyl or halophenyl. Haloalkyl groups with a chain length of 1 to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluo roethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-fluoroprop-2-yl, pentafluoroethyl, 1,1-di-fluorine -2, 2, 2-trichloroethyl, 2, 2, 3, 3-tetrafluoroethyl, and 2,2,2-trichloroethyl, pentafluoroethyl, heptaf1 normal aoropropyl, normal perfluorohexyl; haloalkyl groups in the meanings of R, R 3, and in particular R 5, are preferably trichloromethyl, fluoromethyl, dichlorofluoromethyl, difluorocloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, or normal heptafluoropropyl.
Suitable haloalkyl are monohalogenated or polyhalogenated alkenyl groups, in which halogen is fluorine, chlorine, bromine, and iodine, and in particular fluorine and chlorine, for example 1-chlorovinyl, 2-chlorovinyl, 2,2-difluorovinyl, 2, 2 -difluoroprop-l-en-2-ilo, 2,2-dichloro-rrubile, 3-fluoroprop-1-enyl, chloroprop-l-en-1-yl, 3-oromoprop-l-en-l-yl, 2,3,3-trifluoroprop-2-en -l-yl, 2, 3, 3-trichloroprop-2-en-l-yl, and 4,4,4-trifluorobut-2-en-l-yl. Among the preferred monhalogenated, dihalogenated, or trihalogenated alkenyl groups of 2 to 6 carbon atoms are those having a chain length of 2 to 5 carbon atoms. Suitable haloalkynyl are, for example, monohalogenated or polyhalogenated alkynyl groups, wherein halogen is bromine, iodine, and in particular fluorine and chlorine, for example 3-fluoropropinyl, 3-chloropropinyl, 3-bromopropinyl, 3,3,3- trifluoropropinyl, and 4, 4, 4-trifluorobut-2-en-1-yl. Among the preferred monohalogenated or polyhalogenated alkynyl groups are those having a chain length of 2 to 5 carbon atoms. A cycloalkyl group of 3 to 6 carbon atoms monohalogenated or polyhalogenated is, for example, the group 2, 2-dichlorocyclopropyl, 2,2-
dibromoocyclopropyl, 2, 2, 3, 3-tetrafluorocyclobutyl or 2, 2-difluoro-3, 3-dichlorocyclobutyl. Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, normal butoxy, isobutoxy, secondary butoxy, and tertiary butoxy, and the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxyl normal carbonyl, isobutoxycarbonyl, butoxyl secondary carbonyl, or tertiary butoxyl carbonyl; preferably methoxycarbonyl, ethoxycarbonyl, or tertiary butoxycarbonium. The haloalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Haloalkoxy is, for example, fluoromethoxy, di-fluoromethoxy, trifluoromethoxy, 2,2,2-trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, 1-fluoroexyloxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-fluoroe. coxyl and 2, 2, 2-trichloroethoxy; preferably fluoromethoxy, difluoromethoxy, 2-chloroethoxy, and trifluoromethoxy.
The thioalkyl groups preferably have a chain length of 1 to 8 carbon atoms. Thioalkyl is, for example, thiomethyl, thioethyl, thiopropyl, thioisopropyl, thiobutyl, thiobutyl, secondary thiobutyl, or tertiary thiobutyl, preferably thiomethyl, and thioethyl. Alkylsulfinyl is, for example, methylsulphinyl, ethylsulinyl, propylsulfinyl, isopropylsulfinyl, butyl-sulfinyl butyl, isobutylsulfinyl, secyl butyl trio-sulfinyl, tertiary butyl-sulfinyl; preferably methylsulfinyl and ethylsulphinyl. Alkylsulfonyl is, for example, methylsulphonyl, ethylsulphonyl, propylsulphonyl, isopropylsulfonyl, normal butyl sulfonyl, isobutyl sulphonyl, secondary butyl sulfonyl, or tertiary butyl sulfonyl; preferably methylsulfonyl or ethylsul Añilo. Alkylamino is, for example, methylamino, ethylamine, propyl normal-amino, isopropylamino, or the butylamino isomers. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, propyl, norm1-methylamino, dibutylamino, and diisopropylamino. Alkylamino groups having a chain length of 1 to 4 carbon atoms are preferred. The alkyloxy groups preferably have 1 to 6 carbon atoms.
carbon, Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, propoxyl normal-methyl, propoxyl normal-ethyl, isopropoxymethyl, or isopropoxyethyl. The alkylthioalkyl groups preferably have from 1 to 6 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, normal propyl-Aomethyl, normal propyl thioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl, or butylthiobutyl. Phenyl, also as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, thiophenol, phenylalkyl, phenoxyalkyl, or tosyl, may be in a monosubstituted or polysubstituted form. In this case, the substituents can be in any of the ortho, meta, and / or para positions. Alenyl is, for example, CH_ = C = CH2CH_ = CH-CH2-CH = CH, CH_ = CH-CH_-CH_-CH = CH_ or CH_ = CH-CH2-CH = CH-CHa. The invention also extends to the MJ salts which can form the compounds of the formula I, in particular those compounds of the formula I wherein Rio is 0 ~ MJ preferably with amines, alkali metal bases, alkaline earth metal bases, or quaternary ammonium bases. The following should be emphasized as salt formers between alkali metal bases
and bases of alkaline earth metal: the hydroxides of lithium, sodium, potassium, magnesium, or calcium, in particular those of sodium or potassium. Examples of the amines that are suitable for the ammonium salt formation are not only ammonia, but also alkylamines of 1 to 18 primary carbon atemos, secondary, and tertiary, hydroxyalkylamines of 1 to 4 carbon atoms and alkoxyalkylamines of 2 to 4 carbon atoms, for example methylamine, ethylamine, propyl normal-amine, isopropylamine, the four isomers of butylamine, amyl normal-amine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonilamine, methylpentadecylamine, methyloct.adecylamine, ethylbutylamine, ethylheptylamine, ethylctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, dipropyl normal-amine, di-isopropy sheet, dibutyl normal-amine, diamyl normal-amine, di-isoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, propanol normal-amine, isopropanolamine, N, N-diethanolamine, N-ethylpropanolamine, N- butylethanolamine, allylamine, butenyl normal-2-amine, pentenyl normal-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, exeilo-
normal-2-amine, propylene diamine, trimethylamine, triethylamine, tripropyl normal-amine, tri-isopropylamine, tributyl normal-amine, tri-isobutylamine, tributyl secondary amine, triamyl normal amine, methoxyethylamine, and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquiniline, morpholine, piperidine, pyrrolinin, indoline, quinuclidine, and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m-, p-t.oluidines, phenylenediamines, naphthylamines, and o-, m-, and p-chloroanilines; but in particular triethylamine, isopropylamine, and di-isopropylamine. Examples of quaternary ammonium bases which are suitable for salt formation are, for example, [N (RaRRcRc)] "OH", wherein Ra, Rb, Rc / and R., Independently of each other, are alkyl of 1 to 4 carbon atoms. Other tetra-alkylammonium bases suitable with other anions can be obtained, for example by anion exchange reactions. M ^ preferably represents an ammonium salt, in particular NHJ, or an alkali metal, in particular potassium or sodium. The compounds of the formula I can be present in different tautomeric forms, for example, if R10 is hydroxyl, in the preferred formulation I 'and I "'
I '
I "
Among the compounds of the formula I, those where: p is 0; Rs is haloalkyl of 1 to 6 carbon atoms; R2 is hydrogen, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl from 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms
carbon, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms - sulfinyl, haloalkyl of 1 to 6 carbon atoms - sulfonyl, benzyl - S (0) n -, alkyl of 1 to 6 carbon atoms - amino, dialkyl of 2 to 6 carbon atoms - amino, alkyl of 1 to 6 carbon-aminosulfonyl atoms, dialkyl of 2 to 6 carbon atoms-aminosulfonyl, phenyl, phenoxy, thiophenyl, phenylsulfinyl, or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by alkyl of 1 to 3 carbon atoms , haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or is 0S (0) r; -Rj ?, N (R2 ) S (O) Il 3 -R, cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-S (0) p -alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms; R2 is hydrogen, alkyl of 1 to 6 carbon atoms. haloalkyl of 1 to 6 carbon atoms, alkenium of 2 to 6 carbon atoms, haloalkenyl of 2
to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms , thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfenyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms -sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkyl of 1 to 6 carbon atoms-amino, dialkyl of 2 to 6 carbon atoms-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, dialkyl of 2 to 6 carbon atoms-aminosulfonyl, phenyl, thiophenyl, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible for phenyl to be substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or is -N (R 3) -S (OA-22, cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms S-carbon (0) n-alkyl of 1 to 4 carbon atoms; R4 is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms,
haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxy, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms sulfonyl, haloalkyl of 1 to 4 carbon atoms, formyl, cyano, halogen, phenyl, or phenoxy, it being possible that phenyl, in turn, is substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro; or R4 is a 5 to 10 membered monocyclic or bicyclic fused R5 ring system, which may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being linked by the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, and it is not possible for the ring system to contain more than 2 oxygen atoms, and no more than 2 sulfur atoms, and it is possible that the The ring itself is mono-, di-, or tri-substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms. carbon,. alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxy of 1
at 6 atoms of carbon, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms , thioalkenyl of 3 to 6 carbon atoms, halotiocilkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-thioalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, cyanothioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms sulfinyl carbon, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosulfonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, dialkyl of 2 to 4 carbon atoms - aminosulfonyl, halogen, cyano, ni and phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the
Nitrogen in the heterocyclic ring are different from halogen; R2i and R22, independently of one another, are alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R-.3 /? A / Y independently of one another are hydrogen or alkyl of 1 to 4 carbon atoms; n, nx, n2, n3, and n, independently of each other, are 0, 1 or 2;
wherein R ", Ri, R", and Re, independently of one another, sor hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkene Lo of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carboni Lo, alkyl of 1 to 6 carbon atoms-S (O) r, i7, alkyl of 1 to 6 carbon atoms-NHS (O ) 2, alkyl of 1
to 6 carbon-amino atoms, di- (C 1-6 alkyl) amino, hydroxyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms , hydroxyalkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyloxyalkyl of 1 to 6 carbon atoms, tosyloxyl of 1 to 6 carbon atoms, halogen, cyano, nitro, phenyl, or phenyl which is substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, amino, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 at 4 carbon atoms-S (O) n-8, alkyl of 1 to 4 carbon atoms-S (O) 20, haloalkyl of 1 to 4 carbon atoms-S (O) n 5, haloalkyl of 1 to 4 carbon atoms -S (O) 20, alkyl of 1 to 4 carbon atoms-S (O) 2 NH, alkyl of 1 to 4 carbon atoms-S (0) nis- (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH, or cyano; or R, o and R- adjacent, or Rs and R9 are together - (CH;) n ?; n5, ni7, ni- and ni ?, independently of each other, are 0, 1 or 2; -
m is 2, 3, 4, 5 or 6; W is oxygen, S (0) not / -CRnRi; -, -C (0): 3-; n is 0, 1 or 2; Rn is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl from 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyloxyalkyl of 1 to 4 carbon atoms, tosyloxy.alkyl of 1 to 4 carbon atoms, di- (alkoxy of 1 to 3 carbon atoms-alkyl) methyl, di- (alkyl of 1 to 3 carbon atoms-thioalkyl) methyl, (alkoxy of 1 to 3 carbon atoms-alkyl) - (alkyl of 1 to 3 carbon atoms-thioalkyl) methyl, oxacycloalkyl of 3 to 5 carbon atoms, tiacycloalkyl of 3 to 5 carbon atoms, dioxacycloalkyl of 3 to 4 carbon atoms, dithiacycloalkyl of 3 to 4 carbon atoms, oxatiac: .Calkyl of 3 to 4 carbon atoms, formyl, alkoxy of 1 to 4 carbon atoms-carbonyl, or phenyl, which at the same time it can be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to
4 carbon atoms - carbonyl, alkoxy of 1 to 4 carbon atoms - carbonyl, amino, alkyl of 1 to 4 carbon atoms - amino, dialkyl of 1 to 4 carbon atoms - amino, alkyl of 1 to 4 carbon atoms -S (0) n?, Alkyl of 1 to 4 carbon atoms-S (0) 20, haloalkyl of 1 to 4 carbon atoms-S (0) nt, haloalkyl of 1 to 4 carbon atoms-S (0) ) 0, alkyl of 1 to 4 carbon atoms-S (0) NH, alkyl of 1 to 4 carbon atoms- 5 (0) n 2 (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH, or cyano; ni, n, and n2i, independently of each other, are 0, 1 0 2; or Ri2, together with R9, is a group - (CH) 0-; or is 1, 2, 3, 4 or 5; R: _ is hydrogen, alkyl of 1 to 4 atoms or haloalkyl of 1 to 4 carbon atoms; or R: _, together with Ru, is a group - (CH2) m ?; m4 is 2, 3, 4, 5 or 6; Rui is hydroxyl, 0 ~ MJ halogen, alkoxy of 1 to 12 carbon atoms, alkyl of 1 to 12 carbon atoms, carbonyloxy, alkenyl of 2 to 4 carbon atoms carbonyloxy, cycloalkyl of 3 to 6 carbon atoms -carbonyloxy, alkoxy of 1 to 12 carbon atoms -carbonyloxy, alkyl of 1 to 12 carbon atoms -carbonyloxy, R.23R24N-C (0) 0, alkyl of 1 to 12
carbon atoms-S (0) r; -, haloalkyl of 1 to 4 carbon atoms-S (0) n9-, alkenyl of 2 to 12 carbon atoms-S (0) nio-, 'haloalkenyl of 2 to 12 carbon atoms-S (0) r? -, alkynyl of 2 to 12 carbon atoms-S (0) 22; benzyloxy, phenoxy, thiophenyl, phenylsulfinyl, or phenylsulfonyl, wherein the phenyl group, in turn, may be substituted by alkyl of 1 to 4 carbon atoms. haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, carbonyl of 1 to 4 carbon atoms, alkyl from 1 to 4 carbon-amino atoms, dialkyl of 1 to 4 carbon-amino atoms, alkyl of 1 to 4 carbon atoms-S (0) r 13, alkyl of 1 to 4 carbon atoms -5 (0) 0, haloalkyl of 1 to 4 carbon atoms S (0) r, i4, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0) NH, alkyl of 1 to 4 carbon atoms-S (0) 2N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano, or is alkyl of 1 to 4 carbon atoms-S (0) y, phenyl-S (0) 0, (alkoxy of 1 to 4 carbon atoms) P (0) 0, alkyl of 1 to 4 carbon atoms (alkoxy of 1 to 4 carbon atoms) P (0) 0, or H (alkoxyl of 1 to 4 carbon atoms) P (0) 0; n8, n., n: 0, nn, ni2, n13 and ni4, independently of each other, are 0, 1 or 2;
RIA is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonyl, or phenyl, which in turn can be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 atoms carbon, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbons, alkyl of 1 to 4 carbon atoms, carbonyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-- amino, dialkyl of 1 to 4 carbon-amino atoms, alkyl of 1 to 4 carbon atoms-S (O) n? s / alkyl of 1 to 4 carbons-S (O) 0 atoms, haloalkyl of 1 to 4 carbon atoms-S (O) nie, haloalkyl of 1 to 4 carbon atoms-S (EYO, alkyl of 1 to 4 carbon atoms-S (O) 2 NH, alkyl of 1 to 4 carbon atoms-S (O ) 2N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano; i5 And n? ¿, independently of each other, are 0, 1 or 2; and the agrochemically tolerated M + salts, and all the stereoisomers and tautomers of the compounds of the formula I. In a preferred group of compounds of the formula I, Rio is halogen, thiocyanate, thioalkyl of 1 to
12 carbon atoms, alkyl of 1 to 12 carbon atoms sulfinyl, alkyl of 1 to 12 carbon atoms
sulfonyl, halotioalkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms sulfinyl, haloalkyl of 1 to 12 carbon atoms sulfonyl, thioalkenyl of 1 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms-sulfinyl , alkenyl of 2 to 12 carbon atoms-sulfonyl, halotioalkenyl of 2 to 12 carbon atoms, haloalkenyl of 2 to 12 carbon atoms sulfinyl, haloalkenyl of 2 to 12 carbon atoms-sulfonyl, thioalkynyl of 2 to 12 carbon atoms ,. alkynyl of 2 to 12 carbon atoms sulfinyl, alkynyl of 2 to 12 carbon atoms-sulfonyl, alkoxy of 1 to 4 carbon atoms carboni Lioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 2 carbon atoms-sulfinyl, alkoxy of 1 to 4 carbon atoms carbonyl-alkyl of 1 to 2 sulfur carbon atoms, alkyl of 1 to 3 carbon atoms-S (O) 2 NH, haloalkyl of 1 to 8 carbon atoms -S (O) 2 NH, alkyl of 1 to 8 carbon atoms-S (O) 20, alkyl of 1 to 18 carbon atoms, carbonyloxy, alkenyl of 2 to 18 carbon atoms-carbonyloxy, cycloalkyl of 3 to 6 atoms of carbon-carbonyloxy, alkoxy of 1 to 12 carbon atoms-carbonyloxy, thioalkyl of 1 to 12 carbon atoms-carbonyloxy, R? bR? 7NC (O) O-, R? 6Ri7NC S) 0-, thiobenzyl, benzylsulfinyl,
benzylsulfonyl, thiophenyl, phenylsulfinyl, phenylsulfonyl, phenylsulfonyloxy, or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted as indicated in claim 1; or is an Ari-thio, Ar-sulfinyl, Ari-sulfonyl group, wherein Ari is a 5- or 6-membered monocyclic ring system which may be aromatic or may be partially saturated, and may contain from 1 to 2 selected heteroatoms from the group consisting of nitrogen, oxygen, and sulfur, and which, in turn, may be substituted as indicated in claim 1; or is thienylcarbonyloxy or furylcarbonyloxy, it being possible that these, in turn, are substituted by methyl or halogen, or pyridylenediloxyloxy which in turn may be substituted as indicated in claim 1. In the preferred compounds of formula I, furthermore, Rio is hydroxyl or OAT. Other compounds of formula I that should be emphasized are those in which W is oxygen, -CRnRu-or -C (0) ~, where, in particular, when W is -CRuRi? -, a) Rr¿ is hydrogen , methyl, ethyl, cyano, methoxycarbonyl, ethoxycarbonyl, thiomethyl, methylsulphonyl, methylsulphonyl, or methoxy; and R? , R8, R9, Rn, and R? 2, independently of each other are
hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkenyl of 2 to 3 carbon atoms, or alkynyl of 2 to 3 carbon atoms, or b) adjacent R6 and R7, and / or Rs and R? they are together
- (CAA-, -C (0) 0 (CH2) 2- or S (0)? (CH2) 3-; oc) R6 is hydrogen, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, thiomethyl, methylsuifinyl, methylsulfonyl, or methoxy , and R? 2 together
In addition, the preferred groups of compounds of formula I are those wherein: W is oxygen, and R ?, R7, R ° _ and R? , independently of one another, are hydrogen or alkyl of 1 to 3 carbon atoms; or W is -C (O) - and R, R7, Re, and RQ, independently of one another are alkyl of 1 to 3 carbon atoms; or R2 is hydrogen and R3 is methyl; or R is methyl, ethyl, normal propyl, isopropyl, vinyl, methoxymethyl, methoxycarbonylloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, or cyanomethyl.
Other compounds of the formula I to be emphasized are those wherein R is hydrogen or methyl, or R5 is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl, or difluoromethyl. In a further preferred group of compounds of formula I, R3 is hydrogen, R2 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, cyclopropyl, alkenyl of 2 to 3 carbon atoms, haloalkenyl of 2 to 3 carbon atoms, alkylo of 2 to 3 carbon atoms, alenyl, alkoxy of 1 to 2 carbon atoms alkyl of 1 to 2 carbon atoms, thioalkyl of 1 to 2 carbon atoms-alkyl of 1 to 2 carbon atoms, cyanoalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms-carbonyl Lalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms, carbonyloxyalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, allyloxy, propargyloxy, thioalkyl of 1 to 3 carbon atoms, alkyl of 1 to 3 carbon atoms-sulfinyl, or cyano. The compounds of the formula I, wherein Q is a Qi group can be prepared using the processes that are known per se, for example, those described in European Patent Numbers EP-A-0 353 187 and EP-A-0 316 491, for example, either by:
a) reacting a compound of the formula
III
wherein R2, R3, R, and R5 have the meaning given in formula I, and X is an leaving group, for example halogen or cyano, with a compound of the formula
II.
where R ,. , RT, R8, RQ and W have the meaning given in formula I, in the presence of a base, and in a solvent, to give the compound of formula IV
IV)
and subsequently isomerization of the latter, for example, in the presence of a base, and a catalytic amount of dimethylaminopyridine (DMAP) or a source of cyanide; or b) reacting a compound of formula XVI:
wherein R2, R3, 4, and Rs have the meaning given in formula I, with the compounds of formula II:
wherein Rk, R7, Ra, RQ, and W have the meaning given in formula I, in an inert organic solvent, in the presence of a base and coupling agent, to give the compound of formula IV:
and subsequently isomerizing the latter, for example as described in route a). The preparation of the compounds of the formula I is illustrated in greater detail in the following reaction scheme.
Reaction Scheme 1 Route to
III
I s ornen 2 Base, p
catalyzed
Route b)
solvent for example CH Cl 0-110 C
I sorneation: Base, for example, (C H) N
KCN catalyst
The compounds of the formula I with the group Qi, wherein R, is hydroxyl, can preferably be prepared according to this reaction scheme. The starting material for the preparation of the compounds of the formula I, wherein Q is a group Qi and Rn is hydroxyl, according to reaction scheme 1, route a), are the carboxylic acid derivatives of the formula III , wherein X is an leaving group, for example halogen, for example iodine, bromine, and
particular chlorine, N-oxyphthalimide or N, 0-dimethylhydroxylamino, or part of an activated ester, for example
(formed from dicyclohexylcarbodiimide (DCC), and the corresponding carboxylic acid) or
C -H N = C- H (CH) N (CH) O- (formed from N-ethyl-N '- (3-dimethylaminopropyl) carbodiimide (EDC) and the corresponding carboxylic acid). These are reacted with the dione derivatives of the formula II in an inert organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, and in the presence of a base, for example an alkylamine, preferably triethylamine, an aromatic amine, for example, pyridine, or 4-dimethyl-aminopyridine (DMAP), to give the isomeric enol ethers of formula IV. This esterification is carried out successfully at temperatures from 0 ° C to 110 ° C. The isomerization of the ester derivatives of the formula IV to give the dione derivatives of the
Formula I (wherein RiC is OH) can be carried out, for example, in analogy with European Patents Nos. EP-A-0 353 187 or EP-A-0 315 491, in the presence of a base, for example an alkylamine, for example, triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP, or a catalytic amount of a cyanide source, for example acetone cyanohydrin or potassium cyanide. Both reaction steps can be carried out without the isolation of the intermediates IV, in particular when a cyanide compound of the formula III (X = cyano) is used, or in the presence of a catalytic amount of acetone cyanohydrin or cyanide. potassium According to reaction scheme 1, route b), the desired diones of the formula I (wherein Ri is hydroxyl) can be obtained, for example, in a manner analogous to Chem. Lett. 1975, 1045, by esterification of the carboxylic acids of the formula? Vi with the dione derivatives of the formula II in an inert solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile, or an aromatic hydrocarbon, for example toluene, in the presence of a base, for example an alkylamine, for example triethylamine, and an agent
coupling, for example 2-chloro-1-methylpi-cidinium iodide. Depending on the solvent used, this esterification is carried out successfully at temperatures of 0 ° C to 110 ° C, and first, as is described in route a), the isomeric ester of formula IV is produced, which can be isomerized as it is described in route a), for example, in the presence of a base and a catalytic amount of DMAP, or a source of cyanide, to give the desired dione derivatives of formula I (Rio = hydroxy lo). The activated carboxylic acid derivatives of the formula III in the reaction scheme I (route a), wherein X is an outlet group, for example halogen, for example bromine, iodine, or in particular chlorine, can be prepared by methods conventional known, for example, as described by C. Ferri "Reaktionen der organischen Synthese" ["Reactions in organic synthesis"], Georg Thieme Verlag, Stuttgart, 1978, pages 460 et seq. This is shown in reaction scheme 2 below.
Reaction test 2
According to reaction scheme 2, the compounds of formula III, wherein X has the above-mentioned meaning, are prepared, for example, by the use of a halogenating agent, for example thionyl halides, for example thionyl or thionyl bromide; phosphorus halides or phosphorus oxyhalides, for example phosphorus pentachloride or phosphorus oxychloride, or phosphorus pentabromide or phosphoryl bromide; or oxalyl halides, for example oxalyl chloride, or by the use of a reactant to form activated esters, for example N, N '-dicyclohexylcarbodiimide (DCC), or N-ethyl-N' - (3-dimethylaminopropyl) carbodi-imide (EDC), of the formula XVII. Examples of the meanings of X for the compound of the formula XVII as a halogenating agent, are a leaving group, for example, halogen, for example fluorine, bromine, or iodine, and in particular chlorine, and Wi is, for example , PC12, SOCI, SOBr or CICOCO.
The preferred reaction is carried out in an inert organic solvent, for example in aliphatic, halogenated, aromatic, or aromatic halogenated hydrocarbons, for example, normal hexane, benzene, toluene, xylenes, dichloromethane 1,2-dichloroethane, or chlorobenzene, at temperatures of reaction on the scale from -20 ° C to the reflux temperature of the reaction mixture, preferably from 40 ° C to 150 ° C, and in the presence of a catalytic amount of N, N-dimethylformamide. These reactions are generally known, and different variations with respect to the leaving group X are described in the literature. The compounds of the formula I, wherein Ri0 is different from hydroxyl or halogen, can be prepared by the conversion methods which are in general known from the literature, for example, by acylation or carbamoylation methods, using appropriate acid chlorides, in the presence of a suitable base, starting from the compounds wherein Ri is hydroxyl, or they can be prepared by reactions of nucleophilic substitution on the chlorides of the formula I, wherein R. is halogen, which can also be obtained by known methods, by reaction with a chlorinating agent, such as phosgene, thionyl chloride, or oxalyl chloride.
In this case, examples of the compounds which are used are suitably substituted amines, or directly, hydroxylamines, or alkylsulfonamides, mercaptans, thiophenols, phenols, Ar5-NH2 or Ar2-SH, in the presence of a base, for example 5-ethyl -2-methylpyridine, di-isopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate, or potassium carbonate. The compounds of the formula I in which Ri contains thio groups can be oxidized in analogy to known conventional methods, for example using peracids, for example meta-chloroperbenzoic acid (m-CPEA), or peracetic acid, to give the sulfones and the corresponding sulphoxides of the formula I. The degree of oxidation on the sulfur atom (SO- or S0-) can be controlled by the amount of oxidant. As well, the resulting derivatives of formula I, wherein R? it is different from hydroxyl, it can exist in different isomeric forms which, if appropriate, can be isolated in pure form. Accordingly, the invention also extends to all of these stereoisomeric forms. Examples of these isomeric forms are the formulas I *, I **, and i *** below, where Q is the Qi group (see also note and schematic on page 10 above).
I * * *
All other compounds within the scope of formula I can be prepared easily, taking into consideration the chemical properties of the pyridyl or Q fraction. The final products of formula I can be isolated in the customary manner, by concentration or by solvent, and are purified by recrystallization or trituration of the solid residue in solvents where they are not readily soluble, such as ethers, aromatic hydrocarbons, or chlorinated hydrocarbons, by distillation, or by
column chromatography medium and a suitable eluent. Furthermore, the expert knows in which sequence certain reactions are conveniently carried out in order to avoid secondary reactions. Unless directed synthesis is performed to isolate the pure isomers, the product can be obtained as a mixture of two or more isomers. The isomers can be resolved by methods known per se. The compounds of the formula I, wherein n is
1, that is, the corresponding N-oxides of the formula I, can be synthesized by the reaction of a compound of the formula I, wherein n is 0, with a suitable oxidant, for example with the adduct of H202-urea , in the presence of an acid anhydride, for example trifluoroacetic anhydride. The compounds of the formula I, wherein R in the ortho position in relation to the pyridine nitrogen, is 1-chloro-alkyl of 1 to 2 carbon atoms, 1-hydroxy-1-alkyl of 2 carbon atoms, 1- (C 1-6 alkylcarbonyloxy) -alkyl of 1 to 2 carbon atoms, 1-benzoyloxyalkyl of 1 to 2 carbon atoms, 1- (C 1-4 alkoxycarbonyloxy) - alkyl of 1 to 2 carbon atoms, 1- (thioalkyl of 1 to 4 carbon atoms) -alkyl of 1 to 2
- carbon atoms, 1- (alkyl of 1 to 4 carbon atoms-sulfinyl) -alkyl of 1 to 2 carbon atoms, 1- (alkyl of 1 to 4 carbon atoms-sulfonyl) -alkyl of 1 to 2 atoms of carbon, 1-thiocyanato-alkyl of 1 to 2 carbon atoms, 1-cyano-alkyl of 1 to 2 carbon atoms, can also be prepared, for example, by heating an N-oxide of the formula I under reaction conditions known, for example in the presence of tosyl chloride (see, for example, Parham, E, Sloan, KB, Reddy, K.R., Olson, PE, J. Org Chem 1373, 38, 927) or in the presence of an acid anhydride
(see, for example, Konno, K., Hashimoto, K .; Shirahama, H., Matsumoto, T .; He terocycl is 1986, 24, 2169) and if appropriate, subsequently the product is further reacted. These reaction sequences can be demonstrated with reference to the following example:
(p o r e j C 1 C 0 E t, A c ^ O I or T s C l)
E = O C (0) R, OH, C l E = OC (O) R, C l
The compounds of the formula I, wherein R in the ortho position in relation to the pyridine nitrogen, in particular 1-bromo-alkyl of 1 to 2 carbon atoms, 1-chloro-alkyl of 1 to 2 carbon atoms, 1-fluoro-alkyl of 1 to 2 carbon atoms, 1,1-dibromonetyl, 1,1-dichloromethyl, formyl, 1- (thioalkyl of 1 to 4 carbon atoms) -alkyl of 1 to 2 carbon atoms, 1 - (alkyl of 1 to 4 carbon atoms-sulfinyl) -alkyl of 1 to 2 carbon atoms, 1- (alkyl of 1 to 4 carbon atoms-sulfonyl) -alkyl of 1 to 2 carbon atoms, 1-thioc ? anato-alkyl of 1 to 2 carbon atoms, or 1-cyano-alkyl of 1 to 2 carbon atoms, can also be prepared, for example, by the oxidation of a compound of formula I, wherein Rio is particular chlorine, alkoxy of 1 to 4 carbon atoms-carbonyloxy, or benzoylcarbonyloxy, under known halogenation conditions, for example with N-bromosuccinimide or N-chlorosuccinimide, in the presence of light and a free radical initiator, for
example benzoyl peroxide, to give the compounds of
1-bromo or 1-chloro, 1,1-dibromo or 1,1-dichloro, and subsequently the latter is re-functionalized to give the corresponding derivatives. Again, these sequences. Reaction rates can be demonstrated with reference to the following example.
F = F, Me X = C1, Br; X H, X or aqueous processing
= C1, Br; = H,
The compounds of the formula I can also be synthesized by the reaction of a compound
of the formula I wherein p is 0, and R1C is alkyl of 1 to 6 carbon atoms, with a suitable base, for example di-isop :: lithium opylamide or normal lithium butyl, at temperatures between -100 ° C and 20 ° C (preferably between -70 ° C and -50 ° C), in an inert solvent (for example tetrahydrofuran), to give the corresponding dianion. The person skilled in the art knows how carbanions can be converted by means of electrophilic substitution, for example with a chloroformic ester. This reaction sequence can be demonstrated with reference to the following example:
-100-20A
Electroflio (eg C1CO CH)
E = CO CH E = CO CH
Other compounds within the scope of formula I can be prepared with suitable electrophiles, taking into consideration the chemical properties of the fraction. of pyridyl or Q. The compounds of the formula Illa:
wherein: Rs? i is haloalkyl of 1 to 6 carbon atoms; R30? it is hydrogen; R (1) is hydrogen or alkyl of 1 to 6 carbon atoms, and R2o is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, or vinyl substituted by alkoxy of 1 to 2 carbon atoms-carbonyl or by phenyl, alkynyl of 2 to 6 carbon atoms, or haloalkynyl of 2 to 6 atoms of carbon, or ethynyl or alenyl of 3 to 6 carbon atoms substituted by trimethylsilyl, hydroxy, alkoxy of 1 to 2 atoms
of carbon, alkoxy of 1 to 2 carbon atoms-carbonyl, or by phenyl; or cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by halogen, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-S (O) r, -alkyl of 1 to 4 carbon atoms, cyano-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms, oxiranyl, alkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 4 carbon atoms, dialkyl of 1 to 4 carbon atoms-aninoalkyl of 1 to 4 carbon atoms, hydroxy-alkyl of 1 to 4 atoms of carbon, thioalkyl of 1 to 12 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, or formyl-alkyl of 1 to 4 carbon atoms, or R2u? is a 5 to 10 membered monocyclic or bicyclic fused ring system which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the system being of ring bound with the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, C = C-, -CH20-, -CH2N (alkyl of 1 to 4 carbon atoms) -, -CH2S-, -CH2SO-, or -CH2S02-, and it is not possible that each
ring system contains more than 2 oxygen atoms and more than 2 carbon atoms of sulfur, and it is possible for the ring system itself to be mono-, di-, or tri-substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon-thioalkyl atoms, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms carbon-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosulfonyl , alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms)
carbon) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, carbon, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are different from halogen; and X is halogen or cyano, are novel and were developed specifically for the preparation of the compounds of the formula I, and therefore, are an additional objective of the present invention. The compounds of formula XVIa:
wherein R2oi / R301 / R401 and R501 have the above-mentioned meaning, with the proviso that, if R501 is trifluoromethyl, and simultaneously R30? and R4 ?? are hydrogen, then R 0? is different from alkyl of 1 to 6 carbon atoms, they are novel, and by
consequently, they are an additional objective of the present invention. The compounds of the formula Ch (or formula II) are coroacids and can be prepared by methods similar to those described, for example, in J. Org. Chem (1577) 42, 1163-9, in UK Patent Application Number GB 2205316, in Patent Numbers DE 3902818, GB 8705557, DE 4434987, WO 9213821, and in Aust. J. Chem. (1976), 29 (11), 2525-31, Chem. Commun. (1998), (16), 1691-1692. The compounds of formula XVI (or XVIa and XVIb) are synthesized by methods similar to known methods, for example, as in Heterocycles 46, 129 (1997), or Helvética Chimica Acta 71, 596 (1988), and are characterized in that any of: a) a compound of formula V:
where R3o? it is hydrogen; R4o? is hydrogen, alkyl of 1 to 6 carbon atoms, or phenyl, it being possible that phenyl in turn is -substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to
3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro; or R40? is a 5 to 10 membered monocyclic or bicyclic fused ring system which may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, and it is not possible for the ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or tri-substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms , alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, 1 to 1 alkoxy
4 carbon atoms-thioalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2
carbon atoms, cyanothioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosuifonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms Aminosulfonyl, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible for phenyl and tisbenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are different from halogen, and Ri i is alkyl of 1 to 4 carbon atoms, a compound of the formula VI is acylated
where R o; is haloalkyl of 1 to 6 carbon atoms, to give the compound of formula VII:
wherein R301 / R401 / R501 / and 14 have the above-mentioned meaning, in the presence of a base, for example an aromatic amine, for example pyridine, and the alkoxy group subsequently is exchanged for the amino group with ammonia in an organic solvent, for example a halogenated hydrocarbon, for example dichloromethane, a nitrile, for example acetonitrile. The resulting compound of the formula VI I I:
subsequently it is subjected to a condensation reaction with a compound of the formula IX:
Ri
where R20? is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms- S (0) n4_alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms -carbonyloxyalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, oxiranyl, alkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 4 carbon atoms, di - (alkyl of 1 to 4 carbon atoms) aminoalkyl of 1 to 4 carbon atoms, or formylalkyl of 1 to 4 carbon atoms; or R n? is an Ar "-alkyl group of 1 to 4 carbon atoms, where Ar" is a fused monocyclic or bicyclic ring system of 5 to 10 members which may be aromatic or may be partially saturated, and may contain 1 to 4 heteroatoms selected from the group consisting of
nitrogen, oxygen, and sulfur, it is not possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or tri-substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl , acetyl of 3 to 5 carbonace thioalkyl atoms, alkoxy of 3 to 6 carbon atoms- c arbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon-sulfonyl, aminosul fonyl, alkyl of 1 to 2 carbon atoms-aminosul fonyl, di- (alkyl of 1 to 2 carbon atoms)
carbon) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are different from halogen, and Ri4 has the above-mentioned meaning, and subsequently the resulting compound of formula Xa is hydrolyzed:
to give the compound of formula XVIa
wherein R2oi / soi / R401 and R501 have the above-mentioned meaning; or b) a compound of formula XI:
wherein R 4 has the above-mentioned meaning, it is subjected to a condensation reaction with a compound of the formula XII:
and the resulting compound of formula XIII
(XVIII
wherein R3 R, and R £ have the above-mentioned meaning, and Ri is alkyl of 1 to 4 carbon atoms, is chlorinated to give the compound of the formula XIV:
where R3, R, Rs, and R? they have the above-mentioned meaning (for example using P0C13) / and this compound is subsequently reacted with a nucleus: ofyl of the formula XV:
Z-R15 (XV)
wherein Z is SH, OH, or amino, and R? 5 is alkyl of 1 to or carbon atoms, alkenyl of 3 to 5 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms carbon, haloalkynyl of 3 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms, phenyl, or benzyl, it being possible for the phenyl group, in turn, to be substituted by alkyl from 1 to 3
carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or is alkoxy of 1 to 4 carbon atoms-alkyl from 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinylalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 atoms of carbon-sulfonylalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyl, or di- (alkyl of 1 to 4 carbon atoms) aminosulfonyl, or Ris is a monocyclic or bicyclic fused ring system of 5 to 10 members that may be aromatic or may be partially saturated, and may contain from 1 to 4 het. Or rodents selected from the group consisting? in nitrogen, oxygen, and sulfur, it is not possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or tri- substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms
carbon, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl and 3 to 6 atoms of carbon, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon atoms-thioalkyl, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl or, haloalkyl of 1 to 6 carbon atoms-sulfinyl or, alkyl of 1 to 6 carbon atoms- sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosul fonyl, alkyl of 1 to 2 carbon atoms-aminosul fonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfonyl, (CH2) rRt, NR8R9, halogen , cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl are substituted on the phenyl ring by a alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and the substituents being on it. Nitrogen in the heterocyclic ring other than halogen, in the presence of a base, to give the compounds of the formula Xb:
wherein Ri, R? 5, R3, Ri, R =, and Z have the meanings mentioned above, and the resulting compound is subsequently hydrolyzed to give the compound of the formula XVIb:
H
wherein Ris, R3, R4, R5, and Z have the above-mentioned meaning. The compounds wherein Z-Ris and Z are oxygen, and Ris is alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms ,. haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl
from 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, or alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, can also be reacted, starting from XIII, by alkylation direct with the corresponding alkylating agent L-R15 XVa, wherein L is an leaving group, such as chlorine, bromine, iodine, mesyloxy, or tosylexyl. The compounds of the formula XVIb, wherein Z-R15 is fluorine, are prepared by the reaction of a compound of the formula XIV with potassium fluoride, and if appropriate, a catalytic amount of 18-crown-6 in the presence of a polar aprotic solvent, for example acetonitrile, dimethyl formamide, or sulfolane. Compounds of formula XVIc wherein Z-R15 is hydrogen, are prepared by reducing the chloro group in formula XIV, for example with hydrogen, in the presence of a suitable metal catalyst, or in the form of ammonium, in a solvent suitable. The preparation of the compounds of formula XVI or XVIa, XVIb, and XVIc, are illustrated in greater detail in reaction schemes 3 and 4 below.
Reaction scheme 3
For
XVIa
Reaction scheme 4
Xc XVI C
Reduction e.g MeOH / NH4HC0r MeOH
XV Ib Xb
The compounds of formula XVId, wherein R 2 is bromomethyl, cyanomethyl, thiocyanatomethyl, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, or a vinyl substituted by phenyl, alkynyl of 2 to 6 carbon atoms , haloalkynyl of 2 to 6 carbon atoms, a trimethylsilyl, hydroxyl, alkyl of 1 to 2 carbon atoms-alkoxy of 1 to 2 carbon atoms-carbonyl, or ethynyl substituted by phenyl, alenyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or cycloalkyl of 3 to 6
Mono- or polyhalogenated carbon atoms can be prepared, for example, according to the generally known conversion methods, which are shown in reaction scheme 4a.
Reaction scheme 4a
XI XVld Xm
The intermediates of the formula XVIa, wherein R <2> is CF2C1, are prepared as described in reaction scheme 3, or by the reaction of a compound of formula Xa, wherein R50? is trichloromethyl, with hydrofluoric acid, in a pressurized container, at temperatures between 0 ° C and 220 ° C (preferably 600 ° C to 200 ° C). Compounds of formula XVIa, wherein R501 is CHF;, can be prepared as in reaction scheme 3, or by heating a compound of formula Xa, wherein R301 R 01 Ri4 / and R201 have the above meaning mentioned, and R501 is CFC1, in an inert solvent, for example, toluene or benzene, at temperatures between 25 ° C and 120 ° C (preferably 80 ° C to 120 ° C), with tributyltin hydride or 1, 1,1,3,3, 3-hexamethyl-2- (trimethylsilyl) trisilane, in the presence of a catalytic amount of azoisobutyronitrile, and subsequently the resulting compound is hydrolyzed to give the compound of the formula XVIa wherein R5 ,,? It is CHF. Compounds of the formula XVIa wherein R? O ?, R301 / Rsoi / and S? Have the above-mentioned meaning, can also be prepared by the reaction of a compound of the formula Xc, wherein R? 4, R301 / R401 , and R501 have the meaning above
mentioned, and R20? is CH C1, by nucleophilic substitution, for example with an alkali metal iodide in an inert solvent, to give the corresponding iodides, or by means of hydrobromic acid gas in lower carboxylic acids, such as glacial acetic acid, to give the corresponding bromine derivatives (e.g., in accordance with U.S. Patent No. US-3974166). or by means of alkali metal fluoride in a dipolar solvent, such as sulfolane, to give the corresponding fluorine derivatives, or, to prepare an alkoxy radical Xd, by the reaction of a halogen derivative Xc with an alcohol or phenol, in the presence of a base, such as sodium hydride, or an alkali earth metal oxide or alkaline earth metal carbonate, or directly with an alkali metal alkoxide in an inert solvent, such as formamide dimethyl or in an excess of the alcohol ROH corresponding to the group to be introduced, temperatures between -5 ° C and 160 ° C, or, in order to prepare a corresponding aromatic or aliphatic thioether Xe, by reaction, in a manner analogous to what has been said above, of the halide Xc with an aliphatic thiol or aromatic in the presence of a base, such as hydride
sodium, either with an alkali metal salt of a thiol in an inert solvent, from -10 ° C to 150 ° C, or for the purpose of preparing the corresponding sulfinyl or sulfonyl derivatives Xe, by carrying out the reaction with an oxidant, such as m-chloroperbenzoic acid or sodium periodate or sodium perborate, with the temperature control known in the art, depending on the degree of oxidation (for example, -30 ° C to + 50 ° C for n = 1 ) or from -20 ° C to + 100 ° C for n = 2), in an inert solvent, such as dichloromethane, to give Xf, or, in order to prepare cyanomethylene derivatives of formula Xg, by reaction of a halide of the formula Xc with an alkali metal cyanide or tetra-alkylammonium cyanide or copper cyanide, in an inert solvent, such as dichloromethane, tetrahydrofuran, or ometamethyl form, at temperatures between 0 ° C and 220 ° C . The preparation of the compounds of the formula XVIa (R501 = CF2C1) and of the intermediates of the formulas Xc, Xd, Xe, Xf, and Xg, is illustrated in greater detail in the following reaction schemes 5, 6, and 7.
Reaction scheme 5
Xa Xa (R: F5o: = CC1: í_'li = CC1F.
Reaction scheme 6
i * "p R i Jl
p ClC N R-
Xa (Rsct = CF.CI) «lp-Bu) 3Sn-H? G (R ^ = ^^ XVIa (Rsot = CHF2)
Reaction scheme 7
xg Xd
To prepare all other compounds of formula X and XVI that are functionalized according to the definition of R20? (Z-R15) to R501, a multiplicity of known standard methods are suitable, for example alkylation, halogenation, acylation, amidation, oximation, oxidation, and reduction, depending on the choice of suitable preparation methods, of the properties ( reactivities) of the substituents in the intermediates. The reactions to give the compounds of the formula I are conveniently carried out in inert, aprotic organic solvents. These solvents are hydrocarbons, such as benzene, toluene, xylene, or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloromethane, tetrachloromethane, or chlorobenzene, ethers, such as diethyl ether, ethylene glycol, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran, or dioxane. , nitriles, such as acetonitrile or propionitrile, amides, such as N, N-dimethylformamide, diethyl formamide, or N-methylpyrrolidinone. The reaction temperatures are conveniently between -20 ° C and + 120 ° C. In general, the reactions are slightly exothermic, and as a rule, they can be performed: at room temperature. To reduce the
Reaction time, or otherwise start the reaction, the mixture can be briefly heated up to the boiling point of the reaction mixture. The reaction times can also be reduced by the addition of a few drops of base as the catalyst of the reaction. Suitable bases are, in particular, tertiary amines, such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo [4.3.0] non-5-ene, or 1, 5-diazabicyclo [5.4.0] undec-7-ene. However, inorganic bases, such as hydrides, for example sodium hydride or calcium hydride, hydroxides, for example sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, can also be used as bases. or hydrogen carbonates, such as potassium hydrogen carbonate and sodium hydrogen carbonate, can also be used as bases. The compounds of the formula I can be isolated in the customary manner, by concentration and / or by evaporation of the solvent, and can be purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, hydrocarbons aromatics, or chlorinated hydrocarbons.
All application methods that are conveniently used in agriculture, for example, application before emergence, application after emergence, and seed treatment, as well as different methods and techniques, for example the controlled release of the active ingredients, are suitable for the use according to the invention of the compounds of the formula I or of the compositions comprising them. For this purpose, the active ingredient in solution is applied to mineral carriers for granules, or to polymerized granules (urea / formaldehyde), and dried. If appropriate, an additional coating (coated granules) can be applied, which allows the active ingredient to be released in a controlled manner for a specific period of time. The compounds of formula I can be used as herbicides as such, that is, as obtained from the synthesis. However, it is preferably processed in the usual manner, together with auxiliaries conventionally used in the formulation technique, for example, to give emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, powders. dry, granules, or
microcapsules. These formulations are described, for example, in International Publication Number WO 97/34485 on pages 9 to 13. Application methods, such as spraying, atomizing, dusting, wetting, dispersing, or watering, as well as the type of composition, they are selected to fit the intended objectives and the prevailing circumstances. The formulations, ie the compositions, preparations, or products comprising the active ingredient of the formula I, or at least one active ingredient of the formula I, and as a rule, one or more solid or liquid formulation aids, are prepared from the known manner, for example by intimate mixing and / or grinding of the active ingredients together with the formulation aids, for example solvents or solid carriers. In addition, surface active compounds (surfactants) can additionally be used when preparing the formulations Examples of solvents and solid carriers are indicated, for example, in International Publication Number WO 97/34485 on page 5. Suitable surface activity compounds are, depending on the nature of the
active ingredient of formula I to be formulated: nonionic, cationic, and / or anionic surfactants, and mixtures of surfactants, having good emulsifying, dispersing, and wetting properties. Examples of suitable anionic, nonionic, and cationic surfactants are listed, for example. in International Publication Number WO 97/34485 on pages 7 and 8. The surfactants conventionally used in the formulation art, which are described, among others, in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridge ood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch" ["Guide to Surfactants"], Cari Hanser Verlag, Munich / Vienna, 1981, and M. and J. Ash, "Encyclopedia of Surfactants", volumes I- III, Chemical Publishing Co. , New York, 1980-81, are also further suitable for the preparation of the herbicidal compositions according to the invention. As a rule, the herbicidal formulations comprise from 0.1 to 99 percent by weight, in particular from 0.1 to 95 percent by weight of herbicide, from 1 to 99.9 percent by weight, in particular from 5 to 99.8 percent by weight of an auxiliary of solid or liquid formulation, and from 0 to 25 per cent by weight, in particular from 0.1 to 25 per cent by weight.
one hundred percent by weight of a surfactant. Although concentrated compositions are preferred as commercially available articles, the final consumer uses, as a rule, dilute compositions. The compositions may also comprise additional additives, such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (coconut oil, rapeseed oil, or epoxidized soybean oil), lovers antisp, eg silicone oil, preservatives, regulators. of viscosity, binders, viscosifiers, and fertilizers, or other active ingredients. As a rule, the active ingredients of formula I are applied to the plant or its environment in concentrations of 0.001 to 4 kilograms / hectare, in particular 0.005 to 2 kilograms / hectare. The dosage required for the desired action can be determined by experiment. It depends on the type of action, the stage of development of the crop plant, and the grass, and the application (location, time, method), and, due to these parameters, they can vary within wide limits. The compounds of the formula I are distinguished by their herbicidal and growth inhibiting properties, which allow them to be used in cultures of
useful plants, in particular in cereals, cotton, soy, sugar beet, sugar cane, plantation crops, rapeseed, maize, and rice, and for the non-selective control of herbs. It is also understood that the crops include those that have been made tolerant to herbicides or classes of herbicides by conventional methods of plant breeding or by genetic engineering. The herbs to be controlled can be both mono and di-cotyledonous herbs, such as Stellaria, Nasturtimm, Agrostis, Digitaria, Oats, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rortboellia, Cyperus, Abutilon, Aids, Xanthium, Amaranthus, Chenopodium, Ipomsea, Chrysanthemum, Galium, Viola and Veronica. The following examples illustrate the invention in greater detail, without limiting it.
Preparation Examples:
Example Hl: Preparation of 3-hydroxy-4,4-dimethyl-2- (2-methyl-1-6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone (compound A2-B24):
6.68 grams (0.0305 moles) of methyl 2-methyl-6-trifluoromethylnicotinate (prepared as described in Heterocycles, 46, 129 (1997)) are dissolved in 250 milliliters of methanol / water (3: 1 mixture), and add in 1.92 grams (0.046 moles) of lithium hydroxide hydrate, at a temperature of 22 ° C. After 4 hours at 22 ° C, the reaction mixture is poured into ethyl acetate and 2N hydrochloric acid, and the organic phase is washed three times with water, dried with sodium sulfate, and evaporated, and the residue It is crushed with a small amount of hexane. After filtration, 5.69 grams (90 percent of theory) of 2-methyl-6-tri fluoromethylnicotinic acid of a melting point of 147-149 ° C are obtained. The resulting 2-methyl-6-trifluoromethyl-nicotinic acid (1.026 grams, 0.005 moles) is dissolved in 20 milliliters of oxalyl chloride. Three drops of dimethyl formamide are added, and the mixture is refluxed for 1 hour. The mixture is then concentrated on a rotary evaporator, and the residue (2-methyl-6-trifluoromethylnicotinoyl chloride) is recovered in 100 milliliters of methylene chloride. At a temperature of 0 ° C, 1.6 milliliters (0.0115 moles) of triethylamine and 0.7 grams (0.005 moles) of 4,4-dimethylcyclohexane-1,3-dione are added. After 2 hours at a
temperature of 22 ° C, the solvent is removed on a vacuum rotary evaporator, the remaining residue dissolves; in 55 milliliters of acetonitrile, and 0.15 milliliters (0.0016 moles) of acetone cyanohydrin and 0.79 milliliters (0.0057 moles) of triethylamine are added, in order to subject the intermediate to a reconfiguration reaction. After the reaction solution has been stirred for 4 hours at room temperature, it is evaporated. The remaining syrup is passed through chromatography on silica gel. Elution with a mixture of toluene, ethyl alcohol, dioxane, triethylamine, and water (100: 40: 20: 20: 5 parts by volume) gives a pale yellow viscous oil (Rf = 0.39 over the aforementioned mixture as the mobile phase). ), which is dissolved in dichloromethane, and washed in succession with 75 milliliters of 5 percent hydrochloric acid and 75 milliliters of water.The evaporation to dryness of the organic solution, which has been dried with Ma_S04, produces 1.05 grams (63 percent) pure 3-hydroxy-4,4-dimethyl-2- (2-methyl-6-trifluoromethylpyridin-3-carbonyl) cyclohex-2-enone in the form of white crystals with a melting point of 75 -77 ° C. A-NMR (dh-DMS0, d in ppm): 1342, s, 6H: 2.088, t, J 9Hz, 2H: 2,685, s, 3H: 2,982, t, J 9Hz, 2H: 8.030, d, J d.LHz, IH: 8.094, d, (J. 8.1Hz), 1H.
Example H2: Preparation of 5-methyl-5-trifluoromethylcyclohexane-1,3-dione (compound H-B1066): 0.64 grams of sodium were introduced into 40 milliliters of ethanol, and 3.23 milliliters of methyl acetoacetate and 4.9 grams of ethanol were introduced. Isopropyl 4,4,4-trifluo - "? - 3-methylbut-2-enoate, and the mixture was heated to the boiling point for 18 hours, after which the mixture was divided between dilute hydrochloric acid and acetate. The remaining 2-methyl-4,6-dioxo-2-trifluoro-romethyl-cyclohexanecarboxylate methyl ester is hydrolyzed in a mixture of methanol and water to the boiling point in the presence of 9.1 grams of hydroxide. The mixture is subsequently acidified with hydrochloric acid, and extracted with fresh ethyl acetate.After recrystallization (ethyl acetate), pure 5-methyl-5-trifl-ao-methylcyclohexane-1,3-dione is obtained from a single point. of fusion of 150-152 ° C.
Example H3: Preparation of methyl 2-hydroxy-l-methoxy-5-methyl-4-oxacyclohex-2-enecarboxylate (Example H-B1069):
A 30 percent solution of 35.8 grams of sodium methoxide is introduced into 65 milliliters of dimethyl sulfoxide, and within 20 minutes, it is treated with a mixture of 16.7 grams of 3-methyl-3-buten-2-one and 32.4 grams of dimethyl methoxy alonate at a temperature of 33 ° C at 35 ° C. The mixture is stirred for 1 hour at a temperature of 35 ° C, and then acidified with hydrochloric acid and extracted repeatedly with dichloromethane. The organic phases are washed with water, dried and concentrated. Crystallization from hot ethyl acetate and hexane gives pure methyl 2-hydroxy-l-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate, melting at 117-117.5 ° C.
Example H: Preparation of methyl 2-hydroxy-l-methoxy-5-methyl-3- (2-methyl-1-6-trifluoromethylpyridin-3-carbonyl) -4-oxocyclohex-2-enecarboxylate (compound A2-B1069): 2.23 grams of 2-methyl-6-trifluo-ometilnicot fresh inoyl chloride is added to a mixture of 2.14 grams of methyl 2-hydroxy-l-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate and 2.02 grams of triethylamine in 30 milliliters of acetonitrile After about 30 minutes, 0.065 grams of potassium cyanide are added, and the mixture is stirred for 18 minutes.
hours. At a pH of 2, the mixture is subsequently partitioned between water and ethyl acetate, dried over magnesium sulfate, and evaporated. Filtration over silica gel (ethyl acetate / methanol / triethylamine mobile phase, 85: 10: 5) gives 2-hydroxyl-methoxy-5-methyl-3-3- (2-methyl-6-trifluoromethylpyridin-3-carboni L) -4-oxocyclohex-2-enecarboxylate pure methyl as a viscous oil.
Example H5: Preparation of 3-hydroxy-4-methoxy-6-methyl-2- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone (compound A2-B1070): 1.4 grams of 2-hydroxy methyl-l-methoxy-5-methyl-3- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) -4-oxocyclohex-2-enecarboxylate in dioxane / water (5: 3) are treated with 0.586 grams of potassium hydroxide, and the mixture is stirred for 3 hours. Then mix is acidified (pH 3), and extracted with fresh ethyl acetate. The crude product is purified by chromatography in a manner analogous to Example H4. 3-Hydroxy-4-methoxy-6-methyl-2- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone is obtained as a viscous oil (in accordance with A-NMR, as a mixture of 3 tautomeric forms).
Example H6: 5-chloro-2,6,6,6-tetramethyl-4- (2-methyl-β-trifluoromylpyridine-3-carbonyl) -cyclohex-4-ene-1,3-dione (compound A2-B1105 ) and 6- [chloro- (2-methyl-6-trifluoromethylpyridin-3-yl) methylene] -2,2,4-tetramethylcyclohexane-1, 3,5-trione: 7.0 grams (55 mmol) of oxalyl chloride , are introduced in 18.5 grams (50 millimoles) of 5-hydroxy-2, 2,6,6-tetramethyl-4- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) cyclohex-4-ene-1, 3- dione ((compound A2-B354), dissolved in 50 milliliters of dichloroethane, 5 drops of dimethyl formamide are added, and the mixture is slowly heated to the boiling point.After about 30 minutes, after the peeling is over of gas, the mixture is evaporated, and the product is crystallized by the addition of normal hexane.The main product obtained is 5-chloro-2,2,6,6-tetramethyl-4- (2-methyl-6-trifluoromethylpyridin- 3-carbonyl) cyclohex-4-ene-1,3-dione pure, melting point 119.5-120 ° C. additional separation with high performance liquid chromatography of the mother liquor using 5-10 percent ethyl acetate in hexane, gives the 6-isomer
[chloro- (2-methyl-1-6-trifluoromethyl-1-pyridin-3-yl) methylene] -2,2,4-tetramethyl-cyclohexane-1,3,5-trione, mp 92.5-93 ° C.
Example H7: 5-chloro-2,2,6,6-tetramethyl-4- (2-methyl-1-oxy-6-trifluoromethylpyridin-3-carbonyl) cyclohex-4-ene-1,3-dione (compound A1210-B1105 ): 1.94 grams (5 millimoles) of 5-chloro-2, 2,6,6-tetramethyl-4- (2-methyl-6-trifluoromethylpyridine-3-carboni 1) cyclohex-4-ene-l, 3-dione , they are treated in 20 milliliters of dichloroethane, at a temperature of -10 ° C, with 0.93 grams (10 millimoles) of an adduct of hydrogen peroxide / urea, and 1.89 grams (9 millimoles) of trifluoroacetic anhydride. The reaction mixture is heated to room temperature, with stirring, and maintained; for 4 additional hours at this temperature. The mixture is then partitioned between ethyl acetate and water of a pH of 5, washed with a sodium chloride solution, and evaporated. The residue that is filtered through silica gel is 5-chloro-2, 2,6,6-tetramethyl-4- (2-methyl-1-oxy-6-trifluoromethyl-1-pyridine-3-carboni 1) cyclohex-4 -ne-l, 3-dione pure with a melting point of 145.5-146 ° C.
Example H8: 4- (2-bromomethyl-6-trifluoromethylpyridin-3-carbonyl) -5-chloro-2, 2,6,6-tetramethylcyclohex-4-ene-l, 3-dione (compound A1029-B1105: 0.39 grams (1 millimole) of 5-chloro-2, 2, 6, 6-tetrame ti 1-4- ( 2-methyl-6-trifluoromethylpyridine-3-carboni) cyclohex-4-ene-l, 3-dione and 0.20 grams (1.1 mmol) of N-bromosuccinimide are refluxed in the presence of a catalytic amount of dibenzoyl peroxide in 10 milliliters of carbon tetrachloride After the reaction ceases, the resulting succinimide is removed by filtration, and the crude product is purified by column chromatography (mobile phase: ethyl acetate / hexane 1: 4). Pure 2-bromomethyl-6-trifluoromethylpyridine-3-carbonyl) -5-chloro-2, 2,6,6-tetramethyl-1-cyclohex-4-ene-1,3-dione with a melting point of 94.5-95 ° C .
Example H9: 2- (2-Acetoxymethyl-6-trifluoromethylpyridine-3-carbonyl) -4,4,6,6-tetramethyl-3,5-dioxocyclohex-1-enyl acetate (compound A1099-B1107): 0.4 grams 1 millimole) of 5-chloro-2, 2,6,6,6-tetramethyl-4- (2-methyl-1-1-oxy-6-trifluoromethyl-1-pyridine-3-carbonii) cyclohex-4-ene-1, 3- diona (Example H7), they are
under reflux for 25 minutes in the presence of 3 milliliters of acetic anhydride. The mixture is then concentrated and divided between ethyl acetate and a sodium bicarbonate solution at a pH of 6.5. The crude product, separated on silica gel (mobile phase: ethyl acetate / hexane, 1: 4) yields 2- (2-acetoxymethyl-6-trifluoromethylpyridin-3-carbonyl L) -4, 4, 6 acetate, Pure 6-tetramethyl-3, 5-dioxocyclohex-l-enyl as an oil; At NMR (CDCA): 7.98 d, CH, 7.72 d, CH, 5 62 s, CH2, 2.22 and 2.20 2x OAc, 1.58, s, 2x CH3, 1.44 ppm, s, 2x CH3.
Example H10: 5-hydroxy-2-methyl-4- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) -bicyclo [4.1.0] hept-4-en-3-one (compound A2-D109), and 3-hydroxy-7-methyl-2- (2-methyl-6-trifluoromethylpyridin-3-carbonyl) cyclohepta-2,6-dienone (compound A2-F5): 0.82 grams (2 mmol) of trans-5-hydroxy- 2-Methyl-4- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) -3-oxo-bicyclo [4.1.0] hept-4-en-2-carboxylic acid ethyl ester
(compound A2-D111), is stirred in a 2: 1 dioxane / water mixture, together with 0.254 grams (4.5 millimoles) of potassium hydroxide at room temperature, until
which reacts all the starting material. Then ethyl acetate is added, the mixture is acidified to a pH of 3 using 4 N HCl and the 2 phase mixture is then heated for about 1 hour at a temperature of 40 ° C. The aqueous phase is then separated, which is saturated with sodium chloride. The ethyl acetate extract is evaporated to dryness, and the product is passed through chromatography on silica gel (mobile phase of ethyl acetate / hexane 1: 2). The first fraction that is isolated is 3-hydroxy-7-methyl-2- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) cyclohepta-2,6-dienone as a mixture of pure tautomers, JH-NMR (CDC13) 17.72 and 17.08, 2s, OH, 7.6-7.45, 2 aromatic H, 6.68 and 6.62, ^ 2t, CH, 2.84, m, 2.63, m, 2.52, m, 4H, 2.62 and 2.54, 2s, CH3, 2.03 and 1.77 ppm, 2s CH3. Subsequent elution with 100 percent ethyl acetate gives, as the second fraction, the mixture of isomers and tautomers of 5-hydroxy-2-methyl-4- (2-methyl-6-trifluoromethylpyridine-3-carboni. 4.1.0] hept-4-en-3-one, A-NMR (CDC13): between Drs 17-62 and 17.48, 2s, OH, 7.6-7.45, aromatic 2H, 2.54, m, 2.48, 2s CH ^, 1.22 and 1.14, 2d, CHj, 1.00 to 0.05 ppm, 2H.
Example Hll: 5-hydroxy-2-methansulfinyl-2-methy1-4- (2-methyl-1-6-trifluoromethylpyridin-3-carbonyl) bicyclo [4.1.0] hept-4-en-3-one (compound A2-D114 ): 0.87 grams (2.3 millimoles) of 5-hydroxy-2-methyl-2-methylsulfanyl-4- (2-methyl-6-trifluoromethyl) -methylpyridin-3 -carbonyl) bicyclo [4.1.0] hept-4-en -3-one (compound A2-D113), dissolved in 8 milliliters of methanol, is heated for 3 hours at a temperature of 50 ° C in the presence of 0.56 grams of periodate: or sodium. The mixture is then partitioned between ethyl acetate and a sodium chloride solution, concentrated, and the crude product is purified by chromatography (mobile phase: ethyl acetate / methanol, 19: 1). The pure 5-hydroxy-2-methanesulfinyl-2-methyl-4- (2-methyl-6-trifluoromethylpyridin-3-carboni 1) bicyclo [4.1.0] hept-4-en-3-one is obtained as a mixture of tautomers and isomers with a melting point of 159.5-160 ° C.
Example H12: 2-propyl-2-ynyloxy-6-trifluoromethyl-nicotinic acid (compound A1025): 47 grams (0.2 moles) of 2-oxo-6-trifluoromethyl-1,2-dihydropyridine-3-carboxylic acid, 20 milliliters (0.25 moles) of propargyl bromide, and 43
grams (0.31 moles) of potassium carbonate, heated to a temperature of 75 ° C, in a mixture of 40 milliliters of dimethyl formamide and 80 milliliters of acetonitrile, in the presence of a catalytic amount of 18-crown-6 ether. After 5 hours, the mixture is partitioned between ethyl acetate and a saturated solution of sodium chloride. The crude product is filtered through a column of silica gel using 15 percent ethyl acetate in hexane. The main component, which is obtained in the form of an oil, is pure ethyl 2-prop-2-ynyloxy-6-trifluoromethylnicotinate.; ARMN (CDC13): 8.31, d, CH, 7.38, d, CH, 5.13, d, CH2, 4.41, q, CH2, 2.48, t, CCH, 1.41 ppm, t, CH3. 36.3 grams (0.13 moles) of this product are stirred for a period of 16 hours with a solution of 11.5 grams (0.17 moles) of potassium hydroxide in 50 milliliters of water and 50 milliliters of dioxane. After acidification and extraction with ethyl acetate, crystalline 2-prop-2-ynyloxy-6-trifluoromethylnicotinic acid is obtained; A-NMR (CDC1J: 10.0, b, OH, 8.53, d, CH, 7.44, d, CH, 5.22, d, CH2, 2.54 ppn, t, CCH.
Example H13: 2-thiomethyl-6-trifluoromethyl-nicotinic acid (compound Al5): 9.4 grams (40 mmol) of 2-oxo-6-trifluoromethyl-1-1,2-dihydropyridine-3-carboxylic acid are introduced into a 1-molar solution of 21.7 grams of phosphorus tribromide (80 millimoles) in dichloromethane, at a temperature of 35 ° C. The solvent is then distilled, and the reaction mixture is slowly heated to the boiling point of about 175 ° C. After? of 18 c., the mixture is cooled to 0 ° C, diluted with dichloromethane, and stirred with ice water of a pH of 1.8. The organic phase is then washed with a cold sodium carbonate solution, and with a 15% sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue is ethyl 2-bromo-6-trifluoromethylnicotinate in the form of an oil; A-NMR (CDC13): 8.20, d, CH, 7.72 d, CH, 4.46, q,
CH / 1.42 ppm, t, CH3 of a melting point of 164-166 ° C. 1.0 grams (3.4 millimoles) of this product, dissolved in a small amount of acetonitrile, are heated for 45 minutes at a temperature of 70 ° C, together with 0.26 grams of sodium metantiolate (3.4 millimoles), in the presence of a catalytic amount of ether of 15-crown-5. The solution, which is cooled to room temperature, is then treated with 0.22 grams
(5.5 mmol) of sodium hydroxide and 5 milliliters of water, and stirring is continued for 3 hours. The neutral components are subsequently removed with a small amount of diethyl ether, and the aqueous phase is brought to a pH of 2.5, and extracted twice using ethyl acetate. This gives 2-thiomethyl-6-trifluoromethylnicotinic acid as a crystalline product; A-NMR (CDC13): 846, d, CH, 7.43, d, CH, 2.58 ppm, s, SCH3.
Example H14: 2-methanesulfonylamino-6-trifluoromethyl-nicotinic acid (compound A1203): 0.52 grams of methanesulfonamide are introduced into a tetrahydrofuran suspension of 0.24 grams of 55 percent sodium hydride in oil. After the evolution of hydrogen ceases, 1.5 grams (5 mmol) of ethyl 2-bromo-6-trifluoromethyl-thienotinate, 0.3 grams (5.2 mmol) of potassium fluoride, and a catalytic amount of crown ether are added, and milliliters of N-methylpyrrolidone, and the mixture is heated to the boiling point for 18 hours. Then the reaction mixture is partitioned between ethyl acetate and water, and freed from the neutral organic constituents. The aqueous phase is brought to a pH of 2.9, extracted three times with
Cool ethyl acetate, dry, and concentrate. A crystalline product, ethyl 2-methanesulfonylamino-6-trifluoromethylnicotinate is obtained from ether / hexane; A-NMR (CDC 1 J, 10.48, s, NH, 8.49, d, CH, 7.38, d, CH, 4.45, q, CH :, 3.51, s, S0 CH ,, 1.42 ppm, t, CH3, 0.43 grams (1.4 millimoles) of the previous product, hydrolyzed at room temperature using a 1: 1 solution of 0.22 grams (3.9 millimoles) of potassium hydroxide in dioxane / water, after the solution, which has been acidified to a pH from 2.5, extracted with ethyl acetate, 2-methanesulfonylamino-6-trifluoromethylnicotinic acid is obtained as a crystallized; A-NMR (de-DMSO): 8.62, d, CH, 7.72, d, CH, 3.52 ppm, s , S02CHJ.
Example H15: (3-Methoxycarbonyl-6-trifluoromethylpyridin-2-ylmethyl) triphenylphosphonium bromide: 50 grams (0.23 moles) of methyl 2-methyl-6-trifluoromethylnicotinate, and 49 grams (0.28 moles) of N-bromosuccinimide, heat for 90 minutes at 50 ° C in 500 milliliters of carbon tetrachloride in the presence of a catalytic amount of a, a-azaisobutyronitrile with illumination by a light bulb
150 watts. The precipitated succinimide is filtered, and the product of methyl 2-bromomethyl-6-trifluoromethylnicotinate is then isolated as the main component by column chromatography (mobile phase of ethyl acetate / hexane, 1:15), A- NMR (CDC1 J: 4.01, s, 3H, 5.03, s, 2H, 7.72, d (J 8.2Hz), 1H, 8.43 ppm, d, (J 8.2Hz), 1H, 25.6 grams (35 millimoles) of the previous product , they are recovered in toluene, and treated with 10.6 grams (40 millimoles) of trifemlfosphine. After the mixture is heated for 2 hours at the boiling point, the (3-methoxycarbonyl 1-6-trifluoromethyl bromide is crystallized. pure lpyridin-2-ylmethyl) triphenylphosphonium, with a melting point of 215-217 ° C, on cooling.
Example H16: 2-Vinyl-6-trifluoromethynicotinic acid (compound A21), and 2- (2, 2-dichlorocyclopropyl) -6-trifluoromethyl-nicotinic acid (compound A1092): 5.7 grams (10 millimoles) of (3-methoxycarbonyl) bromide 6-trifluoromethylpyridin-2-ylmethyl) triphenylphosphonium are dissolved at room temperature in a two-phase system of 25 milliliters of chloroform and 2.1 grams (20 millimoles) of carbonate of
sodium, and it is reacted in 10 milliliters of water, with one. 37 percent aqueous solution of 1.7 grams (20 millimoles) of formaldehyde. After 1.5 hours, the organic phase is separated and filtered through silica gel. Methyl 2-vinyl-6-trifluoromethylnicotinate is obtained as an oil. H-NMR (CDC13): 8.31, d, CH, 7.10, dd, CH, 7.09, d, CH, 6.68, dd, CH, 5.68, dd, CH, 3.97 ppm, s, OCH. 0.97 grams (4.1 millimoles) of this product are recovered again in chloroform, and reacted with 6 milliliters of a 50 percent sodium hydroxide solution with vigorous stirring in the presence of 90 milligrams of benzyltrimethylammonium bromide. After 20 hours, the organic phase is separated, concentrated, and purified by high performance liquid chromatography (mobile phase: ethyl acetate / hexane 1: 4). This gives pure methyl 2- (2,2-dichlorocyclopropyl) -6-trifluoromethylnicotinate, A-NMR (CDC13): 8.50, d, CH, 7.70, d ,. CH, 4.08, s, OCH3, 3.68, dd, CH, 2.64, dd, CH, 2.05 ppm, dd, CH. The hydrolysis of the above esters gives, according to the same, 2-vinyl-6-trifluoromethylnicotinic acid, A-NMR (CDCI3): 8.40, d, CH, 7.22, dd, CH, 7.09, d, CH, 6.68 , dd, CH, 5.58 ppm, dd, CH, and 2- (2, 2-dichlorocyclopropyl) -6-
trifluoromethylnicotinic, A-NMR (CDClj): 8.64, d, CH, 7.23, c, CH, 3.78, dd, CH, 2.67, dd, CH, 2.08 ppm, dd, CH.
Example H17: 2-Prone-1,2-dienyl-6-trifluoromethyl-nicotinic acid (A1096), and 2- (3-chloropropenyl) -6-trifluoromethyl-nicotinic acid (compound A1095): 6.7 grams (11 mmol) of bromide (( 3-methoxycarbonyl-6-trifluoromethylpyridin-2-yl) methyl) triphenylphosphonium is reacted with 2 milliliters of a 45 percent aqueous chloroacetaldehyde solution (14 millimoles) and 1.5 grams (14 millimoles) of sodium carbonate with vigorous stirring, in a two-phase system of 20 milliliters of chloroform and 7 milliliters of water. After 2 hours, the organic solution is separated, and washed with a half-saturated solution of sodium chloride. The product is separated on silica gel (mobile phase of ethyl acetate / hexane 1: 4). As the first fraction, methyl 2-propa-l, 2-dienyl-6-trifluoromethylnicotinate is isolated. A-NMR (CDC13) 7.62, m, CH, 7.55, d, CH,
7. 32, d, CH, 7.04, d, CH, 7.02, m, CH, 3.98 ppm, s, OCH3, and 2- (3-chloropropenyl) -6- is isolated
methyl trifluoromethylnicotinate, A-NMR (CDC13): 8.85, d, CH, 7.65, dd, 7.58, d, CH, CH, 7.28, dd, CH, 4.32, d, CH2C1, 3.98 ppm, s, OCH3, as the second fraction. Hydrolysis of the above esters gives 2-propa-l, 2-dienyl-6-trifluoromethylnicotinic acid, melting point 194-196 ° C, and 2- (3-chloropropenyl) -6-trifluoromethylnicotinic acid, melting point 137- 138 ° C.
Example H18: 2-Chloro-4-methyl-6-trifluoromethyl-nicotinic acid (compound A1205): In a pressurized vessel, 7.5 grams (0.03 mole) of ((3-ethoxycarbonyl) -4-methyl-6-trifluoromethyl) pyrid are heated -2-one for 3 hours at a temperature of 170 ° C, in the presence of 5.8 milliliters of phenyl dichlorophosphate. When it is cooled, the reaction solution is filtered directly onto a short silica gel column (mobile phase: ethyl acetate / hexane, 1: 9), and 2-chloro-4-methyl-6-trifluoromethylpyridinone is obtained. 3-ylethyl ester as an oily product. The latter is hydrolyzed in the presence of an aqueous solution of potassium hydroxide in dioxane, at a temperature of 40 ° C. After acidification at a pH of 2.7, extraction with ethyl acetate gives acid-chloro-4-methyl-6-trifluoromethylnicotinic acid as a
crystalline product: A-NMR (CDC13) 9.55, b, OH, 7.55, s, 1H; 3.80, s, CH3, 2.56 ppm, s, CH3.
Example H19: Acid-methyl-6-trifluoromethynicotinic
(compound A531): To a suspension of 0.55 grams of Pd / C at 10 per cent in 20 milliliters of methanol, 3.0 grams (16.8 millimoles) of 2-chloro-4-methyl-6-trifluoromethylpyridine are added to it. 3-ylethyl ester, and, in 2 portions,
a total of 5 grams of ammonium formate, and the mixture is stirred for 24 hours at room temperature. The reaction mixture is then filtered through Celite, and partitioned between ethyl acetate and a sodium chloride solution. Chromatographic purification (phase
mobile, 1: 9) gives 4-methyl-6-trifluoromethylpyridin-3-ylethyl ester in the form of an oil: hydrolysis according to the above processes gives 4-methyl-6-trifluoromethylnicotinic acid: A-NMR ( CDC13): 9.32, s, 1H, 7.62, s, 1H, 2.79 ppm, s, CH3. Example H20: 5-methyl-5-methylsulfanylbicyclo [4.1. Ojheptane-2,4-dione (compound H-D113): A 1-molar solution of 16.7 grams (0.1 mole) of lithium bis rimethylsilylamide in tetrahydrofuran,
- > is added at a temperature of 0 ° C to a solution of
13. 4 grams (0.1 moles) of methyl 2-methylmercaptopropionate in 30 milliliters of tetrahydrofuran. After the mixture is stirred for 1 hour, 11.8 grams (0.1 moles) of 5-chloropent-3-en-2-one are added dropwise over the course of 20 minutes, so that the temperature can be maintained at room temperature. 0 ° C. After the mixture is stirred for an additional 30 minutes, ice water is added, and the mixture is acidified with hydrochloric acid, and extracted with diethyl acetate. The crude product is passed through chromatography with ethyl acetate / hexane, 15/85. This gives methyl 2- (2-acetylchlopropyl) -2-methylsulfanylpropionate, A-NMR (CDC13): 3.74, s, OCH3, 2.19 and 2.14, 2s, SCA, 2.12 and 2.00, 2s, CH3, 2.2-1.9 , 1H, 1.3, s, CH. ,, 1.3 to 1.0 ppm, 21, as a mixture of 3: 7 isomers. 2.45 grams (11 millimoles) of the anteric product, which is enriched in the more polar isomer, are heated with 4.5 grams (25 millimoles) of a 30% sodium ethoxide solution in a mixture of toluene / dimethyl formamide, 19: 1, for 90 minutes, at 115 ° C. The mixture is then taken up in ethyl acetate, and washed with dilute hydrochloric acid at a pH of 3. The residue which is isolated is purified on silica gel (mobile phase of ethyl acetate / lexane 1: 2). This gives isomer I of 5-methyl-5-
methylsulfanylbicyclo [4.1.0] heptane-2,4-dione, ARMN (CDC13) 3.48, d, CH, 3.00, d, CH, 2.21, m, CH, 1.94, m, CH, 1.86, s, CH3, 1.57, s, CH3, 1.44, m, CH, 1.04 ppm, m, CH. The isomer II of 5-methyl-5-methylsulfanylbicyclo [4.1.0] heptane-2,4-dione, A-NMR (CDC13): 3.78, d, CH, 3.14 d, CH, 2.22, m, CH, 1.93, m, CH, 2.08, s, CH3, 1.58, s, CH, 1.6-1.4 ppm, 2H, is obtained from the product that is enriched in apolar isomers.
Example H21: 4-methylene glycon-4-ene-1,3-dione (compound H-F5): 1.0 grams (5.4 millimoles) of the isomers II of 5-methyl-5-methylsulfanylbicyclo [4.1.0] heptane-2, 4-dionei are hydrogenated for 90 minutes under atmospheric pressure in 15 milliliters of methanol, in the presence of 5 grams of Raney nickel. The mixture is concentrated and purified on silica gel (mobile phase ethyl acetate / hexane, 1: 1), and 4-methylcyclohept-4-ene-1,3-dione, A-NMR (CDC13) is obtained: 6.84, m, CH, 3.94, s, CH2, 2 77, n, CH2, 2.59, m, CH2, 1.88 ppm, s, CH3, as an oil.
Example H22: 2-oxaespiro [4.5] decane-1,6,8-trione (compound HE 16): A suspension of sodium hydride (55 percent in oil, 27.5 mmol), in 70 milliliters of anhydrous tetrahydrofuran, cooled to a temperature of -20 ° C, and a solution of 2-acylbutyrolactone (2.69 milliliters, 25 mmol) in 5 milliliters of tetrahydrofuran is subsequently added dropwise. After the reaction mixture is stirred for 1 hour at this temperature, it is treated by dripping with a solution of methyl acrylate (4.5 milliliters)., 50 millimoles) in tetrahydrofuran, at a temperature of -20 ° C. The reaction mixture is subsequently allowed to warm to room temperature, and is stirred for 8 hours. The mixture is then poured into ice water, and acidified with 2N hydrochloric acid, to a pH of 1. After extraction with ethyl acetate, drying over sodium sulfate, and concentration in vacuo, the product is dried. purify by evaporation chromatography (eluent: ethyl acetate / acetic acid 1: 1). This gives 2-oxaespiro [4.5] decane-1, 6, 8-trione in the form of a white powder with a melting point of 145-148 A.
Example H23: Spiro [2.5] octane-, 6-dione (compound H-Cl): 3.4 grams of sodium hydride (55 percent suspension in oil, 78.0 mmol) were introduced into 1 liter of tertiary butanol, and the mixture it is stirred for about 4 minutes at room temperature. Then 2 acylbutyrolactone (100 grams, 0.78 moles) was added, and the reaction mixture was treated with methyl acrylate (67.2 grams, 0.78 millimoles) over a period of 3.5 hours at a temperature of about 30 ° C. The reaction mixture is taken up in diethyl ether, and washed in succession with 75 milliliters of a saturated solution of NaH2P04, water, and a saturated solution of sodium chloride, dried over sodium sulfate, and concentrated. This gave 162 grams of methyl 3- (3-acetyl-2-oxotetrahydrofuran-3-yl) propionate as a colorless oil, which can be further reacted without purification. 2.0 grams (9.3 millimoles) of the previous product, and 2.1 grams of sodium iodide (14.0 millimoles), are dissolved in 10 milliliters of 1,3-dimethyl-2-imidazolidinone, and the solution is heated for 3 hours at 210 ° C. . After cooling, the reaction mixture is poured into a saturated aqueous solution diluted with NaH2P04, and extracted with diethyl ether,
dry over sodium sulfate and concentrate. This gives methyl 3- (1-acetylcyclopropyl) propionate as a colorless oil. 74.5 grams of methyl 3- (l-acetylcyclopropyl) propionate (0.32 moles) are dissolved in 1 liter of tetrahydrofuran, and the solution is treated in portions with 14.3 grams of sodium hydride (55 percent suspension in oil, 0.32 moles). ), at room temperature. After 1 hour, the reaction mixture is diluted with 200 milliliters of dimethyl formamide, and heated to 70 ° C. After 8 hours, the tetrahydrofuran is removed in vacuo, and the residue is poured into 2N hydrochloric acid, and extracted with diethyl ether. The organic phase is dried over sodium sulfate and concentrated, and column chromatography on silica gel (methylene chloride: ethanol 9: 1, as eluent) gives spiro [2.5] octane-4,6-dione in the Form of white crystals with a melting point of 116-118 ° C.
Example H24: 2- (4,6-Dimethoxypyrimidin-2-ylsulfanylmethyl) -6-trifluoromethyl-nicotinic acid (compound Al088): 2.0 grams (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethylnicotinate (prepared from a
Analogously to Heterocycles, 46, 129 (1997), by heating methyl 4-chloro-3-oxobutyrate and 4-amino-1,1,1-trifluorobut-3-en-2-one, in toluene in the presence of trifluoroacetic acid), are introduced into 30 milliliters of acetonitrile and 1.63 g (11.83 millimoles) of K2C? 3, and are reacted with 1.49 grams (8.67 millimoles) of 4,6-dimethoxypyrimidine-2-thiol at room temperature. After 4 hours, the mixture is poured into ethyl acetate / water, the ethyl acetate phase is removed, and the aqueous phase is extracted again with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulfate, concentrated, and purified by recrystallization from ethyl acetate / hexane. This gives methyl 2- (4,6-dimethoxypyrimidin-2-ylsulfanylmethyl) -6-trifluoromethylnicotinate in the form of white crystals with a melting point of 123-124 ° C. The hydrolysis of the above esters (in a manner analogous to Example Hl) gives, according to the foregoing, 2- (4,6-dimethoxypyrimidin-2-ylsulfanylmethyl) -6-trifluoromethylnicotinic acid in the form of white crystals of a single point of fusion of 157-158 ° C. A-NMR (CDC13): 3.96, s, 6H; 3 99, s, 3H; 5.03, s, 2H; 5.72, s, 1H; 7.66, d (J, 8.1Hz), 1H; 8.40 ppm, d (J, 8.1Hz), 1H.
Example H25: 2-Cyanomethyl-6-trifluoromethylnicotinic acid (compound Al103): 2.0 grams (7.89 mmol) of methyl 2-chloromethyl-6-trifluoromethylnicotinate, and 565 milligrams
(8.67 mmol) of potassium cyanide, are reacted in 20 milliliters of a mixture of acetonitrile / water (1: 1), in the presence of 270 milligrams of tetrabutylammonium acid sulfate. After the reaction is complete, the mixture is poured into water, and extracted with ethyl acetate. After the ethyl acetate phase is dried over sodium sulfate and concentrated, the crude product is purified by means of high performance liquid chromatography (ethyl acetate: hexane as eluent). This gives 610 milligrams
(32 percent theory) of methyl 2-cyanomethyl-6-trifluoromethylnicotinate in the form of an oil. A-NMR (CDC13): 3.96, s, 3H; 4.38, s, 2H; 7.72, d (J, 8.1Hz), 1H; 8.48 ppm, d (J, 8.1Hz), 1H. Hydrolysis analogous to the aforementioned methods produces acid-2-cyanomethyl-6-trifluoromethylnicotinic acid in the form of yellow crystals with a melting point of 152-153 ° C. A-NMR
(CDC13): 4.18, s, 2H; 7.72, d (J, 8.1Hz), 1H; 8.52 ppm, d (J, 8.1Hz), 1H.
Example H26: 3- (6-difluoromethyl-2-2-methylpyridin-3-carbonyl) -2-hydroxy-1-methyl-4-oxocyclohex-2-enecarboxylate (compound A124-B34): 200 milligrams (0.516 millimoles) of 3- [6- (Chlorodifluoromethyl) -2-methylpyridin-3-carbonyl] -2-hydroxy-l-methyl-4-oxocyclohex-2-enecarboxylate methyl
(compound A94-B34), are heated for 3 hours at a temperature of 120 ° C in 8 milliliters of toluene, in the presence of 0.18 milliliters (0.62 millimoles) of tris (trimethylsilyl) silane. The remaining viscous residue is passed through chromatography on silica gel. The pale yellow viscous oil that is obtained by elution with a mixture of toluene, ethyl alcohol, dioxane, triethylamine, and water (100: 40: 20: 20: 5 by volume), is dissolved in dichloromethane, and washed in succession with aqueous hydrochloric acid and water. Evaporation of the organic solution which is dried with Na 2 SO 4 yields 140 milligrams (73 percent) of 3- (6-difluoromethyl-2-methylpyridine-3-carbonyl) -2-hydroxy-1-methyl-4-oxocyclohex-2. pure methyl -carboxylate in the form of a pale yellow A-NMR (CDC1): 1.28, s, 3H; 1.79-1.97, m, 1H; 2.39-2.46; m, 1H; 2.43, s, 3H; 2.69, dt (J, 19.2 and 4.8Hz), 1H; 2.82-2.92, m, 1H; 3.67, s, 3H; 6.55, t, (J, 55.5 Hz), 1H; 7.43, d (J,
7. 8Hz), 1H; 7.49, d (J, 7.8Hz), 1H; 17.20 ppm, br, s, 1H.
Example H27: 3-hydroxy-2- (2-methyl-l-oxy-6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone (compound A1210-B1): 16.1 grams (0.054 moles) of 3-hydroxy-2 - (2-methyl-6-trifluoromethyl lpyridin-3-carbonyl) cyclohex-2-enone (Example A2-B1) and 10.2 grams (0.11 mole) of urea complex / hydrogen peroxide, are dissolved in 150 milliliters of chloride of methylene, and subsequently 22.1 milliliters (0.162 moles) of trifluoroacetic anhydride are added dropwise at a temperature of 25 ° C. After the reaction mixture is stirred for 14 hours at a temperature of 25 ° C, it is poured into ethyl acetate and water, and the organic phase is washed twice with water, dried with sodium sulfate, and concentrated . The residue is chromatographed on silica gel (eluent: ethyl acetate / methanol, 9/1). This gives 2.4 grams (14 percent) of the desired product in the form of white crystals (melting point 117-119 ° C). 2 H-NMR (d 6 -DMSO): 1.98, m, 2H; 2.30, s, 3H; 2.60, t (J, 7.25Hz), 4H; 7.32, d (J, 9.8Hz), 1H; 7.92 ppm, d (J, 9.8Hz), 1H.
Example H28: 2- (2-methy1-6-trifluoromethylpyridin-3-carbonyl) -3-phenylsulfanyl-cyclohex-2-enone (compound A2-B1102: 4.0 grams (0.0134 moles) of 3-hydroxy-2- (2-methyl- 6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone (compound A2-B1), are suspended in 25 milliliters of oxalyl chloride, and subsequently 0.1 milliliters of dimethyl formamide are added dropwise. gas, the mixture is maintained for 1.5 hours at a bath temperature of 45 ° C, and subsequently concentrated, and the residue (3-chloro-2- (2-methyl-6-trifluoromethylpyridin-3-carboni 1) -cyclohex -2-enone) is dissolved in 60 milliliters of methylene chloride.Triethylamine (3.7 milliliters, 0.0268 moles), dimethylaminopyridine (160 milligrams, 1.34 millimoles), and 1.5 milliliters (0.0147 moles) of thiophenol are added at a temperature of 0- 5 ° C. After 20 hours at a temperature of 22 ° C., the reaction mixture is concentrated and purified on silica gel (hexane / a ethyl acetate, 5: 1). Trituration in hexane gives pure 2- (2-methyl-6-trifluoromethylpyridin-3-carboni 1) -3-phenylsulfanylcyclohex-2-enone in the form of white crystals with a melting point of 124-125 ° C. A-NMR (CDC13): 1.99, m, 2H; 2.41, m 4H; 2.80, s, 3H; 2.60: 7.40-7.60, m, 6H; 7.80 ppm, d (J, 8.2Hz), 1H.
Example H29: 3-Benzenesulfonyl-2- (2-methyl-6-trifluoromethylpyridine-3-carbonyl) cyclohex-2-enone (compound A2-B1104): 0.8 grams (0.00204 moles) of 2- (2-methyl-6) -trifluoromethylpyridine-3-carbonyl) -3-phenylsulfanyl-cyclohex-2-enone obtained above, are dissolved in 30 milliliters of methylene chloride, and subsequently 1.39 milliliters of peracetic acid are added dropwise (at 39 percent in acetic acid, 0.00816 moles ), at a temperature of 25 ° C. After 4 hours at 25 ° C, the reaction mixture is poured into ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate, and concentrated, and the residue is triturated with a small amount. of hexane and ethyl acetate. Filtration gives 0.72 grams (84 percent of theory) of 3-benzenesulfonyl-2 (2-methyl-6-trifluoromethyl-pyridine-3-carbonyl) cyclohex-2-enone in the form of white crystals of a melting point from 165-167 ° C. A-NMR (CDC13): 2.30, m, 2H; 2.55, t (J, 7Hz), 2H; 2.71, m, 2H; 3.05, s, 3H; : 7.40-7.80, m, 4H; 7.80-8.05 ppm, m, 3H.
Example H30: 6-difluoromethyl-2-methylnicotinic acid (compound A124): 6.1 grams (0.026 moles) of methyl 6- (chlorodifluoromethyl) -2-methylnicotinate (prepared in a manner analogous to Heterocycles, 46, 129
(1997), by heating methyl 3-oxobutyrate and 4-amino-l-chloro-l, 1-difluorobut-3-en-2-one in toluene, in the presence of trifluoroacetic acid), are heated to a temperature of 123 ° C, in the presence of 430 milligrams (0.26 moles) of tris (trimethylsilyl) silane, in 150 milliliters of toluene.
After 1.5 hours, the reaction mixture is concentrated and purified on silica gel (hexane / ethyl acetate 13: 1). This gives 3.8 grams (73 percent of theory) of methyl 6-difluoromethyl-2-methylnicotinate as a colorless oil. Hydrolysis of the above esters (in a manner analogous to Example Hl) gives, according to the foregoing, 6-difluoromethyl-2-methylnicotinic acid in the form of white crystals with a melting point of 135-136 ° C. A-NMR (CDC13): 2.68, s, 3H; 6.583, t (J, 55.2Hz), 1H; 7.54, d (J, 8.1Hz), 1H; 7.54 ppm, d (J, 8.1Hz), 1H.
Example H31: 6- (Chlorodifluoromethyl) -2-methylnicotinic acid (compound A-94): 5.0 grams (18.62 mmol) of methyl 2-methyl-6-trichlomethylnicotinate (prepared in a manner analogous to Heterocycles, 46, 129 (1997 )), they are cooled to a temperature of -40 ° C in a pressurized container, and subsequently 35 grams (1.75 moles) of hydrofluoric acid distilled at this temperature are passed. The mixture is heated for 10 hours at 200 ° C (pressure about 55 bar). After cooling, the pressure is released using a gas flushing system, the HF is removed by suction, and the reaction mixture is poured into ethyl acetate / ice. The ethyl acetate phase is separated, and the aqueous phase is back extracted using ethyl acetate. The combined ethyl acetate phases are washed with water, dried over sodium sulfate, and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. The filtration gives 2.2 grams (53 percent of theory) of 6-chlorodifluoromethyl-2-methylnicotinic acid as pale green crystals with a melting point of 134-135 ° C. : H-NMR (CDC13): 2.987, s, 3H; 7.64, d (J, 8.1Hz), 1H; 8.513 ppm, d (J, 8.1Hz), 1H.
Example H32: 2- [2- (4,6-Dimethoxypyrimidin-2-sulfonylmethyl) -6-trifluoromethylpyridin-3-carbonyl] -3-hydroxycyclohex-2-enone (compound A1090-B1): 100 milligrams of 2- [2 - (4,6-dimethoxypyrimidin-2-ylsulfanylmethyl) -6-trifluoromethylpyridine-3-carbonyl] -3-hydroxycyclohex-2-enone (compound A1088-B1), are dissolved in methylene chloride, and subsequently 0.3 is added dropwise milliliters of peracetic acid (39 percent in acetic acid) at a temperature of 25 ° C. After 15 hours at 25 ° C, the reaction mixture is poured into ethyl acetate and water, and the organic phase is washed with water, dried with sodium sulfate, and concentrated. This gives 95 milligrams of 2- [2- (4,6-dimethoxypyrimidin-2-sulfonylmethyl) -6-trifluoromethylpyridine-3-carbonyl] -3-hydroxycyclohex-2-enone in the form of a resin. "H-NMR (CDC13): 3.79, s, 6H, 3.91, s, 3H, 4.99, s, 2H, 6.09, s, 1H, 7.52, d (J, 9Hz), 1H, 7.68 ppm, d (J, 9Hz), 1H In the following tables, Ph is the phenyl group, and CC is an ethyne group.
Table 1: Compounds of formula XVId:
Cornp. No. A R3 Ri Rs P
Al H H H CF, 0
A2 CH3 H H CF3 0
A3 CH3CH2 H H CF-- 0
A4 (CH3) CH H H CF3 0
A5 (CH3) 3C H H CF3 0
A6 cyclopropyl H H CF3 0
A7 CH3 (CH2) 2 H H CF3 0
A8 CH3OCH2 H H CF3 0
A9 CH3OCH2 H H CF, 0 A10 Ph H H CF 0 All PhO H H CF 0 A12 PhS H H CF3 0 A13 PhSO H H CF3 0 A14 Ph S0 H H CF3 0 A15 CH3S H H CF3 0 Al 6 CH3SO H H CF3 0
Comp. Do not . R2 R3 R Rs P
A17 CF3 H H CF3 0
A18 F2CH H H CF3 0
Al 9 HCC H H CF3 0
A20 CH3CC H H CF3 0
A21 CH2 = CH H H CF. 0
A22 CH2 = CHCH2 H H CF; 0
A23 CH3S02N (CH3) H H CF, 0
A24 (CH3) 2N H H CF-: 0
A25 (CH3) 2NS02 H H CF, 0
A26 C1CH H H CF3 0
A27 CH3SCH2 H H CF, 0
A28 CH3S0CH2 H H CF3 0
A29 CH3S02CH2 H H CF3 0
A30 [1.2. . ] -triazol- 1 -ylmethyl H H CF3 0
A31 CH3 CF3 H CF3 0
A32 CH3 CF3 H CF3 0
A33 H H H CF3CF2 0
A34 CH3 H H CF3CF2 0
A35 CH3CH2 H H CF3CF; 0
A36 cyclopropyl H H CF3CF2 0
A37 (CH3) 3C H H CF3CF2 0
A38 (CH5) AH H H CF3CF2 0
A39 CH3 (CH2) 2 H H CF3CF2 0
A40 CH3OCH2 H H CF3CF2 0
Comp. No. R2 R3 P > 4 Rs P
A41 CH3O (CH2) 2 H H CF3CF2 0
A42 Ph H H CF3CF2 0
A43 PhO H H CF3CF2 0
A44 PhS H H CF3CF2 0
A45 PhSO H H CF3CF2 0
A ^ 6 PhS02 H H CF3CF2 0
A7 CH3S H H CF3CF2 0
A? 8 CH3SO H H CF3CF2 0
AA9 CF3 H H CF3CF2 0
ASO F2CH H H CF3CF2 0
AE 1 HCC H H CF3CF2 0
A53 CH2 = CH H CF3CF2 0
A55 CH3SO2N (CH3) H H CF3CF2 0
A56 (CH3) 2N H H CF3CF2 0
A57 (CH3) 2NS02 H H CF3CF2 0
A58 CICH2 H H CF3CF2 0
A60 CH3SOCH2 H H CF3CF2 0
A61 Cp3S? 2CH2 H H CF3CF2 0
A62 [1.2.4] -triazol-1-ylmet? Lo H H CF3CF2 0
A63 H H H C F3C F2C 2 0
A64 CH3 H H CF3CF2CF2 0
A65 Cri3CH2 H H CF3CF2CF2 0
A66 cyclopropyl H H CF3CF2CF2 0
A67 (CH3) 3C H H C F3C F2C 2 0
A63 (CH3) 2CH H H CF3CF2CF2 0
A69 CH3 (CH2) 2 H H C 3CF2C 0
A70 CH3OCH2 H H CF3CF2CF2 0
A7 I CH3O (CH2) 2 H H F3CF2CF2 0
A7C! PhO H H CF3CF2CF2 0
Comp. No. R2 R3 R4 Rs P
A7 PhS H H CF3CF2CF2 0
A7Í5 PhSO H H CF3CF2CF2 0
A7 (5 PhS02 H H CF3CF2CF2 0
A77 CH3S H H CF3CF2CF2 0
A7H CH3SO H H CF3CF2CF2 0
A79 CF3 H H CF3CF2CF2 0
A80 F2CH H H CF3CF2CF2 0
A81 HCC H H CF3CF2CF2 0
A8_! CH3CC H H CF3CF2CF2 0
A8ÍI CH2 = CH H H CF3CF2CF2 0
A8 ¿Crl2 = CHCH2 H H CF3CF2CF2 0
A85 CH3S02N (CH3) H H CF3CF2CF2 0
A86? (CH3) 2N H H CF3CF2CF2 0
A87 (CH3) 2NS02 H H CF3CF2CF2 0
A8fi CICH2 H H CF3CF2CF2 0
A89 CH3SCH2 H H CF3CF2CF2 0
A90 CH3SOCH2 H H CF3CF2CF2 0
A91 CH3SO2CH2 H H CF3CF2CF2 0
A92 [1.2.4] -triazol-l-ylmethyl H H CF3CF2CF2 0
A93 H H H CF2CI 0
A94 CH3 H H CF2CI 0
A96 cyclopropyl H H CF2CI 0
A97 (CH3) 3C H H CF2CI 0
A98 (CH3) 2CH H H CF2CI 0
A100 CH3OCH2 H H CF2CI 0
A101 CH3O (CH2) 2 H H CF2CI 0
A102 Ph H H CF2CI 0
A103 PhO H H CF2CI 0
A104 PhS H H CF2CI 0
A105 PhSO H H CF2CI 0
A106 PhSO2 H H CF2CI 0
Comp. No. R2 R3 R4 Rs P
A107 CH3S H H CF2Cl 0
A108 CH3SO H H CF2CI 0
A10 & CF3 H H CF2CI 0
A11C F2CH H H CF2CI 0
A111 HCC H H CF2CI 0
A112 CH3CC H H CF2CI 0
A1 12 CH2 = CH H CF2CI 0
A114 CH2 = CHCH2 H H CF2CI 0
A115 CH3SO2N (CH3) H H CF2CI 0
A116 (CH3) 2N H H CF2CI 0
A1 17 (CH3) 2NSO2 H H CF2CI 0
A118 CICH2 H H CF2CI 0
A120 CH3SOCH2 H H CF2CI 0
A121 CH3S02Cri2 H H CF2CI 0
A122 [1.2.4] -tpazol-l-ylmethyl H H CF2CI 0
A123 H H H CHF2 0
A124 CH3 H H CHF2 0
A126 cyclopropyl H H CHF2 0
A127 (CH3) 3C H H CHF2 0
A128 (CH3) 2CH H H CHF2 0
A129 CH3 (CH2) 2 H H CHF2 0
A130 CH3OCH2 H H CHF2 0
A131 CH3O (CH2) 2 H H CHF2 0
A132 Ph H H CHF2 0
A133 PhO H H CHF2 0
A135 PhSO H H CHF2 0
A136 PhSO2 H H CHF2 0
A137 CH3S H H CHF2 0
A138 CH3SO H H CHF2 0
A139 CF3 H H CHF2 0
Comp. No. R2 R3 R4 Rs P
A140 F2CH H H CHF2 0
A141 HCC H H CHF2 0
A14 CH3CC H H CHF2 0
A14S CH2 = CH H H CHF2 0
A144 CH2 = CHCrl2 H H CHF2 0
A145 CH3SO2N (CH3) H H CHF2 0
A146 (CH3) 2N H H CHF2 0
A147 (CH3) 2NS02 H H CHF2 0
A148 CICH2 H H CHF2 0
A151 CH3S? 2CH2 H H CHF2 0
A152 ll.2.4 | -triazol-l-ylmethyl H H CHF2 0
A154 CH3 H H CCI3 0
A155 CH3CH2 H H CCI3 0
A156 cyclopropyl H H CCI3 0
13 A158 (CH3) 2CH H H CCI3 0
A161 CH3O (CH2) 2 H H CCI3 0
A164 PhS H H CCI3 0
A171 HCC H H CCI3 0
: > A172 CH3CC H H CCI3 0
Comp. No. R2 R3 R, Rs P
A173 CH2 = CH H H CCI3 0
A175 CH3SO2N (CH3) H H CCI3 0
A177 (CH3) 2NSO2 H H CCI3 0
A179 CHaSCH2 H H CCI3 0
A18D CH3SOCH2 H H CCI3 0
A 182 [1.2.4] -triazol-l-ylmethyl H H CCI3 0
A183 H H CH3 CF3 0
A184 CH3 H CH3 CF3 0
A18I5 cyclopropyl H CH3 CF3 0
A187 (CH3) 3C H CH3 CF3 0
A1813 (CH3) 2CH H CH3 CF3 0
A189 CH3 (CH2) 2 H CH3 CF3 0
A 190 CH3OCH2 H CH3 CF3 0
A19"l CH3O (CH2) 2 H CH3 CF3 0
A19! Ph H CH3 CF3 0
A193 PhO H CH3 CF3 0
A194 PhS H CH3 CF3 0
A19í¡ PhSO H CH3 CF3 0
A196; PhSO2 H CH3 CF3 0
A 197 CH3S H CH3 CF3 0
A198 CH3SO H CH3 CF3 0
A199 CF3 H CH3 CF3 0
A200 F2CH H CH3 CF3 0
A201 HCC H CH3 CF3 0
A202 CH3CC H CH3 CF3 0
A203 CH2 = CH H CH3 CF3 0
A204 CH2 = CHCH2 H CH3 CF3 0
A205 CH3SO2N (CH3) H CH3 CF3 0
Comp. No. R2 R3 R4 Rs P
A20B (CH3) 2N H CH3 CF3 0
A207 (CH3) 2NS02 H CH3 CF3 0
A203 CICH2 H CH3 CF3 0
A203 CHaSCH2 H CH3 CF3 0
A210 CH3SOCH2 H CH3 CF3 0
A21 1 CH3SO2CH2 H CH3 CF3 0
A21 H H CH3 CF3CF2 0
A21 CH3 H CH3 CF3CF2 0
A21 CH3CH2 H CH3 CF3CF2 0
A21! 5 cyclopropyl H CH3 CF3CF2 0
A2K5 (CH3) 3C H CH3 CF3CF2 0
A21 (CH3) 2CH H CH3 CF3CF2 0
A218 CH3 (CH2) 2 H CH3 CF3CF2 0
A219 CH3OCH2 H CH3 CF3CF2 0
A220 CH30 (CH2) 2 H CH3 CF3CF2 0
A221 Ph H CH3 CF3CF2 0
A22 PhO H CH3 CF3CF2 0
A22ÍI PhS H CH3 CF3CF2 0
A22 PhSO H CH3 CF3CF2 0
A22 £. PhS02 H CH3 CF3CF2 0
A227 CH3SO H CH3 CF3CF2 0
A229 F2CH H CH3 CF3CF2 0
A230 HCC H CH3 CF3CF2 0
A231 CH3CC H CH3 CF3CF2 0
A232 CH2 = CH H CH3 CF3CF2 0
A234 CH3SO2N (CH3) H CH3 CF3CF2 0
A235 (CH3) 2N H CH3 CF3CF2 0
A236 (CH3) 2NSO2 H CH3 CF3CF2 0
A237 CICH2 H CH3 CF3CF2 0
A238 CH3SCH2 H CH3 CF3CF2 0
Comp. No. R2 R3 R4 Rs P
A239 CH3SOCH2 H CH3 CF3CF2 0
A240 CH3S02CH2 H CH3 CF3CF2 0
A241 H H CH3 CF3CF2CF2 0
A242 CH3 H CH3 CF3CF2CF2 0
A243 CH3CH2 H CH3 CF3CF2CF2 0
A244 cyclopropyl H CH3 CF3CF2CF2 0
A245 (CH3) 3C H CH3 CF3CF2CF2 0
A246 (CH3) 2CH H CH3 CF3CF2CF2 0
A247 CH3 (CH2) 2 H CH3 CF3CF2CF2 0
A248 CH3OCH2 H CH3 CF3CF2CF2 0
A249 CH3O (CH2) 2 H CH3 CF3CF2CF2 0
A250 Ph H CH3 CF3CF2CF2 0
A251 PhO H CH3 CF3CF2CF2 0
A252 PhS H CH3 CF3CF2CF2 0
A253 PhSO H CH3 CF3CF2CF2 0
A254 PhS02 H CH3 CF3CF2CF2 0
A255 CH3S H CH3 CF3CF2CF2 0
A256 CH3SO H CH3 CF3CF2CF2 0
A257 CF3 H CH3 CF3CF2CF2 0
A258 F2CH H CH3 CF3CF2CF2 0
A259 HCC H CH3 CF3CF2CF2 0
A260 CH3CC H CH3 CF3CF2CF2 0
A261 CH2 = CH H CH3 CF3CF2CF2 0
A262 CH2 = CHCH2 H CH3 CF3CF2CF2 0
A263 CH3S02N (CH3) H CH3 CF3CF2CF2 0
A264 (CH3) 2N H CH3 CF3CF2CF2 0
A265 (CH3) 2NSO2 H CH3 CF3CF2CF2 0
A266 CICH2 H CH3 CF3CF2CF2 0
A267 CH3SCH2 H CH3 CF3CF2CF2 0
A268 CH3SOCH2 H CH3 CF3CF2CF2 0
A269 CH3S? 2CH2 H CH3 CF3CF2CF2 0
A270 H H CH3 CF2CI 0
A271 CH3 H CH3 CF2CI 0
Comp. No. R2 R3 R4 Rs P
A272 CH3CH2 H CH3 CF2CI 0
A273 cyclopropyl H CH3 CF2CI 0
A274 (CH3) 3C H CH3 CF2CI 0
A275 (CH3) 2CH H CH3 CF2CI 0
A276 CH3 (CH2) 2 H CH3 CF2CI 0
A277 CH3OCH2 H CH3 CF2CI 0
A278 CH3O (CH2) 2 H CH3 CF2CI 0
A279 Ph H CH3 CF2CI 0
A280 PhO H CH3 CF2CI 0
A281 PhS H CH3 CF2CI 0
A282 PhSO H CH3 CF2CI 0
A283 PhS02 H CH3 CF2CI 0
A284 CH3S H CH3 CF2CI 0
A285 CH3SO H CH3 CF2CI 0
A286 CF3 H CH3 CF2CI 0
A287 F2CH H CH3 CF2CI 0
A288 HCC H CH3 CF2CI 0
A289 CH3CC H CH3 CF2CI 0
A290 CH2 = CH H CH3 CF2CI 0
A291 CH2 = CHCH2 H CH3 CF2CI 0
A292 CH3SO2N (CH3) H CH3 CF2CI 0
A293 (CH3) 2N H CH3 CF2CI 0
A294 (CH3) 2NS02 H CH3 CF2CI 0
A295 CICH2 H CH3 CF2CI 0
A296 CH3SCH2 H CH3 CF2CI 0
A297 CH3SOCH2 H CH3 CF2CI 0
A298 CH3SO2CH2 H CH3 CF2CI 0
A299 H H CH3 CHF2 0
A300 CH3 H CH3 CHF2 0
A301 CH3CH2 H CH3 CHF2 0
A302 cyclopropyl H CH3 CHF2 0
A303 (CH3) 3C H CH3 CHF2 0
A304 (CH3) 2CH H CH3 CHF2 0
Comp. No. R2 R3 R4 Rs P
A305 CH3 (CH2) 2 H CH3 CHF2 0
A306 CH3OCH2 H CH3 CHF2 0
A307 CH30 (CH2) 2 H CH3 CHF2 0
A308 Ph H CH3 CHF2 0
A309 PhO H CH3 CHF2 0
A310 PhS H CH3 CHF2 0
A311 PhSO H CH3 CHF2 0
A312 PhS02 H CH3 CHF2 0
A313 CH3S H CH3 CHF2 0
A314 CH3SO H CH3 CHF2 0
A315 CF3 H CH3 CHF2 0
A316 F2CH H CH3 CHF2 0
A317 HCC H CH3 CHF2 0
A318 CH3CC H CH3 CHF2 0
A319 CH2 = CH H CH3 CHF2 0
A320 CH2 = CHCH H CH3 CHF2 0
A321 CH3S02N (CH3) H CH3 CHF2 0
A322 (CH3) 2N H CH3 CHF2 0
A323 (CH3) 2NS02 H CH3 CHF2 0
A324 CICH2 H CH3 CHF2 0
A325 CH3SCH2 H CH3 CHF2 0
A326 CH3SOCH2 H CH3 CHF2 0
A327 CH3S02CH2 H CH3 CHF2 0
A328 H H CH3 CGI3 0
A329 CH3 H CH3 CCI3 0
A330 CH3CH2 H CH3 CCI3 0
A331 (CH3) 3C H CH3 CCI3 0
A332 (CH3) 2CH H CH3 CCI3 0
A333 cyclopropyl H CH3 CCI3 0
A334 CH3 (CH2) 2 H CH3 CCI3 0
A335 CH3OCH2 H CH3 CCI3 0
A336 CH30 (CH2) 2 H CH3 CCI3 0
A337 Ph H CH3 CCI3 0
Comp. No. R2 R3 4 Rs P
A33I3 PhO H CH3 CCI3 0
A339 PhS H CH3 CCI3 0
A340 PhSO H CH3 CCI3 0
A34 I PhS02 H CH3 CCI3 0
A342 CH3S H CH3 CCI3 0
A343 CH3SO H CH3 CCI3 0
A344 CF3 H CH3 CCI3 0
A34I »F2CH H CH3 CCI3 0
A34ÍI HCC H CH3 CCI3 0
A347 CH3CC H CH3 CCI3 0
A34 CH = CHCH2 H CH3 CCI3 0
A35C CH3S02N (CH3) H CH3 CCI3 0
A351 (CH3) 2N H CH3 CCI3 0
A352 (CH3) 2NS02 H CH3 CCI3 0
A355 CH3SOCH2 H CH3 CCI3 0
A356 CH3S02CH2 H CH3 CCI3 0
A357 H H Ph CF3 0
A358 CH3 H Ph CF3 0
A360 cyclopropyl H Ph CF3 0
A361 (CH3) 3C H Ph CF3 0
A362 (CH3) 2CH H Ph CF3 0
A363 CH3 (CH2) 2 H Ph CF3 0
A364 CH3OCH2 H Ph CF3 0
A365 CH3? (CH2) 2 H Ph CF3 0
A366 Ph H Ph CF3 0
A367 PhO H Ph CF3 0
A368 PhS H Ph CF3 0
A369 PhSO H Ph CF3 0
A370 PhS02 H Ph CF3 0
Comp. No. R2 R3 R4 Rs P
A371 CH3S H Ph CF3 0
A37 CH3SO H Ph CF3 0
A373 CF3 H Ph CF3 0
A374 F2CH H Ph CF3 0
A37! "HCC H Ph CF3 0
A37 (3 CH3CC H Ph CF3 0
A377 CH2 = CH H Ph CF3 0
A378 CH2 = CHCH2 H Ph CF3 0
A37Í) CH3S02N (CH3) H Ph CF3 0
A380 (CH3) 2N H Ph CF3 0
A381 (CH3) 2NS02 H Ph CF3 0
A382! CICH2 H Ph CF3 0
A38 CH3SCH2 H Ph CF3 0
A38 CH3SOCH2 H Ph CF3 0
A385 CH3S02CH2 H Ph CF3 0
A387 CH3 H Ph CF3CF2 0
A38S CH3CH2 H Ph CF3CF2 0
A38S cyclopropyl H Ph CF3CF2 0
A390 (CH3) 3C H Ph CF3CF2 0
A391 (CH3) 2CH H Ph CF3CF2 0
A392 CH3 (CH2) 2 H Ph CF3CF2 0
A393 CH3OCH2 H Ph CF3CF2 0
A394 CH30 (CH2) 2 H Ph CF3CF2 0
A395 Ph H Ph CF3CF2 0
A396 PhO H Ph CF3CF2 0
A397 PhS H Ph CF3CF2 0
A398 PhSO H Ph CF3CF2 0
A399 PhS02 H Ph CF3CF2 0
A400 CH3S H Ph CF3CF2 0
A401 CH3SO H Ph CF3CF2 0
A402 CF3 H Ph CF3CF2 0
A403 F2CH H Ph CF3CF2 0
Comp. No. R2 R3 R4 Rs P
A404 HCC H Ph CF3CF2 0
A405 CH3CC H Ph CF3CF2 0
A406 CH2 = CH H Ph CF3CF2 0
A407 CH2 = CHCH2 H Ph CF3CF2 0
A408 CH3S02N (CH3) H Ph CF3CF2 0
A409 (CH3) 2N H Ph CF3CF2 0
A410 (CH3) 2NS02 H Ph CF3CF2 0
A411 CICH2 H Ph CF3CF2 0
A412 CH3SCH2 H Ph CF3CF2 0
A413 CH3SOCH2 H Ph CF3CF2 0
A414 CH3S02CH2 H Ph CF3CF2 0
A415 H H Ph CF3CF2CF2 0
A416 CH3 H Ph CF3CF2CF2 0
A417 CH3CH2 H Ph CF3CF2CF2 0
A418. cyclopropyl H Ph CF3CF2CF2 0
A419 (CH3) 3C H Ph CF3CF2CF2 0
A420 (CH3) 2CH H Ph CF3CF2CF2 0
A421 CH3 (CH2) 2 H Ph CF3CF2CF2 0
A422 CH3OCH2 H Ph CF3CF2CF2 0
A423 CH30 (CH2) 2 H Ph CF3CF2CF2 0
A424 Ph H Ph CF3CF2CF2 0
A425 PhO H Ph CF3CF2CF2 0
A426 PhS H Ph CF3CF2CF2 0
A427 PhSO H Ph CF3CF2CF2 0
A428 PhS02 H Ph CF3CF2CF2 0
A429 CH3S H Ph CF3CF2CF2 0
A430 CH3SO H Ph CF3CF2CF2 0
A431 CF3 H Ph CF3CF2CF2 0
A432 F2CH H Ph CF3CF2CF2 0
A433 HCC H Ph CF3CF2CF2 0
A434 CH3CC H Ph CF3CF2CF2 0
A435 CH2 = CH H Ph CF3CF2CF2 0
A436 CH2 = CHCH2 H Ph CF3CF2CF2 0
Comp. No. R2 R3 R4 Rs P
A437 CH3S02N (CH3) H Ph CF3CF2CF2 0
A438 (CH3) 2N H Ph CF3CF2CF2 0
A439 (CH3) 2NS02 H Ph CFaCF2CF2 0
A440 CICH2 H Ph v_ i 3 r "(- r 2 0
A441 CH3SCH2 H Ph C 3C r2 i-2 0
A442 CH3SOCH2 H Ph C F3C F2C F2 0
A443 CH3S02CH2 H Ph? 3t F 2 F2 0
A444 H H Ph CF2CI 0
A445 CH3 H Ph CF2CI 0
A446 CH3CH2 H Ph CF2CI 0
A447 cyclopropyl H Ph CF2CI 0
A448 (CH3) 3C H Ph CF2CI 0
A449 (CH3) 2CH H Ph CF2CI 0
A450 CH3 (CH2) 2 H Ph CF2CI 0
A451 CH3OCH2 H Ph CF2CI 0
A452 CH30 (CH2) 2 H Ph CF2CI 0
A453 Ph H Ph CF2CI 0
A454 PhO H Ph CF2CI 0
A455 PhS H Ph CF2CI 0
A456 PhSO H Ph CF2CI 0
A457 PhS02 H Ph CF2CI 0
A458 CH3S H Ph CF2CI 0
A459 CH3SO H Ph CF2CI 0
A460 CF3 H Ph CF2CI 0
A461 F2CH H Ph CF2CI 0
A462 HCC H Ph CF2CI 0
A463 CH3CC H Ph CF2CI 0
A464 CH2 = CH H Ph CF2CI 0
A465 CH2 = CHCH H Ph CF2CI 0
A466 CH3S02N (CH3) H Ph CF2CI 0
A467 (CH3) 2N H Ph CF2CI 0
A468 (CH3) 2NS02 H Ph CF2CI 0
A469 CICH2 H Ph CF2CI 0
Comp. No. R2 R3 'R4 Rs P
A470 CH3SCH2 H Ph CF2CI 0
A471 CH3SOCH2 H Ph CF2CI 0
A472 CH3S? 2CH2 H Ph CF2CI 0
A473 H H Ph CHF2 0
A474 CH3 H Ph CHF2 0
A475 CH3CH2 H Ph CHF2 0
A476 cyclopropyl H Ph CHF2 0
MU (CH3) 3C H Ph CHF2 0
A478 (CH3) 2CH H Ph CHF2 0
A479 CH3 (CH2) 2 H Ph CHF2 0
A480 CH3OCH2 H Ph CHF2 0
A481 CH30 (CH2) 2H Ph CHF2 0
A482 Ph H Ph CHF2 0
A483 PhO H Ph CHF2 0
A484 PhS H Ph CHF2 0
A485 PhSO H Ph CHF2 0
A486 PhS02 H Ph CHF2 0
A487 CH3S H Ph CHF2 0
A488 CH3SO H Ph CHF2 0
A489 CF3 H Ph CHF2 0
A490 F2CH H Ph CHF2 0
A491 HCC H Ph CHF2 0
A492 CH3CC H Ph CHF2 0
A493 CH2 = CH H Ph CHF2 0
A494 CH2 = CHCH H Ph CHF2 0
A495 CH3S02N (CH3) H Ph CHF2 0
A496 (CH3) 2N H Ph CHF2 0
A497 (CH3) 2NS02 H Ph CHF2 0
A498 CICH2 H Ph CHF2 0
A499 CH3SCH2 H Ph CHF2 0
A500 CH3SOCH2 H Ph CHF2 0
A501 CH3SO2CH2 H Ph CHF2 0
A502 H H Ph CCI3 0
Comp. No. R2 R3 R4 Rs P
A503 CH3 H Ph CCI3 0
A504 CH3CH2 H Ph CCI3 0
A505 cyclopropyl H Ph CCI3 0
A50I3 (CH3) 3C H Ph CCI3 0
A507 (CH3) 2CH H Ph CCI3 0
A50I3 CH3 (CH2) 2 H Ph CCI3 0
A509 CH3OCH2 H Ph CCI3 0
A510 CH30 (CH2) 2 H Ph CCI3 0
A51 I Ph H Ph CCI3 0
A512 PhO H Ph CCI3 0
A51 PhS H Ph CCI3 0
A514 PhSO H Ph CCI3 0
A51Í1 PhS02 H Ph CCI3 0
A51 S F2CH H Ph CCI3 0
A520 HCC H Ph CCI3 0
A521 CH3CC H Ph CCI3 0
A522 CH2 = CH H Ph CCI3 0
A523 CH2 = CHCH2 H Ph CCI3 0
A524 CH3S02N (CH3) H Ph CCI3 0
A525 (CH3) 2N H Ph CCI3 0
A526 (CH3) 2NS02 H Ph CCI3 0
A527 CICH2 H Ph CCI3 0
A528 CH3SCH2 H Ph CCI3 0
A529 CH3S0CH2 H Ph CCI3 0
A530 CH3S02CH2 H Ph CCI3 0
A531 H CH3 H CF3 0
A532 H CH3CH2 H CF3 0
A533 H cyclopropyl H CF3 0
A534 H (CH3) 3CH H CF3 0
A535 H (CH3) 2CH H CF3 0
Comp. Mo. R2 R3 R4 Rs P
A53I5 H CH3 (CH2) 2 H CF3 0
A53"'H CH3OCH2 H CF3 0
A53I3 H CH30 (CH2) 2 H CF3 0
A539 H Ph H CF3 - 0
A540 H PhO H CF3 0
A54"! H PhS H CF3 0
A542 H PhSO H CF3 0
A543 H PhS02 H CF3 0
A544 H CH3S H CF3 0
A54í¡ H CH3SO H CF3 0
A54e »H CF3 H CF3 0
A547 H F2CH H CF3 0
A54ÍI H HCC H CF3 0
A54ÍI H CH3CC H CF3 0
A550 H CH2 = CH H CF3 0
A551 H CH2 = CHCH2 H CF3 0
A552 'H CH3S02N (CH3) H CF3 0
A55Ó H (CH3) 2N H CF3 0
A55A H (CH3) 2NS02 H CF3 0
A55E H CH3SCH2 H CF3 0
A55e H CH3SOCH2 H CF3 0
A558 H CH3 H CF3CF2 0
A55S H CH3CH2 H CF3CF2 0
A560 H cyclopropyl H CF3CF2 0
A561 H (CH3) 3C H CF3CF2 0
A562 H (CH3) 2CH H CF3CF2 0
A563 H CH3 (CH2) 2 H CF3CF2 0
A564 H CH3OCH2 H CF3CF2 0
A565 H CH30 (CH2) 2 H CF3CF2 0
A566 H Ph H CF3CF2 0
A567 H PhO H CF3CF2 0
A568 H PhS H CF3CF2 0
Comp. No. R2 R3 R4 Rs P
A570 H PhS02 H CF3CF2 0
A571 H CH3S H CF3CF2 0
A572 H CH3SO H CF3CF2 0
A573 H CF3 H CF3CF2 0
A574 H F2CH H CF3CF2 0
A575 H HCC H CF3CF2 0
A576 H CH3CC H CF3CF2 0
A577 H CH2 = CH H CF3CF2 0
A578 H CH2 = CHCH2 H CF3CF2 0
A579 H CH3S02N (CH3) H CF3CF2 0
A580 H (CH3) 2N H CF3CF2 0
A581 H (CH3) 2NS02 H CF3CF2 0
A582 H CH3SCH2 H CF3CF2 0
A583 H CH3SOCH2 H CF3CF2 0
A584 H CH3SO2CH2 H CF3CF2 0
A586 H CH3CH2 H C F3C F2C F2 0
A587 H cyclopropyl - H C F3C F2C F2 0
A588 H (CH3) 3C H CF3CF2CF2 0
A589 H (CH3) 2CH H CF3CF2CF2 0
A590 H CH3 (CH) 2 H C 3CF2CF2 0
A591 H CH3OCH2 H CF3CF2CF2 0
A592 H CH30 (CH2) 2 H CF3CF CF2 0
A593 H Ph H C F3C F C F2 0
A594 H PhO H C F3C F C F2 0
A595 H PhS H CF3CF2CF2 0
A596 H PhSO H CF3CF2CF2 0
A597 H PhS02 H 3 (- # F2'- '' 2 0
A599 H CH3SO H CF3CF2CF2 0
A600 H CF3 H CF3CF2CF2 0
A601 H F2CH H C F3C F2C F 0
Comp. No. R2 R3 R4 Rs P
A602 H HCC H C F3C F C F2 0
A603 H CH3CC H CF3CF2CF2 0
A604 H CH2 = CH H CF3CF2CF2 0
A605 H CH2 = CHCH2 H CF3CF2CF2 0
A606 H CH3S02N (CH3) H C F3C F2C F2 0
A607 H (CH3) 2N H CF3CF2CF2 0
A608 H (CH3) 2NS02 H C F3C F2C F2 0
A609 H CH3SCH2 H CF3CF CF2 0
A610 H CH3SOCH2 H CF3CF2CF2 0
A61 1 H CH3S02CH2 H CF3CF2CF2 0
A612 H CH3 H CF2CI 0
A613 H CH3CH2 H CF2CI 0
A614 H cyclopropyl H CF2CI 0
A615 H (CH3) 3C H CF2CI 0
A616 H (CH3) 2CH H CF2CI 0
A617 H CH3 (CH2) 2 H CF2CI 0
A618 H CH3OCH2 H CF2CI 0
A619 H CH30 (CH2) 2 H CF2CI 0
A620 H Ph H CF2CI 0
A621 H PhO H CF2CI 0
A622 H PhS H CF2CI 0
A623 H PhSO H CF2CI 0
A624 H PhS02 H CF2CI 0
A625 H CH3S H CF2CI 0
A626 H CH3SO H CF2CI 0
A627 H CF3 H CF2CI 0
A628 H F2CH H CF2CI 0
A629 H HCC H CF2CI 0
A630 H CH3CC H CF2CI 0
A631 H CH2 = CH H CF2CI 0
A632 H CH2 = CHCH2 H CF2CI 0
A633 H CH3S02N (CH3) H CF2CI 0
A634 H (CH3) 2N H CF2Cl 0
Comp. ND R2 R3 R4 Rs P
A635 H (CH3) 2NS02 H CF2Cl 0
A636 H CH3SCH2 H CF2CI 0
A637 H CH3SOCH2 H CF2CI 0
A638 H CH3S02CH2 H CF2CI 0
A639 H CH3 H CHF2 0
A640 H CH3CH2 H CHF2 0
A641 H cyclopropyl H CHF2 0
A642 H (CH3) 3C H CHF2 0
A643 H (CH3) 2CH H CHF2 0
A644 H CH3 (CH2) 2 H CHF2 0
A645 H CH3OCH2 H CHF2 0
A646 H CH30 (CH2) 2 H CHF2 0
A647 H Ph H CHF2 0
A648 H PhO H CHF2 0
A649 H PhS H CHF2 0
A650 H PhSO H CHF2 0
A651 H PhS02 H CHF2 0
A652 H CH3S H CHF2 0
A653 H CH3SO H CHF2 0
A654 H CF3 H CHF2 0
A655 H F2CH H CHF2 0
A656 H HCC H CHF2 0
A657 H CH3CC H CHF2 0
A658 H CH2 = CH H CHF2 0
A659 H CH2 = CHCH2 H CHF2 0
A660 H CH3S02N (CH3) H CHF2 0
A661 H (CH3) 2N H CHF2 0
A662 H (CH3) 2NS02 H CHF2 0
A663 H CH3SCH2 H CHF2 0
A664 H CH3SOCH2 H CHF2 0
A666 H CH3 H CCI3 0
A667 H CH3CH2 H CCl3 0
Comp. No. R2 R3 R4 Rs P
A6e¡8 H cyclopropyl H CCI3 0
A6É 9 H (CH3) 3C H CCI3 0
A670 H (CH3) 2CH H CCI3 0
A6 2 H CH3OCH2 H CCI3 0
A673 H CH30 (CH2) 2 H CCI3 0
A674 H Ph H CCI3 0
A675 H PhO H CCI3 0
A676 H PhS H CCI3 0
A678 H PhS02 H CCI3 0
A679 H CH3S H CCI3 0
A681 H CF3 H CCI3 0
A683 H HCC H CCI3 0
A687 H CH3S02N (CH3) H CCI3 0
A68I3 H (CH3) 2N H CCI3 0
A68 H (CH3) 2NS02 H CCI3 0
A690 H CH3SCH2 H CCI3 0
A69 I H CH3SOCH2 H CCI3 0
A693 H CH3 CH3 CF3 0
A69f¡ H cyclopropyl CH3 CF3 0
A69ÍI H (CH3) 3C CH3 CF3 0
A69 H (CH3) 2CH CH3 CF3 0
A696 H CH3 (CH2) 2 CH3 CF3 0
A69 H CH3OCH2 CH3 CF3 0
A700 H CH30 (CH2) 2 CH3 CF3 0
Comp. Mo. R2 R3 R4 Rs P
A701 H Ph CH3 CF3 0
A702 H PhO CH3 CF3 0
A703 H PhS CH3 CF3 0
A704 H PhSO CH3 CF3 0
A705 H PhS02 CH3 CF3 0
A706 H CH3S CH3 CF3 0
A707 H CH3SO CH3 CF3 0
A708 H CF3 CH3 CF3 0
A709 H F2CH CH3 CF3 0
A710 H HCC CH3 CF3 0
A711 H CH3CC CH3 CF3 0
A712 H CH2 = CH CH3 CF3 0
A713 H CH2 = CHCH2 CH3 CF3 0
A714 H CH3S02N (CH3) CH3 CF3 0
A715 H (CH3) 2N CH3 CF3 0
A716 H (CH3) 2NS02 CH3 CF3 0
A717 H CH3SCH2 CH3 CF3 0
A718 H CH3SOCH2 CH3 CF3 0
A719 H CH3S02CH2 CH3 CF3 0
A720 H CH3 CH3 CF3CF2 0
A721 H CH3CH2 CH3 CF3CF2 0
A722 H cyclopropyl CH3 CF3CF2 0
A723 H (CH3) 3C CH3 CF3CF2 0
A724 H (CH3) 2CH CH3 CFiCF2 0
A725 H CH3 (CH2) 2 CH3 CF3CF2 0
A726 H CH3OCH2 CH3 CF3CF2 0
A727 H CH30 (CH2) 2 CH3 CF3CF2 0
A728 H Ph CH3 CF3CF2 0
A729 H PhO CH3 CF3CF2 0
A730 H PhS CH3 CF3CF2 0
A731 H PhSO CH3 CF3CF2 0
A732 H PhS02 CH3 CF3CF2 0
A733 H CH3S CH3 CF3CF2 0
A734 H CH3SO CH3 CF3CF2 0
A735 H CF3 CH3 CF3CF2 0
A736 H F2CH CH3 CF3CF2 0
A737 H HCC CH3 CF3CF2 0
A738 H CH3CC CH3 CF3CF2 0
A739 H CH2 = CH CH3 CF3CF2 0
A740 H CH2 = CHCH2 CH3 CF3CF2 0
A741 H CH3S02N (CH3) CH3 CF3CF2 0
A742 H (CH3) 2N CH3 CF3CF2 0
A743 H (CH3) 2NS02 CH3 CF3CF2 0
A744 H CH3SCH2 CH3 CF3CF2 0
A745 H CH3SOCH2 CH3 CF3CF2 0
A746 H CH3S02CH CH3 CF3CF2 0
A747 H CH3 CH3 CF3CF2CF2 0
A748 H CH3CH2 CH3 CF3CF2CF2 0
A749 H cyclopropyl CH3 CF3CF2CF2 0
A750 H (CH3) 3C CH3 CF3CF2CF2 0
A751 H (CH3) 2CH CH3 (- 3 (- / i 2 1"2 0
A752 H CH3 (CH2) 2 CH3 C F3C F2C F2 0
A753 H CH3OCH2 CH3 C F3C F2C 2 0
A754 H CH30 (CH2) 2 CH3 CF3CF2CF2 0
A755 H Ph CH3 C F3C F2C 2 0
A756 H PhO CH3 C F3C F2C F2 0
A757 H PhS CH3 CF3CF2CF2 0
A758 H PhSO CH3 C 3L F2C F2 0
A759 H PhS02 CH3 CF3CF2CF2 0
A760 H CH3S CH3 C F3C F2C F2 0
A761 H CH3SO CH3 CF3CF2CF2 0
A762 H CF3 CH3 CF3CF2CF2 0
A763 H F2CH CH3 CF3CF2CF2 0
A764 H HCC CH3 CF3CF2CF2 0
A765 H CH3CC CH3 C F3C F2C F2 0
A766 H CH2 = CH CH3 C F3C F2C F2 0
Comp. No. R2 R3 R4 Rs P
A767 H CH2 = CHCH2 CH3 CF3CF CF 0
A76 £ H CH3S02N (CH3) CH3 CF3CF2CF2 0
A76S H (CH3) 2N CH3 C F3C F2C F2 0
A77C H (CH3) 2NS02 CH3 CF3CF2CF2 0
A771 H CH3SCH2 CH3 CF3CF2CF2 0
A772 H CH3SOCH2 CH3 CF3CF2CF2 0
A773 H CH3S02CH2 CH3 CF3CF2CF2 0
A774 H CH3 CH3 CF2CI 0
A775 H CH3CH2 CH3 CF2CI 0
A776 H cyclopropyl CH3 CF2CI 0
A777 H (CH3) 3C CH3 CF2CI 0
A778 H (CH3) 2CH CH3 CF2CI 0
A779 H CH3 (CH2) 2 CH3 CF2CI 0
A780 H CH3OCH2 CH3 CF2CI 0
A781 H CH30 (CH2) 2 CH3 CF2CI 0
A782 H Ph CH3 CF2CI 0
A783 H PhO CH3 CF2CI 0
A784 H PhS CH3 CF2CI 0
A785 H PhSO CH3 CF2CI 0
A786 H PhS02 CH3 CF2CI 0
A787 H CH3S CH3 CF2CI 0
A788 H CH3SO CH3 CF2CI 0
A789 H CF3 CH3 CF2CI 0
A790 H F2CH CH3 CF2CI 0
A791 H HCC CH3 CF2CI 0
A792 H CH3CC CH3 CF2CI 0
A793 H CH2 = CH CH3 CF2CI 0
A795 H CH3S02N (CH3) CH3 CF2CI 0
A796 H (CH3) 2N CH3 CF2CI 0
A797 H (CH3) 2NS02 CH3 CF2CI 0
A798 H CH3SCH2 CH3 CF2CI 0
A799 H CH3SOCH2 CH3 CF2CI 0
or
> > > > > > > 00 00 00 00 > > > > > > > > > > > > > > > > > > > > > > > > > > or
OO 00 oo? ? ? ? O to t M r ooo or Mo or Mo oo oo oo oo oo oo oo oo oo oo oo oo oo oo o o oo oo oo oo oo oo oo 3 or or or or 73 to or CO 00 rn rn t Ko o o l ro ro X X X X X X X X X X X X X X X X X X X X R X X X X X X X X X X R X X
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o x x x x x x x x x x x x x x x x x x x x x x x x x
o o n o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o O, oy ^ o ^ o, o ^ ^ o x? x? t? tt -p t? x-? x? xt? -p? -p -p -p xt? x-p x? x-p xtt x-p xt? 1-p 1? 1t? 1-p 1? 1-ri ^ o1
o o o o o o o o o o o o o o o o o o -?
Comp. No. R2 R3 4 Rs P
A833 H CH3 (CH2) 2 CH3 CCI3 0
A834 H CH3OCH2 CH3 CCI3 0
A83I5 H CH30 (CH2) 2 CH3 CCI3 0
A83 (5 H Ph CH3 CCI3 0
A837 H PhO CH3 CCI3 0
A838 H PhS CH3 CCI3 0
A83 H PhSO CH3 CCI3 0
A841 H CH3S CH3 CCI3 0
A849 H CH3S02N (CH3) CH3 CCI3 0
A851 H (CH3) 2NS02 CH3 CCI3 0
A853 H CH3SOCH2 CH3 CCI3 0
A854 H CH3S? 2CH2 CH3 CCI3 0
A855 H CH3 Ph CF3 0
A856 H CH3CH2 Ph CF3 0
A857 H (CH3) 2CH Ph CF3 0 0 A858 H (CH3) 2CH Ph CF3 0
A859 H cyclopropyl Ph CF3 0
A861 H CH3OCH2 Ph CF3 0
A862 H CH30 (CH2) 2 Ph CF3 0
A863 H Ph Ph. CF3 0
A864 H PhO Ph CF3 0 * A865 H PhS Ph CF3 0
Comp. No. R2 R3 R4 Rs P
A866 H PhSO Ph CF3 0
A867 H PhS02 Ph CF3 0
A868 H CH3S Ph CF3 0
A869 H CH3SO Ph CF3 0
A870 H CF3 Ph CF3 0
A871 H F2CH Ph CF3 0
A872 H HCC Ph CF3 0
A873 H CH3CC Ph CF3 0
A874 H CH2 = CH Ph CF3 0
A875 H CH2 = CHCH2 Ph CF3 0
A876 H CH3S02N (CH3) Ph CF3 0
A877 H (CH3) 2N Ph CF3 0
A878 H (CH3) 2NS02 Ph CF3 0
A879 H CH3SCH2 Ph CF3 0
A880 H CH3SOCH2 Ph CF3 0
A881 H CH3S02CH2 Ph CF3 0
A882 H CH3 Ph CF3CF2 0
A884 H cyclopropyl Ph CF3CF2 0
A885 H (CH3) 3C Ph CF3CF2 0
A886 H (CH3) 2CH Ph CF3CF2 0
A887 H CH3 (CH2) 2 Ph CF3CF2 0
A888 H CH3OCH2 Ph CF3CF2 0
A889 H CH30 (CH2) 2 Ph CF3CF2 0
A890 H Ph Ph CF3CF2 0
A891 H PhO Ph CF3CF2 0
A892 H PhS Ph CF3CF2 0
A893 H PhSO Ph CF3CF2 0
A894 H PhS02 Ph CF3CF2 0
A895 H CH3S Ph CF3CF2 0
A896 H CH3SO Ph CF3CF2 0
A897 H CF3 Ph CF3CF2 0
A898 H F2CH Ph CF3CF2 0
íomp. Mo. R2 R3 R4 Rs P
A899 H HCC Ph CF3CF2 0
A900 H CH3CC Ph CF3CF2 0
A901 H CH2 = CH Ph CF3CF2 0
A902 H CH2 = CHCH2 Ph CF3CF2 0
A903 H CH3S02N (CH3) Ph CF3CF2 0
A904 H (CH3) 2N Ph CF3CF2 0
A905 H (CH3) 2NS02 Ph CF3CF2 0
A906 H CH3SCH2 Ph CF3CF2 0
A907 H CH3SOCH2 Ph CF3CF2 0
A908 H CH3S02CH2 Ph CF3CF2 0
A909 H CH3 Ph CF3CF2CF2 0
A910 H CH3CH2 Ph C F3C F2C F2 0
A91 1 H cyclopropyl Ph CF3CF2CF2 0
A912 H (CH3) 3C Ph C F3C F C F2 0
A913 H (CH3) 2CH Ph CF3CF2CF2 0
A914 H CH3 (CH2) 2 Ph C F3C F2C F2 0
A915 H CH3OCH2 Ph CF3CF2CF2 0
A916 H CH30 (CH2) 2 Ph C F3C F2C F2 0
A917 H Ph Ph C F3C F2C F2 0
A918 H PhO Ph CF3CF2CF2 0
A919 H PhS Ph C F3C F2C F2 0
A920 H PhSO Ph C F3C F2C F2 0
A921 H PhS02 Ph CF3CF2CF2 0
A922 H CH3S Ph CF3CF2CF2 0
A923 H CH3SO Ph C F3C F2C F2 0
A924 H CF3 Ph C F3C F2C F 0
A925 H F2CH Ph CF3CF2CF2 0
A926 H HCC Ph CF3CF2CF2 0
A927 H CH3CC Ph CF3CF2CF2 0
A929 H CH2 = CHCH2 Ph C F3C F C F2 0
A930 H CH3S02N (CH3) Ph CF3CF2CF2 0
A931 H (CH3) 2N Ph CF3CF2CF2 0
Comp. No. R2 R3 R4 Rs P
A932 H (CH3) 2NS02 Ph CF3CF2CF2 0
A933 H CH3SCH2 Ph CF3CF2CF2 0
A934 H CH3SOCH2 Ph CF3CF2CF2 0
A935 H CH3S02CH2 Ph C V- r 2 (- i 2 0
A936 H CH3 Ph CF2CI 0
A937 H CH3CH2 Ph CF2CI 0
A938 H cyclopropyl Ph CF2CI 0
A939 H (CH3) 3C Ph CF2CI 0
A940 H (CH3) 2CH Ph CF2CI 0
A941 H CH3 (CH2) 2 Ph CF2CI 0
A942 H CH3OCH2 Ph CF2CI 0
A943 H CH30 (CH2) 2 Ph CF2CI 0
A944 H Ph Ph CF2CI 0
A945 H PhO Ph CF2CI 0
A946 H PhS Ph CF2CI 0
A947 H PhSO Ph CF2CI 0
A948 H PhS02 Ph CF2CI 0
A949 H CH3S Ph CF2CI 0
A950 H CH3SO Ph CF2CI 0
A951 H CF3 Ph CF2CI 0
A952 H F2CH Ph CF2CI 0
A953 H HCC Ph CF2CI 0
A954 H CH3CC Ph CF2CI 0
A955 H CH2 = CH Ph CF2CI 0
A956 H CH2 = CHCH2 Ph CF2CI 0
A957 H CH3S02N (CH3) Ph CF2CI 0
A958 H (CH3) 2N Ph CF2CI 0
A959 H (CH3) 2NS02 Ph CF2CI 0
A960 H CH3SCH2 Ph CF2CI 0
A961 H CH3SOCH2 Ph CF2CI 0
A962 H CH3S02CH2 Ph CF2CI 0
A963 H CH3 Ph CHF2 0
A964 H CH3CH2 Ph CHF2 0
Comp. No. R2 R3 R4 Rs P
A965 H (CH3) 3C Ph CHF2 0
A966 H (CH3) 2CH Ph CHF2 0
A967 H cyclopropyl Ph CHF2 0
A968 H CH3 (CH2) 2 Ph CHF2 0
A969 H CH3OCH2 Ph CHF2 0
A97D H CH30 (CH2) 2 Ph CHF2 0
A971 H Ph Ph CHF2 0
A972 H PhO Ph CHF2 0
A973 H PhS Ph CHF2 0
A974 H PhSO Ph CHF2 0
A975 H PhS02 Ph CHF2 0
A976 H CH3S Ph CHF2 0
A977 H CH3SO Ph CHF2 0
A973 H CF3 Ph CHF2 0
A979 H F2CH Ph CHF2 0
A980 H HCC Ph CHF2 0
A98 I H CH3CC Ph CHF2 0
A98 H CH2 = CH Ph CHF2 0
A983 H CH2 = CHCH2 Ph CHF2 0
A984 H CH3S02N (CH3) Ph CHF2 0
A985 H (CH3) 2N Ph CHF2 0
A98I3 H (CH3) 2NS02 Ph CHF2 0
A987 H CH3SCH2 Ph CHF2 0
A98IJ H CH3S0CH2 Ph CHF2 0
A989 H CH3S02CH2 Ph CHF2 0
A990 H CH3 Ph CCI3 0
A993 H (CH3) 2CH Ph CCI3 0
A994 H cyclopropyl Ph CCI3 0
A99 £ ¡H CH3 (CH2) 2 Ph CCI3 0
A997 H CH30 (CH2) 2 Ph CCI3 0
> > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > 3 o CD CO -§ o o to o o to t o o? ro o o o o O O fO o- -, o- * o - w o O - - o - -. or -Jb or _ "or _ _ o_ - O O O O or CD 00 -J O) cp? tto ro O trt m v-? m in r r i _ O O O O or co co
O o TJ r O O o z J TI 5 * O I X o O o x o? X 22 X X II or C? Z "^ O TI X X X X X X X X X X X X X X X X X X X X
Or C? X X O O O C? o x O
I X X X X X X X X X X X
x x x x x x x x x x x x x x TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ TJ r z z r r r - 3- z - zr
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o -p t? t? t? -p t? -p t? -p? t? -p t? -p? ? ? O O O O O O O O O O O O O O O x
o o o o o o o o o o o o o TJ
Comp. N D. R2 R3 R Rs P
A1031 CHF2CH2 H H CF3 0
A 1033 fl.3] -imidazol-l-ylmethyl H H CF3 0
A 1034 CHCI2CH2 H H CF3 0
A 1035 CICH = CH H H CF3 0
A1036 CI2C = CH H H CF3 0
A1037 CF3CH = CH H H CF3 0
A 1038 CICC H H CF3 0
A 1039 PhCH2 H H CF3 0
A 1040 CH3CH2 CH3 H CF3 0
A1041 CH3 OH H CF3 0
A 1042 CH3 F H CF3 0
A1043 CH3 Cl H CF3 0
A1044 F CH3 H CF3 0
A 1045 Cl CH3 H CF3 0
A 1046 H F H CF3 0
A 1047 H Cl H CF3 0
A 1048 H Br H CF3 0
A 1049 H OH H CF3 0
A 1050 H OCH3 H CF3 0
A1051 H OCHF2 H CF3 0
A 1052 H OS02CH3 H CF3 0
A 1053 H OS02CF3 H CF3 0
A 1054 H CICH2 H CF3 0
A 1055 H BrCH2 H CF3 0
A 1056 H FCH2 H CF3 0
A 1057 H CHF2CH2 H CF3 0
A1058 H C 3CH2 H CF3 0
A1059 H triazolimetil H CF3 0
A1061 H CICH = CH H CF3 0
A 1062 H CI2C = CH H CF3 0
A 1063 H CF3CH = CH H CF3 0
Comp. No. R2 R3 R4 Rs P
A1064 H CICC H CF3 0
A106 H CH3C (0) H CF3 0
A106 (5 H Ph H CF3 0
A 1067 H S02CH3 H CF3 0
A1068 H S02CF3 H CF3 0
A1069 H NC H CF3 0
A1070 H N02 H CF3 0
A1071 CH3 H F CF3 0
A1072 'CH3 H Cl CF3 0
A1073 CH3 H Br CF3 0
A 107 ¿CH3 H NC CF3 0
A 1075 CH3 H CH30 CF3 0
A1076 CH3 H CH3S CF3 0
A 1077 CH3 H CH3SO CF3 0
A 1078 CH3 H CH3S02 CF3 0
A 1079 CH3CH2OCH2 H H CF3 0
A 1080 PhOCH2 H H CF3 0
A 1082 (CH3) 2CH2OCH2 H H CF3 0
A 1083 BrCH2CH2 H H CF3 0
A 1084 FCH2CH2 H H CF3 0 \ .N SCH, A1085 XX H H CF3 0 I
Comp. No. R2 R3 R4 Rs P
A109 I Cyclopropyl-CH2 H H C CFF33 0 0
A109 2.2-dichlorocycloprop- 1 - H H C CFF33 0 0 ilo A1093 CH3OC (0) CH = CH H H C CFF33 0 0
A1094 CH3CH2OC (0) CH = CH H H C CFF33 0 0
A1095 CICH2CH = CH H H C CFF33 0 0
A1096 CH = C = CH H H C CFF33 0 0
A1097 (CH3) 2NCH2 H H C CFF33 0 0
A1098 HOCH2 H H C CFF33 0 0
A109 CH3C (0) OCH2 H H C CFF33 0 0
A1100 PhC (0) OCH2 H H C CFF33 0 0
A1101 PhCH2CH2 H H C CFF33 0 0
A1102! CH3OC (0) CH2 H H C CFF33 0 0
A110ÍÍ NCCH2 H H C CFF33 0 0
A1104 CH3 (CH2) 7SCH2 H H C CFF33 0 0
A1 10E CH3 (CH2) 7SOCH2 H H f- C CFF33 .. 0 0
A1106 CH3 (CH2) 7S02CH2 H H C CFF33 0 0
A1108 CICH2CC H H CF3 0
A1109 CHF2CH2CH2 H H CF3 0
A11 10 CHCI2CH2CH2 H H CF3 0
A111 1 CF3S020 H H CF3 0
Comp. No. R2 R3 R4 Rs P
A1114 H H CF3 0
A1115 O "'H H CF3 0
A1117 iXc "'H H CF3 0
A1118 CH3ON = CHCH2 H H CF3 0
A1119 0 = CHCH2 H H CF3 0
A1120 CH3CH2OCH2 H H CF2CI 0
A1121 PhOCH2 H H CF2CI 0
A1122 N ^ ° CH- H H CF2CI 0
A1123 (CH3) 2CH2OCH2 H H CF2CI 0
A1124 BrCH2 H H CF2CI 0
A1125 FCH2 H H CF2CI 0
A1129 ^ XNJ ySCH 'H H CF2CI 0
A1130 / O? sow, H H CF2CI 0
A1132 cyclopropyl-CH2 H H CF2CI 0
A1133 H H CF2CI 0
2. 2-dichlorocycloprop-l-yl
Comp. No. R2 R3 R4 R5 P
A1 134 CH30C (0) CH = CH H CF2CI 0
A1 135 CH3CH2OC (0) CH = CH H CF2CI 0
A1136 CICH2CH = CH H H CF2CI 0
A1 137 CH = C = CH H H CF2CI 0
A1 138 (CH3) 2NCH2 H H CF2CI 0
A1139 HOCH2 H H CF2CI 0
A1140 CH3C (0) OCH2 H H CF2CI 0
A1141 PhC (0) OCH2 H H CF2CI 0
A1 142 PhCH2 H H CF2CI 0
A1 143 CH3OC (0) CH2 H H CF2CI 0
A1144 NCCH2 H H CF2CI 0
A1 145 CH3 (CH2) 7SCH2 H H CF2CI 0
A1 146 CH3 (CH2) 7SOCH2 H H CF2CI 0
A1147 CH3 (CH2) 7S02CH2 H H CF2CI 0
A1149 CICH2CC H H CF2CI 0
A1150 Br H H CF2CI 0
A1151 Cl H H CF2CI 0
A1 152 CF3S020 H H CF2CI 0
A1156 cr H H CF2CI 0
A1157 • or H H CF2CI 0
A1159 CH3ON = CHCH2 H H CF2CI 0
Comp. No. R2 R3 R4 RRss P P
A1160 0 = CHCH2 H H C CFF22CCII 0 0
A1161 CH3CH2OCH2 H H C CFF22HH 0 0
A1 162 PhOCH2 H H C CFF22HH 0 0
A1 164 (CH3) 2CH2OCH2 H H CF2H 0
A1165 BrCH2 H H CF2H 0
A1166 FCH2 H H CF2H 0
A1170 H H CF2H K¿-N and
A1 173 c? Cloprop? L-CH2 H H CF2H 0
A1174 2.2-dichlorocycloprop- 1- H H CF2H 0 ilo A1175 CH3OC (0) CH = CH H H CF2H 0
A1176 CH3CH2OC (0) CH = CH H H CF2H 0
A1 177 CICH2CH = CH H H CF2H 0
A1178 CH = C = CH H CF2H 0
A1179 (CH3) 2NCH2 H H CF2H 0
A1180 HOCH2 H H CF2H 0
AA11118811 CCHH33CC ((00)) OOCCHH22 H H CF2H 0
A1182 PhC (0) OCH2 H H CF2H 0
Q. O O O O O O O O O O
X X X X X X X X X X X X X X X X X X
LL LL LL LL LL LL LL
LL LL LL LL LL LL LL LL LL LL LL LL O O CJ ü ü O ü CJ O ü O O O ü O ü O ü O O ü ü ü O ü ü
tf x x x x x x X X X X x x x i x g x x x x
X X X X X X X X X X X x x x x x g x x x
o _ ta. 'r ^ CG C T cu ^ - 00 CD O CM CO • vt 0 CO Oi O) O) O) n i O) s > O) O) m. 8 00 00 00 oo 0 co r- CO a. i- o o O O O O o o M o t_ - "- CM CM CM CM CM CM CM CM CM CM
< < < < < < < < < < < < < < < < < < < < or i <
or. or
LL LL LL LL LL LL LL LL LL LL LL LL LL LL LL LL LL LL LL
X O Ü P O O Ü O Ü Ü O O Ü Ü Ü Ü Ü O O P Ü Ü Ü O P Ü P O O
rf X X X X X X X X X X X X X X X X X X x x x x x x x
rf x x x x x x x x x LL X X X X X X X X ü x x x x x x x
z cr > or i- CM co ^ r lO COvv-OO O O ^ M C í- in go. O u) < JJ T- T- T- T- T- CM CM CM CM CM CM CM CM CM CM co D. CM CM CM CM CM CM CO CO CO CO CO CO CO CO CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM OJ C \ J OJ CM CM CM < < < < < < < < < < < CJ
Comp. No. R2 R3 R4 Rs P
A1238 Cl H H CF3 1
A1239 0 = CHCH2 H H CF3 1
A1240 CH3 H H CF2CI 1
A1242 cyclopropyl H H CF2CI 1
A 1243 CH3 (CH2) 2 H H CF2CI 1
A 1244 CH3OCH2 H H CF2CI 1
A 1245 CF3 H H CF2CI 1
A1246 F2CH H H CF2CI 1
A 1247 CICH2 H H CF2CI 1
A1248 CH3S02CH2 H H CF2CI 1
A1249 CH3 CF3 H CF2CI 1
A1250 CH3CH2OCH2 H H CF2CI 1
A1251 PhOCH2 H H CF2CI 1
A1252 (CH3) 2CH2OCH2 H H CF2CI 1
A1253 BrCH2 H H CF2CI 1
A 1254 FCH2 H H CF2CI 1
/ O- / SO.CH, A1256 x H H CF2CI 1
and A 1257 cyclopropyl-CH2 H H CF2CI 1
A1258 2.2-d? Chlorocycloprop-1-H H CF.2Cl 1 yl A1259 (CH3) 2NCH2 H H CF2CI 1
A1260 HOCH2 H H CF2CI 1
A1261 CH3C (0) OCH2 H H CF2CI 1
A 1262 PhC (0) OCH2 H H CF2CI 1
A1263 • PhCH2 H H CF2CI 1
A 1264 CH3OC (0) CH2 H H CF2CI 1
A1265 NCCH2 H H CF2CI 1
A1266 CH3 (CH2) 7S02CH2 H H CF2CI 1
Comp. No. R2 R3 R4 Rs P
A1267 Br H H CF2CI 1
A12613 Cl H H CF2CI 1
A 1269 0 = CHCH2 H H CF2CI 1
A1270 CH3 H H CF2H 1
A127 I CH3CH2 H H CF2H 1
A1272 cyclopropyl H H CF2H 1
A1273 CH3 (CH2) 2 H H CF2H 1
A1274 CH3OCH2 H H CF2H 1
A1275 CF3 H H CF2H 1
A1276 F2CH H H CF2H 1
A 1277 CICH2 H H CF2H 1
A1276I CH3S? 2CH2 H H CF2H 1
A127 CH3 CF3 H CF2H 1
A128C CH3CH2OCH2 H H CF2H 1
A1281 PhOCH2 H H CF2H 1
A 1282 (CH3) 2CH2OCH2 H H CF2H 1
A1283 BrCH2 H H CF2H 1
A 1284 FCH2 H H CF2H 1
A1286 / ° ^ N ^ SO, CH2 H H CF2H 1
A1287 cyclopropyl-CH2 H H CF2H 1
A1288 2.2-dichlorocycloprop-1-H H CF2H 1 yl A1289 (CH3) 2NCH2 H H CF2H 1
A1290 HOCH2 H H CF2H 1
A1291 CH3C (0) OCH2 H H CF2H 1
At 1292 PhC (0) OCH2 H H CF2H 1
A1293 PhCH2 H H CF2H 1
A 1294 CH3OC (0) CH2 H H CF2H 1
A1295 NCCH2 H H CF2H 1
Comp. No. R2 R3 R4 Rs P
A129S CH3 (CH2) 7S02CH2 H H CF2H A1297 Br H H CF2H A1293 Cl H H CF2H A1299 0 = CHCH2 H H CF2H A1300 CH3 H H CF3CF2 A130 I HO H Ph CF3 0
A130 CH3 H CH2 = CH CF3 0
A1303 CH3 H CH3CH20 CF3 0
A1304 HO CH3 H CF3 0
A1305 HO H H CF3 0
A1306 (CH3CH2) 2N (0) CO H H CF3 0
A1307 CH3 H Tosil-O CF3 0
A 1308 CH3 H CH3CC CF3 0
A1309 CH3 H HCC CF3 0
A1310 CH3 H CICH2CC CF3 0
A1311 CH3 H PhCH20 CF3 0
A1312! CH3 H CF3S020 CF3 0
A1313 CH3 H (CH3) 2N CF3 0
A1314 CH3 H CH3C (0) 0 CF3 0
A1315 CH3 H CH3CH2C (0) 0 CF3 0
A1316 CH3 H PhC (0) 0 CF3 0
A1317 CH3 H 3-Pyridyl CF3 0
A1318 CH3OCH2OCH2 H H CF2CI 0
A1319 CH3OCH2OCH2 H H CF2H 0
A 1320 CH3OCH2OCH2 H H CF2CF3 0
A1321 CH3OCH2OCH2 H H CF3 1
A 1322 CH3O H CH3 CF3 0
In the following Table 2, Q is Q:
"> •,
and QL = the following radicals B Table 2: Radicals B: Radice l R6 Ry R8 9 R10
B1 H H H H OH CH2
B2 CH3 H H OH OH CH2
B3 CH3CH2 H H OH OH CH2
B4 CH3CH2CH2 H H OH OH CH2
B5 (CH3) 2CH H H OH OH CH2
B6 (CH3) 3C H H OH OH CH2
B7 CH3S H H OH OH CH2
B8 CH3SO H H OH OH CH2
B9 CH3S02 H H OH OH CH2
B10 Ph H H OH OH CH2
B11 CH30 H H OH OH CH2
B12 CH3OC (0) H H OH OH CH2
B13 CH3CH2OC (0) H H OH OH CH2
B14 CH2 = CHCH2 H H OH OH CH2
B15 HCCCH2 H H OH OH CH2
B16 CF3 H H OH OH CH2
B17 (CH3) 2NS02 H H OH OH CH2
B18 (CH3) 2N H H OH OH CH2
B19 PhO H H OH OH CH2
B20 PhS H H OH OH CH2
B21 PhSO H H OH OH CH2
B22 PhS02 H H OH OH CH2
Radical Re R7 R8 R9 R10 W
B23 CN H H OH OH CH2
B24 CH3 CH3 H H OH CH2
B25 CHsCH? CH3 H H OH CH2
B26 CH3CH2CH2 CH3 H H OH CH2
B27 (CH3) 2CH CH3 H OH OH CH2
B28 (CH3) 3C CH3 H OH OH CH2
B29 CH3S CH3 H H OH CH2
B30 CH3SO CH3 H H OH CH2
B31 CH3S02 CH3 H H OH CH2
B32 Ph CH3 H H OH CH2
B33 CH30 CH3 H H OH CH2
B34 CH3OC (0) CH3 H H OH CH2
B35 CH3CH2OC (0) CH3 H H OH CH2
836 CH2 = CHCH2 CH3 H H OH CH2
B37 HCCCH2 CH3 H H OH CH2
B38 CF3 CH3 H H OH CH2
B39 (CH3) 2NS02 CH3 H H OH CH2
B40 (CH3) 2N CH3 H H OH CH2
B41 PhO CH3 H H OH CH2
B42 PhS CH3 H H OH CH2
B43 PhSO CH3 H H OH CH2
B44 PhS02 CH3 H H OH CH2
B45 CN CH3 H H OH CH2
B46 CH3 H CH3 H OH CH2
B47 CH3CH2 H CH3 H OH CH2
B48 CH3CH2CH2 H CH3 H OH CH2
B49 (CH3) 2CH H CH3 H OH CH2
B50 (CH3) 3C H CH3 H OH CH2
B51 CH3S H CH3 H OH CH2
B52 CH3SO H CH3 H OH CH2
B53 CH3S02 H CH3 H OH CH2
B54 Ph H CH3 H OH CH2
B55 CH3O H CH3 H OH CH2
Radical Re R7 R8 R9 Ric- W
B56 CH3OC (0) H CH3 H OH CH2
B57 CH3CH2OC (0) H CH3 H OH CH2
B58 CH2 = CHCH2 H CH3 H OH CH2
B59 HCCCH2 H CH3 H OH CH2
B60 CF3 H CH3 H OH CH2
B61 (CH3) 2NS? 2 H CH3 H OH CH2
B62 (CH3) 2N H CH3 H OH CH2
B63 PhO H CH3 H OH CH2
B64 PhS H CH3 H OH CH2
B65 PhSO H CH3 H OH CH2
B66 PhS02 H CH3 H OH CH2
B67 CN H CH3 H OH CH2
B68 CH3 CH3 CH3 H OH CH2
B69 CH3CH2 CH3 CH3 H OH CH2
B70 CH3CH2CH2 CH3 CH3 H OH CH2
B71 (CH3) 2CH CH3 CH3 H OH CH2
B72 (CH3) 3C CH3 CH3 H OH CH2
B73 CH3S CH3 CH3 H OH CH2
B74 CH3SO CH3 CH3 H OH CH2
B75 CH3S02 CH3 CH3 H OH CH2
B76 Ph CH3 CH3 H OH CH2
B77 CH30 CH3 CH3 H OH CH2
B78 CH3OC (0) CH3 CH3 H OH CH2
B79 CH3CH2OC (0) CH3 CH3 H OH CH2
B80 CH2 = CHCH2 CH3 CH3 H OH CH2
B81 HCCCH2 CH3 CH3 H OH CH2
B82 CF3 CH3 CH3 H OH CH2
B83 (CH3) 2NS02 CH3 CH3 H OH CH2
B84 (CH3) 2N CH3 CH3 H OH CH2
B85 PhO CH3 CH3 H OH CH2
B86 PhS CH3 CH3 H OH CH2
B87 PhSO CH3 CH3 H OH CH2
B88 PhS02 CH3 CH3 H OH CH2
3 rd 5o 5 5 2 5 5 5 5 2 3 5 - * o co oo Oi Ol? ro - ••
o ^^^ o X or O X o o J_ o O O O X X O
X TJ X? o O X O o o X o o X O T X X O J- T) o rr TJ TJ O O O o X O X? T "O u C? ± C? C? ZJ- X 11 TI O O X TJ? X or X O
T X or? X O n rn Z z o X or X 1T? (n? X or X O x o o o -J- o o o o O C? o O O C? O X or X z 10 O O O C? X O o O o o X o x X o X
ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox ox X
x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x 4 _ -t, 0 0 0 0 0 0 X X X X X x x x x x x x x x x 0x 0x 0x 0 X x 0x 0x 0x 0x 0x 0x 0x 0x 0x 0x 0x 0x _x ^ -rj
O O O O O O O O O o o o o o X x x x x x x x x x x x x x x y x x x x x x x x x x x x x x x x 3
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o < x x x x x x x x x x x x x x x x x x x x x x x x x x <
Radical Re R7 RB R9 R10 W
B122 CH3CH2OC (0) CH3CH2 H H OH CH2
B124 HCCCH2 CH3CH2 H H OH CH2
B126 (CH3) 2NS02 CH3CH2 H H OH CH2
B127 (CH3) 2N CH3CH2 H H OH CH2
B128 PhO CH3CH2 H H OH CH2
B129 PhS CH3CH2 H H OH CH2
B130 PhSO CH3CH2 H H OH CH2
B131 PhS02 CH3CH2 H H OH CH2
B132 CN CH3CH2 H H OH CH2
B133 H H H OH OH CHCH3
B134 CH3 H H OH OH CHCH3
B135 CH3CH2 H H OH OH CHCH3
B136 CH3CH2CH H H OH OH CHCHa
B137 (CH3) 2CH H H OH OH CHCH3
B138 (CH3) 3C H H OH OH CHCHa
B139 CH3S H H OH OH CHCHa
B140 CH3SO H H OH OH CHCH3
B141 CH3S02 H H OH OH CHCH3
B142 Ph H H OH OH CHCH3
B143 CH3O H H OH OH CHCH3
B144 CH3OC (0) H H OH OH CHCH3
B145 CH3CH20C (0) H H OH OH CHCH3
B146 CH2 = CHCH2 H H OH OH CHCH3
B147 HCCCH2 H H OH OH CHCH3
B148 CF3 H H OH OH CHCH3
B149 (CH3) 2NS02 H H OH OH CHCH3
B150 (CH3) 2N H H OH OH CHCH3
B151 PhO H H OH OH CHCH3
B152 PhS H H H OH CHCH3
B153 PhSO H H OH OH CHCH3
B154 PhS02 H H OH OH CHCH3
Radical Re R7 Rβ R9 R10 W B155 CN H H OH OH CHCH3 B156 CH3 CH3 H OH OH CHCH3 B157 CH3CH2 CH3 H OH OH CHCH3 B158 CH3CH2CH2 CH3 H OH OH CHCH3 B15 £? (CH3) 2CH CH3HH OH CHCH3 B160 (CH3) 3C CH3 H OH CHCH3 B161 CH3S CH3 H OH OH CHCH3 B162 CH3SO CH3 H OH OH CHCH3 B163 CH3S02 CH3 H H OH CHCH3 B164 Ph CH3 H H OH CHCH3 B165 CH3O CH3 H H OH CHCH3
B166 CH3OC (0) CH3 H H OH CHCH3
B167 CH3CH2OC (0) CH3 H H OH CHCH3
B168 CH2 = CHCH2 CH3 H OH OH CHCH3
B169 HCCCH2 CH3 H H OH CHCH3
B170 CF3 CH3 H OH OH CHCH3
B171 (CH3) 2NS02 CH3 H OH OH CHCH3
B172 (CH3) 2N CH3 H H OH CHCHa
B173 PhO CH3 H H OH CHCHa
B174 PhS CH3 H H OH CHCH3
B175 PhSO CH3 H H OH CHCH3
B176 PhS02 CH3 H H OH CHCH3
B177 CN CH3 H OH OH CHCH3
B178 CH3 H CH3 H OH CHCH3
B179 CH3CH2 H CH3 H OH CHCH3
2 (1 B180 CH3CH2CH H CH3 H OH CHCH3
B181 (CH3) 2CH H CH3 H OH CHCH3
B182 (CH3) 3C H CH3H OH CHCH3
B183 CH3S H CH3 H OH CHCH3
B184 CH3SO H CH3 H OH CHCH3
B185 CH3S02 H CH3 H OH CHCH3"-, B186 Ph H CH3 H OH CHCH3
B187 CH3O H CH3 H OH CHCH3
Radies 1 Re R7 Rß R9 R-io W
B188 CH3OC (0) H CH3 H OH CHCH3
B189 CH3CH2OC (0) H CH3H OH CHCHa
B190 CH2 = CHCH2 H CH3 H OH CHCHa
B191 HCCCH2 H CH3 H OH CHCHa
B192 CF3 H CH3 H OH CHCH3
B193 (CH3) 2NS02H CH3H OH CHCH3
B194 (CH3) 2N H CH3H OH CHCHa
B195 PhO H CH3 H OH CHCH3
B196 PhS H CH3 H OH CHCH3
B197 PhSO H CH3 H OH CHCH3
B198 PhS02 H CH3 H OH CHCH3
B199 CN H CH3 H OH CHCH3
B200 CH3 CH3 CH3 H OH CHCH3
B201 CH3CH2 CH3 CH3 H OH CHCHa
B202 CH3CH2CH2 CH3 CH3 H OH CHCHa
B203 (CH3) 2CH CH3 CH3H OH CHCH3
B204 (CH3) 3C CH3 CH3H OH CHCH3
B205 CH3S CH3 CH3 H OH CHCH3
B206 CH3SO CH3 CH3 H OH CHCH3
B207 CH3S02 CH3 CH3 H OH CHCH3
B208 Ph CH3 CH3 H OH CHCHa
B209 CH30 CH3 CH3 H OH CHCH3
B210 CH3OC (0) CH3 CH3 H OH CHCH3
B211 CH3CH2OC (0) CH3 CH3 H OH CHCH3
B212 CH2 = CHCH2 CH3 CH3 H OH CHCH3
B213 HCCCH2 CH3 CH3 H OH CHCH3
B214 CF3 CH3 CH3 H OH CHCH3
B215 (CH3) 2NS02 CH3 CH3 H OH CHCH3
B216 (CH3) 2N CH3 CH3 H OH CHCH3
B217 PhO CH3 CH3 H OH CHCH3
B218 PhS CH3 CH3 H OH CHCH3
B219 PhSO CH3 CH3 H OH CHCH3
B220 PhS02 CH3 CH3 H OH CHCH3
Radical Re R7 Rß R9 R10 W
B221 CN CH3 CH3 H OH CHCH3
B222 CH3 CH3 CH3 CH3 OH CHCH3
B223 CH3CH2 CH3 CH3 CH3 OH CHCH3
B224 CH3CH2CH2 CH3 CH3 CH3 OH CHCH3
B225 (CH3) 2CH CH3 CH3 CH3 OH CHCH3
B226 (CH3) 3C CH3 CH3 CH3 OH CHCH3
B227 CH3S CH3 CH3 CH3 OH CHCH3
B228 CH3SO CH3 CH3 CH3 OH CHCHa
B229 CH3S02 CH3 CH3 CH3 OH CHCH3
B230 Ph CH3 CH3 CH3 OH CHCHa
B231 CH30 CH3 CH3 CH3 OH CHCH3
B232 CH3OC (0) CH3 CH3 CH3 OH CHCH3
B233 CH3CH2OC (0) CH3 CH3 CH3 OH CHCH3
B234 CH2 = CHCH2 CH3 CH3 CH3 OH CHCHa
B235 HCCCH2 CH3 CH3 CH3 OH CHCH3
B236 CF3 CH3 CH3 CH3 OH CHCH3
B237 (CH3) 2NS02 CH3 CH3 CH3 OH CHCH3
B238 (CH3) 2N CH3 CH3 CH3 OH CHCH3
B239 PhO CH3 CH3 CH3 OH CHCH3
B240 PhS CH3 CH3 CH3 OH CHCH3
B241 PhSO CH3 CH3 CH3 OH CHCH3
B242 PhS02 CH3 CH3 CH3 OH CHCH3
B243 CN CH3 CH3 CH3 OH CHCH3
B244 CH3CH2 CH3CH2 H OH OH CHCH3
B245 CH3CH2CH2 CH3CH2 H H OH CHCH3
B246 (CH3) 2CH CH3CH2 H OH OH CHCH3
B247 (CH3) 3C CH3CH2 H OH OH CHCH3
B248 CH3S CH3CH2 H OH OH CHCH3
B249 CH3SO H3CH2 H OH OH CHCH3
B250 CH3S02 CH3CH2 H OH OH CHCH3
B251 Ph CH3CH2 H OH OH CHCH3
B252 CH3O CH3CH2 H OH OH CHCH3
B253 CH3OC (0) CH3CH2 H H OH CHCH3
Radical Re R7 Rß "R9 River W
B254 CH3CH2OC (0) CH3CH2 H OH OH CHCH3
B255 CH2 = CHCH2 CH3CH2 H OH OH CHCH3
B256 HCCCH2 CH3CH2 H H OH CHCH3
B257 CF3 CH3CH2 H OH OH CHCH3
B258 (CH3) 2NS02 CH3CH2 H OH OH CHCH3
B259 (CH3) 2N CH3CH2 H H OH CHCH3
B260 PhO CH3CH2 H OH OH CHCH3
B261 PhS CH3CH2 H H OH CHCH3
B262 PhSO CH3CH2 H OH OH CHCH3
B263 PhS02 CH3CH2 H OH OH CHCH3
B264 CN CH3CH2 H OH OH CHCH3
B265 H H H H OH C = 0
B266 CH3 H H OH OH c = o
B267 CH3CH2 H H OH OH C = 0
B268 CH3CH2CH2 H H OH OH C = 0
B269 (CH3) 2CH H H OH OH = 0
B270 (CH3) 3C H H OH OH =
B271 CH3S H H OH OH C = 0
B272 CH3SO H H OH OH C = 0
B273 CH3S02 H H OH OH C = 0
B274 Ph H H H OH C = 0
B275 CH30 H H OH OH C = 0
B276 CH3OC (0) H H OH OH =
B277 CH3CH2OC (0) H H OH OH = 0
B278 CH2 = CHCH2 H H OH OH = 0
B279 HCCCH2 H H OH OH C = 0
B280 CF3 H H OH OH C = 0
B281 (CH3) 2NS02 H H OH OH = 0
B282 (CH3) 2N H H OH OH = 0
B283 PhO H H H OH C = 0
B284 PhS H H H OH C = 0
B285 PhSO H H H OH C = 0
B286 PhS02 H H OH OH C = 0
Radical Re R7 Rß R9 R10 W
B287 CN H H H OH c = o
B288 CH3 CH3 H H OH C = 0
B289 CH3CH2 CH3 H OH OH c = o
B290 CH3CH2CH2 CH3 H H OH c = o
B291 (CH3) 2CH CH3 H H OH C = 0
B292 (CH3) 3C CH3 H H OH C = 0
B293 CH3S CH3 H H OH C = 0
B294 CH3SO CH3 H H OH C = 0
B295 CH3S02 CH3 H H OH C = 0
B296 Ph CH3 H H OH C = 0
B297 CH3O CH3 H H OH C = 0
B298 CH3OC (0) CH3 H H OH C = 0
B299 CH3CH2OC (0) CH3 H H OH C = 0
B300 CH2 = CHCH2 CH3 H H OH C = 0
B301 HCCCH2 CH3 H H OH C = 0
B302 CF3 CH3 H H OH C = 0
B303 (CH3) 2NS02 CH3 H H OH C = 0
B304 (CH3) 2N CH3 H H OH C = 0
B305 PhO CH3 H H OH c = o
B306 PhS CH3 H H OH C = 0
B307 PhSO CH3 H H OH C = 0
B308 PhS02 CH3 H H OH C = 0
B309 CN CH3 H H OH C = 0
B310 CH3 H CH3 H OH C = 0
B312 CH3CH2CH2 H CH3 H OH C = 0
B313 (CH3) 2CH H CH3 H OH C = 0
B314 (CH3) 3C H CH3H OH C = 0
B315 CH3S H CH3 H OH C = 0
B316 CH3SO H CH3 H OH C = 0
B317 CH3S02 H CH3 H OH C = 0
B318 Ph H CH3 H OH C = 0
B319 CH30 H CH3 H OH C = 0
Radical Re R7 Re Rg R10 W
B320 CH3OC (0) H CH3 H OH c = o
B321 CH3CH2OC (0) H CH3 H OH C = 0
B322 CH2 = CHCH2 H CH3 H OH C = 0
B323 HCCCH2 H CH3 H OH C = 0
B324 CF3 H CH3 H OH C = 0
B325 (CH3) 2NS02H CH3H OH c = o
B326 (CH3) 2N H CH3 H OH C = 0
B327 PhO H CH3 H OH C = 0
B328 PhS H CH3 H OH C = 0
B329 PhSO H CH3 H OH C = 0
B330 PhS02 H CH3 H OH c = o
B331 CN H CH3 H OH C = 0
B332 CH3 CH3 CH3 H OH C = 0
B333 CHsCH2 CH3 CH3 H OH C = 0
B334 CH3CH2CH2 CH3 CH3 H OH C = 0
B335 (CH3) 2CH CH3 CH3H OH c = o
B336 (CH3) 3C CH3 CH3 H OH C = 0
B337 CH3S CH3 CH3 H OH c = o
B338 CH3SO CH3 CH3 H OH C = 0
B339 CH3SO2 CH3 CH3 H OH c = o
B340 Ph CH3 CH3 H OH c = o
B341 CH30 CH3 CH3 H OH C = 0
B342 CH3OC (0) CH3 CH3 H OH C = 0
B343 CH3CH2OC (0) CH3 CH3 H OH C = 0
B345 HCCCH2 CH3 CH3 H OH c = o
B346 CF3 CH3 CH3 H OH c = o
B347 (CH3) 2NSOz CH3 CH3H OH c = o
B348 (CH3) 2N CH3 CH3 H OH C = 0
B349 PhO CH3 CH3 H OH C = 0
B350 PhS CH3 CH3 H OH C = 0
B351 PhSO CH3 CH3 H OH C = 0
B352 PhS02 CH3 CH3 H OH C = 0
Radical Re R7 Rs R9 R10 W
B353 CN CH3 CH3 H OH c = o
B354 CH3 CH3 CH3 CH3 OH C = 0
B355 CH3CH2 CH3 CH3 CH3 OH c = o
B356 CH3CH2CH2 CH3 CH3 CH3 OH c = o
B357 (CH3) 2CH CH3 CH3 CH3 OH C = 0
B358 (CH3) 3C CH3 CH3 CH3 OH C = 0
B359 CH3S CH3 CH3 CH3 OH C = 0
B360 CH3SO CH3 CH3 CH3 OH c = o
B361 CH3S02 CH3 CH3 CH3 OH C = 0
B362 Ph CH3 CH3 CH3 OH C = 0
B363 CH30 CH3 CH3 CH3 OH C = 0
B364 CH3OC (0) CH3 CH3 CH3 OH C = 0
B365 CH3CH2OC (0) CH3 CH3 CH3 OH c = o
B366 CH2 = CHCH2 CH3 CH3 CH3 OH C = 0
B367 HCCCH2 CH3 CH3 CH3 OH C = 0
B368 CF3 CH3 CH3 CH3 OH C = 0
B369 (CH3) 2NS02 CH3 CH3 CH3 OH C = 0
B370 (CH3) 2N CH3 CH3 CH3 OH c = o
B371 PhO CH3 CH3 CH3 OH C = 0
B372 PhS CH3 CH3 CH3 OH c = o
B373 PhSO CH3 CH3 CH3 OH C = 0
B374 PhSOz CH3 CH3 CH3 OH c = o
B375 CN CH3 CH3 CH3 OH C = 0
B376 CH3CH2 CH3CH2 H H OH C = 0
B377 - H3? 2? 2 CH3CH2 H H OH C = 0
B378 (CH3) 2CH CH3CH2 H H OH C = 0
B379 (CH3) 3C CH3CH2 H H OH C = 0
B380 CH3S CH3CH2 H H OH C = 0
B381 CH3SO C? 3 (_ H2 H H OH C = 0
B382 CH3S02 CH3CH2 H H OH C = 0
B383 Ph CH3CH2 H H OH C = 0
B384 CH30 CH3CH2 H H OH C = 0
B385 CH3OC (0) CH3CH2 H H OH C = 0
Radical Re R7 Rß R9 River W
B386 CH3CH2OC (0) CH3CH2 H H OH C = 0
B387 CH2 = CHCH2 CH3CH2 H H OH c = o
B388 HCCCH2 CH3CH2 H H OH c = o
B389 CF3 CH3CH2 H H OH C = 0
B390 (CH3) 2NS02 CH3CH2 H H OH C = 0
B391 (CH3) 2N CH3CH2 H H OH C = 0
B392 PhO CHsCH2 H H OH C = 0
B393 PhS CH3CH2 H H OH c = o
B394 PhSO CH3CH2 H H OH C = 0
B395 PhS02 CH3CH2 H H OH C = 0
B396 CN CH3CH2 H H OH C = 0
B397 'H H H H OH N-CH3
B398 CH3 H H OH OH N-CH3
B399 CH3CH2 H H OH OH N-CH3
B400 CH3CH2CH2 H H OH OH N-CH3
B401 (CH3) 2CH H H OH OH N-CH3
B402 (CH3) 3C H H OH OH N-CH3
B403 CH3S H H OH OH N-CH3
B404 CH3SO H H OH OH N-CH3
B405 CH3S02 H H OH OH N-CH3
B406 Ph H H OH OH N-CH3
B407 CH30 H H OH OH N-CH3
B408 CH3OC (0) H H OH OH N-CH3
B409 CH3CH2OC (0) H H OH OH N-CH3
B410 CH2 = CHCH2 H H OH OH N-CH3
B41 1 HCCCH2 H H OH OH N-CH3
B412 CF3 H H OH OH N-CH3
B413 (CH3) 2NS02 H H OH OH N-CH3
B414 (CH3) 2N H H OH OH N-CH3
B415 PhO H H OH OH N-CH3
B416 PhS H H OH OH N-CH3
B417 PhSO H H H OH N-CHa
B418 PhS02 H H OH OH N-CH3
Radical Re R7 Rβ Rg R10 W B419 CN H H OH OH N-CH3
B421 CH3CH2 CH3 H OH OH N-CH3
B422 CH3CH2CH2 CH3 H OH OH N-CH3
B423 (CH3) 2CH CH3 H OH OH N-CH3
B424 (CH3) 3C CH3 H H OH N-CH3
B425 CH3S CH3 H OH OH N-CH3
B426 CH3SO CH3 H OH OH N-CH3
B427 CH3S02 CH3 H H OH N-CH3
B428 Ph CH3 H H OH N-CH3
B429 CH30 CH3 H OH OH N-CH3
B430 CHaOC (O) CH3 H H OH N-CH3
B431 CH3CH2OC (0) CH3 H H OH N-CH3
B432 CH2 = CHCH2 CH3 H OH OH N-CH3
B433 HCCCH2 CH3 H H OH N-CH3
B434 CF3 CH3 H OH OH N-CH3
B435 (CH3) 2NS02 CH3 H OH OH N-CH3
B436 (CH3) 2N CH3 H OH OH N-CH3
B437 PhO CH3 H H OH N-CH3
B438 PhS CH3 H H OH N-CH3
B439 PhSO CH3 H H OH N-CHa
B440 PhS02 CH3 H H OH N-CH3
B441 CN CH3 H OH OH N-CH3
B442 CH3 H CH3 H OH N-CH3
B443 CH3CH2 H CH3 H OH N-CH3
B444 CH3CH2CH2 H CH3 H OH N-CH3
B445 (CH3) 2CH H CH3H OH N-CH3
B446 (CH3) 3C H CH3H OH N-CH3
B447 CH3S H CH3 H OH N-CH3
B448 CH3SO H CH3 H OH N-CH3
B449 CH3S02 H CH3 H OH N-CH3"> - B450 Ph H CH3 H OH N-CH3
B451 CH30 H CH3 OH OH N-CH3
Radical Re R7 Re Rg R10 W
B452 CH3OC (0) H CH3 H OH N-CH3
B453 CH3CH2OC (0) H • CH3 H OH N-CH3
B454 CH2 = CHCH2 H CH3 H OH N-CH3
B455 HCCCH2 H CH3 H OH N-CH3
B456 CF3 H CH3 H OH N-CH3
B457 (CH3) 2NS02H CH3H OH N-CH3
B458 (CH3) 2N H CH3H OH N-CH3
B459 PhO H CH3 H OH N-CH3
B460 PhS H CH3 H OH N-CH3
B461 PhSO H CH3 H OH N-CH3
B462 PhS02 H CH3 H OH N-CH3
B463 CN H CH3 H OH N-CH3
B464 CH3 CH3 CH3 H OH N-CH3
B465 CH3CH2 CH3 CH3 H OH N-CH3
B466 CH3CH CH2 CH3 CH3 H OH N-CHa
B467 (CH3) 2CH CH3 CH3H OH N-CH3
B468 (CH3) 3C CH3 CH3H OH N-CH3
B469 CH3S CH3 CH3 H OH N-CH3
B470 CH3SO CH3 CH3 H OH N-CH3
B471 CH3S02 CH3 CH3 H OH N-CH3
B472 Ph CH3 CH3 H OH N-CH3
B473 CH3O CH3 CH3 H OH N-CH3
B474 CH3OC (0) CH3 CH3 H OH N-CH3
B475 CH3CH20C (0) CH3 CH3 H OH N-CH3
B476 CH2 = CHCH2 CH3 CH3 H OH N-CH3
B477 HCCCH2 CH3 CH3 H OH N-CH3
B478 CF3 CH3 CH3 H OH N-CH3
B479 (CH3) 2NS02 CH3 CH3 H OH N-CH3
B480 (CH3) 2N CH3 CH3H OH N-CH3
B481 PhO CH3 CH3 H OH N-CH3
B482 PhS CH3 CH3 H OH N-CH3
B483 PhSO CH3 CH3 H OH N-CH3
B484 PhS02 CH3 CH3 H OH N-CH3
Radical Re R7 Rß 9 R10 W
B485 CN CH3 CH3 H OH N-CH3
B486 CH3 CH3 CH3 CH3 OH N-CH3
B487 CH3CH2 CH3 CH3 CH3 OH N-CH3
B488 CH3CH2CH2 CH3 CH3 CH3 OH N-CH3
B489 (CH3) 2CH CH3 CH3 CH3 OH N-CH3
B490 (CH3) 3C CH3 CH3 CH3 OH N-CH3
B491 CH3S CH3 CH3 CH3 OH N-CH3
B492 CH3SO CH3 CH3 CH3 OH N-CH3
B493 CH3S02 CH3 CH3 CH3 OH N-CH3
B494 Ph CH3 CH3 CH3 OH N-CH3
B495 CH3O CH3 CH3 CH3 OH N-CH3
B496 CH3OC (0) CH3 CH3 CH3 OH N-CH3
B497 CH3CH2OC (0) CH3 CH3 CH3 OH N-CH3
B498 CH = CHCH2 CH3 CH3 CH3 OH N-CH3
B499 HCCCH2 CH3 CH3 CH3 OH N-CH3
B500 CF3 CH3 CH3 CH3 OH N-CH3
B501 (CH3) 2NS02 CH3 CH3 CH3 OH N-CH3
B502 (CH3) 2N CH3 CH3 CH3 OH N-CH3
B503 PhO CH3 CH3 CH3 OH N-CH3
B504 PhS CH3 CH3 CH3 OH N-CH3
B505 PhSO CH3 CH3 CH3 OH N-CH3
B506 PhS02 CH3 CH3 CH3 OH N-CH3
B507 CN CH3 CH3 CH3 OH N-CH3
B508 CHsCH2 CH3CH2 H OH OH N-CH3
B509 CH3CH2CH2 CH3CH2 H H OH N-CH3
B510 (CH3) 2CH CH3CH2 H H OH N-CH3
B511 (CH3) 3C CH3CH2 H OH OH N-CH3
B512 CH3S CH3CH2 H OH OH N-CH3
B513 CH3SO CH3CH2 H OH OH N-CH3
B514 CH3S02 CH3CH2 H H OH N-CH3
B515 Ph CH3CH2 H H OH N-CH3
B516 CH30 CH3CH2 H OH OH N-CH3
B517 CHaOC (O) CH3CH2 H H OH N-CH3
Radical Re R7 Rß Rg R10 W
B518 CH3CH2OC (0) CH3CH2 H H OH N-CH3
B519 CH2 = CHCH2 CH3CH2 H OH OH N-CH3
B520 HCCCH2 CH3CH2 H H OH N-CH3
B521 CF3 CH3CH2 H OH OH N-CH3
B522 (CH3) 2NS? 2 CH3CH2 H H OH N-CH3
B523 (CH3) 2N CH3CH2 H OH OH N-CH3
B524 PhO CH3CH2 H H OH N-CH3
B525 PhS CH3CH2 H H OH N-CH3
B526 PhSO CH3CH2 H H OH N-CH3
B527 PhS02 CH3CH2 H H OH N-CH3
B528 CN CH3CH2 H H OH N-CH3
B529 H H H H OH 0
B530 CH3 H H OH 0
B531 CH3CH2 H H OH 0
B532 CH3CH2CH2 H H OH 0
B533 (CH3) 2CH H H OH 0
B534 (CH3) 3C H H OH 0
B535 CH3S H H OH 0
B536 CH3SO H H OH 0
B537 CH3S02 H H OH 0
B538 Ph H H H OH 0
B539 CH30 H H OH 0
B540 CH3OC (0) H H OH 0
B541 CH3CH2OC (0) H H OH 0
B542 CH2 = CHCH2 H H OH 0
B543 HCCCH2 H H OH 0
B544 CF3 H H H OH 0
B545 (CH3) 2NS02 H H OH 0
B546 (CH3) 2N H H OH 0
B547 PhO H H H OH 0
B548 PhS H H H OH 0
B549 PhSO H H OH 0
B550 PhS02 H H OH 0
Radical Re R7 Rß R9 R10 w
B551 CN H H H OH or
B552 CH3 CH3 H H OH or
B553 CH3CH2 CH3 H H OH or
B554 CH3CH2CH2 CH3 H H OH or
B555 (CH3) 2CH CH3HH OH or
B556 (CH3) 3C CH3HH OH or
B557 CH3S CH3 H H OH or
B558 CH3SO CH3 H H OH or
B559 CH3S02 CH3 H H OH or
B560 Ph CH3 H H OH o
B561 CH30 CH3 H H OH or
B562 CH3OC (0) CH3 H H OH or
B563 CH3CH2OC (0) CH3 H H OH or
B564 CH2 = CHCH2 CH3 H H OH or
B565 HCCCH2 CH3 H H OH or
B566 CF3 CH3 H H OH or
B567 (CH3) 2NS02 CH3 H H OH or
B568 (CH3) 2N CH3HH OH or
B569 PhO CH3 H H OH o
B570 PhS CH3 H H OH or
B571 PhSO CH3 H H OH or
B572 PhS02 CH3 H H OH or
B573 CN CH3 H H OH or
B574 CH3 H CH3 H OH or
B575 CH3CH2 H CH3 H OH or
B576 CH3CH2CH2 H CH3 H OH or
B577 (CH3) 2CH H CH3H OH or
B578 (CH3) 3C H CH3H OH or
B579 CH3S H CH3 H OH or
B580 CH3SO H CH3 H OH or
B581 CH3S02 H CH3 H OH or
B582 Ph H CH3 H OH or
B583 CH3O H CH3 H OH or
Radici? Re R7 Rß Rg River W B584 CH3OC (0) H CH3 H OH O B585 CH3CH20C (0) H CH3 H OH 0 B586 CH2 = CHCH2 H CH3 H OH O B587 HCCCH2 H CH3 H OH 0 B588 CF3 H CH3 H OH OR B589 (CH3) 2NS02 H CH3 H OH 0
B590 (CH3) 2N H CH3 H OH 0
B591 PhO H CH3 H OH 0
B592 PhS H CH3 H OH 0
B593 PhSO H CH3 H OH 0
B594 PhS02 H CH3 H OH 0
B595 CN H CH3 H OH 0
B596 CH3 CH3 CH3 H OH 0
B597 CH3CH2 CH3 CH3 H OH 0
B598 CH3CH2CH2 CH3 CH3 H OH 0
B599 (CH3) 2CH CH3 CH3 H OH 0
B600 (CH3) 3C CH3 CH3 H OH 0
B601 CH3S CH3 CH3 H OH 0
B602 CH3SO CH3 CH3 H OH O
B603 CH3S02 CH3 CH3 H OH O
B604 Ph CH3 CH3 H OH 0
B605 CH30 CH3 CH3 H OH 0
B606 CH3OC (0) CH3 CH3 H OH 0
B607 CH3CH2OC (0) CH3 CH3 H OH 0
B608 CH2 = CHCH2 CH3 CH3 H OH 0
B609 HCCCH2 CH3 CH3 H OH 0
B610 CF3 CH3 CH3 H OH 0
B611 (CH3) 2NS02 CH3 CH3 H OH 0
B612 (CH3) 2N CH3 CH3 H OH 0
B613 PhO CH3 CH3 H OH 0
B614 PhS CH3 CH3 H OH 0
- > B615 PhSO CH3 CH3 H OH 0
B616 PhS02 CH3 CH3 H OH 0
Radical Re R7 Re Rg R10 w B617 CN CH3 CH3 H OH or B618 CH3 CH3 CH3 CH3 OH or B619 CH3CH2 CH3 CH3 CH3 OH or B620 CH3CH2CH2 CH3 CH3 CH3 OH or B621 (CH3) 2CH CH3 CH3 CH3 OH or B622 (CH3) 3C CH3 CH3 CH3 OH or B623 CH3S CH3 CH3 CH3 OH or B624 CH3SO CH3 CH3 CH3 OH or B625 CH3S02 CH3 CH3 CH3 OH or B626 Ph CH3 CH3 CH3 OH or B627 CH30 CH3 CH3 CH3 OH or
B628 CH3OC (0) CH3 CH3 CH3 OH or B629 CH3CH2OC (0) CH3 CH3 CH3 OH or B630 CH2 = CHCH CH3 CH3 CH3 OH or B631 HCCCH2 CH3 CH3 CH3 OH or B632 CF3 CH3 CH3 CH3 OH or B633 (CH3) 2NS02 CH3 CH3 CH3 OH or B634 (CH3) 2N CH3 CH3 CH3 OH or
B635 PhO CH3 CH3 CH3 OH or B636 PhS CH3 CH3 CH3 OH or B637 PhSO CH3 CH3 CH3 OH or B638 PhS02 CH3 CH3 CH3 OH or B639 CN CH3 CH3 CH3 OH or B640 CH3CH2 CH3CH2 H H OH or B641 CH3CH2CH2 CH3CH2 H H OH or
B642 (CH3) 2CH CH3CH2 H H OH or B643 (CH3) 3C CH3CH2 H H OH or B644 CH3S CH3CH2 H H OH or B645 CH3SO CH3CH2 H H OH or B646 CH3S02 CH3CH2 H H OH or B647 Ph CH3CH2 H H OH or
:? B648 CH3O CH3CH2 H H OH or B649 CH3OC (0) CH3CH2 H H OH or
Radical Re R7 Rß Rg River W
B650 CH3CH2OC (0) CH3CH2 H H OH O
B651 CH2 = CHCH2 CH3CH2 H OH 0
B652 HCCCH2 CH3CH2 H H OH 0
B653 CF3 CHsCH? H H OH 0
B654 (CH3) 2NS02 CH3CH2 H H OH or
B655 (CH3) 2N CHsCH2 H OH 0
B656 PhO CH3CH2 H H OH 0
B657 PhS CHsCH2 H H OH 0
B658 PhSO CH3CH2 H H OH 0
B659 PhS02 CHsCH2 H H OH 0
B660 CN CHsCH2 H H OH or
B661 H H H OH OH
B662 CH3 H H H OH s
B663 CH3CH2 H H H OH s
B664 CH3CH2CH2 H H H OH s
B665 (CH3) 2CH H H OH OH s
B666 (CH3) 3C H H H OH s
B667 CH3S H H H OH s
B668 CH3SO H H OH OH s
B669 CH3S02 H H H OH s
B670 Ph H H H OH s
B671 CH30 H H OH OH s
B672 CH3OC (0) H H OH OH s
B673 CH3CH2OC (O) H H OH OH s
B675 HCCCH2 H H OH OH s
B676 CF3 H H H OH s
B677 (CH3) 2NS02 H H OH OH s
B678 (CH3) 2N H H OH OH s
B679 PhO H H H OH s
B680 PhS H H H OH s
B681 PhSO H H H OH s
B682 PhS02 H H H OH s
Radical Re R7 Rß Rg River w
B683 CN H H H OH s
B684 CH3 CH3 H H OH s
B685 CH3CH2 CH3 H H OH s
B686 CH3CH2CH2 CH3 H H OH s
B687 (CH3) 2CH CH3 H H OH s
B688 (CH3) 3C CH3 H H OH s
B689 CH3S CH3 H H OH s
B690 CH3SO CH3 H H OH s
B691 CH3S02 CH3 H H OH s
B692 Ph CH3 H H OH s
B693 CH30 CH3 H H OH s
B694 CH3OC (0) CH3 H H OH s
B695 CH3CH2OC (0) CH3 H H OH s
B696 CH2 = CHCH2 CH3 H H OH s
B697 HCCCH2 CH3 H H OH s
B698 CF3 CH3 H H OH s
B699 (CH3) 2NS02 CH3 H H OH s
B700 (CH3) 2N CH3 H H OH s
B701 PhO CH3 H H OH s
B702 PhS CH3 H H OH s
B703 PhSO CH3 H H OH s
B704 PhS02 CH3 H H OH s
B705 CN CH3 H H OH s
B706 CH3 H CH3 H OH s
B707 CH3CH2 H CH3 H OH s
B708 CH3CH2CH2 H CH3 H OH s
B709 (CH3) 2CH H CH3 H OH s
B710 (CH3) 3C H CH3 H OH s
B71 1 CH3S H CH3 H OH s
B712 CH3SO H CH3 H OH s
B713 CH3S02 H CH3 H OH s
B714 Ph H CH3 H OH s
B715 CH30 H CH3 H OH s
Radical Re R7 Rß Rg R10 W
B71 c > CH3OC (0) H CH3 H OH S
B717 CH3CH2OC (0) H CH3 H OH S
B71 £ 'HCCCH2 H CH3 H OH S
B720 CF3 H CH3 H OH S
B721 (CH3) 2NS02 H CH3 H OH S
B722 (CH3) 2N H CH3 H OH S
B723 PhO H CH3 H OH S
B724 PhS H CH3 H OH S
B725 PhSO H CH3 H OH S
B726 PhS02 H CH3 H OH S
B727 CN H CH3 H OH S
B728 CH3 CH3 CH3 H OH S
B729 CH3CH2 CH3 CH3 H OH S
B730 CH3CH2CH2 CH3 CH3 H OH S
B731 (CH3) 2CH CH3 CH3 H OH S
B732 (CH3) 3C CH3 CH3 H OH S
B733 CH3S CH3 CH3 H OH S
B734 CH3SO CH3 CH3 H OH s
B735 CH3S02 CH3 CH3 H OH s
B736 Ph CH3 CH3 H OH s
B737 CH3O CH3 CH3 H OH s
B738 CH3OC (0) CH3 CH3 H OH s
B739 CH3CH2OC (0) CH3 CH3 H OH s
B740 CH2 = CHCH2 CH3 CH3 H OH s
B741 HCCCH2 CH3 CH3 H OH s
B742 CF3 CH3 CH3 H OH s
B743 (CH3) 2NS02 CH3 CH3 H OH s
B744 (CH3) 2N CH3 CH3 H OH s
B745 PhO CH3 CH3 H OH s
B746 PhS CH3 CH3 H OH s
B747 PhSO CH3 CH3 H OH s
B748 PhS02 CH3 CH3 H OH s
Radical Re R7 Rß Rg River w
B749 CN CH3 CH3 H OH s
B750 CH3 CH3 CH3 CH3 OH s
B751 CH3CH2 CH3 CH3 CH3 OH s
B752 CH3CH2CH2 CH3 CH3 CH3 OH s
B753 (CH3) 2CH CH3 CH3 CH3 OH s
B754 (CH3) 3C CH3 CH3 CH3 OH s
B755 CH3S CH3 CH3 CH3 OH s
B756 CH3SO CH3 CH3 CH3 OH s
B757 CH3SOz CH3 CH3 CH3 OH s
B758 Ph CH3 CH3 CH3 OH s
B759 CH30 CH3 CH3 CH3 OH s
B760 CH3OC (0) CH3 CH3 CH3 OH s
B761 CH3CH2OC (0) CH3 CH3 CH3 OH s
B762 CH2 = CHCH2 CH3 CH3 CH3 OH s
B763 HCCCH2 CH3 CH3 CH3 OH s
B764 CF3 CH3 CH3 CH3 OH s
B765 (CH3) 2NS02 CH3 CH3 CH3 OH s
B766 (CH3) 2N CH3 CH3 CH3 OH s
B767 PhO CH3 CH3 CH3 OH s
B768 PhS CH3 CH3 CH3 OH s
B769 PhSO CH3 CH3 CH3 OH s
B770 PhS02 CH3 CH3 CH3 OH s
B771 CN CH3 CH3 CH3 OH s
B772 CH3CH2 CH3CH2 H H OH s
B773 CH3CH2CH2 CH3CH2 H H OH s
B774 (CH3) 2CH CH3CH2 H H OH s
B775 (CH3) 3C CH3CH2 H H OH s
B776 CH3S CH3CH2 H H OH s
B777 CH3SO CH3CH2 H H OH s
B778 CH3S02 CH3CH2 H H OH s
B779 Ph CH3CH2 H H OH s
B781 CH3OC (0) CH3CH2 H H OH s
Radical Re R7 R8 Rg River W
B782 CH3CH2OC (0) CH3CH H H OH s
B783 CH2 = CHCH2 CH3CH2 H H OH s
B784 HCCCH2 CH3CH2 H H OH s
B785 CF3 CH3CH2 H H OH s
B786 (CH3) 2NS02 CH3CH2 H H OH s
B787 (CH3) 2N CH3CH2 H H OH s
B788 PhO CH3CH2 H H OH s
B789 PhS CH3CH2 H H OH s
B790 PhSO CH3CH2 H H OH s
B791 PhS02 CH3CH2 H H OH s
B792 CN CH3CH2 H H OH s
B793 H H H H OH so2
B794 CH3 H H OH OH2
B795 CH3CH2 H H OH OH2
B796 CH3CH2CH2 H H OH OH2
B797 (CH3) 2CH H H OH OH2
B798 (CH3) 3C H H OH OH2
B799 CH3S H H OH OH2
B800 CH3SO H H OH OH2
B801 CH3S02 H H OH OH2
B802 Ph H H H OH so2
B803 CH30 H H OH OH2
B804 CH3OC (0) H H OH OH2
B805 CH3CH2OC (0) H H OH OH2
B806 CH2 = CHCH2 H H OH OH2
B807 HCCCH2 H H OH OH2
B808 CF3 H H OH OH2
B809 (CH3) 2NS02 H H OH OH2
B810 (CH3) 2N H H OH OH2
B811 PhO H H OH OH2
B812 PhS H H OH OH2
B813 PhSO H H OH OH2
B814 PhS02 H H OH OH2
Radical Re R7 Rß Rg R-io w
B815 CN H H H OH so2
B816 CH3 CH3 H OH OH2
B817 CH3CH2 CH3 H H OH so2
B818 CH3CH2CH2 CH3 H H OH so2
B819 (CH3) 2CH CH3 H OH OH2
B820 (CH3) 3C CH3 H OH OH2
B821 CH3S CH3 H OH OH2
B822 CH3SO CH3 H H OH so2
B823 CH3S02 CH3 H H OH so2
B824 Ph CH3 H H OH so2
B825 CH30 CH3 H OH OH2
B826 CHaOC (O) CH3 H H OH so2
B827 CH3CH2OC (0) CH3 H H OH so2
B828 CH2 = CHCH2 CH3 H H OH so2
B829 HCCCH2 CH3 H H OH so2
B830 CF3 CH3 H OH OH2
B831 (CH3) 2NS02 CH3 H H OH so2
B832 (CH3) 2N CH3 H OH OH2
B833 PhO CH3 H H OH so2
B834 PhS CH3 H H OH so2
B835 PhSO CH3 H H OH so2
B836 PhS02 CH3 H H OH so2
B837 CN CH3 H OH OH2
B838 CH3 H CH3 H OH so2
B840 CH3CH2CH2 H CH3 H OH so2
B841 (CH3) 2CH H CH3 H OH so2
B842 (CH3) 3C H CH3H OH so2
B843 CH3S H CH3 H OH so2
B844 CH3SO H CH3 H OH so2
B845 CH3S02 H CH3 H OH so2
B846 Ph H CH3 H OH so2
B847 CH30H CH3H OH so2
Radical Re R7 Rß Rg R10 W
B848 CH3OC (0) H CH3 H OH S02
B849 CH3CH2OC (0) H CH3 H OH so2
B850 CH2 = CHCH H CH3 H OH so2
B851 HCCCH2 H CH3 H OH so2
B852 CF3 H CH3 H OH so2
B853 (CH3) 2NS02H CH3H OH so2
B854 (CH3) 2NH CH3H OH so2
B855 PhO H CH3 H OH so2
B856 PhS H CH3 H OH so2
B857 PhSO H CH3 H OH so2
B858 PhS02 H CH3 H OH so2
B859 CN H CH3 H OH so2
B860 CH3 CH3 CH3 H OH so2
B861 CH3CH2 CH3 CH3 H OH so2
B862 CH3CH2CH2 CH3 CH3 H OH so2
B863 (CH3) 2CH CH3 CH3 H OH so2
B864 (CH3) 3C CH3 CH3H OH so2
B865 CH3S CH3 CH3 H OH so2
B866 CH3SO CH3 CH3 H OH so2
B867 CH3S02 CH3 CH3 H OH so2
B868 Ph CH3 CH3 H OH so2
B869 CH3O CH3 CH3 H OH so2
B870 CH3OC (0) CH3 CH3 H OH so2
B871 CH3CH2OC (0) CH3 CH3 H OH SO2
B873 HCCCH2 CH3 CH3 H OH so2
B874 CF3 CH3 CH3 H OH so2
B875 (CH3) 2NS02 CH3 CH3H OH so2
B876 (CH3) 2N CH3 CH3 H OH so2
B877 PhO CH3 CH3 H OH so2
B878 PhS CH3 CH3 H OH so2
B879 PhSO CH3 CH3 H OH so2
B880 PhSOz CH3 CH3 H OH so2
Radical Re R7 RB R9 R10 W
B881 CN CH3 CH3 H OH S02
B882 CH3 CH3 CH3 CH3 OH S02
B883 CH3CH2 CH3 CH3 CH3 OH S02
B884 CH3CH2CH2 CH3 CH3 CH3 OH so2
B885 (CH3) 2CH CH3 CH3 CH3 OH S02
B886 (CH3) 3C CH3 CH3 CH3 OH S02
B887 CH3S CH3 CH3 CH3 OH S02
B888 CH3SO CH3 CH3 CH3 OH so2
B889 CH3S02 CH3 CH3 CH3 OH S02
B890 Ph CH3 CH3 CH3 OH S02
B891 CH30 CH3 CH3 CH3 OH so2
B892 CH3OC (0) CH3 CH3 CH3 OH so2
B893 CH3CH2OC (0) CH3 CH3 CH3 OH so2
B894 CH2 = CHCH2 CH3 CH3 CH3 OH so2
B895 HCCCH2 CH3 CH3 CH3 OH so2
B896 CF3 CH3 CH3 CH3 OH so2
B897 (CH3) 2NS02 CH3 CH3 CH3 OH so2
B898 (CH3) 2N CH3 CH3 CH3 OH so2
B899 PhO CH3 CH3 CH3 OH so2
B900 PhS CH3 CH3 CH3 OH so2
B901 PhSO CH3 CH3 CH3 OH so2
B902 PhS02 CH3 CH3 CH3 OH so2
B903 CN CH3 CH3 CH3 OH so2
B904 CH3CH2 CH3CH2 H H OH so2
B905 CH3CH2CH2 CH3CH2 H H OH so2
B906 (CH3) 2CH CH3CH2 H OH OH2
B907 (CH3) 3C CH3CH2 H OH OH2
B908 CH3S CH3CH2 H H OH so2
B909 CH3SO CH3CH H H OH so2
B910 CH3S02 CH3CH2 H H OH so2
B911 Ph CH3CH2 H H OH so2
B912 CH30 CH3CH2 H H OH so2
B913 CH3OC (0) CH3CH2 H H OH so2
Radical Re R7 Rß Rg R10 W
B914 CH3CH2OC (0) CH3CH2 H H OH so2
B916 HCCCH2 CHsCH2 HH OH so2 B917 CF3 CH3CH2 HH OH so2 B918 (CH3) 2NS02 CH3CH2 HH OH so2 B919 (CH3) 2N CH3CH2 HH OH so2 B920 PhO CH3CH2 HH OH so2 B921 PhS CH3CH2 HH OH so2 B922 PhSO CH3CH2 HH OH so2 B923 PhS02 CH3CH2 HH OH so2 B924 CN CH3CH2 HH OH so2 B925 HHHH OH CHC (0) OCH2CH3
B926 CH3 H H OH OH CHC (0) OCH2CH3
B927 CHsCH2 H H OH OH CHC (0) OCH2CH3
B928 CH3CH2CH2 H H OH OH CHC (0) OCH2CH3
B929 (CH3) 2CH H H OH OH CHC (0) OCH2CH3
B930 (CH3) 3C H H OH OH CHC (0) OCH2CH3
B931 CH3S H H OH OH CHC (0) OCH2CH3
B932 CH3SO H H OH OH CHC (0) OCH2CH3
B933 CH3S02 H H OH OH CHC (0) OCH2CH3
B934 Ph H H OH OH CHC (0) OCH2CH3
B935 CH3O H H OH OH CHC (0) OCH2CH3
B936 CH3OC (0) H H OH OH CHC (0) OCH2CH3
B937 CH3CH20C (0) H H OH OH CHC (0) OCH2CH3
B938 CH2 = CHCH2 H H OH OH CHC (0) OCH2CH3
B939 HCCCH2 H H OH OH CHC (0) OCH2CH3
B940 CF3 H H OH OH CHC (0) OCH2CH3
B941 (CH3) 2NS02 H H OH OH CHC (0) OCH2CH3
B942 (CH3) 2N H H OH OH CHC (0) OCH2CH3
B943 PhO H H OH OH CHC (0) OCH2CH3
B944 PhS H H OH OH CHC (0) OCH2CH3
B945 PhSO H H OH OH CHC (0) OCH2CH3
B946 PhS02 H H OH OH CHC (0) OCH2CH3
Radical Re R7 Rβ Rg River W B947 CN H H OH OH CHC (0) OCH2CH3
B948 CH3 CH3 H OH OH CHC (0) OCH2CH3
B949 CH3CH2 CH3 H OH OH CHC (0) OCH2CH3
B950 CH3CH2CH2 CH3 H OH OH CHC (0) OCH2CH3
B951 (CH3) 2CH CH3 H OH OH CHC (0) OCH2CH3
B952 (CH3) 3C CH3 H OH OH CHC (0) OCH2CH3
B953 CH3S CH3 H OH OH CHC (0) OCH2CH3
B954 CH3SO CH3 H OH OH CHC (0) OCH2CH3
B955 CH3S02 CH3 H OH OH CHC (0) OCH2CH3
B956 Ph CH3 H H OH CHC (0) OCH2CH3
B957 CH30 CH3 H OH OH CHC (0) OCH2CH3
B958 CH3OC (0) CH3 H H OH CHC (0) OCH2CH3
B959 CH3CH2OC (0) CH3 H OH OH CHC (0) OCH2CH3
B960 CH2 = CHCH2 CH3 H OH OH CHC (0) OCH2CH3
B961 HCCCH2 CH3 H H OH CHC (0) OCH2CH3
B962 CF3 CH3 H OH OH CHC (0) OCH2CH3
B963 (CH3) 2NS02 CH3 H OH OH CHC (0) OCH2CH3
B964 (CH3) 2N CH3 H H OH CHC (0) OCH2CH3
B965 PhO CH3 H OH OH CHC (0) OCH2CH3
B966 PhS CH3 H H OH CHC (0) OCH2CH3
B967 PhSO CH3 H OH OH CHC (0) OCH2CH3
B968 PhS02 CH3 H OH OH CHC (O) OCH2CH3
B969 CN CH3 H OH OH CHC (0) OCH2CH3
B970 CH3 H CH3 H OH CHC (0) OCH2CH3
B971 CH3CH2 H CH3 H OH CHC (0) OCH2CH3
B972 CH3CH2CH2H CH3H OH CHC (0) OCH2CH3
B973 (CH3) 2CH H CH3H OH CHC (0) OCH2CH3
B974 (CH3) 3C H CH3 OH OH CHC (0) OCH2CH3
B975 CH3S H CH3 H OH CHC (0) OCH2CH3
B976 CH3SO H CH3 H OH CHC (0) OCH2CH3
B977 CH3S02H CH3H OH CHC (0) OCH2CH3
B978 Ph H CH3 OH OH CHC (0) OCH2CH3
B979 CH30H CH3H OH CHC (0) OCH2CH3
Radical Re R7 Rβ R9 R10 W B980 CH3OC (0) H CH3H OH CHC (0) OCH2CH3
B981 CH3CH2OC (0) H CH3 H OH CHC (0) OCH2CH3
B982 CH = CHCH2 H CH3 H OH CHC (0) OCH2CH3
B983 HCCCH2 H CH3 H OH CHC (0) OCH2CH3
B984 CF3 H CH3 OH OH CHC (0) OCH2CH3
B985 (CH3) 2NS02H CH3H OH CHC (0) OCH2CH3
B986 (CH3) 2NH CH3H OH CHC (0) OCH2CH3
B987 PhO H CH3 H OH CHC (0) OCH2CH3
B988 PhS H CH3 H OH CHC (0) OCH2CH3
B989 PhSO H CH3 H OH CHC (0) OCH2CH3
B990 PhS02 H CH3 H OH CHC (0) OCH2CH3
B991 CN H CH3 OH OH CHC (0) OCH2CH3
B992 CH3 CH3 CH3 H OH CHC (0) OCH2CH3
B993 CH3CH2 CH3 CH3 H OH CHC (0) OCH2CH3
B994 CH3CH2CH2 CH3 CH3 H OH CHC (0) OCH2CH3
B995 (CH3) 2CH CH3 CH3H OH CHC (0) OCH2CH3
B996 (CH3) 3C CH3 CH3H OH CHC (0) OCH2CH3
B997 CH3S CH3 CH3 H OH CHC (0) OCH2CH3
B998 CH3SO CH3 CH3 H OH CHC (0) OCH2CH3
B999 CH3S02 CH3 CH3 H OH CHC (0) OCH2CH3
B1000 Ph CH3 CH3 H OH CHC (0) OCH2CH3
B1001 CH3O CH3 CH3 H OH CHC (0) OCH2CH3
B1002 CH3OC (0) CH3 CH3 H OH CHC (0) OCH2CH3
B1003 CH3CH2OC (0) CH3 CH3 H OH CHC (0) OCH2CH3
B1004 CH2 = CHCH2 CH3 CH3 H OH CHC (0) OCH2CH3
B1005 HCCCH2 CH3 CH3 H OH CHC (0) OCH2CH3
B1006 CF3 CH3 CH3 H OH CHC (0) OCH2CH3
B1007 (CH3) 2NS02 CH3 CH3 H OH CHC (0) OCH2CH3
B1008 (CH3) 2N CH3 CH3H OH CHC (0) OCH2CH3
B1009 PhO CH3 CH3 H OH CHC (0) OCH2CH3
B1010 PhS CH3 CH3 H OH CHC (0) OCH2CH3
B1011 PhSO CH3 CH3 H OH CHC (0) OCH2CH3
B1012 PhS02 CH3 CH3 H OH CHC (0) OCH2CH3
Radical Re R7 Rb Rg R10 W B101 CN CH3 CH3 H OH CHC (0) OCH2CH3
B1014 CH3 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1015 CH3CH2 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B101CÍ CH3CH2CH2 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1017 (CH3) 2CH CH3 CH3 CH3 OH CHC (0) OCH2CH3
B101 I (CH3) 3C CH3 CH3 CH3 OH CHC (0) OCH2CH3
B101 CH3S CH3 CH3 CH3 OH CHC (0) OCH2CH3
B102C CH3SO CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1021 CH3S02 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1022 Ph CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1023 CH30 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1024 CH3OC (0) CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1025 CH3CH2OC (0) CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1026 CH2 = CHCH2 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1027 HCCCH2 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1028 CF3 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1029 (CH3) 2NS02 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1030 (CH3) 2N CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1031 PhO CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1032 PhS CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1033. PhSO CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1034 PhS02 CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1035 CN CH3 CH3 CH3 OH CHC (0) OCH2CH3
B1036 CH3CH2 CH3CH2 H H OH CHC (0) OCH2CH3
B1037 CH3CH2CH2 CH3CH2 H OH OH CHC (0) OCH2CH3
B1038 (CH3) 2CH CH3CH2 H OH OH CHC (0) OCH2CH3
B1039 (CH3) 3C CH3CH2 H H OH CHC (0) OCH2CH3
B1040 CH3S CH3CH2 H H OH CHC (0) OCH2CH3
B1041 CH3SO CH3CH2 H OH OH CHC (0) OCH2CH3
B1042 CH3S02 CH3CH2 H H OH CHC (0) OCH2CH3
B1043 Ph CH3CH2 H H OH. CHC (0) OCH2CH3
B1044 CH30 CH3CH H OH OH CHC (0) OCH2CH3
B1045 CH3OC (0) CH3CH H OH OH CHC (0) OCH2CH3
Radical Re R7 Rβ Rg River W B1046 CH3CH2OC (0) CH3CH2 H H OH CHC (0) OCH2CH3
B1047 CH2 = CHCH2 CH3CH2 H H OH CHC (0) OCH2CH3
B1048 HCCCH2 CH3CH2 H OH OH CHC (0) OCH2CH3
B1049 CF3 CH3CH2 H OH OH CHC (0) OCH2CH3
B1050 (CH3) 2NS02 CH3CH2 H H OH CHC (0) OCH2CH3
B1051 (CH3) 2N CH3CH2 H OH OH CHC (0) OCH2CH3
B1052 PhO CH3CH2 H OH OH CHC (0) OCH2CH3
B1053 PhS CH3CH2 H H OH CHC (0) OCH2CH3
B1054 PhSO CH3CH2 H OH OH CHC (0) OCH2CH3
B1055 PhS02 CH3CH2 H OH OH CHC (0) OCH2CH3
B1056 CN CH3CH2 H OH OH CHC (0) OCH2CH3
B1057 CH3OC (0) H H OH OH CHPh
B1058 H H H H OH CHPh
B1059 H H H OH OH CH (CH2CH3)
B1060 H H H OH OH CH (CH2CH2CH3)
B1061 H H H OH OH CH (CH (CH3) 2)
B1062 H H H OH OH CH (C (CH3) 3)
B1063 H H H OH OH C (CH3) 2
B1064 H H H OH OH CH (CF3)
B1065 CH3OC (0) H H OH OH (CH3) (CF3)
B1066 H H H OH OH (CH3) (CF3)
B1067 CH3OC (0) CH30 H H OH CH2
B1068 H CH30 H H OH CH2
B1069 CH30 CH3OC (0) H CH3 OH CH2
B1070 CH3O H CH3 H OH CH2
B1071 Cl H H OH OH CH2
B1072 F H H H OH CH2
B1073 H H H OH OH CH (OCH 3) 2
B1074 H H H OH OH CH2OSO2CH3
B1075 CH3 CH3 CH3 CH3 OH S (O)
B1076 CICH2CH2 H H OH OH CH2
B1077 HO (CH2) 2 H H OH OH CH2
B1078 MsO (CH2) 2 H H OH OH CH2
Radical Re R7 Rß Rg River W
B1079 HOCH (CH3) CH2 H H OH OH CH2
B1080 MsOCH (CH3) CH2 H H OH OH CH2
B1081 (CH3) 2CH H CH3 CH3 OH CH2
B1082 HCCCH2 H CH3 CH3 OH CH2
B1083 H C = CCH2 H CH3 CH3 OH CH2
B1084 H2C = C (CH3) H H OH OH CHCH3
B1085 H H H H OH CHCONHCH2Ph
B1087 CH3OC (0) CH3 H H OH C (CH3) 2
B1089 CH3CH2 H CH3 CH3 OH CH2
B1090 CH3OC (0) H H OH OH CF3CH2CH2
B1091 CHsCH2S CH3CH2 CH3 H OH CH2
B1092 CH3S Ph CH3 H OH CH2
B1093 CH3CH2 CH3CH2 CH3 H OH CH2
B1094 CH3OC (0) H H OH OH (CH3) 2
B1095 CH3 H H OH C (CH3) 2
B1096 H H H OH OH NCOCH2SCH3
B1097 to "H H H OH CH2
B1098 l.l-dimethylvinyl H H OH OH CH2
B1 100 H H H H -ONH + (CH 2 CH 3) 3 CH 2
B1 101 H H H H -ONH + (CH 2 CH 3) 3 CH (CH 3)
B1 102 H H H H PhS CH2
B1 103 H H H H PhSO CH2
B1 104 H H H H Ph S02 CH2
B1 105 CH3 CH3 CH3 CH3 Cl C = 0
B1 106 H H H OH OH CHCH2CH (CH3) 2
Radical Re R7 Rß R9 R10 w
B1107 CH3 CH3 CH3 CH3 CH3C (0) OR C = 0
B1108 CH3OC (0) CH2 HHH OH CH2 B1109 CH3OC (0) CH2 CH3 HH OH CH2 B1 110 CH3OC (0) CH2 CH3 CH3 H OH CH2 B111 1 CH3OC (0) CH2 CH3 CH3 CH3 OH CH2 B1112 CH3OC (0) CH2 H CH3 CH3 OH CH2 B1113 CH3OC (0) CH2 HHH OH CH (CH3) B1 114 CH3OC (0) CH2 CH3 HH OH CH (CH3) B1115 CH3OC (0) CH2 CH3 CH3 H OH CH (CH3) B1 116 CH3OC (0) CH2 CH3 CH3 CH3 OH CH (CH3) B1 117 CH30C (0) CH2 H CH3 CH3 OH CH (CH3) B1 118 CH3OC (0) CH2 HHH OH C (CH3) 2 B1 119 CH30C (0) CH2 CH3 HH. OH C (CH3) 2 B1120 CH3OC (0) CH2 CH3 CH3 H OH C (CH3) 2 B1 121 CH3OC (0) CH2 CH3 CH3 CH3 OH C (CH3) 2 B1122 CH30C (0) CH2 H CH3 CH3 OH C (CH3 ) 2 B1 123 CH3CH2OC (0) CH2 HHH OH CH2 B1124 CH3CH2OC (0) CH2 CH3 HH OH CH2 B1 125 CH3CH2OC (0) CH2 CH3 CH3 H OH CH2 B1 126 CH3CH2OC (0) CH2 CH3 CH3 CH3 OH CH2 B1 127 CH3CH2OC ( 0) CH2 H CH3 CH3 OH CH2 B1 128 3H3CH2OC (0) CH2HHH OH CH (CH3) B1 129 CH3CH2OC (0) CH2 CH3HH OH CH (CH3) B1 130 CH3CH2OC (0) CH2 CH3 CH3 H OH CH (CH3) B1131 CH3CH2OC (0) CH2 CH3 CH3 CH3 OH CH (CH3) B1 132 CH3CH2OC (0) CH2 H CH3 CH3 OH CH (CH3) B1133 CH3CH2OC (0) CH2HHH OH C (CH3) 2 B1 134 CH3CH2OC (0) CH2 CH3 HH OH C (CH3) 2 B1135 CH3CH2OC (0) CH2 CH3 CH3 H OH C (CH3) 2 B1 136 CH3CH2OC (0) CH2 CH3 CH3 CH3 OH C (CH3) 2 B1 137 CH3CH2OC (0) CH2 H CH3 CH3 OH C (CH3) 2 B1 138 CH3 HH OH CH2 CH, CH, O or
or? ol _X _X or? or? or? _X _Xr or? or? or? _Xr. _Xr. or o ?? _ ._ O ?? or ?? X X x Ox Ox _ _ or x_ X? or? or? _I _X or? or? or? _X? ? co o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o -rj ov? X X? x? X X? x? X X? x? X X? x? X X? x? X X? x? X X óF X X
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o x
X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X S
o I oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX oX < ^ -
Radical Re R7 Rß R9 R10 W
B1172 CH3OCH2 CH3 CH3 CH3 OH CH2
B1173 CH3OCH2 H CH3 CH3 OH CH2
B1174 PhCH2 H H OH OH CH2
B1175 PhCH2 CH3 H H OH CH2
B1176 PhCH2 CH3 CH3 H OH CH2
B1177 PhCH2 CH3 CH3 CH3 OH CH2
B1178 PhCH2 H CH3 CH3 OH CH2
B1179 H H H H O-K + CH2
B1180 H H H H S (CH2) 7CH3 CH2
B1181 H H H H S (CH2) 7CH3 CH2
B1182 H H H H SO (CH2) 7CH3 CH2
B1183 H H H H S02 (CH2) 7CH3 CH2
B1184 H H H H NHSO2CH3 CH2
B1185 H H H H NH (CO) S (CH 2) 7 CH 3 CH 2
B1186 H H H H Cl CH2
B1187 H H H H NH2 CH2
B1188 H H H H OC (0) C (CH 3) 3 CH 2
B1189 H H H H 0C (0) CH3 CH2
B1190 H H H H OC (0) Ph CH2
B1191 H H H H OC (0) -cyclopropyl CH2
B1192 H H H H OC (0) CH2CH3 CH2
B1193 H H H H OC (0) CH = CH2 CH2
B1194 H H H H OC (0) CH = CHCH3 CH2
B1195 H H H H OC (0) SCH3 CH2
B1196 H H H H OC (0) S (CH2) 7CH3 CH2
B1197 H H H H OC (0) OCH2CH3 CH2
B1198 H H H H OC (0) N (CH 2 CH 3) 2 CH 2
B1199 H H H H S- (4-Cl-phenyl) CH 2
B1200 H H H H SO - (- 4-Cl-phenyl) CH 2
B1201 H H H H S 2- (4-CF3-phenyl) CH2
B1202 H H H H S- (4-CF 3 -phenyl) CH 2
B1203 H H H H SO- (4-CF 3 -phenyl) CH 2
B1204 H H H H S 2- (4-CF3-phenyl) CH2
you roped ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro ro x 0 ro ro ro to M o o to Ql_L. or co co CD co co co D co cn co 00 00 00 oo 00 oo ca 00 00 oo v | o o o o o o o CD 00 vi cn cp -C-. ? ro o co oo i cn cp J? ro - O co ro - * O co 00 v | cn cn U)
o o o o o o o o o o o o o o o o o o o o o o o o o o X X X X X X X X X X I X X X X X X X X X X X X X X X F
o o o o o o o o o o o o o o o o o o o o o o o o o x x x x x x x x x x x x x x x x x x x i x x x
X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X X F
o o o o o o o o o o o o o o o o o o o o o o o o O X O O O x x x x x x x x x x x x x x x x x x x X X or x x x x x x x x x x x x x x x x
Radical Re R7 Rß R9 River W
B1201 CH3 CH3 H H S? 2- (-CF3-phenyl) CH2
B1202 CH3 CH3 H H S- (4-CF3-phenyl) CH2
B1203 CH3 CH3 H H SO- (4-CF3-phenyl) CH2
B1204 CH3 CH3 H H S? 2- (4-CF3-femlo) CH2
B1205 CH3 CH3 H H S- (4-N? 2-phenyl) CH2
B1206 CH3 CH3 H H SO- (4-N? 2-phenyl) CH2
B1207 CH3 CH3 H H S? 2- (4-N? 2-phenyl) CH2
B1208 CH3 CH3 H H s- t CH2
B1209 CH3 CH3 H H s CH2
B1210 CH3 CH3 H H li T CH2
B121 1 CH3 CH3 H H Tf CH2
B1213 H H H OH OH-CH2CH2 '
B1214 CH3 H H OH OH-CH2CH2-
B1215 CH3 CH3 H OH OH-CH2CH2- B1216 CH3 CH3 CH3 OH OH -CH2CH2- B1217 CH3 CH3 CH3 CH3 OH -CH2CH2-
In the following Table 3, Q is Q;
and Q2 = the following radicals C: Table 3: Radicals C:
Radical R7 Rl6 RlO P w
Radical Re R7 Laughs Rio P W
C1 H H OH 1 CH2
C2 CH3 H H OH 1 CH2
C3 CH3CH2 H H OH 1 CH2
C4 CH3CH2CH2 H H OH 1 CH2
C5 (CH3) 2CH H OH 1 CH2
C6 (CH3) 3C H OH 1 CH2
C7 CH3S H H OH 1 CH2
C8 CH3SO H H OH 1 CH2
C9 CH3S02 H H OH 1 CH2
C10 Ph H H OH 1 CH2
C11 CH30 H OH 1 CH2
C12 CH3OC (0) H H OH 1 CH2
C13 CH3CH2OC (0) H H OH 1 CH2
C14 CH2 = CHCH2 H H OH 1 CH2
C15 HCCCH2 H H OH 1 CH2
C16 CF3 H H OH 1 CH2
C17 (CH3) 2NS02 H H OH 1 CH2
C18 (CH3) 2N H H OH 1 CH2
C19 PhO H H OH 1 CH2
C20 PhS H H OH 1 CH2
C21 PhSO H H OH 1 CH2
C22 PhS02 H H OH 1 CH2
C23 CN H H OH 1 CH2
C24 CH3 CH3 H OH 1 CH2
C25 CH3CH2 CH3 H OH 1 CH2
C26 CH3CH2CH2 CH3 H OH 1 CH2
C27 (CH3) 2CH CH3 H OH 1 CH2
C28 (CH3) 3C CH3 H OH 1 CH2
C29 'CH3S CH3 H OH 1 CH2
C30 CH3SO CH3 H OH 1 CH2
C31 CH3S02 CH3 H OH 1 CH2
C32 Ph CH3 H OH 1 CH2
Radical R6 R7 R e River P W
C33 CH30 CH3 H OH 1 CH2
C34 CH3OC (0) CH3 H OH 1 CH2
C35 CH3CH2OC (0) CH3 H OH 1 CH2
C36 CH2 = CHCH2 CH3 H OH 1 CH2
C37 HCCCH2 CH3 H OH 1 CH2
C38 CF3 CH3 H OH 1 CH2
C39 (CH3) 2NS02 CH3 H OH 1 CH2
C40 (CH3) 2N CH3H OH 1 CH2
C41 PhO CH3 H OH 1 CH2
C42 PhS CH3 H OH 1 CH2
C43 PhSO CH3 H OH 1 CH2 C44 PhS02 CH3 H OH 1 CH2
C45 CN CH3 H OH 1 CH2
C46 H H OH OH 4 CH2
C47 CH3 H OH OH 4 CH2
C48 CH3CH2 H H OH 4 CH2
C49 CH3CH2CH2 H H OH 4 CH2
C 50 (CH 3) 2 H H OH 4 CH 2 C 51 (CH 3) 3 C H H OH 4 CH 2
C52 CH3S H OH OH 4 CH2
C53 CH3SO H H OH 4 CH2
C54 CH3S02 H H OH 4 CH2
C55 Ph H H OH 4 CH2
C56 CH30 H OH OH 4 CH2
C57 CH3OC (0) H H OH 4 CH2
C58 CH3CH2OC (0) H H OH 4 CH2
C59 CH2 = CHCH2 H H OH 4 CH2
C60 HCCCH2 H H OH 4 CH2
C61 CF3 H H OH 4 CH2
C62 (CH3) 2NS02 H H OH 4 CH2
C63 (CH3) 2N H OH OH 4 CH2 C64 PhO H OH OH 4 CH2
C65 PhS H H OH 4 CH2
Radical Re R7 Laughs Rio P W
C66 PhSO H H OH 4 CH2
C67 PhS02 H H OH 4 CH2
C68 CN H H OH 4 CH2
C69 CH3 CH3 H OH 4 CH2
C 70 CH 3 CH 2 CH 3 H OH 4 CH 2 C71 CH 3 CH 2 CH 2 CH 3 H OH 4 CH 2
C72 (CH3) 2CH CH3 H OH 4 CH2
C73 (CH3) 3C CH3 H OH 4 CH2
C74 CH3S CH3 H OH 4 CH2
C75 CH3SO CH3 H OH 4 CH2
C76 CH3S02 CH3 H OH 4 CH2
C77 Ph CH3 H OH 4 CH2
C78 CH30 CH3 H OH 4 CH2
C79 CH3OC (0) CH3 H OH 4 CH2
C80 CH3CH2OC (0) CH3 H OH 4 CH2
C81 CH2 = CHCH2 CH3 H OH 4 CH2
C82 HCCCH2 CH3 H OH 4 CH2
C83 CF3 CH3 H OH 4 CH2 C84 (CH3) 2NS02 CH3 H OH 4 CH2
C85 (CH3) 2N CH3 H OH 4 CH2
C86 PhO CH3 H OH 4 CH2
C87 PhS CH3 H OH 4 CH2
C88 PhSO CH3 H OH 4 CH2
C89 PhS02 CH3 H OH 4 CH2
C90 CN CH3 H OH 4 CH2 C91 H H OH 3 CH2
C92 CH3 H OH 3 CH2
C93 CH3CH2 H OH 3 CH2
C94 CH3CH2CH2 H H OH 3 CH2
C95 (CH3) 2CH H OH 3 CH2
C96 (CH3) 3C H OH 3 CH2
C97 CH3S H OH 3 CH2
C98 CH3SO H H OH 3 CH2
Radical R6 R7 íe Rio P W
C99 CH3S02 H H OH 3 CH2
C100 Ph H H OH 3 CH2
C101 CH30 H OH 3 CH2
C102 CH3OC (0) H H OH 3 CH2
C103 CH3CH2OC (0) H H OH 3 CH2
C104 CH2 = CHCH2 H OH 3 CH2
C105 HCCCH2 H H OH 3 CH2
C106 CF3 H OH 3 CH2
C107 (CH3) 2NS02 H OH 3 CH2
C108 (CH3) 2N H OH 3 CH2
C109 PhO H OH 3 CH2
C110 PhS H H OH 3 CH2
C1 11 PhSO H H OH 3 CH2
C1 12 PhS02 H H OH 3 CH2
C113 CN H H OH 3 CH2
C1 14 CH3 CH3 H OH 3 CH2
C1 15 CH3CH2 CH3 H OH 3 CH2
C1 16 CH3CH2CH2 CH3 H OH 3 CH2 C1 17 (CH3) 2CH CH3 H OH 3 CH2
C118 (CH3) 3C CH3 H OH 3 CH2
C1 19 CH3S CH3 H OH 3 CH2
C120 CH3SO CH3 H OH 3 CH2
C121 CH3S02 CH3 H OH 3 CH2
C122 Ph CH3 H OH 3 CH2
C123 CH30 CH3 H OH 3 CH2
C124 CHaOC (O) CH3 H OH 3 CH2
C125 CH3CH2OC (0) CH3 H OH 3 CH2
C126 CH2 = CHCH2 CH3 H OH 3 CH2
C127 HCCCH2 CH3 H OH 3 CH2
C128 CF3 CH3 H OH 3 CH2
C129 (CH3) 2NS02 CH3 H OH 3 CH2
C130 (CH3) 2N CH3H OH 3 CH2
C131 PhO CH3 H OH 3 CH2
Radical Re R7 Rl6 River P W
C132 PhS CH3 H OH 3 CH2
C133 PhSO CH3 H OH 3 CH2
C134 PhS02 CH3 H OH 3 CH2
C135 CN CH3 H OH 3 CH2
C136 CH3CH2 CH3CH2 H OH 1 CH2
C137 H H OH 1 CH (CH3)
C138 CH3 H OH 1 CH (CH3)
C139 CH3 CH3 H OH 1 CH (CH3)
0140 CH2CH3 H H OH 1 CH (CH3)
C141 CH2CH3 CH3 H OH 1 CH (CH3)
C142 CH3CH2 CH3CH2 H OH 1 CH (CH3)
C143 H H CH3 OH 1 CH2
C144 CH3 CH3 CH3 OH 1 CH2
C145 CH3CH2 CH3CH2 CH3 OH 1 CH2
C146 H H OH 2 CH2
C147 CH3 CH3 H OH 2 CH2
C148 CH3CH2 CH3CH2 H OH 2 CH2
C149 H H OH OH 5 CH2
C150 CH3 CH3 H OH 5 CH2
C151 CH3CH2 CH3CH2 H OH 5 CH2
C152 CH3 H H OH 2 CH2
In the following Table 4, Q is Q--
and Cb = the following radicals D: Table 4: Radicals D:
Radical R6 RB RI2 R 10
Radical R6 R7 R8 R «Rio o
D1 H H H OH 2
D2 CH3 H H OH 2
D3 CH3CH H H OH 2
D4 CH3CH2CH2 H H OH 2
D5 (CH3) 2CH H H OH 2
D6 (CH3) 3C H H OH 2
D7 CH3S H H OH 2
D8 CH3SO H H OH 2
D9 CH3S02 H H OH 2
D10 Ph H H OH 2
D1 1 CH30 H H OH 2
D12 CH2 = CHCH2 H H OH 2
D13 HCCCH2 H H OH 2
D14 CF3 H H OH 2
D15 PhO H H OH 2
D16 PhS H H OH 2
D17 PhSO H H OH 2
D18 PhS02 H H OH 2
D19 CH3 CH3 H OH 2
D21 CH3CH CH2 CH3 H H OH 2
D22 (CH3) 2CH CH3 H OH 2
D23 (CH3) 3C CH3 H OH 2
D24 CH3S CH3 H OH 2
D25 CH3SO CH3 H OH 2
D26 CH3S02 CH3 H H OH 2
D27 Ph CH3 H H OH 2
D28 CH30 CH3 H OH 2
D29 CH2 = CHCH2 CH3 H OH 2
D30 HCCCH2 CH3 H H OH 2
D31 CF3 CH3 H OH 2
D32 PhO CH3 H H OH 2
Radical Re R7 R1 l2 River or D132 CH3CH2OC (0) CH3 CH3 H OH 1 D133 CH30 CH3 CH3 H OH 1 D134 CH3S CH3 CH3 H OH 1 D135 CH3SO CH3 CH3 H OH 1 D136 CH3S02 CH3 CH3 H OH 1 D137 HHH CH3 OH 1 D138 CH3 HH CH3 OH 1 D139 HH CH3 CH3 OH 1 D140 CH3CH2OC (0) CH3 HH OH 4
In the following Table 5, Q is Q
and Qj = the following radicals E: Table 5: Radicals E:
Radical Re R7 River X Y W q
E1 H OH OH S CH2 CH2 2
E2 CH3 H OH S CH2. CH2 2
E3 CH3 CH3 OH S CH2 CH2 2
E4 CH3OC (0) H OH S CH2 CH2 2
E5 CH3 CH3OC (0) OH S CH2 CH2 2
E6 H OH OH SO CH2 CH2 2
E7 CH3 OH OH SO CH2 CH2 2
E8 CH3 CH3 OH SO CH2 CH2 2
E9 CH3OC (0) H OH SO CH2 CH2 2
E10 CH3 CH3OC (0) OH SO CH2 CH2 2
E1 1 H OH OH S02 CH2 CH2 2
Radical Re R7 Rß R ¡? R10 0
D99 CH2 = CHCH2 CH3 H OH OH 4
D100 HCCCH2 CH3 H H OH 4
D101 CF3 CH3 H OH OH 4
D102 PhO CH3 H H OH 4
D103 PhS CH3 H H OH 4
D104 PhSO CH3 H H OH 4
D105 PhS02 CH3 H H OH 4
D106 H H H CH 3, OH 4
D107 H H H CH 3, OH 3
D108 H H H OH 1
D109 CH3 H H OH 1
D1 10 CH3OC (0) CH3 H OH 1
D1 11 CH3CH2OC (0) i CH3 H OH 1
D1 12 CH30 CH3 H OH 1
D113 CH3S CH3 H H OH 1
D1 14 CH3SO CH3 H H OH 1
D1 15 CH3S02 CH3 H OH 1
D116 CH3CH2 H H OH 1
D117 CH3OC (0) CH3CH2 H OH 1
D118 CH3CH2OC (0) CH3CH2 H OH 1
D119 CH30 CH3CH2 H OH 1
D120 CH3S CH3CH2 H H OH 1
D121 CH3SO CH3CH2 H OH 1
D122 CH3S02 CH3CH2 H OH 1
D123 CH3CH2S CH3 H OH 1
D124 CH3CH2SO CH3 H H OH 1
D125 CH3CH2S02 CH3 H OH 1
D126 CH3CH S CH3CH2 H OH 1
D127 CH3CH2SO CH3CH2 H OH 1
D128 CH3CH2S02 H3CH2 H OH 1
D129 H H CH3 H OH 1
D130 CH3 H CH3 H OH 1
D131 CH3OC (0) CH3 CH3 H OH 1
Radical Re R7 Rβ R12 Rio o
D66 CF3 CH3 H OH 3
D67 PhO CH3 H H OH 3
D68 PhS CH3 H OH 3
D69 PhSO CH3 H OH 3
D70 PhS02 CH3 H OH 3
D71 H H H OH 4
D72 CH3 H H OH 4
D73 CH3CH2 H H OH 4
D74 CH3CH2CH2 H H OH OH 4
D75 (CH3) 2CH H H OH 4
D76 (CH3) 3C H H OH 4
D77 CH3S H H OH 4
D78 CH3SO H H OH 4
D79 CH3S02 H H OH 4
D80 Ph H H OH OH 4
D81 CH30 H H OH 4
D82 CH2 = CHCH2 H H OH OH 4
D83 HCCCH2 H H OH 4
D84 CF3 H H OH 4
D85 PhO H H OH 4
D86 PhS H H H OH 4
D87 PhSO H H OH 4
D88 PhS02 H H H OH 4
D89 CH3 CH3 H OH OH 4
D90 CH3CH2 CH3 H OH OH 4
D91 CH3CH2CH2 CH3 H OH OH 4
D92 (CH3) 2CH CH3 H OH OH 4
D93 (CH3) 3C CH3 H OH 4
D94 CH3S CH3 H OH OH 4
D95 CH3SO CH3 H OH OH 4
D96 CH3S02 CH3 H H OH 4
D97 Ph CH3 H H OH 4
D98 CH30 CH3 H OH OH 4
Radical Re R7 Rß Rl2 Rio or
D33 PhS CH3 H H OH 2
D34 PhSO CH3 H H OH 2
D35 PhS02 CH3 H H OH 2
D36 H H H OH 3
D37 CH3 H H OH 3
D38 CH3CH2 H H OH 3
D39 CH3CH2CH2 H H OH 3
D40 (CH3) 2CH H H OH 3
D41 (CH3) 3C H H OH 3
D42 CH3S H H OH 3
D43 CH3SO H H OH 3
D44 CH3S02 H H OH 3
D45 Ph H H OH 3
D46 CH30 H H OH 3
D47 CH2 = CHCH2 H H OH 3
D48 HCCCH2 H H OH 3
D49 CF3 H H OH 3
D50 PhO H H OH 3
D51 PhS H H OH 3
D52 PhSO H H OH 3
D53 PhS02 H H OH 3
D54 CH3 CH3 H OH 3
D55 CH3CH2 CH3 H OH 3
D56 CH3CH2CH2 CH3 H OH 3
D57 (CH3) 2CH CH3 H OH 3
D58 (CH3) 3C CH3 H OH 3
D59 CH3S CH3 H OH 3
D60 CH3SO CH3 H OH 3
D61 CH3S02 CH3 H OH 3
D62 Ph CH3 H OH 3
D63 CH30 CH3 H OH 3
D64 CH2 = CHCH2 CH3 H OH 3
D65 HCCCH2 CH3 H OH 3
Radical Re R7 River X Y w q
E12 CH3 H OH S02 CH2 CH2 2 H2 2
E13 CH3 CH3 OH S02 CH2 C E14 CH3OC (0) H OH S02 CH2 CH2 2
E15 CH3 CH3OC (0) OH S02 CH2 CH2 2 CH2 2
E16 H OH OH O E17 CH3 H OH CO O CH2 2
E18 CH3 CH3 OH CO or CH2 2
E19 CHaOC (O) H OH CO O CH2 2
E20 CH3 CH3OC (0) OH CO or CH2 2
E21 H H OH CO O CH2 2
E22 CH 3 H OH CO O CH 2 2 CH 3 O OH CO O CH 2 2
E23 CH3 E24 CH3OC (0) H OH CO O CH2 2
E25 CH3 CH3OC (0) OH CO or CH2 2
E26 H H OH CO or CH2 2
E27 CH3 H OH CO or CH2 2
E28 CH3 CH3 OH CO 0 CH2 2
E29 CH3OC (0) H OH CO or CH2 2
E30 CH3 CH3OC (0) OH CO or CH2 2
In the following Table 6, Q is Q:
and Qs = the following radicals F: Table 6: Radicals F:
Radical Re R7 Rß River F1 H H OH OH F2 CH3 H OH
Radical Re R7 Rß River F3 CH3 CH3 H OH F4 CH3 CH3 CH3 OH F5 H H CH3 OH F6 H CH3 CH3 OH
Table 7: Compounds of the Formula
Comp. R2 R3 Qi P
No. A1 H H H CF3 B24 0
A2 CH3 H H CF3 B24 0
A3 CH3CH2 H H CF3 B24 0
A4 (CH3) 2CH H H CF3 B24 0
A5 (CH3) 3C H H CF3 B24 0
A6 cyclopropyl H H CF3 B24 0
A7 CH3 (CH2) H H CF3 B24 0
A8 CH3OCH2 H H CF3 B24 0
A9 CH30 (CH2) 2 HH CF3 B24 0 A10 Ph HH CF3 B24 0 A11 PhO HH CF3 B24 0 A12 PhS HH CF3 B24 0 A13 PhSO HH CF3 B24 0 A14 PhS02 HH CF3 B24 0 A15 CH3S HH CF3 B24 0 A16 CH3SO HH CF3 B24 0 A17 CF3 HH CF3 B24 0 A18 F2CH HH CF3 B24 0
A20 CH3CC H H CF3 B24 0
A21 CH2 = CH H H CF3 B24 0
A22 CH2 = CHCH2 H H CF3 B24 0
A23 CH3S02N (CH3) H H CF3 B24 0
A24 (CH3) 2N H H CF3 B24 0
A25 (CH3) 2NS02 H H CF3 B24 0
A26 CICH2 H H CF3 B24 0
A27 CH3SCH2 H H CF3 B24 0
A28 CH3SOCH2 H H CF3 B24 0
A29 CH3S02CH H H CF3 B24 0
A30 [1.2.4] -triazole-l- H H CF3 B24 0 ilmethyl A31 CH3 CF3 H CH3 B24 0
A32 CH3 CH3 H CF3 B24 0
A33 H H H CF3CF2 B24 0
A34 CH3 H H CF3CF2 B24 0
A35 CH3CH2 H H CF3CF2 B24 0
A36 cyclopropyl H H CF3CF2 B24 0
A37 (CH3) 3C H H CF3CF2 B24 0
A38 (CH3) 2CH H H CF3CF2 B24 0
A39 CH3 (CH2) 2 H H CF3CF2 B24 0
A40 CH3OCH2 H H CF3CF2 B24 0
A41 CH30 (CH2) 2 H H CF3CF2 B24 0
A42 Ph H H CF3CF2 B24 0
A43 PhO H H CF3CF2 B24 0
A44 PhS H H CF3CF2 B24 0
A45 PhSO H H CF3CF2 B24 0
A46 PhS02 H H CF3CF2 B24 0
A47 CH3S H H CF3CF2 B24 0
A48 CH3SO H H CF3CF2 B24 0
A49 CF3 H H CF3CF2 B24 0
ijomp. p2 R4 Rs Q1 P
No. A50 F2CH H H CF3CF2 B24 0
A51 HCC H H CF3CF2 B24 0
A52 CH3CC H H CF3CF2 B24 0
A53 CH2 = CH H CF3CF2 B24 0
A54 CH2 = CHCH H H CF3CF2 B24 0
A55 CH3S02N (CH3) H H CF3CF2 B24 0
A56 (CH3) 2N H H CF3CF2 B24 0
A57 (CH3) 2NS02 H H CF3CF2 B24 0
A58 CICH2 H H CF3CF2 B24 0
A59 CH3SCH2 H H CF3CF2 B24 0
A60 CH3SOCH2 H H CF3CF2 B24 0
A61 CH3SO2CH2 H H CF3CF2 B24 0
A62 [1.2.4] -triazole-l- H H CF3CF2 B24 0 ilmethyl A63 H H H CF3CF2CF2 B24 0
A64 CH3 H H CF3CF2CF2 B24 0
A65 CH3CH2 H H CF3CF2CF2 B24 0
A66 cyclopropyl H H CF3CF2CF2 B24 0
A67 (CH3) 3C H H CF3CF2CF2 B24 0
A68 (CH3) 2CH H H CF3CF2CF2 B24 0
A69 CH3 (CH2) 2 H H CF3CF2CF2 B24 0
A70 CH3OCH2 H H CF3CF2CF2 B24 0
A71 CH30 (CH2) 2 H H CF3CF2CF2 B24 0
A72 Ph H H CF3CF2CF2 B24 0
A73 PhO H H CF3CF2CF2 B24 0
A74 PhS H H CF3CF2CF2 B24 0
A75 PhSO H H CF3CF2CF2 B24 0
A76 PhS02 H H CF3CF2CF2 B24 0
A77 CH3S H H CF3CF2CF2 B24 0
A78 CH3SO H H CF3CF2CF2 B24 0
A79 CF3 H H CF3CF2CF2 B24 0
A80 F2CH H H CF3CF2CF2 B24 0
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No. A174 CH2 = CHCH2 H H CCI3 B24 0
A175 CH3S02N (CH3) H H CCI3 B24 0
A176 (CH3) 2N H H CCI3 B24 0
A177 (CH3) 2NS02 H H CCI3 B24 0
A178 CICH2 H H CCI3 B24 0
A179 CH3SCH2 H H CCI3 B24 0
A180 CH3SOCH2 H H CCI3 B24 0
A181 CH3S02CH2 H H CCI3 B24 0
A182 [1 2 4] -tnazol-l- H H CCI3 B24 0 ummethyl A183 H H CH3 CF3 B24 0
A184 CH3 H CH3 CF3 B24 0
A185 CH3CH2 H CH3 CF3 B24 0
A186 cyclopropyl H CH3 CF3 B24 0
A187 (CH3) 3C H CH3 CF3 B24 0
A188 (CH3) 2CH H CH3 CF3 B24 0
A189 CH3 (CH2) 2 H CH3 CF3 B24 0
A190 CH3OCH2 H CH3 CF3 B24 0
A191 CH30 (CH2) 2 H CH3 CF3 B24 0
A192 Ph H CH3 CF3 B24 0
A193 PhO H CH3 CF3 B24 0
A194 PhS H CH3 CF3 B24 0
A195 PhSO H CH3 CF3 B24 0
A196 PhS02 H CH3 CF3 B24 0
A197 CH3S H CH3 CF3 B24 0
A198 CH3SO H CH3 CF3 B24 0
A199 CF3 H CH3 CF3 B24 0
A200 F2CH H CH3 CF3 B24 0
A201 HCC H CH3 CF3 B24 0
A202 CH3CC H CH3 CF3 B24 0
A203 CH2 = CH H CH3 CF3 B24 0: »A204 H2- C HC H H CH3 CF3 B24 0
Comp. R2 R3 R4 Q1 No. A205 CH3S02N (CH3; H CH3 CF3 B24 0
A206 (CH3) 2N H CH3 CF3 B24 0
A207 (CH3) 2NS02 H CH3 CF3 B24 0
A208 CICH2 H CH3 CF3 B24 0
A209 CH3SCH2 H CH3 CF3 B24 0
A210 CH3S0CH2 H CH3 CF3 B24 0
A21 1 CH3S02CH2 H CH3 CF3 B24 0
A212 H H CH3 CF3CF2 B24 0
A213 CH3 H CH3 CF3CF2 B24 0
A214 CH3CH2 H CH3 CF3CF2 B24 0 0 A215 cyclopropyl H CH3 CF3CF2 B24 0
A216 (CH3) 3C H CH3 CF3CF2 B24 0
A217 (CH3) 2CH H CH3 CF3CF2 B24 0
A218 CH3 (CH2) 2 H CH3 CF3CF2 B24 0
A219 CH3OCH2 H CH3 CF3CF2 B24 0
A220 CH30 (CH2) 2 H CH3 CF3CF2 B24 0
A221 Ph H CH3 CF3CF2 B24 0
A222 PhO H CH3 CF3CF2 B24 0
A223 PhS H CH3 CF3CF2 B24 0
A224 PhSO H CH3 CF3CF2 B24 0
A225 PhS02 H CH3 CF3CF2 B24 0
A226 CH3S H CH3 CF3CF2 B24 0
A227 CH3SO H CH3 CF3CF2 B24 0
A228 CF3 H CH3 CF3CF2 B24 0
A229 F2CH H CH3 CF3CF2 B24 0
A230 HCC H CH3 CF3CF2 B24 0
A231 CH3CC H CH3 CF3CF2 B24 0
A232 CH2 = CH H CH3 CF3CF2 B24 0
A234 CH3S02N (CH3) H CH3 CF3CF2 B24 0
? • > A235 (CH3) 2N H CH3 CF3CF2 B24 0
A236 (CH3) 2NS02 H CH3 CF3CF2 B24 0
Comp. R2 R4 Rs Q1 P
No. A237 CICH2 H CH3 CF3CF2 B24 0
A238 CHaSCH2 H CH3 CF3CF2 B24 0
A239 CH3SOCH2 H CH3 CF3CF2 B24 0
A240 CHsS02CH2 H CH3 CF3CF2 B24 0
A241 H H CH3 CF3CF2CF2 B24 0
A242 CH3 H CH3 CF3CF2CF2 B24 0
A243 CHsCH2 H CH3 CF3CF2CF2 B24 0
A244 cyclopropyl H CH3 CF3CF2CF2 B24 0
A245 (CH3) 3C H CH3 CF3CF2CF2 B24 0
A246 (CH3) 2CH H CH3 CF3CF2CF2 B24 0
A248 CH3OCH2 H CH3 CF3CF2CF2 B24 0
A249 CH30 (CH2) 2 H CH3 CF3CF2CF2 B24 0
A250 Ph H CH3 CF3CF2CF2 B24 0
A251 PhO H CH3 CF3CF2CF2 B24 0
A252 PhS H CH3 CF3CF2CF2 B24 0
A253 PhSO H CH3 CF3CF2CF2 B24 0
A254 PhS02 H CH3 CF3CF2CF2 B24 0
A255 CH3S H CH3 CF3CF2CF2 B24 0
A256 CH3SO H CH3 CF3CF2CF2 B24 0
A257 CF3 H CH3 CF3CF2CF2 B24 0
A258 F2CH H CH3 CF3CF2CF2 B24 0
A259 HCC H CH3 CF3CF2CF2 B24 0
A260 CH3CC H CH3 CF3CF2CF2 B24 0
A261 CH2 = CH H CH3 CF3CF2CF2 B24 0
A262 CH2 = CHCH2 H CH3 CF3CF2CF2 B24 0
A263 CH3S02N (CH3) H CH3 CF3CF2CF2 B24 0
A264 (CH3) 2N H CH3 CF3CF2CF2 B24 0
A265 (CH3) 2NSOz H CH3 CF3CF2CF2 B24 0
A266 CICH2 H CH3 CF3CF2CF2 B24 0
A267 CH3SCH2 H CH3 CF3CF2CF2 B24 0
A268 CH3SOCH2 H CH3 CF3CF2CF2 B24 0
No. A269 CH3S02CH2 H CH3 CF3CF2CF2. B24 0
A272 CH3CH2 H CH3 CF2CI B24 0
A273 cyclopropyl H CH3 CF2CI B24 0
A274 (CH3) 3C H CH3 CF2CI B24 0
A275 (CH3) 2CH H CH3 CF2CI B24 0
A276 CHs (CH2) 2 H CH3 CF2CI B24 0
A277 CH3OCH2 H CH3 CF2CI B24 0
A278 CH30 (CH2) 2 H CH3 CF2CI B24 0
A279 Ph H CH3 CF2CI B24 0
A280 PhO H CH3 CF2CI B24 0
A281 PhS H CH3 CF2CI B24 0
A282 PhSO H CH3 CF2CI B24 0
A283 PhS02 H CH3 CF2CI B24 0
A284 CH3S H CH3 CF2CI B24 0
A285 CH3SO H CH3 CF2CI B24 0
A286 CF3 H CH3 CF2CI B24 0
A287 F2CH H CH3 CF2CI B24 0
A288 HCC H CH3 CF2CI B24 0
A289 CH3CC H CH3 CF2CI B24 0
A290 CH2 = CH H CH3 CF2CI B24 0
A291 CH2 = CHCH2 H CH3 CF2CI - B24 0
A292 CH3S02N (CH3) H CH3 CF2CI B24 0
A293 (CH3) 2N H CH3 CF2CI B24 0
A294 (CH3) 2NS02 H CH3 CF2CI B24 0
A295 CICH2 H CH3 CF2CI B24 0
A296 CHsSCH2 H CH3 CF2CI B24 0
A297 CH3SOCH2 H CH3 CF2CI B24 0
A298 CHsS02CH2 H CH3 CF2CI B24 0
A299 H H CH3 CHF2 B24 0
A300 CH3 H CH3 CHF2 B24 0
Comp. R2 R4 Q1 P
No. A301 CHsCH2 H CH3 CHF2 B24 0
A302 cyclopropyl H CH3 CHF2 B24 0
A303 (CH3) 3C H CH3 CHF2 B24 0
A304 (CH3) 2CH H CH3 CHF2 B24 0
A305 CHs (CH2) 2 H CH3 CHF2 B24 0
A306 CH3OCH2 H CH3 CHF2 B24 0
A307 CH30 (CH2) 2 H CH3 CHF2 B24 0
A308 Ph H CH3 CHF2 B24 0
A309 PhO H CH3 CHF2 B24 0
A310 PhS H CH3 CHF2 B24 0
PhSO H CH3 CHF2 B24 0
A31 1 A312 PhS02 H CH3 CHF2 B24 0
A313 CH3S H CH3 CHF2 B24 0
A314 CH3SO H CH3 CHF2 B24 0
A315 CF3 H CH3 CHF2 B24 0
A316 F2CH H CH3 CHF2 B24 0
A317 HCC H CH3 CHF2 B24 0
A318 CH3CC H CH3 CHF2 B24 0
A319 CH2 = CH H CH3 CHF2 B24 0
A320 CH2 = CHCH2 H CH3 CHF2 B24 0
A321 CH3S02N (CH3) H CH3 CHF2 B24 0
A322 (CH3) 2N H CH3 CHF2 B24 0
A323 (CH3) 2NS02 H CH3 CHF2 B24 0
A324 CICH2 H CH3 CHF2 B24 0
A325 CH3SCH2 H CH3 CHF2 B24 0
A326 CH3SOCH2 H CH3 CHF2 B24 0
A327 CH3S02CH H CH3 CHF2 B24 0
A330 CHs H2 H CH3 CCI3 B24 0
A332 (CH3) 2CH H CH3 CCI3 B24 0
Comp. R2 FU Q1 P
No. A333 cyclopropyl H CH3 CCI3 B24 0
A334 CH3 (CH2) 2 H CH3 CCI3 B24 0
A335 CH3OCH2 H CH3 CCI3 B24 0
A336 CH30 (CH2) 2 H CH3 CCI3 B24 0
A337 Ph H CH3 CCI3 B24 0
A338 PhO H CH3 CCI3 B24 0
A341 PhS02 H CH3 CCI3 B24 0
A342 CH3S H CH3 CCI3 B24 0
A346 HCC, H CH3 CCI3 B24 0
A347 CH3CC H CH3 CCI3 B24 0
A348 CH2 = CH H CH3 CCI3 B24 0
A349 CH2 = CHCH2 H CH3 CCI3 B24 0
A350 CH3S02N (CH3) H CH3 CCI3 B24 0
A351 (CH3) 2N H CH3 CCI3 B24 0
A352 (CH3) 2NS02 H CH3 CCI3 B24 0
A353 CICH2 H CH3 CCI3 B24 0
A354 CH3SCH2 H CH3 CCI3 B24 0
A355 CH3SOCH2 H CH3 CCI3 B24 0
A356 CH3S02CH2 H CH3 CCI3 B24 0
A357 H H Ph CF3 B24 0
A358 CH3 H Ph CF3 B24 0
A359 CH3CH2 H Ph CF3 B24 0
A360 cyclopropyl H Ph CF3 B24 0
A361 (CH3) 3C H Ph CF3 B24 0
A362 (CH3) 2CH H Ph CF3 B24 0
A363 CH3 (CH2) 2 H Ph CF3 B24 0
A364 CH3OCH2 H Ph CF3 B24 0
Comp. R2 R3 F Rs Qi P
No. A365 CH30 (CH2) 2 H Ph CF3 B24 0
A366 Ph H Ph CF3 B24 0
A367 PhO H Ph CF3 B24 0
A368 PhS H Ph CF3 B24 0
A369 PhSO H Ph CF3 B24 0
A370 PhS02 H Ph CF3 B24 0
A371 CH3S H Ph CF3 B24 0
A372 CH3SO H Ph CF3 B24 0
A373 CF3 H Ph CF3 B24 0
A374 F2CH H Ph CF3 B24 0
A375 HCC H Ph CF3 B24 0
A376 CH3CC H Ph CF3 B24 0
A377 CH2 = CH H Ph CF3 B24 0
A378 CH2 = CHCH2 H Ph CF3 B24 0
A379 CH3S02N (CH3) H Ph CF3 B24 0
A380 (CH3) 2N H Ph CF3 B24 0
A381 (CH3) 2NS02 H Ph CF3 B24 0
A382 CICH2 H Ph CF3 B24 0
A383 CH3SCH2 H Ph CF3 B24 0
A384 CH3SOCH2 H Ph CF3 B24 0
A385 CH3S? 2CH2 H Ph CF3 B24 0
A386 H H Ph CF3CF2 B24 0
A387 CH3 H Ph CF3CF2 B24 0
A388 CH3CH2 H Ph CF3CF2 B24 0
A389 cyclopropyl H Ph CF3CF2 B24 0
A390 (CH3) 3C H Ph CF3CF2 B24 0
A391 (CH3) 2CH H Ph CF3CF2 B24 0
A392 CH3 (CH2) 2 H Ph CF3CF2 B24 0
A393 CH3OCH2 H Ph CF3CF2 B24 0
A394 CH30 (CH2) 2 H Ph CF3CF2 B24 0
A395 Ph H Ph CF3CF2 B24 0
A396 PhO H Ph CF3CF2 B24 0
Comp. R2 R3 R4 Q1 P
No. A397 PhS H Ph CF3CF2 B24 0
A398 PhSO H Ph CF3CF2 B24 0
A399 PhS02 H Ph CF3CF2 B24 0
A400 CH3S H Ph CF3CF2 B24 0
A401 CH3SO H Ph CF3CF2 B24 0
A402 CF3 H Ph CF3CF2 B24 0
A403 F2CH H Ph CF3CF2 B24 0
A404 HCC H Ph CF3CF2 B24 0
A405 CH3CC H Ph CF3CF2 B24 0
A406 CH2 = CH H Ph CF3CF2 B24 0
A407 CH2 = CHCH2 H Ph CF3CF2 B24 0
A408 CH3S02N (CH3) H Ph CF3CF2 B24 0
A409 (CH3) 2N H Ph CF3CF2 B24 0
A410 (CH3) 2NS02 H Ph CF3CF2 B24 0
A411 CICH2 H Ph CF3CF2 B24 0
A412 CH3SCH2 H Ph CF3CF2 B24 0
A413 CH3SOCH2 H Ph CF3CF2 B24 0
A414 CH3S? 2CH2 H Ph CF3CF2 B24 0
A415 H H Ph CF3CF2CF2 B24 0
A416 CH3 H Ph C F3C F2C F B24 0
A417 L / 1 I3CH2 H Ph CF3CF2CF2 B24 0
A418 cyclopropyl H Ph 3 2 r2 B24 0
A419 (CH3) 3C H Ph C F3C F2C F2 B24 0
A420 (CH3) 2CH H Ph C F3C F C F2 B24 0
A421 CH3 (CH2) 2 H Ph C F3C F2C F2 B24 0
A422 CH3OCH2 H Ph CF3CF2CF2 B24 0
A423 CH30 (CH2) 2 H Ph C F3C F2C F B24 0
A424 Ph H Ph CF3CF2CF2 B24 0
A425 PhO H Ph C F3C F2C F2 B24 0
A426 PhS H Ph C F3C F2C F2 B24 0
A427 PhSO H Ph CF3CF2CF2 B24 0
A428 PhSOz H Ph C F3C F2C F2 B24 0
Comp. R2 R3 R4 Qi P
No. A429 CH3S H Ph CF3CF2CF2 B24 0
A430 CH3SO H Ph CF3CF2CF2 B24 0
A431 CF3 H Ph CF3CF2CF2 B24 0
A432 F2CH H Ph CF3CF2CF2 B24 0
A433 HCC H Ph CF3CF2CF2 B24 0
A434 CH3CC H Ph CF3CF2CF2 B24 0
A435 CH2 = CH H Ph CF3CF2 F2 B24 0
A437 CH3S02N (CH3) H Ph CF3CF2CF2 B24 0
A438 (CH3) 2N H Ph C F3C F2C F B24 0
A439 (CH3) 2NS02 H Ph CF3CF2CF2 B24 0
A440 CICH2 H Ph CF3CF2CF2 B24 0
A441 CH3SCH2 H Ph CF3CF2CF B24 0
A442 CH3SOCH2 H Ph C F3C F2C F2 B24 0
A443 CH3S02CH2 H Ph CF3CF2CF2 B24 0
A444 H H Ph CF2CI B24 0
A445 CH3 H Ph CF2CI B24 0
A446 CH3CH H Ph CF2CI B24 0
A447 cyclopropyl H Ph CF2CI B24 0
A448 (CH3) 3C H Ph CF2CI B24 0
A449 (CH3) 2CH H Ph CF2CI B24 0
A450 CH3 (CH2) 2 H Ph CF2CI B24 0
A451 CH3OCH2 H Ph CF2CI - B24 0
A452 CH30 (CH2) 2 H Ph CF2CI B24 0
A453 Ph H Ph CF2CI B24 0
A454 PhO H Ph CF2CI B24 0
A455 PhS H Ph CF2CI B24 0
A456 PhSO H Ph CF2CI B24 0
A457 PhS02 H Ph CF2CI B24 0
A458 CH3S H Ph CF2CI B24 0
A459 CH3SO H Ph CF2CI B24 0
A460 CF3 H Ph CF2CI B24 0
Comp. R2 R4 Rs Qi P
No. A461 F2CH H Ph CF2CI B24 0
A462 HCC H Ph CF2CI B24 0
A463 CH3CC H Ph CF2CI B24 0
A464 CH2 = CH H Ph CF2CI B24 0
A465 CH2 = CHCH2 H Ph CF2CI B24 0
A466 CH3S02N (CH3) H Ph CF2CI B24 0
A467 (CH3) 2N H Ph CF2CI B24 0
A468 (CH3) 2NS02 H Ph CF2CI B24 0
A469 CICH2 H Ph CF2CI B24 0
A470 CH3SCH2 H Ph CF2CI B24 0
A471 CH3SOCH2 H Ph CF2CI B24 0
A472 CH3S02CH2 H Ph CF2CI B24 0
A473 H H Ph CHF2 B24 0
A474 CH3 H Ph CHF2 B24 0
A475 CH3CH2 H Ph CHF2 B24 0
A476 cyclopropyl H Ph CHF2 B24 0
A477 (CH3) 3C H Ph CHF2 B24 0
A478 (CH3) 2CH H Ph CHF2 B24 0
A479 CH3 (CH2) 2 H Ph CHF2 B24 0
A480 CH3OCH2 H Ph CHF2 B24 0
A481 CH30 (CH2) 2H Ph CHF2 B24 0
A482 Ph H Ph CHF2 B24 0
A483 PhO H Ph CHF2 - B24 0
A484 PhS H Ph CHF2 B24 0
A485 PhSO H Ph CHF2 B24 0
A486 PhSOz H Ph CHF2 B24 0
A487 CH3S H Ph CHF2 B24 0
A488 CH3SO H Ph CHF2 B24 0
A489 CF3 H Ph CHF2 B24 0
A490 F2CH H Ph CHF2 B24 0
A491 HCC H Ph CHF2 B24 0
A492 CH3CC H Ph CHF2 B24 0
Comp. R2 R4 R5 Qi P
No. A493 CH2 = CH H Ph CHF2 B24 0
A494 CH2 = CHCH2 H Ph CHF2 B24 0
A495 CH3S02N (CH3) H Ph CHF2 B24 0
A496 (CH3) 2N H Ph CHF2 B24 0
A497 (CH3) 2NS02 H Ph CHF2 B24 0
A498 CICH2 H Ph CHF2 B24 0
A499 CH3SCH2 H Ph CHF2 B24 0
A500 CH3SOCH2 H Ph CHF2 B24 0
A501 CH3S02CH2 H Ph CHF2 B24 0
A502 H H Ph CCI3 B24 0
A503 CH3 H Ph CCI3 B24 0
A504 CH3CH2 H Ph CCI3 B24 0
A505 cyclopropyl H Ph CCI3 B24 0
A506 (CH3) 3C H Ph CCI3 B24 0
A507 (CH3) 2CH H Ph CCI3 B24 0
A508 CH3 (CH2) 2 H Ph CCI3 B24 0
A509 CH3OCH2 H Ph CCI3 B24 0
A510 CH30 (CH2) 2 H Ph CCI3 B24 0
A511 Ph H Ph CCI3 B24 0
A512 PhO H Ph CCI3 B24 0
A513 PhS H Ph CCI3 B24 0
A514 PhSO H Ph CCI3 B24 0
A515 PhS02 H Ph CCI3 B24 0
A516 CH3S H Ph CCI3 B24 0
A517 CH3SO H Ph CCI3 B24 0
A518 CF3 H Ph CCI3 B24 0
A519 F2CH H Ph CCI3 B24 0
A520 HCC H Ph CCI3 B24 0
A521 CH3CC H Ph CCI3 B24 0
A522 CH2 = CH H Ph CCI3 B24 0
A523 CH2 = CHCH2 H Ph CCI3 B24 0
A524 CH3S02N (CH3) H Ph CCI3 B24 0
Comp. R2 R3 R4 Rs Q1 P
No. A525 (CH3) 2N H Ph CCI3 B24 0
A526 (CH3) 2NSOz H Ph CCI3 B24 0
A527 CICH2 H Ph CCI3 B24 0
A528 CH3SCH2 H Ph CCI3 B24 0
A529 CH3SOCH2 H Ph CCI3 B24 0
A530 CH3S02CH2 H Ph CCI3 B24 0
A531 H CH3 H CF3 B24 0
A532 H CH3CH2 H CF3 B24 0
A533 H cyclopropyl H CF3 B24 0
A534 H (CH3) 3CH H CF3 B24 0
A535 H (CH3) 2CH H CF3 B24 0
A536 H CH3 (CH2) 2 H CF3 B24 0
A537 H CH3OCH2 H CF3 B24 0
A538 H CH30 (CH2) 2 H CF3 B24 0
A539 H Ph H CF3 B24 0
A540 H PhO H CF3 B24 0
A541 H PhS H CF3 B24 0
A542 H PhSO H CF3 B24 0
A543 H PhS02 H CF3 B24 0
A544 H CH3S H CF3 B24 0
A545 H CH3SO H CF3 B24 0
A546 H CF3 H CF3 B24 0
A547 H F2CH H CF3 - B24 0
A548 H HCC H CF3 B24 0
A549 H CH3CC H CF3 B24 0
A550 H CH2 = CH H CF3 B24 0
A551 H CH2 = CHCH2 H CF3 B24 0
A552 H CH3S02N (CH3) H CF3 B24 0
A553 H (CH3) 2N H CF3 B24 0
A554 H (CH3) 2NS02 H CF3 B24 0
A555 H CH3SCH2 H CF3 B24 0
A556 H CH3SOCH2 H CF3 B24 0
Comp. R2 R4 Rs Qi P No. A557 H CH3S02CH2 H CF3 B24 0 A558 H CH3 H CF3CF2 B24 0 A559 H CH3CH2 H CF3CF2 B24 0 A560 H cyclopropyl H CF3CF2 B24 0 A561 H (CH3) 3C H CF3CF2 B24 0 A562 H (CH3) 2CH H CF3CF2 B24 0 A563 H CH3 (CH2) 2 H CF3CF2 B24 0 A564 H CH3OCH2 H CF3CF2 B24 0 A565 H CH30 (CH2) 2 H CF3CF2 B24 0 A566 H Ph H CF3CF2 B24 0 A567 H PhO H CF3CF2 B24 0 A568 H PhS H CF3CF2 B24 0 A569 H PhSO H CF3CF2 B24 0 A570 H PhS02 H CF3CF2 B24 0 A571 H CH3S H CF3CF2 B24 0 A572 H CH3SO H CF3CF2 B24 0 A573 H CF3 H CF3CF2 B24 0 A574 H F2CH H CF3CF2 B24 0 A575 H HCC H CF3CF2 B24 0 A576 H CH3CC H CF3CF2 B24 0 A577 H CH2 = CH H CF3CF2 B24 0 A578 H CH2 = CHCH2 H CF3CF2 B24 0 A579 H H3S02N (CH3) H CF3CF2 - B24 0 A580 H (CH3) 2N H CF3CF2 B24 0 A581 H (CH3) 2NS02 H CF3CF2 B24 0 A582 H CH3SCH2 H CF3CF2 B24 0 A583 H CH3SOCH2 H CF3CF2 B24 0 A584 H CH3S02CH2 H CF3CF2 B24 0 A585 H CH3 HC F3C F2C F2 B24 0 A586 H CH3CH2 HC F3C FC F2 B24 0 A587 H cyclopropyl H CF3CF2CF2 B24 0 A588 H (CH3) 3C H 3 F2C 2 B24 0
Comp. R2 R3 R4 H5 U, p
No. A589 H (CH3) 2CH H CF3CF2CF2 B24 0
A590 H CH3 (CH2) 2 H CF3CF2CF2 B24 0
A591 H CH3OCH2 H CF3CF2CF2 B24 0
A592 H CH30 (CH2) 2 H CF3CF2CF2 B24 0
A593 H Ph H CF3CF2CF2 B24 0
A594 H PhO H CF3CF2CF2 B24 0
A595 H PhS H CF3CF2CF2 B24 0
A596 H PhSO H CF3CF2CF2 B24 0
A597 H PhS02 H CF3CF2CF2 B24 0
A598 H CH3S H CF3CF2CF2 B24 0
A599 H CH3SO H CF3CF2CF2 B24 0
A600 H CF3 H CF3CF2CF2 B24 0
A601 H F2CH H CF3CF2CF2 B24 0
A602 H HCC H CF3CF2CF2 B24 0
A603 H CH3CC H CF3CF2CF2 B24 0
A604 H CH ^ CH H CF3CF2CF2 B24 0
A605 H CH2 = CHCH2 H CF3CF2CF2 B24 0
A606 H CH3S02N (CH3) H CF3CF2CF2 B24 0
A607 H (CH3) 2N H CF3CF2CF2 B24 0
A608 H (CH3) 2NS02 H CF3CF2CF2 B24 0
A609 H CH3SCH2 H CF3CF2CF2 B24 0
A610 H CH3SOCH2 H CF3CF2CF2 B24 0
A61 1 H CH3S02CH2 H CF3CF2CF2 B24 0
A612 H CH3 H CF2CI B24 0
A613 H CH3CH2 H CF2CI B24 0
A614 H cyclopropyl H CF2CI B24 0
A615 H (CH3) 3C H CF2CI B24 0
A616 H (CH3) 2CH H CF2CI B24 0
A617 H CH3 (CH2) 2 H CF2CI B24 0
A618 H CH3OCH2 H CF2CI B24 0
A619 H CH30 (CH2) 2 H CF2CI B24 0
A620 H Ph H CF2CI B24 0
Comp. R2 R3 R4 Rs Q1 P
No. A621 H PhO H CF2CI B24 0
A622 H PhS H CF2CI B24 0
A623 H PhSO H CF2CI B24 0
A624 H PhS02 H CF2CI B24 0
A625 H CH3S H CF2CI B24 0
A626 H CH3SO H CF2CI B24 0
A627 H CF3 H CF2CI B24 0
A628 H F2CH H CF2CI B24 0
A629 H HCC H CF2CI B24 0
A630 H CH3CC H CF2CI B24 0
A631 H CH2 = CH H CF2CI B24 0
A632 H CH2 = CHCH2 H CF2CI B24 0
A633 H CH3S02N (CH3) H CF2CI B24 0
A634 H (CH3) 2N H CF2CI B24 0
A635 H (CH3) 2NS02 H CF2CI B24 0
A636 H CH3SCH2 H CF2CI B24 0
A637 H CH3SOCH2 H CF2CI B24 0
A638 H CH3S02CH2 H CF2CI B24 0
A639 H CH3 H CHF2 B24 0
A640 H CH3CH2 H CHF2 B24 0
A641 H cyclopropyl H CHF2 B24 0
A642 H (CH3) 3C H CHF2 B24 0
A643 H (CH3) 2CH H CHF2 B24 0
A644 H CH3 (CH2) 2 H CHF2 B24 0
A645 H CH3OCH2 H CHF2 B24 0
A646 H CH30 (CH2) 2 H CHF2 B24 0
A647 H Ph H CHF2 B24 0
A648 H PhO H CHF2 B24 0
A649 H PhS H CHF2 B24 0
A650 H PhSO H CHF2 B24 0
A651 H PhSOz H CHF2 B24 0
A652 H CH3S H CHF2 B24 0
Comp. R2 R4 Rs Qi P No. A653 H CH3SO H CHF2 B24 0 A654 H CF3 H CHF2 B24 0 A655 H F2CH H CHF2 B24 0 A656 H HCC H CHF2 B24 0 A657 H CH3CC H CHF2 B24 0 A658 H CH2 = CH H CHF2 B24 0 A659 H CH2 = CHCH2 H CHF2 B24 0 A660 H CH3S02N (CH3) H CHF2 B24 0 A661 H (CH3) 2N H CHF2 B24 0 A662 H (CH3) 2NS02 H CHF2 B24 0 A663 H CH3SCH2 H CHF2 B24 0 A664 H CH3SOCH2 H CHF2 B24 0 A665 H CH3S02CH2 H CHF2 B24 0 A666 H CH3 H CCI3 B24 0 A667 H CH3CH2 H CCI3 B24 0 A668 H cyclopropyl H CCI3 B24 0 A669 H (CH3) 3C H CCI3 B24 0 A670 H (CH3) 2CH H CCI3 B24 0 A671 H CH3 (CH2) 2 H CCI3 B24 0 A672 H CH3OCH2 H CCI3 B24 0 A673 H CH30 (CH2) 2 H CCI3 B24 0
A679 H CH3S H CCI3 B24 0
A681 H CF3 H CCI3 B24 0 A682 H F2CH H CCI3 B24 0
A684 H CH3CC H CCI3 B24 0
Comp. R2 R4 Rs Qi P No.
A686 H CH2 = CHCH2 H CC B24 0 A687 H CH3S02N (CH3) H CCI3 B24 0 A688 H (CH3) 2N H CCI3 B24 0 A689 H (CH3) 2NS02 H CCI3 B24 0 A690 H CHsSCH2 H CCI3 B24 0 A691 H CH3SOCH2 H CCI3 B24 0 A692 H CH3S02CH2 H CCI3 B24 0 A693 H CH3 CH3 CF3 B24 0 A694 H CHsCH2 CH3 CF3 B24 0 A695 H cyclopropyl CH3 CF3 B24 0 A696 H (CH3) 3C CH3 CF3 B24 0 A697 H (CH3) 2CH CH3 CF3 B24 0 A698 H CHs (CH2) 2 CH3 CF3 B24 0 A699 H CH30CH2 CH3 CF3 B24 0 A700 H CH30 (CH2) 2 CH3 CF3 B24 0 A701 H Ph CH3 CF3 B24 0 A702 H PhO CH3 CF3 B24 0 A703 H PhS CH3 CF3 B24 0 A704 H PhSO CH3 CF3 B24 0 A705 H PhS02 CH3 CF3 B24 0 A706 H CH3S CH3 CF3 B24 0 A707 H CH3SO CH3 CF3 - B24 0 A708 H CF3 CH3 CF3 B24 0 A709 H F2CH CH3 CF3 B24 0 A710 H HCC CH3 CF3 B24 0 A711 H CH3CC CH3 CF3 B24 0 A712 H CH2 = CH CH3 CF3 B24 0
A714 H CH3S02N (CH3) CH3 CF3 B24 0 A715 H (CH3) 2N CH3 CF3 B24 0 A716 H (CH3) 2NS02 CH3 CF3 B24 0
Comp. R4 Q1 P No. A717 H CH3SCH2 CH3 CF3 B24 0 A718 H CH3SOCH2 CH3 CF3 B24 0 A719 H CH3S02CH2 CH3 CF3 B24 0 A720 H CH3 CH3 CF3CF2 B24 0 A721 H CH3CH2 CH3 CF3CF2 B24 0 A722 H cyclopropyl CH3 CF3CF2 B24 0 A723 H ( CH3) 3C CH3 CF3CF2 B24 0 A724 H (CH3) 2CH CH3 CF3CF2 B24 0 A725 H CH3 (CH2) 2 CH3 CF3CF2 B24 0 A726 H CH3OCH2 CH3 CF3CF2 B24 0 A727 H CH30 (CH2) 2 CH3 CF3CF2 B24 0 A728 H Ph CH3 CF3CF2 B24 0 A729 H PhO CH3 CF3CF2 B24 0 A730 H PhS CH3 CF3CF2 B24 0 A731 H PhSO CH3 CF-3CF2 B24 0 A732 H PhS02 CH3 CF3CF2 B24 0 A733 H CH3S CH3 CF3CF2 B24 0 A734 H CH3SO CH3 CF3CF2 B24 0 A735 H CF3 CH3 CF3CF2 B24 0 A736 H F2CH CH3 CF3CF2 B24 0 A737 H HCC CH3 CF3CF2 B24 0 A738 H CH3CC CH3 CF3CF2 B24 0 A739 H CH2 = CH CH3 CF3CF2 - B24 0 A740 H CH2 = CHCH2 CH3 CF3CF2 B24 0 A741 H CH3S02N (CH3) CH3 CF3CF2 B24 0 A742 H (CH3) 2N CH3 CF3CF2 B24 0 A743 H (CH3) 2NS02 CH3 CF3CF2 B24 0 A744 H CH3SCH2 CH3 CF3CF2 B24 0 A745 H CH3SOCH2 CH3 CF3CF2 B24 0 A746 H CH3S02CH2 CH3 CF3CF2 B24 0 A747 H CH3 CH3 C F3C F2C F2 B24 0 A748 H CH3CH2 CH3 C F3C F2C F2 B24 0
Comp. R? R4 Qi P No. A749 H cyclopropyl CH3 CF3CF2CF2 B24 0 A750 H (CH3) 3C CH3 CF3CF2CF2 B24 0 A751 H (CH3) 2CH CH3 CF3CF2CF2 B24 0 A752 H CH3 (CH2) 2 CH3 CF3CF2CF2 B24 0 A753 H CH3OCH2 CH3 rr3O? 2 (- I 2 B24 0 A754 H CH30 (CH2) 2 CH3 CF3CF2CF2 B24 0 A755 H Ph CH3 CF3CF2CF2 B24 0 A756 H PhO CH3 F3C r2L »? 2 B24 0 A757 H PhS CH3 CF3CF2CF2 B24 0 A758 H PhSO CH3 C 3CF2 F2 B24 0 A759 H PhS02 CH3 CF3CF2CF2 B24 0 A760 H CH3S CH3 CF3CF2CF2 B24 0 A761 H CH3SO CH3 CF3CF2CF2 B24 0 A762 H CF3 CH3 CF3CF2CF2 B24 0 A763 H F2CH CH3 C F3C F2 F2 B24 0 A764 H HCC CH3 CF3CF2CF2 B24 0 A765 H CH3CC CH3 C F3C F2C F2 B24 0 A766 H CH2 = CH CH3 Cr3 F2 (- * F2 B24 0 A767 H CH2 = CHCH2 CH3 CF3CF2CF2 B24 0 A768 H CH3S02N (CH3) CH3 CF3CF2CF2 B24 0 A769 H (CH3) 2N CH3 CF3CF2CF2 B24 0 A770 H (CH3) 2NS02 CH3 CF3CF2CF2 B24 0 A771 H CH3SCH2 CH3 CF3CF2CF2 B24 0 A772 H CH3SOCH2 CH3 C F3C F2C F2 B24 0 A773 H CH3S02CH2 CH3 C F3C F2C F2 B24 0 A774 H CH3 CH3 CF2CI B24 0 A775 H CH3CH2 CH3 CF2CI B24 0 A776 H cyclopropyl CH3 CF2CI B24 0 A777 H (CH3) 3C CH3 CF2CI B24 0 A778 H (CH3) 2CH CH3 CF2CI B24 0 A779 H CH3 (CH2) 2 CH3 CF2CI B24 0 A780 H CH3OCH2 CH3 CF2CI B24 0
Comp. R2 R3 R4 Rs Qi p
No. A781 H CH30 (CH2) 2 CH3 CF2CI B24 0
A782 H Ph CH3 CF2CI B24 0
A783 H PhO CH3 CF2CI B24 0
A784 H PhS CH3 CF2CI B24 0
A785 H PhSO CH3 CF2CI B24 0
A786 H PhS02 CH3 CF2CI B24 0
A787 H CH3S CH3 CF2CI B24 0
A788 H CH3SO CH3 CF2CI B24 0
A789 H CF3 CH3 CF2CI B24 0
A790 H F2CH CH3 CF2CI B24 0
A791 H HCC CH3 CF2CI B24 0
A792 H CH3CC CH3 CF2CI B24 0
A793 H CH2 = CH CH3 CF2CI B24 0
A794 H CH2 = CHCH2 CH3 CF2CI B24 0
A795 H CH3S02N (CH3) CH3 CF2CI B24 0
A796 H (CH3) 2N CH3 CF2CI B24 0
A797 H (CH3) 2NS02 CH3 CF2CI B24 0
A798 H CH3SCH2 CH3 CF2CI B24 0
A799 H CH3SOCH2 CH3 CF2CI B24 0
A800 H CH3S02CH2 CH3 CF2CI B24 0
A801 H CH3 CH3 CHF2 B24 0
A802 H CH3CH2. CH3 CHF2 B24 0
A803 H cyclopropyl CH3 CHF2 - B24 0
A804 H (CH3) 3C CH3 CHF2 B24 0
A805 H (CH3) 2CH CH3 CHF2 B24 0
A806 H CH3 (CH2) 2 CH3 CHF2 B24 0
A807 H CH3OCH2 CH3 CHF2 B24 0
A808 H CH30 (CH2) 2 CH3 CHF2 B24 0
A809 H Ph CH3 CHF2 B24 0
A810 H PhO CH3 CHF2 B24 0
A811 H PhS CH3 CHF2 B24 0
A812 H PhSO CH3 CHF2 B24 0
24?
Comp. Rs Qi P No. A813 H PhS02 CH3 CHF2 B24 0 A814 H CH3S CH3 CHF2 B24 0 A815 H CH3SO CH3 CHF2 B24 0 A816 H CF3 CH3 CHF2 B24 0 A817 H F2CH CH3 CHF2 B24 0 A818 H HCC CH3 CHF2 B24 0 A819 H CH3CC CH3 CHF2 B24 0 A820 H CH2 = CH CH3 CHF2 B24 0 A821 H CH2 = CHCH2 CH3 CHF2 B24 0 A822 H CH3S02N (CH3) CH3 CHF2 B24 0 A823 H (CH3) 2N CH3 CHF2 B24 0 A824 H (CH3) 2NS02 CH3 CHF2 B24 0 A825 H CH3SCH2 CH3 CHF2 B24 0 A826 H CH3SOCH2 CH3 CHF2 B24 0 A827 H CH3S02CH2 CH3 CHF2 B24 0
A829 H CH3CH2 CH3 CCI3 B24 0 A830 H cyclopropyl CH3 CCI3 B24 0 A831 H (CH3) 3C CH3 CCI3 B24 0 A832 H (CH3) 2CH CH3 CCI3 B24 0 A833 H CHs (CH2) 2 CH3 CCI3 B24 0 A834 H CH3OCH2 CH3 CCI3 B24 0 A835 H CH30 (CH2) 2 CH3 CCI3 - B24 0 A836 H Ph CH3 CCI3 B24 0 A837 H PhO CH3 CCI3 B24 0 A838 H PhS CH3 CCI3 B24 0 A839 H PhSO CH3 CCI3 B24 0 A840 H PhS02 CH3 CCI3 B24 0 A841 H CH3S CH3 CCI3 B24 0 A842 H CH3SO CH3 CCI3 B24 0 A843 H CF3 CH3 CCI3 B24 0 A844 H F2CH CH3 CCI3 B24 0
Comp. R2 R4 Rs Q1 P No.
A846 H CH3CC CH3 CCI3 B24 0 A847 H CH2 = CH CH3 CCI3 B24 0 A848 H CH2 = CHCH2 CH3 CCI3 B24 0 A849 H CH3S02N (CH3) CH3 CCI3 B24 0 A850 H (CH3) 2N CH3 CCI3 B24 0 A851 H (CH3) 2NS02 CH3 CCI3 B24 0 A852 H CH3SCH2 CH3 CCI3 B24 0 A853 H CH3SOCH2 CH3 CCI3 B24 0 A854 H CH3S02CH2 CH, CCI3 B24 0 A855 H CH3 Ph CF3 B24 0 A856 H CH3CH2 Ph CF3 B24 0 A857 H (CH3) 2CH Ph CF3 B24 0 A858 H (CH3) 2CH Ph CF3 B24 0 A859 H cyclopropyl Ph CF3 B24 0 A860 H CH3 (CH2) 2 Ph CF3 B24 0 A861 H CH3OCH2 Ph CF3 B24 0 A862 H CH30 (CH2) 2 Ph CF3 B24 0 A863 H Ph Ph CF3 B24 0 A864 H PhO Ph CF3 B24 0 A865 H PhS Ph CF3 B24 0 A866 H PhSO Ph CF3 B24 0 A867 H PhS02 Ph CF3 B24 0 A868 H CH3S Ph CF3 B24 0 A869 H CH3SO Ph CF3 B24 0 A870 H CF3 Ph CF3 B24 0 A871 H F2CH Ph CF3 B24 0 A872 H HCC Ph CF3 B24 0 A873 H CH3CC Ph CF3 B24 0 A874 H CH2 = CH Ph CF3 B24 0 A875 H CH2 = CHCH2 Ph CF3 B24 0 A876 H CH3S02N (CH3) Ph CF3 B24 0
Comp. R2 R4 Rs Qi P No. A877 H (CH3) 2N Ph CF3 B24 0 A878 H (CH3) 2NS02 Ph CF3 B24 0 A879 H CH3SCH2 Ph CF3 B24 0 A880 H CH3S0CH2 Ph CF3 B24 0 A881 H CH3S02CH2 Ph CF3 B24 0 A882 H CH3 Ph CF3CF2 B24 0 A883 H CH3CH2 Ph CF3CF2 B24 0 A884 H cyclopropyl Ph CF3CF2 B24 0 A885 H (CH3) 3C Ph CF3CF2 B24 0 A886 H (CH3) 2CH Ph CF3CF2 B24 0 A887 H CH3 (CH2) 2 Ph CF3CF2 B24 0 A888 H CH3OCH2 Ph CF3CF2 B24 0 A889 H CH30 (CH2) 2 Ph CF3CF2 B24 0 A890 H Ph Ph CF3CF2 B24 0 A891 H PhO Ph CF3CF2 B24 0 A892 H PhS Ph CF3CF2 B24 0 A893 H PhSO Ph CF3CF2 B24 0 A894 H PhS02 Ph CF3CF2 B24 0 A895 H CH3S Ph CF3CF2 B24 0 A896 H CH3SO Ph CF3CF2 B24 0 A897 H CF3 Ph CF3CF2 B24 0 A898 H F2CH Ph CF3CF2 B24 0 A899 H HCC Ph CF3CF2 B24 0 A900 H CH3CC Ph CF3CF2 B24 0 A901 H CH2 = CH Ph CF3CF2 B24 0 A902 H CH2 = CHCH2 Ph CF3CF2 B24 0 A903 H CH3S02N (CH3) Ph CF3CF2 B24 0 A904 H (CH3) 2N Ph CF3CF2 B24 0 A905 H (CH3) 2NS02 Ph CF3CF2 B24 0 A906 H CH3SCH2 Ph CF3CF2 B24 0
A908 H CH3SO2CH2 Ph CF3CF2 B24 0
Comp. R2 R3 R4 Rs Q1 P
No. A909 H CH3 Ph CF3CF2CF2 B24 0
A910 H CH3CH2 Ph CF3CF2CF2 B24 0
A911 H cyclopropyl Ph CF3CF2CF2 B24 0
A912 H (CH3) 3C Ph CF3CF2CF2 B24 0
A913 H (CH3) 2CH Ph CF3CF2CF2 B24 0
A914 H CH3 (CH2) 2 Ph CF3CF2CF2 B24 0
A915 H CH3OCH2 Ph CF3CF2CF2 B24 0
A916 H CH3O (CH2) 2 Ph CF3CF2CF2 B24 0
A917 H Ph Ph CF3CF2CF2 B24 0
A918 H PhO Ph CF3CF2CF2 B24 0
A919 H PhS Ph CF3CF2CF2 B24 0
A920 H PhSO Ph CF3CF2CF2 B24 0
A921 H PhS02 Ph CF3CF2CF2 B24 0
A922 H CH3S Ph CF3CF2CF2 B24 0
A923 H CH3SO Ph CF3CF2CF2 B24 0
A924 H CF3 Ph CF3CF2CF2 B24 0
A925 H F2CH Ph CF3CF2CF2 B24 0
A926 H HCC Ph CF3CF2CF2 B24 0
A927 H CH3CC Ph CF3CF2CF2 B24 0
A928 H CH2 = CH Ph CF3CF2CF2 B24 0
A929 H CH2 = CHCH2 Ph CF3CF2CF2 B24 0
A930 H CH3S02N (CH3) Ph CF3CF2CF2 B24 0
A931 H (CH3) 2N Ph CF3CF2CF2 B24 0
A932 H (CH3) 2NS02 Ph CF3CF2CF2 B24 0
A933 H CH3SCH2 Ph CF3CF2CF2 B24 0
A934 H CH3SOCH2 Ph CF3CF2CF2 B24 0
A935 H CH3SO2CH2 Ph CF3CF2CF2 B24 0
A936 H CH3 Ph CF2CI B24 0
A937 H CH3CH2 Ph CF2CI B24 0
A938 H cyclopropyl Ph CF2CI B24 0
A939 H (CH3) 3C Ph CF2CI B24 0
A940 H (CH3) 2CH Ph CF2CI B24 0
No. CF2C B24 0 A941 H CH3 (CH2) 2 Ph CF2C B24 0 A942 H CH3OCH2 Ph A943 H CH30 (CH2) 2 Ph CF2C B24 0 A944 H Ph Ph CF2C B24 0 A945 H PhO Ph CF2C B24 0 A946 H PhS Ph CF2C B24 0 A947 H PhSO Ph CF2C B24 0 A948 H PhS02 Ph CF2C B24 0 A949 H CH3S Ph CF2C B24 0 A950 H CH3SO Ph CF2C B24 0 A951 H CF3 Ph CF2C B24 0 A952 H F2CH Ph CF2C B24 0 A953 H HCC Ph CF2C B24 0 A954 H CH3CC Ph CF2C B24 0 A955 H CH2 = CH Ph CF2C B24 0 A956 H CH2 = CHCH2 Ph CF2CI B24 0 A957 H CH3S02N (CH3) Ph CF2CI B24 0 A958 H (CH3) 2N Ph CF2C B24 0 A959 H (CH3 ) 2NS02 Ph CF2C B24 0 A960 H CH3SCH2 Ph CF2C B24 0 A961 H CH3SOCH2 Ph CF2CI B24 0 A962 H CH3S02CH2 Ph CF2C B24 0 A963 H CH3 Ph CHF2 B24 0 A964 H CH3CH2 Ph CHF2 B24 0 A965 H (CH3) 3C Ph CHF2 B24 0 A966 H (CH3) 2CH Ph CHF2 B24 0 A967 H cyclopropyl Ph CHF2 B24 0 A968 H CH3 (CH2) 2 Ph CHF2 B24 0 A969 H CH3OCH2 Ph CHF2 B24 0 A970 H CH30 (CH2) 2 Ph CHF2 B24 0 A971 H Ph Ph CHF2 B24 0 A972 H PhO Ph CHF2 B24 0
Comp. Rz R3 R4 Rs Qi P No. A973 H PhS Ph CHF2 B24 0 A974 H PhSO Ph CHF2 B24 0 A975 H PhS02 Ph CHF2 B24 0 A976 H CH3S Ph CHF2 B24 0 A977 H CH3SO Ph CHF2 B24 0 A978 H CF3 Ph CHF2 B24 0 A979 H F2CH Ph CHF2 B24 0 A980 H HCC Ph CHF2 B24 0 A981 H CH3CC Ph CHF2 B24 0 A982 H CH2 = CH Ph CHF2 B24 0 A983 H CH2 = CHCH2 Ph CHF2 B24 0 A984 H CH3S02N (CH3) Ph CHF2 B24 0 A985 H (CH3) 2N Ph CHF2 B24 0 A986 H (CH3) 2NS02 Ph CHF2 B24 0 A987 H CHsSCH2 Ph CHF2 B24 0 A988 H CH3SOCH2 Ph CHF2 B24 0 A989 H CH3S02CH2 Ph CHF2 B24 0
A991 H CHsCH2 Ph CCI3 B24 0 A992 H (CH3) 3C Ph CCI3 B24 0 A993 H (CH3) 2CH Ph CCI3 B24 0 A994 H cyclopropyl Ph CCI3 B24 0 A995 H CH3 (CH2) 2 Ph CCI3 - B24 0 A996 H CH3OCH2 Ph CCI3 B24 0 A997 H CH30 (CH2) 2 Ph CCI3 B24 0
A1002 H PhS02 Ph CCI3 B24 0
A 1004 H CH3SO Ph CCI3 B24 0
Comp. R2 R3 R4 Rs Q1 P
No. A1005 H CF3 Ph CCI3 B24 0
A1006 H F2CH Ph CCI3 B24 0
A 1007 H HCC Ph CCI3 B24 0
A1008 H CH3CC Ph CCI3 B24 0
A1009 H CH2 = CH Ph CCI3 B24 0
A1010 H CH2 = CHCH2 Ph CCI3 B24 0
A101 1 H CH3S02N (CH3) Ph CCI3 B24 0
A1012 H (CH3) 2N Ph CCI3 B24 0
A1013 H (CH3) 2NS02 Ph CCI3 B24 0
A1014 H CH3SCH2 Ph CCI3 B24 0
A1015 H CH3SOCH2 Ph CCI3 B24 0
A1016 H CH3S02CH2 Ph CCI3 B24 0
A1017 F H H CF3 B24 0
A1018 Cl H H CF3 B24 0
A1019 Br H H CF3 B24 0
A1020 NC H H CF3 B24 0
A1021 CH3S020 H H CF3 B24 0
A1022 CH30 H H CF3 B24 0
A 1023 CH3CH2O H H CF3 B24 0
A1024 CH2CH = CH20 H H CF3 B24 0
A1025 HCCCH2O H H CF3 B24 0
A1026 PhCH2S H H CF3 B24 0
A 1027 PhCH2S02 H H CF3 - B24 0
A 1028 CICH2CH2 H H CF3 B24 0
A1029 BrCH2 H H CF3 B24 0
A1030 FCH2 H H CF3 B24 0
A1031 CHF2CH2 H H CF3 B24 0
A1032 CF3CH2 H H CF3 B24 0
A 1033 [1.3] -imidazole-l- H H CF3 B24 0 ilmethyl A 1034 CHCI2CH2 H H CF3 B24 0
A1035 CICH = CH H H CF3 B24 0
Comp. R2 R3 R4 Rs Qi P
No. A103C CI2C = CH H CF3 B24 0
A1037 CF3CH = CH H CF3 B24 0
A103E CICC H H CF3 B24 0
A103S PhCH2 H H CF3 B24 0
A 1040 CH3CH2 CH3 H CF3 B24 0
A1041 CH3 OH H CF3 B24 0
A 1042 CH3 F H CF3 B24 0
A1043 CH3 Cl H CF3 B24 0
A1044 F CH3 H CF3 B24 0
A1045 Cl CH3 H CF3 B24 0
A1046 H F H CF3 B24 0
A1047 H Cl H CF3 B24 0
A 1048 H Br H CF3 B24 0
A 1049 H OH H CF3 B24 0
A 1050 H OCH3 H CF3 B24 0
A1051 H OCHF2 H CF3 B24 0
A1052 H OSO2CH3 H CF3 B24 0
A1053 H OS02CF3 H CF3 B24 0
A1054 H CICH2 H - CF3 B24 0
A1055 H BrCH2 H CF3 B24 0
A 1056 H FCH2 H CF3 B24 0
A 1057 H CHF2CH2 H CF3 B24 0
A 1058 H CF3CH2 H CF3 - B24 0
A1059 H tpazohmethyl H CF3 B24 0
At 1060 H CHCI2CH2 H CF3 B24 0
A1061 H CICH = CH H CF3 B24 0
A 1062 H CI2C = CH H CF3 B24 0
A 1063 H CF3CH = CH H CF3 B24 0
A 1064 H CICC H CF3 B24 0
A1065 H CH3C (0) H CF3 B24 0
A 1066 H Ph H CF3 B24 0
A1067 H SO2CH3 H CF3 B24 0
oooooooooo Tf Tf Tf "vt f Tf t Tf Tf Tf Tf Tf Tf Tf Tf t T t Tf Tf Tf Tf sm CM OW CM CM OW CM Ol CM CM OJ OJ Ol Ol OJ Ol OJ Ol Ol OJ CM Ol CM Q? CQ CQ CQQ CCQQ CQ CQ CQ CQ CQ CQ CQ CQ CQ CQ CQ CQ
LL LL LL LL LL LL LL
O O O O O O O O O O O O O P P P P P P
is X X X LL or CQ ° XB W X, S _ £? S t T X X T X X X X - o1- or - X X o o
LL o or O X X X X X X X X X X X X X X X or C? z
t-L CO CD | v r. (v | v rv rv tv v f rv oo 8 s e -i o o o 8 8 o o o o o o o o ro o 8 o o o o o o o o O o o o O O Z o o < < < < < < < < < < < < < < < < < <
Comp. H2"s P. Qi P
No. A1091 cyclopropyl-CH2 H H CF3 B24 0
A1092 2.2-d? Chlorocycloprop- 1 - H H CF3 B24 0 ilo A1093 CH3OC (0) CH = CH H H CF3 B24 0
A1094 CH3CH2OC (0) CH = CH H CF3 B24 0
A1095 CICH2CH = CH H CF3 0
A1096 CH = C = CH H H CF3 B24 0
A1097 (CH3) 2NCH2 H H CF3 B24 0
A1098 HOCH2 H H CF3 B24 0
A1099 CH3C (0) OCH2 H H CF3 B24 0
A1100 PhC (0) OCH2 H H CF3 B24 0
A1101 PhCH2CH2 H H CF3 B24 0
A1102 CH3OC (0) CH2 H H CF3 B24 0
A1 103 NCCH2 H H CF3 B24 0
A1104 CH3 (CH2) SCH2 H H CF3 B24 0
A1105 CH3 (CH2) 7SOCH2 H H CF3 B24 0
A1106 CH3 (CH2) 7S? 2CH2 H H CF3 B24 0
A1108 CICH2CC H H CF3 B24 0
A1109 CHF2CH2CH2 H H CF3 B24 0
A11 10 CHCI2CH2CH2 H H CF3 B24 0
A1 1 1 1 CF3S020 H H CF3 'B24 0
A1115 to rJV-CH 'H H CF3 B24 0
Comp. R2 R4 Qi P
No. A1116 c H H CF3 B24 0
A1117 ryeH- H H CF3 B24 0
CH3ON = CHCH2 H H CF3 B24
A1118 0 A1119 0 = CHCH2 H H CF3 B24 0 A1120 CH3CH20CH2 H H CF2CI B24 0 A1121 PhOCH2 H H CF2CI B24 0
A1123 (CH3) 2CH2OCH2 H H CF2CI B24 0 A1124 BrCH2 H H CF2CI B24 0 A1125 FCH2 H H CF2CI B24 0
/ N -r- ^ S-OCH, A1 127 H H CF2CI B24 0
A1 130 H H CF2CI B24 0
A1 132 cyclopropyl-CH2 H H CF2CI B24 0
A1 133 2.2-dichloroc? Cloprop- 1 - H H CF2CI B24 0 ilo A1 134 CH3OC (0) CH = CH H H CF2CI B24 0
A1135 CH3CH2OC (0) CH = CH H CF2CI B24 0
Comp. R3 R4 Q1 P
DO NOT. A1136 CICH2CH = CH HH CF2CI B24 0 A1 137 CH = C = CH HH CF2CI B24 0 A1138 (CH3) 2NCH2 HH CF2CI B24 0 A1139 HOCH2 HH CF2CI B24 0 A1140 CH3C (0) OCH2 HH CF2CI B24 0 A1141 PhC (0) OCH2 HH CF2CI B24 0 A1142 PhCH2 HH CF2CI B24 0 A1143 CH3OC (0) CH2 HH CF2CI B24 0 A1144 NCCH2 HH CF2CI B24 0 A1 145 CH3 (CH2) 7SCH2 HH CF2CI B24 0 A1146 CH3 (CH2) 7SOCH2 HH CF2CI B24 0 A1147 CH3 ( CH2) 7S02CH2 HH CF2CI B24 0
A1149 H H CF2CI B24 0 A1150 H H CF2CI B24 0 A1151 H H CF2CI B24 0 A1152 H H CF2CI B24 0
A1156 aCH 'H H CF2CI B24 0
A1157 -sCH 'H H CF2CI B24 0
A1158 H H CF2CI B24 0
A1 159 CH3ON = CHCH2 H H CF2CI B24 0
A1160 0 = CHCH2 H H CF2CI B24 0
Comp. R2 R3 R4 Rs Qi P
No. A1161 CH3CH2OCH2 H H CF2H B24 0 A1162 PhOCH2 H H CF2H B24 0 N ^ OCH, A1163 H H CF2H B24 0
A1 164 (CH3) 2CH2OCH2 H H CF2H B24 0
A1165 BrCH2 H H CF2H B24 0 A1 16I5 FCH2 H H CF2H B24 0
A116IJ V SOCH, H H CF2H B24 0
N ^ -SO.CH, A1 169 H H CF2H B24 0
A1 170 Y NV SCH, H H CF2H B24 0
A1 171 /°y".?S0CH, H H CF2H B24 0
A1 172 O ^ N ^ SOjCH, HH CF2H B24 0 O A1 17G: cyclopropyl-CH2 HH CF2H B24 0 A1174 2.2-d? Chloro? Cloprop-l- HH CF2H B24 0 Ilo A1 175 CH3OC (0) CH = CH HH CF2H B24 0 A1 176 CH3CH2OC (0) CH = CH HH CF2H B24 0 A1 177 CICH2CH = CH HH CF2H B24 0
A1178 CH = C = CH H CF2H B24 0 A1179 (CH3) 2NCH2 H H CF2H B24 0 A1180 HOCH2 H H CF2H B24 0 A1181 CH3C (0) OCH2 H H CF2H B24 0 A1182 PhC (0) OCH2 H H CF2H B24 0
to. o o O O O O O O O O O o o O O O O O O O O
Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf Tf T Tf T T T T T T T T T T T T T T T T T T T T T T T T T T T OJ? CQ CQ CQ? CQ CQ CQ CQ CQ or m CQ? CQ CQ CQ CQ CQ? CQ CQ CQ?
X X X X X X X X X X X X X X X X X
LL LL LL LL LL LL LL
X IX. IX. IX. IX. LL LL LL LL IX. LL IX. IX. IX LL IX. LL IX. LL o o o P o o O o o o O O O
c £ X X X X X X X X X X X X X X 5 X
X X X X X X X X X X X x x x x x x x x
Comp. R2 «3 R4 Rs Q1 P
No. A1208 CH3CH2OC (0) OCH2 H H CF3 B24 0
A1209 CH3OCH2OCH2 H H CF3 B24 0
A1210 CH3 H H CF3 B24 1
A1211 CHsCH2 H H CF3 B24 1
A1212 cyclopropyl H H CF3 B24 1
A1213 CHs (CH2) 2 H H CF3 B24 1
A1214 CH3OCH2 H H CF3 B24 1
A1215 CF3 H H CF3 B24 1
A1216 F2CH H H CF3 B24 1
A1217 CICH2 H H CF3 B24 1
A1218 CH3SÜ2CH2 H H CF3 B24 1
A1219 CH3 CF3 H CH3 B24 1
A1220 CH3CH2? CH2 H H CF3 B24 1
A1221 PhOCH2 H H CF3 B24 1
A 1222 (CH3) 2CH2OCH2 H H CF3 B24 1
A 1223 BrCH2 H H CF3 B24 1
A1224 FCH2 H H CF3 B24 1
^ O ^ N ^ SO.CH, A1226 H H CF3 B24 1
A1227 cyclopropyl-CH? H H CF3. B24 1
A1228 2.2-d? Chloroc? Cloprop- 1 - H H CF3 B24 1 l A1229 (CH3) 2NCH2 H H CF3 B24 1
A1230 HOCH2 H H CF3 B24 1
A1231 CH3C (0) OCH2 H H CF3 B24 1
A 1232 PhC (0) OCH2 H H CF3 B24 1
A1233 PhCH2 H H CF3 B24 1
A 1234 CH3OC (0) CH2 H H CF3 B24 1
A1235 NCCH2 H H CF3 B24 1
Comp. R2 R3 R4 Rs Q1 P
No. A1236 CH3 (CH2) 7S02CH2 H H CF3 B24 1
A1237 Br H H CF3 B24 1
A1238 Cl H H CF3 B24 1
A1239 0 = CHCH2 H H CF3 B24 1
A1240 CH3 H H CF2CI B24 1
A1241 CH3CH2 H H CF2CI B24 1
A1242 cyclopropyl H H CF2CI B24 1
A1243 CH3 (CH2) 2 H H CF2CI B24 1
A1244 CH3OCH2 H H CF2CI B24 1
A1245 CF3 H H CF2CI B24 1
A1246 F2CH H H CF2CI B24 1
A1247 CICH2 H H CF2CI B24 1
A1248 CH3S? 2CH2 H H CF2CI B24 1
A1249 CH3 CF3 H CF2CI B24 1
A1250 CH3CH2? CH2 H H CF2CI B24 1
A1251 PhOCH2 H H CF2CI B24 1
A1252 (CH3) 2CH2OCH2 H H CF2CI B24 1
A1253 BrCH2 H H CF2CI B24 1
A 1254 FCH2 H H CF2CI B24 1
A1255 V 8? H H CF2CI B24 1
I
A1257 cyclopropyl-CH2 H H CF2CI B24 1
A1258 2.2-dichlorocycloprop-l-H H CF2CI B24 1 ilo A1259 (CH3) 2NCH2 H H CF2CI B24 1
A1260 HOCH2 H H CF2CI B24 1
A1261 CH3C (0) OCH2 H H CF2CI B24 1
A1262 PhC (0) OCH2 H H CF2CI B24 1
A1263 PhCH2 H H CF2CI B24 1
Comp. R2 R3 R4 Rs Q1 P
No. A1264 CH3OC (0) CH2 H H CF2CI B24 1
A1265 NCCH2 H H CF2CI B24 1
A 1266 CH3 (CH2) 7S02CH2 H H CF2CI B24 1
A 1267 Br H H CF2CI B24 1
A1268 Cl H H CF2CI B24 1
A1269 0 = CHCH2 H H CF2CI B24 1
A1270 CH3 H H CF2H B24 1
A1271 CH3CH2 H H CF2H B24 1
A1272 cyclopropyl H H CF2H B24 1
A1273 CH3 (CH2) 2 H H CF2H B24 1
A 1274 CH3OCH2 H H CF2H B24 1
A1275 CF3 H H CF2H B24 1
A 1276 F2CH H H CF2H B24 1
A 1277 CICH2 H H CF2H B24 1
A 1278 CH3S02CH2 H H CF2H B24 1
A 1279 CH3 CF3 H CF2H B24 1
A1280 CH3CH OC H2 H H CF2H B24 1
A1281 PhOCH2 H H CF2H B24 1
A 1282 (CH3) 2CH2OCH2 H H CF2H B24 1
A 1283 BrCH2 H H CF2H B24 1
A1284 FCH2 H H CF2H B24 1
A1286 / 0? N S0? CH, H H CF2H B24 1
Kf? "
A 1287 cyclopropyl-CH2 H H CF2H B24 1
A1288; 2.2-dichlorocycloprop- 1 - H H CF2H B24 1 ilo A 1289 (CH3) 2NCH2 H H CF2H B24 1
A 1290 HOCH2 H H CF2H B24 1
A1291 CH3C (0) OCH2 H H CF2H B24 1
Comp. R. H. H4 «5. μ
No. At 1292 PhC (O iOCH? H H CF2H B24 1
A1293 PhCH2 H H CF2H. B24 1
At 294 CH3OC (0) CH2 H H CF? H B24 1
A1295 NCCH2 H H CF2H B24 1
A 1296 CH3 (CH2) 7S02CHj H H CF2H B24 1
A12S7 Br H H CF2H B24 1
A 1298 Cl H H CF2H B24 1
A 1299 0 = CHCH2 H H CF2H B24 1
A 1300 CH3 H H CF3CF2 B24 1
A1301 HO H Ph CF3 B24 0
A 1302 CH3 H CH- ^ CH CF3 B24 0
A 1303 CH3 H CH3CH, 0 CF3 B24 O
A 1305 HO H H CF3 B24 0
A 1306 (CH3CH2) 2N (0) CO H H CF3 B24 0
A1307 CH3 H Cough-1 CF; B24 0
A 1308 CH3 H CHjCC CF2 B24 0
A1 31 0 Crí, H CICHjCC C- i B2á 0
A13 H CH, H PhCH20 CF, B24 0
At 31 2 CH3 H CF3SO J CF3 B24 0
A131 3 CX) H (CH. -N CF, 824 0
A * .31 4 CH3 H CHJC (0) 0 CF3 B24 0
A1 31 5 CH3 H CH3CH? C (0) CF3 B24 0 O A1316 CH3 H P C (0) 0 CF3 B24 0
A1317 CH3 H 3-P? R? D? Io CF3 B24 O
A1318 CHjOCH-OCH2 H H CF2CI B24 0
A1319 CHjOCHsOCHj H H CF2H B24 0
A 1320 CHjOCH2OCH- H H CF2CF3 B24 0
A 1322 CH3Q H CH3 CF3 B24 0
In the formulaic representations of the tables (for example, Table 7, compound A 1088, substituents R2), the pyridine ring binding site is on the right side of the formulaic representation. The terminal valencies are a methyl group.
Table 8: Composition of the formula Ib (p is 0 or 1
I heard Qi Oi Qi Qi Qi Qi Qi Qi Oi Oi Oi
B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12
B13 B14 B15 B16 B17 B18 B19 B19 B20 B21 B22 B23 - B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36
B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84
B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96
B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108
B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132
B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144
B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 182 B183 B184 B185 B186 B187 B188 B189 B190- B191 B192
B193 E1194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204
B205 E'206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216
B217 E1218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228
B229 IE230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240
B241 E242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252
B253 E254 B255 B256 B257 B258 B259 B260 B261 B262 B263 B264
B265 E266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276
B277 EI278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288
B289 E.290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B301 B302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312
B313 B314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324
B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360
B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372
B373 B374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384
B385 B386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396
B397 B398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420
B421 B422 B423 B424 B425 B426 B438 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444
B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456
B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468
B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480
B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492
B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504
B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516
B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528
B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540
B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552
B553 3554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564
B565 3566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576
B577 3578 B579 B580 B581 B582 B583 B584 B585 B586 'B587 B588
B589 I3590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600
B601 I3602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612
B613 13614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624
B625 I3626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636
B637 I3638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648
B649 I3650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 I3662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784
B785 13786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796
QJ QJ QJ QJ QJ QJ QJ Q-I Q-Y J I QJ
B797 b798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 b849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 b869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 B882 B883 b884 B885 B886 B887 B888 B889 B890 B891 B892 B893 B894 B895 B896 B897 B898 B899 B909 B909 B909 B901 B909 B909 B909 B905 B905 B905 B909 B905 B905 B959 B928 B928 B928 B928 B929 B930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940 B941 B942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952 B953 B954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964 B965 B966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976 B977 B978 B979 B980 B981 B982 B983 B984 B985 B986 B987 B988 B989 B990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B108? B1083 B1084 B1085 B1086 B1087 B1088 B1089 B1090 B1090 B1010 B1091 B1092 B1093 B1010 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1167 B1168 B1168 B1169 B1171 B1171 B1171 B1172 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192
QQ QJ QJ QJ QJ QI QJ Q-I 0-! 0-! 0-! 0-!
B1193 B1194 B1195 B1196 B1197 B1198 B1198 B1199 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216
B1217
Table 9: Compue s of the formula l e (p e s 0 or 1):
Qi Q? Q? Qi I heard I heard Qi I heard I heard Ql Ql Ql
B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12
B13 B14 B15 B16 B17 B18 B19 B19 B20 B21 B22 B23 - B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36
B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 879 B80 B81 B82 B83 B84
B85 B86 B87 B88 B89 B90 B91 B92 B93 B94 B95 B96
B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108
B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132
B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144
B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 B191 B192
B193 B194 B195 B196 B197 B198 B199 B200 B201 B202 B203 B204
B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216
B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228
B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240
B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252
QJ QJ QJ QI QI J QJ QJ J QJ QJ ^
B253 3254 B255 B256 B256 B257 B252 B273 B274 B275 B276 B277 I3278 B279 B280 B281 B282 B283 B284 B285. B286 B287 B288
B289 3290 B291 B292 B293 B294 B295 B296 B297 B298 B299 B300
B301 ¡3302 B303 B304 B305 B306 B307 B308 B309 B310 B311 B312
B313 13314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324
B325 I3326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
B337 I3338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 I3350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360
B361 I3362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372
B373 I3374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384 B385 13386 B387 B388 B389 B390 B391 B392 B393 B394 B395 B396
B397 I3398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 13410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420
B421 I3422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432
B433 I3434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444
B445 I3446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456
B457 B458 B459 B460 B461 B462 B463 B475 B475 B477 B478 B479 B480
B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B491 B492
B493 B494 B495 B496 B497 B498 B499 B500 B501 B502 B503 B504
B505 E3506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516
B517 E3518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528
B529 E5530 B531 B532 B533 B534 B535 B536 B537 B538 - B539 B540
B541 EJ542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552
B553 E5554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564
B565 E5566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576
B577 E5578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 E5590 B591 B592 B593 B594 B595 B596 B597 B598 B599 B600
B601 E1602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612
B613 E1614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624
B625 E1626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636
B637 E638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648
Qj Q¿ _taU Qj Qj Qj Qj Qj Q-? Q? Qj j
B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660 B661 B662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672 B773 B774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 B786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796 B797 b798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808 B809 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832 B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844 B845 B846 B847 B848 b849 B850 B851 B852 B853 B854 B855 B856 B857 B858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868 b869 B870 B871 B872 B873 B888 B886 B887 B896 B896 B886 B885 B886 B888 B889 B888 B889 B909 B909 B909 B902 B903 B905 B905 B909 B909 B909 B909 B910 B910 B910 B912 B912 B912 B913 B914 B915 B916 B917 3918 B919 B920 B921 B923 B923 B923 B923 B923 B923 B923 B923 B923 B936 B936 B936 B936 B936 B936 B939 B939 B609 B951 B953 B953 B953 B955 B956 B957 B958 B959 B960 B951 B962 B953 B964 B965 B967 B967 B968 B968 B970 B971 B972 B973 B973 B974 B974 B975 B976 B995 B997 B997 B998 B999 B1000 B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 61062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 E1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 E1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096 B1097 B1Ó98 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 B1134 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144
Qi Qi Qi Qi Qi Qi Qi Qi Qi j Q Qj
B1145 B1146 B1147 B1148 B1148 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1158 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193 B1194 B1195 B1196 B1ig7 B1ig8 B1ig9 B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 10: Compounds of the formula Id (p is 0 or 1
Qi Oi Oi Qi Qi Qi Qi Qi Qi Qi Oi Qi
B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12
B13 B14 B15 B16 B17 B18 B19 B19 B20 B21 B22 B23 - B25 B26 B27 B28 B2 B30 B31 B32 B33 B34 B35 B36
B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B5g B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84
B85 B86 B87 B88 B88 B90 B91 B92 B93 B84 B85 B96
B97 B98 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108
B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132
B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144
B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 B182 B183 B184 B185 B186 B187 B188 B188 B180 B191 B192
B193 B194 B185 B186 B197 B198 B199 B200 B201 B202 B203 B204
B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216
B217 B218 B219 B220 B221 B222 B223 B224 B225 B226 B227 B228
B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240
B241 B242 B243 B244 B245 B246 B247 B248 B249 B250 B251 B252
B253 B254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
B265 B266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276
B277 B278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288
B289 B290 B291 B292 B293 B294 B2g5 B296 B297 B298 B28g B300
B301 B302 B303 B304 B305 B306 B307 B308 B30 B310 B311 B312
B313 B314 B315 B316 B317 B318 B318 B320 B321 B322 B323 B324
B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
K, B337 3338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 3350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360
B361 3362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372
B373 I3374 B375 B376 B377 B378 B379 B380 B381 B382 B383 B384
B385 I3386 B387 B388 B389 B390 B391 B392 B393 B394 B3g5 B396
B397 I3398 B399 B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 13410 B411 B412 B413 B424 B415 B415 B416 B417 B418 B419 B431 B420 B421 B421 B427
B433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444
B445 I3446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456
B457 I3458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468
B469 I3470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480
B481 I3482 B483 B484 B485 B486 B487 B487 B488 B489 B450? B4 and B492 0 B493 I344 B495 B496 B497 B498 B489 B500 B501 B502 B503 B504
B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516
B517 E3518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528
B529 E3530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540
B541 E3542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552
B553 E3554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564
B565 E) 566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576 5 B577 E3578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 ES590 B591 B592 B593 B594 B595 B596 B597 B5 ß B58 B600
Qi Qi Qi Qi Qi Qi Qi Qj Qtai Qj Qvi Qj
B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612
B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624
B625 3626 B627 B628 B629 B630 B631 B632 B633 B634 B635 B636
B637 3638 B639 B640 B641 B642 B643 B644 B645 B646 B647 B648
B649 13650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 I3662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672
B773 I3774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784
B785 I3786 B787 B788 B789 B790 B791 B792 B793 B794 B795 B796
B797 I3798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808
B809 13810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820
B821 I3822 B823 B824 B825 B826 B827 B827 B828 B829 B830 B831 B832 B833 13834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844
B845 I3846 B847 B848 B849 B850 B851 B852 B853 B854 B855 B856
B857 13858 B859 B860 B861 B862 B863 B864 B865 B866 B867 B868
B869 E3870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880
B881 E3882 B883 B884 B885 B886 B887 B888 B889 B890 B891 B892
B893 E3894 B895 B896 B897 B898 B899 B900 B901 B902 B903 B904
B905 E3906 B907 B908 B909 B910 B911 B912 B913 B914 B915 B916
B917 E5918 B919 B920 B921 B922 B923 B924 B925 B926 B927 B928
B929 E? 930 B931 B932 B933 B934 B935 B936 B937 B938 B939 B940
B941 E942 B943 B944 B945 B946 B947 B948 B949 B950 B951 B952
B953 EI954 B955 B956 B957 B958 B959 B960 B961 B962 B963 B964
B965 E1966 B967 B968 B969 B970 B971 B972 B973 B974 B975 B976
B977 E1978 B979 B980 B981 B982 B983 B984 B985 B986 - B987 B988
B989 E; 990 B991 B992 B993 B994 B995 B996 B997 B998 B999 B1000
B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012
B1013 B1010 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1021 B1023 B1023 B1023
B1025 B1025 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036
B1037 BI038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048
B1049 BI050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060
B1061 B1061 B1067 B1067 B1067 B1067 B1067 B1067 B1067 B1067 B1076 B1076 B1079 B1079 B1079 B1079 B1071 B1071 B1087 B1083 B1083
B1085 B1086 B1087 B1088 B1089 B1090 B1091 B1092 B1093 B1094 B1095 B1096
QJ QI QI QI QI QI QI QI QI I QI QJ
B107 B108 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B110931110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 31122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 31134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B114531146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157131158 B1159 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169131170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 131182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1190 B1191 B1192 B1193131194 B1195 B1196 B1197 B1198 B1igg B1200 B1201 B1202 B1203 B1204 B1205131206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 11: Compounds of the formula le (p is 0 or 1):
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B1 B2 B3 B4 B5 B6 B7 B8 eg B10 B11 B12
B13 B14 B15 B16 B17 B18 B20 B20 B21 B23 B23 B25 B26 B27 B28 B28 B28 B30 B32 B32 B33 B34 B35 B36
B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 'B47 B48
B B4499 B B5500 B B5511 B B5522 B B5533 B B5544 B B5555 B56 B57 B58 B5 B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B7g B80 B81 B82 B83 B84
B85 B86 B87 B88 B89 B80 Bgi B92 B93 B84 B95 B96
B97 B98 B99 B100 B101 B102 B103 B109 13110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 13122 B123 B124 B125 B126 B127 B127 B128 B129 B130 B131 B132 B133 13134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144
B145 13146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
Qj Qj Qj Qj Qj Qj Q-i Q-i -i Q-i -i Qj
B157 B157 B158 B159 B179 B175 B177 B178 B179 B180 B181 B182 B183 B183 B185 B186 B187 B188 B189 B or B191 B192 Bi 3 Big4 B6 Big B197 Bi B7 Big B200 B201 B202 B203 B204 B205 B206 B207 B207 B208 B209 B210 B211 B211 B212 B213 B214 B215 B216 B216 B217 B218 B218 B220 B220 B221 B222 B223 B224 B225 B226 B227 B229 B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252 B253 B254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264 B265 B266 B267 B268 B268 B270 B271 B272 B273 B274 B275 B276 B277 B278 B278 B280 B281 B282 B282 B282 B283 B283 B283 B283 B285 B286 B306 B307 B309 B309 B303 B310 B312 B312 B312 B313 B316 B316 B316 B317 B318 B318 B318 B320 B321 B322 B323 B324 B325 B326 B326 B327 B327 B328 B328 B345 B347 B348 B348 B345 B350 B351 B352 B353 B354 B355 B356 B357 B357 B358 B359 B360 B361 B362 B363 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B37g B380 B381 B382 B383 B384
B385 B386 B387 B388 B388 B3? B391 B3g2 B393 B394 B395 B396 B397 b398 B389 B400 B401 B402 B403 B404 B405 B406 B407 B408 B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420 B421 B422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432 B433 B434 B435 B436 B437 B438 B438 B440 B441 B452 B454 B453 B454 B460 B460 B460 B464 B465 B466 B466 B467 B468 B469 B470 B471 B472 B473 B474 B475 B476 B476 B478 B479 B479 B480 B481 B482 B483 B484 B485 B486 B487 B488 B489 B490 B4 i 8492 B504 B50 B50 B50 B50 B50 B50 B505 B505 B505 B506 B508 B508 B508 B510 B510 B512 B512 B513 B514 B515 B516 B517 B518 B519 B519 B531 B532 B533 B534 B535 B536 B53 B538 B538 B540 B541 B542 B543 B544 B545 B546 B547 B548 B548 B550 B551 B552
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B553 13554 B560 B560 B575 B575 B575 B575 B575 B575 B575 B575 B575 B575 B575 B580 B581 B582 B583 B584 B585 B586 B587 B587 B588 B588 I3590 B5g B5g2 B5g3 B5g4 B595 B596 B596 B57 B5g B58g B600
B601 E3602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612
B613 E3614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624
B625 E3626 B627 B628 B628 B630 B631 B632 B633 B634 B635 B636
B637 E3638 B638 B640 B641 B642 B643 B644 B645 B646 B647 B648
B649 E3650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 EJ662 B663 B664 B665 B666 B667 B668 B669 B670 B671 B672
B773 EJ774 B775 B776 B777 B778 B779 B780 B781 B782 B783 B784 B785 EJ786 B787 B788 B789 B790 B791 B792 B7g3 B74 B7g5 B796
B797 E1798 B7gg B800 B801 B802 B803 B804 B805 B806 B807 B808
B809 E1810 B811 B812 B813 B814 B815 B816 B817 B818 B818 B820
B821 EI822 B823 B824 B825 B826 B827 B828 B828 B830 B831 B832
B833 E834 B835 B836 B837 B838 B838 B840 B841 B842 B843 B844
B845 E.846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 E1858 B858 B860 B861 B862 B863 B864 B865 B866 B867 B868
B869 E1870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880
B881 E882 B883 B884 B885 B886 B887 B888 B888 B880 B881 B882
B893 E894 B885 B886 B887 B888 B899 B900 B901 B902 B903 B904
B905 E906 B907 B908 B90g BgiO Bgi1 B912 B913 Bgi4 Bgi5 Bgi6
B917 E918 B9ig Bg20 Bg21 B922 B923 B 24 B925 B926 B927 B928
B929 B930 B931 B932 B933 B934 B 35 B936 B937 B 38- B83g B 40
B941 B942 B943 B 44 Bg45 Bg46 B 47 Bg48 B84g Bg50 Bg51 B 52
B953 B954 B955 B956 B957 B958 B85g Bg60 Bg61 B 62 B 63 B 64
B965 B966 B967 Bg68 B969 Bg70 Bg71 B972 B973 B974 Bg75 Bg76
B977 B978 B97g B980 B981 B982 B883 Bg84 Bg85 B886 B887 B888
B989 B990 Bg9i B992 B g3 B994 B g5 Bggß Bg 7 B998 Bggg B1000
B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B100g B1010 B1011 B1012
B1013 B1014 B1014 B1015 B1016 B1017 B1018 B1018 B1020 B1021 B1022 B1023 B1023 B1025 B1025 B1027 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1036
B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048
QJ QJ QJ QI QI QI QJ Q-! 0-! Qi Qi Qi
B104g B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B106g B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084 B1085 B1086 B1087 B1088 B1088 B1090 B1091 B10g2 B10g3 B1084 B1095 B1096 B1097 B1098 B1089 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 BI110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 BI122 B1123 B1124 B1125 B1126 B1127 B1128 B1129 B1130 B1131 B1132 B1133 BI134 B1135 B1136 B1137 B1138 B1138 B1140 B1141 B1142 B1143 B1144 B1145 BI146 B1147 B1148 B114g B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 BI158 B1158 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1178 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1189 B1180 B1191 B1ig2 B1193 B1184 B1ig5 B1ig6 B1ig7 B1ig8 B1igg B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B121 5 B1216 B1217
Table: .2: Compounds of the formula If (p is 0 or 1
Qi íli Qi Qi Oí Qi Oí Qi Qi Qi Ql Qi
B1 E.2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12
B13 B14 B15 B16 B17 B18 B19 B19 B20 B21 B22 B23 - B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36
B37 B38 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60
B61 B (> 2 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B7g B80 B81 B82 B83 B84
B85 BEI6 B87 B88 B88 B90 B91 B92 B83 B94 B85 B96
B97 B8 B99 B100 B101 B102 B103 B104 B105 B106 B107 B108
Qj Qj Qj Qj Qj Qi -i Q-i -i j Qj Qj
B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 B122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132
B133 B134 B135 B136 B137 B138 B139 B140 B141 B142 B143 B144
B145 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 B182 B183 B184 B185 B186 B187 B188 B188 BigO Bigi Big2
Big3 Bi 4 Bi 5 Bi 6 Big7 B198 B199 B200 B201 B202 B203 B204
B205 B206 B207 B208 B209 B210 B211 B212 B213 B214 B215 B216
B217 B218 B218 B220 B221 B222 B223 B224 B225 B226 B227 B228
B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252
B253 B254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
B265 B266 B267 B268 B268 B270 B271 B272 B273 B274 B275 B276
B277 B278 B278 B280 B281 B282 B283 B284 B285 B286 B287 B288
B288 B290 B291 B292 B2g3 B294 B295 B296 B297 B298 B28g B300
B301 B302 B303 B304 B305 B306 B307 B308 B308 B310 B311 B312
B313 B314 B315 B316 B317 B318 B318 B320 B321 B322 B323 B324
B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 B350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360
B361 B362 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372
B373 B374 B375 B376 B377 B378 B378 B380 B381 B382 B383 B384
B385 3386 B387 B388 B389 B390 B3gi B392 B393 B3g4 - B395 B3g6
B37 3398 B39g B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 13410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420
B421 I3422 B423 B424 B425 B426 B427 B428 B429 B430 B431 B432
B433 I3434 B435 B436 B437 B438 B438 B440 B441 B442 B443 B444
B445 I3446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456
B457 I3458 B459 B460 B475 B475 B477 B477 B479 B480 B481 B482 B483 B483 B484 B485 B485 B486 B487 B488 B489 B489 B490 B490 B4 and B492
B493 E3494 B495 B496 B47 B4g B489 B500 B501 B502 B503 B504
Qj Qj Qj Qj Qj Qj Qj Q Qj Q-i j Qj
B505 B506 B507 B508 B508 B510 B511 B512 B513 B514 B515 B516
B517 B518 B5ig B520 B521 B522 B523 B524 B525 B526 B527 B528
B529 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540
B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552
B553 B554 B555 B556 B557 B558 B558 B560 B561 B562 B563 B564
B565 B566 B567 B568 B568 B570 B571 B572 B573 B574 B575 B576
B577 B578 B578 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 B590 B5gi B52 B5g3 B5g4 B55 B56 B5g7 B5 ß B58g B600
B601 B602 B603 B604 B605 B606 B607 B608 B609 B610 B611 B612
B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624
B625 B626 B627 B628 B628 B630 B631 B632 B633 B634 B635 B636
B637 B638 B638 B640 B641 B642 B643 B644 B645 B646 B647 B648
B648 B650 B651 B652 B653 B654 B655 B656 B657 B658 B658 B660
B661 B662 B663 B664 B665 B666 B667 B668 B668 B670 B671 B672
B773 B774 B775 B776 B777 B778 B778 B780 B781 B782 B783 B784
B785 B786 B787 B788 B788 B7g? B7 i B7g2 B7g3 B7g4 B75 B7g6
B797 B798 B799 B800 B801 B802 B803 B804 B805 B806 B807 B808
B808 B810 B811 B812 B813 B814 B815 B816 B817 B818 B818 B820
B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832
B833 B834 B835 B836 B837 B838 B839 B840 B841 B842 B843 B844
B845 B846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 B858 B858 B860 B861 B862 B863 B864 B865 B866 B867 B868
B869 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880
B881 B882 B883 B884 B885 B886 B887 B888 B889 B890 'B891 B892
B893 B894 B895 B896 B897 B888 B88g BgOO Bg01 Bg02 B903 B904
B905 B906 B7 Bgoß B909 Bgi Bgu Bgi2 Bgi3 B i4 Bgi5 B i6
B917 B918 B8ig Bg20 B 21 Bg22 B923 B924 Bg25 Bg26 Bg27 Bg28
B929 Bg30 Bg31 Bg32 Bg33 Bg34 Bg35 Bg36 B937 B938 B939 B940
B941 B942 B943 B944 B945 B946 Bg47 Bg48 B84g Bg50 B 51 Bg52
B 53 Bg54 Bg55 Bg56 B 57 Bg58 B959 B960 Bg61 Bg62 B 63 B 64
B65 Bg66 Bg67 Bg68 B86g B970 B971 B972 Bg73 Bg74 B975 B976 B977 B978 B87g B980 B981 B882 B883 B884 B885 B886 B887 B988
B989 Bg9o B991 B992 B93 B g4 Bgg5 Bggß B997 B gß eg 9 B1000
QI QI QI QI QI QI QJ QI J J Q QJ
B1001 81002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 81014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1048 e11050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1058 B1060
B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1068 B1070 B1071 B1072
B1073 B1074 B1075 B1076 B1077 B1078 B1079 B1080 B1081 B1082 B1083 B1084
B1085 B1086 B1087 B1088 B1089 B1090 B10gi B10g2 B1093 B1094 B10g5 B1096
B10g7 B10g8 B1099 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108
B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120
B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1128 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1139 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1149 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 E1158 B115g B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 E1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1183 B1184 B1185 B1186 E1182 B1187 B1188 B1189 B1190 B1193 B1igi B1ig2 B1196 B1197 E1194 B1i 5 B1189 B1200 B1201 B1202 B1ig8 B1203 B1204 B1205 B1207 B1208 B1209 B1210 E1206 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 13: Compounds of the formula Ig (p is 0 or 1
I heard Qi Oi Qi Oi Oi Qi Oi Ql Ql Qi Qi
B1 B2 B3 B4 B5 B6 B7 B8 eg B10 B11 B12
B13 1314 B15 B16 B17 B18 B19 B19 B20 B21 B22 B23 - B25 I326 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36
B37 I338 B39 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 I350 B51 B52 B53 B54 B55 B56 B57 B58 B59 B60
B61 I362 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
QJ QJ QJ QI I QI Q-I QI QJ Qi Qi Qi
B73- B74 B75 B76 B77 B78 B78 B80 B81 B82 B83 B84
B85 B86 B87 B88 B88 B90 B91 B 2 Bg3 B84 B85 B96
B97 B98 Bgg B100 B101 B102 B103 B104 B105 B106 B107 B108
B109 13110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 13122 B123 B124 B125 B126 B127 B128 B129 B130 B131 B132
B133 13134 B135 B136 B137 B138 B138 B140 B141 B142 B143 B144
B145 13146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156
B157 13158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 BAO B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 E3182 B183 B184 B185 B186 B187 B188 B188 BigO Bigi Bi 2
B193 E3194 B195 B196 Big7 Big B18g B200 B201 B202 B203 B204
B205 E3206 B207 B208 B208 B210 B211 B212 B213 B214 B215 B216
B217 E3218 B218 B220 B221 B222 B223 B224 B225 B226 B227 B228
B228 E3230 B231 B232 B233 B234 B235 B236 B237 B238 B238 B240
B241 EJ242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252
B253 E1254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
B265 E266 B267 B268 B269 B270 B271 B272 B273 B274 B275 B276
B277 E1278 B279 B280 B281 B282 B283 B284 B285 B286 B287 B288 B289 E1290 B291 B292 B293 B294 B2g5 B26 B2g7 B2g B28g B300
B301 EI302 B303 B304 B305 B306 B307 B308 B308 B310 B311 B312
B313 E314 B315 B316 B317 B318 B318 B320 B321 B322 B323 B324
B325 E326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
B337 E338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 E350 B351 B352 B353 B354 B355 B356 B357 B358 - B359 B360
B361 B362 B363 B364 B365 B366 B367 B368 B368 B370 B371 B372
B373 B374 B375 B376 B377 B378 B378 B380 B381 B382 B383 B384
B385 B386 B387 B388 B388 B3g? B3gi B3g2 B3g3 B3g4 B3g5 B3g6
B37 B3g B38g B400 B401 B402 B403 B404 B405 B406 B407 B408
B40g B410 B411 B412 B413 B414 B415 B416 B417 B418 B4ig B420
B421 B422 B423 B424 B425 B426 B427 B428 B42g B430 B431 B432
B433 B 34 B435 B436 B437 B438 B438 B440 B441 B442 B443 B444
B445 B446 B447 B448 B44g B450 B451 B452 B453 B454 B455 B456
B457 B458 B458 B460 B461 B462 B463 B464 B465 B466 B467 B468
S? fi? S? í3? fi? fi? S? fi? fi? S? fi? 9?
B468 B470 B471 B472 B473 B474 B475 B476 B477 B478 B479 B480 B481 B482 B483 B484 B485 B486 B486 B487 B488 B488 B4g? B4gi B4g2 B4g3 B4g4 B4g5 B4g6 B4g7 B4g8 B48g B500 B501 B502 B503 B504 B505 B506 B507 B508 B509 B510 B511 B512 B513 B514 B515 B516 B517 B518 B519 B520 B521 B522 B523 B524 B525 B526 B527 B528 B528 B530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540 B541 B542 B543 B544 B545 B546 B547 B548 B549 B550 B551 B552 B553 B554 B555 B556 B557 b558 B55g B560 B561 B562 B563 B564 B565 B566 B567 B568 B568 B570 B571 B572 B573 B574 B575 B576 B577 B578 B578 B580 B581 B582 B583 B584 B585 B586 B587 B588 B588 B590 B591 B5g2 B5g3 B54 B5g5 B56 B5g7 B58 B589 B600 B601 B602 B603 B604 B605 B606 B607 B608 B60G B610 B611 B612 B613 B614 B615 B616 B617 B618 B619 B620 B621 B622 B623 B624 B625 B626 B627 B628 B628 B630 B631 B632 B633 B634 B635 B636 B637 B638 B63G B640 B641 B642 B643 B643 B644 B660 B663 B663 B665 B666 B666 B667 B668 B668 B670 B671 B672 B773 B774 B775 B776 B777 B778 B777 B780 B781 B782 B783 B784 B785 B786 B787 B788 B788 B7 ? B7gi B792 B793 B7g4 B75 B7g6 B7g7 B7 ß B78g B800 B801 B802 B803 B804 B805 B806 B807 B808 B808 B810 B811 B812 B813 B814 B815 B816 B817 B818 B819 B820 B821 B822 B823 B824 B825 B826 B827 B828 B828 B830 B831 B832 B833 B834 B835 B836 B837 B838 B838 B840 B841 B842 B842 B843 B841 B844 B845 B846 B865 B866 B867 B868 B868 B870 B871 B872 B873 B874 B875 B876 B877 B878 B879 B880 B881 3882 B883 B884 B885 B886 B887 B888 B888 B8g? B881 B82 B905 B883 B9495 B889 B889 B886 B887 B889 B889 B889 B889 B910 B910 B910 B910 B927 B927 B923 B927 B927 B927 B927 B927 B927 B927 B927 B927 B927 B932 B932 B933 B933 B933 B935 B937 B839 Bg40 B941 B942 B 43 Bg44 B 45 Bg46 B947 B948 B949 B950 Bg51 Bg52 B953 I3954 B955 B956 B957 Bg58 B85 BgSo Bg61 B962 B963 B964
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
Bg65 B966 B967 B967 B968 B882 B884 Bg4 B885 B886 B887 B 88 Eg Bg0 B9 B9 B9 B9 B9 B7 B7 B B B B B B B B B B B B B B B B B B B B B 6
B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1008 B1010 B1011 B1012
B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024
B1025 B1026 B1027 B1028 B1029 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B103g B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1057 B1058 B1059 B1060 B1061 B1062 B1063 B1064 B1065 B1066 B1067 B1068 B1069 B1070 B1071 B1072 B1073 B1074 B1075 B1076 B1076 B1077 B1077 B1076 B10g10 B10g3 B10g4 B10g5 B106 B10g7 B10g8 B1089 B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108
B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1118 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1128 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1138 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1148 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1158 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1168 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1178 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B118g B1190 B1191 B1ig2 B1193 B1194 B1ig5 B1ig6 B1ig7 B1igß B1igg B1200 B1201 B1202 B1203 B1204 B1205 B1206 B1207 B1208 B1208 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 14: Compounds of the formula Ih (p is 0 or 1):
Qi Qi Qj Q? I heard Qi Q? Q? Q? Qi Q? Qi
B1 B2 B3 B4 B5 B6 B7 B8 B B10 B11 B12
B13 B14 B15 B16 B17 B18 B18 B18 B20 B21 B22 B23.
Qi Qi Qi Qi Qi Qj Qi Q? -3b Qi Qi Ql
B25 B26 B27 B28 B29 B30 B31 B32 B33 B34 B35 B36
B37 B38 B38 B40 B41 B42 B43 B44 B45 B46 B47 B48
B49 B50 B51 B52 B53 B54 B55 B56 B57 B58 B5g B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B78 B80 B81 B82 B83 B84
B85 B86 B87 B88 B89 B80 B91 B92 B 3 Bg4 B85 B96
B87 B88 B89 B B110000 BB110011 B102 B103 B104 B105 B106 B107 B108
B108 B110 B111 B112 B113 B114 B115 B116 B117 B118 B118 B120
B121 B122 B123 B124 B125 B126 B127 B128 B128 B130 B131 B132
B133 B134 B135 B136 B137 B138 B13g B140 B141 B142 B143 B144
B145 B146 B146 B147 B148 B149 B150 B151 B152 B153 B154 B155 B156 B157 B158 B159 B160 B161 B162 B163 B164 B165 B166 B167 B168
B169 B170 B171 B172 B173 B174 B175 B176 B177 B178 B179 B180
B181 B182 B183 B184 B185 B186 B187 B188 B188 BigO Bigi Big2
Big3 Big4 Big5 Big6 Bi 7 Bigß Big B200 B201 B202 B203 B204
B205 B206 B207 B208 B208 B210 B211 B212 B213 B214 B215 B216
B217 B218 B218 B220 B221 B222 B223 B224 B225 B226 B227 B228
B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240 B241 B242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252
B253 B254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
B265 B266 B267 B268 B268 B270 B271 B272 B273 B274 B275 B276
B277 3278 B278 B280 B281 B282 B283 B284 B285 B286 B287 B288
B289 3290 B291 B2g2 B293 B24 B2g5 B2g6 B2g7 B2gß B289 B300
B301 3302 B303 B304 B305 B306 B307 B308 B309 B310-B311 B312
B313 3314 B315 B316 B317 B318 B3ig B320 B321 B322 B323 B324
B325 I3326 B327 B328 B328 B330 B331 B332 B333 B334 B335 B336
B337 I3338 B338 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 I3350 B351 B352 B353 B354 B355 B356 B357 B358 B359 B360
B361 I3362 B363 B364 B365 B366 B367 B368 B368 B370 B371 B372
B373 I3374 B375 B376 B377 B378 B378 B380 B381 B382 B383 B384
B385 I3386 B387 B388 B388 B3g? B391 B3g2 B3g3 B3g4 B35 B396
B3g7 I33gß B389 B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420
QI QI QI QI QI Q -I Q QJ QJ QI YES
B421 B423 B423 B423 B423 B423 B446 B442 B443 B444 B446 B446 B446 B447 B448 B448 B450 B451 B452 B453 B454 B455 B456 B457 B457 3458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468
B468 3470 B471 B472 B473 B474 B475 B476 B477 B478 B47g B480
B481 I3482 B483 B484 B485 B486 B487 B488 8488 B480 B4gi B4g2
B4g3 I3494 B4g5 B4g6 B4g7 B4g B498 B500 B501 B502 B503 B504
B505 I3506 B507 B508 B508 B510 B511 B512 B513 B514 B515 B516
B517 13518 B518 B520 B521 B522 B523 B524 B525 B526 B527 B528
B529 I3530 B531 B532 B533 B534 B535 B536 B537 B538 B539 B540
B541 I3542 B543 B544 B545 B546 B547 B548 B548 B550 B551 B552
B553 I3554 B555 B556 B557 B558 B559 B560 B561 B562 B563 B564
B565 I3566 B567 B568 B569 B570 B571 B572 B573 B574 B575 B576
B577 E3578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 E3590 B5gi B5g2 B5g3 B5g4 B55 B5g6 B5g7 B5g B58g B600
B601 E3602 B603 B604 B605 B606 B607 B608 B608 B610 B611 B612
B613 IE614 B615 B616 B617 B618 B6IG B620 B621 B622 B623 B624
B625 E5626 B627 B628 B628 B628 B630 B631 B632 B633 B634 B634 B635 B636 B637 B637 B638 B638 B640 B646 B647 B648
B649 E1650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 E-662 B663 B664 B665 B666 B667 B668 B668 B670 B671 B672
B773 EI774 B775 B776 B777 B778 B778 B780 B781 B782 B783 B784
B785 EI786 B787 B788 B788 B7g? B791 B792 B793 B794 B795 B7g6
B797 E798 B799 B800 B801 B802 B803 B804 B805 B806 'B807 B808
B809 E810 B811 B812 B813 B814 B815 B816 B817 B818 B818 B820
B821 E822 B823 B824 B825 B826 B827 B828 B828 B830 B831 B832
B833 B834 B835 B836 B837 B838 B838 B840 B841 B842 B843 B844
B845 B846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 B858 B858 B860 B861 B862 B863 B864 B865 B866 B867 B868
B868 B870 B871 B872 B873 B874 B875 B876 B877 B878 B878 B880
B881 B882 B883 B884 B885 B886 B887 B888 B888 B880 B881 B8g2
B893 BB84 B85 B896 B897 B888 B88g BgOO Bg01 Bg02 Bg03 Bg04
Bg05 B906 Bg07 Bg08 B80g BgiO Bgi1 Bgi2 B i3 Bgi4 Bgi5 B916
Qj Qj Qj Qj Qj Qj -j Qj j -! 0-! 0-!
B i7 B i8 B8i B920 B921 B 22 Bg23 B924 B925 Bg26 B927 B928
B929 B930 Bg31 Bg32 B933 B934 Bg35 Bg36 Bg37 Bg38 Bg3g B940
Bg41 Bg42 Bg43 Bg44 Bg45 Bg46 Bg47 Bg48 B849 B950 Bg51 Bg52
Bg53 Bg54 B 55 Bg56 Bg57 Bg58 B85 Bg60 B 61 B 62 Bg63 Bg64
Bg65 Bg66 B967 B968 B 6g Bg70 Bg71 Bg72 Bg73 Bg74 Bg75 B 76
Bg77 Bg78 B87g B 80 B881 B882 B883 B884 B885 Bg86 B887 B888
B889 B9go Bggi eg 2 B9g3 Bg 4 Bggs B ß Bgg7 Bggs B99g BIOOO
B1001 EJ1002 B1003 B1004 B1005 B1006 B1007 B1008 B100g B101081011 B1012 B1013 EI1014 B1015 B1016 B1017 B1018 B1018 B1020 B1021 B1022 B1023 B1024 B1025 EI1026 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 EI1038 B1038 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1048 EI1050 B1051 B1052 B1053 B1054 B1054 B1055 B1056 B1056 B1071 B1072 B1073 B1075 B1075 B1076 B1077 B1077 B1077 B107g B1080 B1081 B1082 B1083 B1084 B1085 E1086 B1087 B1088 B1088 B1? G? B10gi B10g2 B10g3 B10g4 B10g5 B1096 B1097 E1098 B108g B1100 B1101 B1102 B1103 B1104 B1105 B1106 B1107 B1108 B1109 B1110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B1128 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1138 B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1148 B1150 B1151 B1152 B1153 B1154 B1155 B1156 B1157 B1158 B1158 B1160 B1161 B1162 B1163 B1164 B1165 B1166 B1167 B1168 B1169 B1170 B1171 B1172 B1173 B1174 B1175 B1176 B1177 B1178 B1179 B1180 B1181 B1182 B1183 B1184 B1185 B1186 B1187 B1188 B1188 B1ig ? B1191 B1ig2 B1193 B1194 B1ig5 B1ig6 B1ig7 B1ig8 B118g B1200 B1201 B1202B1203 B1204 B1205 B1206 B1207 B1208 B1208 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 15: Compounds of the formula Ik (p is 0 or 1):
I heard Qi Oi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B1 B2 B3 B4 B5 B6 B7 B8 B9 B10 B11 B12
B13 B14 B15 B16 B17 B18 B20 B20 B21 B23 B23 B25 B26 B27 B28 B28 B28 B30 B32 B32 B33 B34 B35 B36
B37 B38 B3 B40 B41 B42 B43 B44 B45 B46 B47 B48
B4g B50 B51 B52 B53 B54 B55 B56 B57 B58 B5g B60
B61 B62 B63 B64 B65 B66 B67 B68 B69 B70 B71 B72
B73 B74 B75 B76 B77 B78 B79 B80 B81 B82 B83 B84
B85 B86 B87 B88 B88 B80 Bgi B82 B3 Bg4 B85 B86
B97 B98 egg B100 B101 B102 B103 B104 B105 B106 B107 B108
B108 B110 B111 B112 B113 B114 B115 B116 B117 B118 B118 B120
B121 B122 B123 B124 B125 B126 B127 B128 B129 B129 B130 B131 B132 B133 B134 B135 B136 B137 B138 B138 B140 B141 B142 B143 B144
B145 B146 B147 B148 B148 B150 B151 B152 B153 B154 B155 B156
B157 B158 B158 B160 B161 B162 B163 B164 B165 B166 B167 B168
B168 B170 B171 B172 B173 B174 B175 B176 B177 B178 B178 B180
B181 B182 B183 B184 B185 B186 B187 B188 B189 B190 Big Big2
Big3 Bi 4 Big5 B196 B197 B198 Bigg B200 B201 B202 B203 B204
B205 B206 B207 B208 B208 B210 B211 B212 B213 B214 B215 B216 B217 B218 B218 B220 B221 B222 B223 B224 B225 B226 B227 B228
B228 B230 B231 B232 B233 B234 B235 B236 B237 B238 B238 B240
B241 B242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252
B253 B254 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
B265 B266 B267 B268 B26g B270 B271 B272 B273 B274 B275 B276
B277 B278 B278 B280 B281 B282 B283 B284 B285 B286 'B287 B288
B288 B2g? B2gi B2g2 B2g3 B2 4 B2g5 B2g6 B2g7 B2g8 B28g B300
B301 B302 B303 B304 B305 B306 B307 B308 B308 B310 B311 B312
B313 B314 B315 B316 B317 B318 B318 B320 B321 B322 B323 B324
B325 B326 B327 B328 B329 B330 B331 B332 B333 B334 B335 B336
B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B348 B350 B351 B352 B353 B354 B355 B356 B357 B358 B358 B360
B361 B362 B363 B364 B365 B366 B367 B368 B368 B370 B371 B372 B373 B374 B375 B376 B377 B378 B37g B380 B381 B382 B383 B384
B385 B386 B387 B388 B389 B390 B3 and B3g2 B3g3 B3g4 B3g5 B36
Q? Q? Q? Q? 9? Q? Q? Q? Q? 9? Q? Q?
B387 B3g8 B38g B400 B401 B402 B403 B404 B405 B406 B407 B408
B408 B410 B411 B412 B413 B414 B415 B416 B417 B418 B418 B420
B421 3422 B423 B424 B425 B426 B427 B428 B42g B430 B431 B432
B433 I3434 B435 B436 B437 B438 B43g B440 B441 B442 B443 B444
B445 3446 B447 B448 B44g B450 B451 B452 B453 B454 B455 B456
B457 3458 B45g B460 B461 B462 B463 B464 B465 B466 B467 B468
B468 I3470 B471 B472 B473 B474 B475 B476 B477 B478 B47g B480
B481 I3482 B483 B484 B485 B486 B487 B488 B488 B490 B491 B4g2
B493 I3494 B495 B496 B497 B4g8 B4gg B500 B501 B502 B503 B504
B505 I3506 B507 B508 B50g B510 B511 B512 B513 B514 B515 B516
B517 13518 B518 B520 B521 B522 B523 B523 B525 B526 B526 B527 B528 B52 13530 B531 B532 B533 B534 B535 B536 B537 B538 B53g B540
B541 13542 B543 B544 B545 B546 B547 B548 B54g B550 B551 B552
B553 6554 B555 B556 B557 B558 B558 B560 B561 B562 B563 B564
B565 E3566 B567 B568 B568 B570 B571 B572 B573 B574 B575 B576
B577 E3578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 E35g? B5 i B5g2 B53 B5g4 B5g5 B5g6 B5g7 B5g B5 B600
B601 EJ602 B603 B604 B605 B606 B607 B608 B608 B610 B611 B612
B613 E5614 B615 B616 B617 B618 B6ig B620 B621 B622 B623 B624
B625 E1626 B627 B628 B628 B630 B631 B632 B633 B634 B635 B636
B637 E! 638 B638 B640 B641 B642 B643 B644 B645 B646 B647 B648
B649 E! 650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 EI662 B663 B664 B665 B666 B667 B668 B668 B670 B671 B672
B773 E1774 B775 B776 B777 B778 B77g B780 B781 B782 - B783 B784
B785 E786 B787 B788 B788 B7g? B7gi B7g2 B7g3 B7g4 B75 B796
B797 E798 B789 B800 B801 B802 B803 B804 B805 B806 B807 B808
B809 E810 B811 B812 B813 B814 B815 B816 B817 B818 B818 B820
B821 E822 B823 B824 B825 B826 B827 B828 B828 B830 B831 B832
B833 B834 B835 B836 B837 B838 B838 B840 B841 B842 B843 B844
B845 B846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 B858 B858 B860 B861 B862 B863 B864 B865 B866 B867 B868
B868 B870 B871 B872 B873 B874 B875 B876 B877 B878 B878 B880
B881 B882 B883 B884 B885 B886 B887 B888 B888 B880 B881 B8g2
Qj Qj Q Q-i Qj - -i Qi i j j Q-! B883 38g4 B8g5 B8g6 B897 Bß ß Bßg9 Bgoo Bgoi Bg02 Bg03 ego4 Bgo5 3go6 Bgo7 egoß ßgog Bgio Bgn egi2 Bgi3 and i4 B i5 egi6
Bgi7 3918 B9ig Bg20 B 21 Bg22 Bg23 6g24 B 25 B926 B927 B928 B929 B 399 B931 B 32 Bg33 Bg34 Bg35 Bg36 B 37 B 38 B83g B 40 B941 3942 B943 Bg44 Bg45 Bg46 Bg47 Bg48 Bg48 Bg4g Bg50 Bg51 Bg52
Bg53 I3954 B955 Bg56 Bg71 Bg57 Bg58 885g Bg60 B961 B961 B961 Bg64 Bg64 Bg6 B 65 I3966 B 67 Bg68 B86g 8g70 B971 B972 Bg73 Bg74 Bg74 Bg75 Bg76 Bg77 B3977 B979 B8083 B881 B77 Bg83 Bg84 B885 Bg86 Bg87 Bg87 Bg88
Bgß9 I3990 Bggi Bgg2 B993 B g4 Bggs Bgg6 Bgg7 Bggß Bggg B1000
B1001 61002 B1003 B1004 B1005 B1006 B1007 B1008 B1008 B1010 B1011 B1012 610,136,101,481,015 B1016 B10176101881018 B1020 B1021 B1022 B1023 B1024 0 B1025 E1026 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 E1038 B1038 B104081041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B104g B1050 B1051 B1052 B1053 B1054 B1055 B1056 B1056 B105781058 B1058 B1060 B1074 B1075 B1077 B1077 B1078 B1078 B1080 B1080 B1081 B1084 B1084 B1084 B1085 B1088 B1088 B108861? G? B10gi B10g28103 B10g4 B10g5610g6
Biog7 Biogß eiogg BUOO BUOI 81102 B1103 B110481105 B1106 B1107 Buot 5 B1109 B1110 B1111 B1112 B1113 B1114 B111581116 B1117 B1118 B1119 B1120 B1121 B1122 B1123 B1124 B1125 B1126 B1127 B1128 B112881130 B1131 B1132 81133 B1134 B1135611366113781138 B1138 B114061141 81142 B1143 B1144 B1145 B1146 B1147 B1148 B114g B1150 B1151 B115261153 B1154 B1155 B1155 B1156 B1157 B1157 B1173 B1174 B1175 B117681177 B1178B1179 B1180 B1181 B1181 B1181 B1183 B1184 B1185 B1186 B1187 B1188 B1188 B1? B1191 B1ig2 () B1i 3 BI194 B1195 B1196 B119761198 B1199 B120061201 B1202 B1203 B1204 B1205 BI206 B1207 B1208 B1209 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 16: Compounds of the formula Im (p is 0 or 1):
Qi Qi Qi Oi Qi Qi Qi Qi Oi Qi Qi Qi
B1 B2 B3 B4 B5 B6 B7 B8 eg B10 B11 B12
B13 B14 B15 B16 B17 B18 B20 B20 B21 B23 B23 B25 B26 B27 B28 B28 B28 B30 B32 B32 B33 B34 B35 B36
B37 B38 B38 B40 B41 B42 B43 B44 B45 B46 B47 B48
848 B50 B51 B52 B53 B54 B55 B56 B57 B58 B5 B60
B61 B62 B63 B64 B65 866 B67 B68 B6g B70 B71 B72
B73 B74 B75 B76 B77 B78 B7g B80 B81 B82 B83 B84
685 B86 B87 B88 B88 B80 Bgi B82 Bg3 B84 B 5 B86
B87 B88 Bgg B100 B101 B102 B103 B104 B105 B106 B107 B108
B109 B110 B111 B112 B113 B114 B115 B116 B117 B118 B119 B120
B121 B122 B123 B124 B125 B126 B127 6128 612g B130 B131 B132
B133 B134 B135 B136 B137 B138 B138 B140 B141 B142 B143 B144
B145 B146 B147 B148 B148 B150 B151 B152 B153 B154 B155 B156
B157 B158 B15g B160 B161 B162 6163 B164 B165 6166 8167 B168
B168 8170 B171 B172 B173 B174 B175 B176 B177 B178 B178 8180
B181 B182 B183 B184 B185 B186 B187 B188 B188 BigO Bigi Big2
Big3 Big4 Big5 Big6 Big7 Bigß Bigg B200 B201 B202 B203 B204
B205 B206 B207 B208 B208 B210 B211 B212 B213 B214 B215 B216 6217 B218 6218 6220 B221 B222 6223 8224 B225 B226 8227 B228
B229 B230 B231 B232 B233 B234 B235 B236 B237 B238 B239 B240
B241 3242 B243 B244 B245 B246 8247 B248 B248 8250 B251 B252
B253 I3254 6255 8256 B257 B258 B25g B260 B261 B262 B263 B264
B265 3266 B267 B268 B26g B270 B271 B272 B273 B274 B275 B276
B277 I3278 B27g B280 B281 B282 B283 B284 B285 B286 B287 B288
B288 I32 0 B2gi B2g2 B2g3 B2 4 B2g5 B2 6 B2g7 B2gß B289 B300
B301 I3302 B303 6304 6305 B306 B307 B308 B309 B310 B311 B312
B313 I3314 B315 B316 B317 B318 B319 B320 B321 B322 B323 B324
QJ QJ QJ QJ QJ I Q-I QJ Q-! 0-! 0 ^ 0-!
B325 B326 B326 B327 B323 B328 B326 B347 B348 B349 B349 B350 B351 B352 B353 B355 B355 B356 B357 B358 B359 B360 B361 B362 B363 B363 B364 B365 B366 B367 B368 B369 B370 B371 B372 B373 B374 B375 B376 B377 B378 B378 B380 B381 B382 B383 B384
B385 B386 B387 B388 B388 B3g? B3gi B3g2 B3g3 B3g4 B3g5 B3g6
B397 B398 B38 6400 6401 6402 6403 6404 6405 B406 B407 B408
B409 B410 B411 B412 B413 B414 B415 B416 B417 B418 B419 B420
B421 B422 B423 B424 8425 B426 B427 8428 B429 B430 B431 B432
6433 B434 B435 B436 B437 B438 B439 B440 B441 B442 B443 B444
B445 B446 B447 B448 B449 B450 B451 B452 B453 B454 B455 B456 B456 B457 B458 B459 B460 B461 B462 B463 B464 B465 B466 B467 B468
B469 B470 B471 B472 B473 B474 B475 B476 B477 B478 B478 B480
B481 B482 B483 B484 B485 B486 B487 B488 B488 B4g? B4gi 84g2
B4g3 B4g4 645 B4g6 B4g7 B4g8 B48g B500 B501 B502 B503 B504
B505 B506 8507 B508 B508 B510 B511 B512 B513 B514 B515 B516
B517 6518 B518 B520 8521 B522 B523 8524 B525 B526 B527 B528
6529 B530 B531 8532 B533 B534 8535 B536 B537 6538 6539 8540
B541 B542 6543 8544 B545 B546 B547 B548 6549 8550 B551 B552
8553 B554 B555 6556 B557 B558 6559 B560 B561 B562 B563 B564
B565 B566 B567 B568 B569 B570 B571 B572 6573 8574 B575 B576
B577 B578 B579 B580 B581 B582 B583 B584 B585 B586 B587 B588
B589 8590 6591 6592 6593 B594 B55 B5g6 B5g7 B5gß B58g B600
6601 6602 8603 8604 6605 6606 6607 8608 B608 B610"B611 B612
8613 6614 8615 6616 6617 6618 6618 6620 B621 B622 B623 B624
B625 6626 B627 B628 8628 B630 B631 B632 B633 B634 B635 B636
B637 B638 B638 6640 6641 B642 B643 B644 B645 B646 B647 B648
B649 B650 B651 B652 B653 B654 B655 B656 B657 B658 B659 B660
B661 B662 B663 B664 6665 6666 B667 B668 866g B670 B671 B672
B773 B774 B775 B776 B777 B778 B778 B780 B781 B782 B783 B784
B785 B786 B787 B788 B788 B7g? B7gi B7g2 B7g3 B7g4 B7g5 B7g6 B77 87gb B7gg B800 8801 B802 B803 B804 6805 B806 B807 B808
B808 B810 6811 B812 B813 8814 B815 B816 B817 B818 B818 B820
Qi Qi Qi Qi Qi Qi Qi Qi Qi
B821 B822 B823 8824 8825 6826 B827 B828 B829 B830 B831 8832
B833 B834 6835 8836 8837 B838 B838 B840 B841 B842 B843 B844
B845 B846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 B858 B858 B860 B861 B862 B863 B864 B865 B866 B867 B868
B868 B870 B871 6872 8873 8874 6875 B876 B877 6878 6878 B880
B881 6882 8883 B884 B885 B886 B887 B888 B888 B890 Bßgi B882 B893 B894 8885 B886 B887 B888 Bßg BgOO B 01 Bg02 Bg03 B904
B905 B6 Bgo7 Bgoß Bgog Bgio egn ßgi2 Bgi3 Bgi4 egi5 Bgi6 B77 Bgid egg eg20 eg2i B 22 B23 Bg2 Bg25 B26 eg27 Bg28
Bg2 Bg30 B931 B932 Bg33 Bg34 B935 B936 B 37 Bg38 Bg3g Bg40
B 41 B942 B943 8944 B945 B946 B947 Bg48 Bg4g Bg50 Bg51 Bg52 B953 3954 B955 Bg56 Bg57 Bg58 B85g Bg60 Bg61 Bg62 B 63 B 64
Bg65 3g66 6g67 Bg68 B969 8g70 Bg71 Bg72 Bg73 Bg74 B 75 Bg76
B 77 3g78 Bg7g 6980 B981 B982 B983 Bg84 B885 Bg86 Bg87 Bg88
Bgß 3ggo eggi B992 Bgg3 8994 B995 eggß eg97 Bg98 B9gg 81000
B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1009 B1010 B1011 B1012 B1013 B1014 B1015 B1016 B1017 B1018 B1019 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B103761038 B1038 B1040 B1041 B1042 B1043 B1044 B1045 B1046 B1047 B1048 B1049 E1050 B1051 B1052 B1053 B1054 B1054 B1055 B1068 B1070 B1057 B1072 B1058 B1075 B1075 B1076 B1076 B1077 B1077 B107g B1080 B1081 B1082 B1083 B1084 B1084 B1085 B1086 B1087 B1088 B1088 B1? G? B10gi B10g2 B10g3 B10g46109581096 B1097 B10988l08g B1100 B1101 B1102 B110381104 B1105 B1106B1107 b1108 B110961110 B1111 B1112 B1113 B1114 B1115 B1116 B1117 B1118 B1118 B1120 61121 61122 B1123 B112461125 B1126 B112761128 B1129 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B113g B1140 B1141 B1142 B1143 B1144 B1145 B1146 B1147 B1148 B1148 B1150 B1154 B1155 B1155 B1157 B1152 B1167 B1153 B1154 B1154 B1175 B1167 B1171 B1171 B1173 B1173 B1173 B1176 B1176 B1176 B1176 B1178 B1178 B1181 B1181 B1181 B1183 B1184 B1184 B1185 B1186 B1187 B1188 B1188 B1ig? B1i i B1i 2 B1193 BI194 B1ig5 B1ig6 B1197 B1198 B1igg B1200 B1201 B1202 B1203 B1204 B1205 BI206 B1207 B1208 B120g 81210 B1211 B1212 B1213 B1214 B1215 B1216
Qj Qj Qj Qj Q-i Q-i Qj Q- 0-! 0-! 0-! 0-!
B1217
Table 17: Compounds of the formula In (p is 0 or 1):
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B1 B2 83 B4 B5 B6 87 B8 Bg B10 B11 B12
B13 B14 B15 B16 B17 B18 B18 B19 B20 B21 B22 B23 - B25 326 B27 B28 B28 B30 B31 B32 633 B34 B35 B36
B37 338 638 B40 B41 B42 B43 B44 845 B46 B47 B48
B4g 350 851 B52 B53 B54 B55 B56 B57 B58 B5g B60
B61 362 B63 B64 B65 B66 B67 B68 B6 B70 B71 B72
B73 I374 B75 B76 B77 B78 B7 B80 B81 B82 B83 B84
B85 I386 687 B88 B89 890 B i B82 683 B84 B 5 B86
B87 I388 egg B100 B101 6102 B103 B104 B105 6106 B107 B108
B108 6110 B111 B112 B113 B114 B115 B116 B117 B118 B1ig B120
B121 E122 B123 B124 B125 B126 6127 6128 B128 B130 B131 B132
B133 E134 B135 B136 B137 B138 B138 B140 B141 B142 B143 B144
B145 B146 B147 B148 B148 B150 B151 B152 B153 B154 B155 B156
B157 B158 6158 6160 B161 B162 B163 B164 B164 B165 B166 B167 B167 B168 B160 B170 B171 B172 B172 B174 B174 B175 B176 B176 B177 B178 B17g B180
B181 B182 B183 B184 B185 B186 B187 B188 B188 BigO Bigi Bi 2
Bi 3 Bi 4 Big5 B196 B197 Bigß 81gg B200 B201 8202 B203 B204
B205 8206 B207 B208 8208 B210 B211 8212 B213 B214 6215 B216
B217 B218 B218 B220 B221 B222 B223 B224 B225 B226 B227 B228
B228 B230 B231 B232 B233 B234 B235 B236 B237 B238 B23g B240
B241 B242 B243 B244 B245 B246 B247 B248 B248 B250 B251 B252
B253 B 54 B255 B256 B257 B258 B258 B260 B261 B262 B263 B264
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
8265 B266 B267 B267 B268 B268 B268 B268 B277 B272 B272 B287 B287 B287 B220 B29 B2g3 B27 B27 B27 B27 B27 B29 B297 B302 B303 B302 B303 B303 B304 B304 B306 B307 B307 B307 B303 B303
B313 B314 B315 B316 B317 B318 B3ig B320 B321 B322 B323 B324
B325 B326 B327 B328 B32g B330 B331 B332 B333 B334 B335 B336
B337 B338 B339 B340 B341 B342 B343 B344 B345 B346 B347 B348
B349 B350 B351 6352 6353 8354 B355 B356 B357 B358 B359 B360
8361 8362 8363 B364 B365 B366 B367 B368 B369 B370 B371 B372
B373 B374 B375 B376 6377 B378 B37g 8380 B381 B382 B383 B384
B385 B386 B387 B388 B388 B3g? B3gi B3g2 B3g3 B3g4 B35 B36 B3g7 B3g8 B389 B400 B401 B402 B403 B404 B405 B406 B407 B408
B409 B410 B411 B412 6413 B414 B415 B416 B417 B418 B419 B420
B421 B422 B423 B424 B425 B426 B427 B428 B428 8430 B431 B432
8433 B434 B435 B436 B437 B438 B438 B440 B441 B442 B443 B444
B445 B446 B447 B448 6449 B450 B451 8452 B453 B454 B455 6456
B457 B458 B458 6460 8461 B462 B463 B464 B465 B466 B467 8468
B469 B470 B471 8472 B473 B474 8475 B476 B477 B478 B478 B480
B481 3482 B483 B484 B485 B486 B487 6488 B488 B480 8481 B4g2
B4g3 34g4 84g5 B4g6 B4g7 84 ß B4 B500 6501 B502 B503 B504
B505 I3506 B507 B508 B50g B510 B511 B512 6513 6514 6515 8516
6517 13518 651 g 6520 B521 B522 B523 8524 B525 B526 8527 B528
B529 I3530 6531 8532 B533 B534 8535 8536 B537 B538 6539 6540
6541 I3542 6543 6544 6545 B546 B547 B548 B549 B550 - B551 B552
B553 I3554 B555 B556 B557 B558 B55g B560 B561 B562 B563 6564
B565 I3566 B567 B568 B568 B570 8571 B572 B573 8574 6575 8576
B577 B578 B578 B580 B581 B582 8583 B584 B585 8586 B587 B588
8588 E3580 85gi B52 B5g3 85g4 B5g5 B56 85g7 B5gß B5gg B600
B601 E3602 B603 B604 B605 B606 B607 B608 B608 B610 B611 B612
B613 E3614 B615 B616 B617 B618 B618 B620 B621 B622 B623 B624
B625 EJ626 B627 B628 B628 B630 B630 B631 B632 B633 B634 B635 B636 B637 EJ638 B638 B640 B641 B642 B643 B644 B645 B646 B647 B648
B648 E1650 B651 B652 B653 B654 B655 B656 B657 B658 B65g B660
Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi Qi
B661 B662 B663 B664 B665 B666 6667 B668 B66g B670 B671 B672
B773 B774 B775 B776 B777 B778 B77g B780 B781 B782 B783 B784
B785 B786 B787 B788 B788 B7g? B7gi B7g2 B7g3 B7g4 B7g5 B76
B797 B798 B79g B800 B801 B802 8803 B804 B805 B806 B807 B808
B808 B810 B811 B812 B813 B814 B815 B816 B817 8818 B819 B820
B821 B822 B823 B824 B825 B826 B827 B828 B829 B830 B831 B832
B833 8834 B835 B836 6837 B838 B838 B840 B841 B842 B843 B844
B845 B846 B847 B848 B848 B850 B851 B852 B853 B854 B855 B856
B857 B858 B858 B860 B861 B862 B863 B864 B865 B866 B867 6868
8869 B870 B871 6872 8873 B874 B875 B876 B877 B878 B879 B880
B881 B882 B883 B884 B885 B886 B887 8888 B889 B880 B881 B82
B893 B894 B895 B86 B897 B888 B89g BgOO Bg01 Bg02 Bg03 Bg04
Bg05 Bg06 B907 B908 B909 BgiO Bgi1 B i2 Bgi3 Bgi4 B i5 B916
B917 B918 B8ig 820 Bg21 Bg22 6g23 B 24 B 25 8g26 Bg27 Bg28
B829 6930 ßg31 B932 B933 634 Bg35 B936 8937 B938 B839 B940
B941 B942 B943 B944 B945 B946 Bg47 6948 B94g Bg50 B 51 B952
B953 Bg54 8g55 6g56 B957 B958 B85g B960 B961 Bg62 Bg63 B964
B965 B966 Bg67 B968 B96g Bg70 Bg71 B 72 Bg73 Bg74 Bg75 Bg76
B 77 Bg78 B979 BgSO B881 B982 6983 B984 B985 6986 B987 B988
B989 B9 or Bggi Bgg2 egg3 Bg94 B9 s B996 Bgg7 Bggß eggg BIOOO
B1001 B1002 B1003 B1004 B1005 B1006 B1007 B1008 B1008 B1010 B1011 B1012 B1013 B1014 B101561016 B1017 B1018 B1018 B1020 B1021 B1022 B1023 B1024 B1025 B1026 B1027 B1028 B1028 B1030 B1031 B1032 B1033 B1034 B1035 B1036 B1037 B1038 B1039 B1040 B1041 B1042 B1043 B1044 B1045 B1046"B1047 B1048 B1049 B1050 B1051 B1052 B1053 B1054 B1054 B1055 B1070 B1071 B1071 B1057 B1075 B1075 B1076 B1076 B1077 B1078 B1078 B1080 B1081 B1082 B1083 B1084 81085 B1086 B10876108861088 BIOgO B10gi B10g2 B10g3 B10g4 Bl? G5810g6
Biog7 Biogß eiogg BHOO BUOI 61102 B1103 B1104 B1105 B1106 B1107 Buoß
B1110 B1111 B1113 61112 6110g B11146111581116 B1117 B1120 B1121 B1122 B1123 B111861119 B1124 B1125 B1126 B1127 B1128 B1128 B1130 B1131 B1132 B1133 B1134 B1135 B1136 B1137 B1138 B1138 B1140 B1141 B1144 B1145 B1146 B1147 6114261143 B1148 B1148 B1150 B1151 B1152 B1153 B1154 B1155 B1156
Q? Q? Q? Q? Q? Q? Q? 9? 9? Q? Q? Q?
B1157131158 B1158 B1160 B1167 B1161 B1161 B1161 B1176 B1176 B1176 B1176 B1176 B1176 B1176 B1176 B1176 B1181 B1181 B1181 B1181 B1183 B1184 B1187 B1187 B1187 B1188 B1188 B1188 B1 B1191 B1ig2 B1ig3 E31194 B1ig5 B1ig6 B1ig7 B1ig8 B1igg B1200 B1201 B1202 B1203 B1204 B1205131206 B1207 B1208 B1208 B1210 B1211 B1212 B1213 B1214 B1215 B1216 B1217
Table 18: Compounds of the formula lo (p is 0 or 1]
Qs ih Q¿ z Qz QQ Q Q Q Q Q Q Q C1 C2 C3 C4 C5 C6 C7 C8 C8 C28 C28 C28 C30 C31 C32 C33 C3 C40 C52 C53 C55 C56 C57 C58 C58 C60 C61 C32 C63 C64 C65 C66 C67 C68 C6g C70 C71 C72 C73 C74 C75 C76. C77 C78 C78 C80 C81 C82 C83 C84 C85 C36 C87 C88 C88 CGO C91 C82 Ng3 Ng4 C95 CGSS C87 ci) 8 CGG C100C101 C102C103 C104 C105 C106 C107 C108 c? Ogcuoc? U C112C113 C114C115 C116C117C118C118C120 C121 C122C123 C124C125 C126C127 C128 C128 C130 C131 C132 C133C134C135 C136C137 C138C138 C140 C141 C142 C143 C144 C145C146C147 C148C148 C150C151
Table 19: Compounds of the formula Iq (p is 0 or 1
0-2 £ 2 Q, Q, Q.2 Qz Cfe A Qz 0.2 z &
C1 C2 C3 C4 C5 C6 C7 C8 cg C10 C11 C12
C13 C14 C15 C16 C17 C18 C18 C20 C21 C22 C23 C24
C25 C 6 C27 C28 C29 C30 C31 C32 C33 C34 C35 C36
C37 C 8 C38 C40 C41 C42 C43 C44 C45 C46 C47 C48
C4g C50 C51 C52 C53 C54 C55 C56 C57 C58 C59 C60
C61 C (2 C63 C64 C65 C66 C67 C68 Cg C70 C71 C72
C73 C74 C75 C76 C77 C78 C79 C80 C81 C82 C83 C84
C85 CEI6 C87 C88 C89 C80 C91 C82 C83 C94 C95 C86
C87 C 8 Cgg C100 C101 C102 C103 C104 C104 C105 C106 C107 C108 Cyclo C110 C111 C112 C113 C114 C115 C116 C117 C118 eng C120
C121 C1 2 C123 C124 C125 C126 C127 C128 ci2g C130 C131 C132
C133 C1 4 C135 C136 C137 C138 C13g CU14 C141 C142 C143 C144
C145 C146 C147 C148 C14g C150 C151
Tabl a 20: Co mpositions of. the faith í) rmu. The Ir (p is C) or 1):
Q3 Q3 Q3 Q3 Q3 Q3 Q3 QJ Q3 Q3 Q3 Q3 Q3 Q1 D2 D3 D4 D5 D6 D7 D8 D8 D8 D8 D10 D11 D12 D12 D13 D14 D15 D16 D17 D17 D18 D18 D20 D20 D20 D24 D24 D24 D24 D25 D2 D27 D28 D28 D2g D30 D31 D32 D32 D33 D34 D35 D36 D36 D37 D38 D3 D40 D41 D42 D43 D44 D45 D46 D47 D48
Q5 Q3 D3 D49 D52 D52 D52 D53 D54 D55 D55 D56 D57 D57 D57 D57 D58 D60 D60 D61 D52 D63 D64 D75 D75 D75 D75 D75 D77 D75 D75 D80 D80 D81 D81 D82 D83 D84 D85 D6 D87 D88 D88 D88 D90 D91 D92 D93 D 4 D85 D96 D97 D98 D9g D100 D101 D102 D103 D104 D105 D106 D107 D108
D109 D110 D111 D112 D113 D114 D115D116 D117 D118 D119 D120
D121 D122 D123 D124 D125 D126 D127 D128 D12g D130 D131 D132
D133 D134 D135 D136 D137D138 D139 D140
Table 21: Compounds of the formula Is (p is 0 or 1)
Q3 Q < Q. Qty Qty Qty Qty Q1 Q2 D2 Q3 D5 D5 D7 D7 D7 D9 D9 D9 D10 D11 D11 D12 D12 D14 D15 D16 D16 D17 D18 D19 D19 D20 D20 D20 D23 D24 D25 D26 D26 D27 D28 D2g D30 D31 D32 D33 D33 D34 D35 D36 D37 D38 D3 D40 D41 D42 D42 D42 D42 D42 D44 D45 D64 D65 D66 D66 D68 D70 D70 D71 D70 D75 D75 D75 D75 D77 D77 D78 D79 D80 D80 D81 D82 D83 D84 D85 D85 D8S D87 D88 D88 D80 D91 D92 D92 D3 D111 D111 D113 D114 D115 D115 D116 D117 D118 D119 D120 D121 D122 D123 D124 D125 D126 D126 D127 D128 D128 D130 D131 D132 D133 D134 D134 D135 D136 D137 D138 D139 DMO
Table 22: Computes Bstos of the formula It (p is 0 or 1):
Qi Qi i Qi Q? Qá i Qá i i i é i? E1 E2 E3 E4 E5 E6 E7 E8 E8 E8 E10 E11 E12 E13 E14 E15 E16 E17 E18 E18 E18 E20 E28 E28 E2 E30
Table 23: Compounds of the formula Iu (p is 0 or 1
Qi to Q? Qi Q Q Q Q Q Q Q Q Q Q Q Q Q Q
E1 E2 E3 E4 E5 E6 E7 E8 Eg E10 E11 E12 E13 E14 E15 E16 E17 E18 E18 E20 E20 E22 E23 E23 E24 E25 E26 E27 E28 E2g E30
Table 24: Compounds of the formula Iv (p is 0 or 1
F1 F2 F3 F4 F5 F6
Table 25: Compounds of the formula Iw (p is 0 or 1 5
Qs Q_ Q_ Qs Qs Qs Fl F2 F3 F4 F5 F6
Table 26: Physical data of intermediaries
Melting points are indicated in ° C
Compound Data Físc. Compound Data Físc. A17 99-100 A1025 crystalline A7 105-106 A1206 94-95 A9 73-74 A1022 oil A6 148-150 A1203 crystalline A26 143-144 A21 amorphous A34 170-171 A1023 110-111 A1026 crystalline A1085 188-191 A1304 crystalline A1088 157 -158 A1301 crystalline A1092 crystalline A1018 110-111 A1095 136-138 Al 195-197 A1096 194-196 A2 150-151 A124 135-136 A15 164-166 A31 209-210 A27 107-108 H-B1057 166-167 A29 173 -174 H-B1058 crystalline A32 145-146 H-B1061 crystalline
Dat compound Físc. Dat compound Físc. A30 178-181 H-B1063 Crystalline A4 143-144 H-B1065 oil A3 148-149 H-B1066 150-152 A10 166-167 H-B1067 122-123 A8 123-124 H-B1069 117-118 A5 81-82 H-B1070 crystalline A154 108-110 H-Cl 116-118 A64 134-135 H-C24 172-175 A94 134-135 A1205 crystalline A531 crystalline H-D113 oil A1045 crystalline H-F5 oil A1322 crystalline H-E16 145-148 A184 146-147 A1088 157-158 A358 155-156 A1103 152-153
Table 2 '': Physical data for the compounds of formula I indicated in the previous tables: (Melting points are indicated in ° C)
Compound No. p.f. Físc data Compound No. p.f. Físc data
A2-B1 90-92 crystalline A34-B1 53-54 crystalline
A2-B1082 - resin A9-B1 oil
A2-B1083 crystalline resin A184-B1 98-99
A2-B90 resin A184-B24 101-102 crystalline
A2-B68 120-121 crystalline A7-B24 oil
A2-B24 75-76 crystalline A3-B24 oil
A2-B1 crystalline oil A34-B24 51-52
A2-B73 resin A2-B1091 oil
A2-B75 amorphous A2-B1092 oil
Compound o. P- f. Físc data Compound No. p.f. Físc data
A2-B95 106--107 crystalline A8-B24 52-53 crystalline
A2-B93 95--96 crystalline A18-B24 - oil
A8-B1 97--98 crystalline A2-B552 - resin
A2-B925 oil A2-C152 - oil
A3-B1 42--44 crystalline A2-B69 - resin
A94-B1 57--58 crystalline A2-D36 - resin
A2-B1057 amorphous A2-B618 - resin
A2-B1063 oil A2-B49 - resin
A2-B1061 oil A2-D71 - resin
A2-B133 58--60 crystalline A2-B1093 - resin
A2-B1058 89--91 crystalline A2-B26 - oil
A64-B24 80--82 crystalline A2-B33 - resin
A64-B1 49--51 crystalline A2-B34 - wax
A2-B1089 oil A2-B35 - wax
A2-B31 151--153 crystalline A2-B1087 - viscous
A2-B1090 139--140 crystalline A2-B1094 - viscous
A154-B L 94--95 crystalline A2-B1088 108-109 crystalline
A2-B46 (cis) 61--62 crystalline A531-B24 - viscous
A2-B46 (traus) 83--84 crystalline A2-B1099 94-96 crystalline
A2-B91 resin A2-B1095 - viscous
A2-B2 resin A2-B1097 - oil
A2-B29 87--88 crystalline A2-B1098 92-93 crystalline
A2-B1066 viscous A2-C147 - resin
A2-B25 oil A2-B70 - resin
A2-B1067 resin A2-B49 - resin
A2-B1069 oil A2-C1 - oil
A2-B1068 viscous A2-B1096 - resin
A2-B1070 viscous A2-B1085 176-177 crystalline
A2-B5 resin A1022-B24 - oil
A2-C149 crystalline resin A2-C47 107-110
A2-C146 crystalline A2-B1100 oil 128-130
Compound No. p.f. Físc data Compound No. p.f. Físc data
A2-B112 resin A8-B2 70-71 crystalline
A2-D140 oil A8 -B1064 resin
A2-B35 139-140 crystalline A2-B45 resin
A2-E1 solid A2 -B10 viscous
A6-B1 123-124 crystalline A8-B133 68-69 crystalline
A6-B24 A8 oil -B1101 113-114 crystalline
A1322-E 24 oil A8-B1106 oil
A2-B1101 124-125 crystalline A2-D111 (trans) oil
A2-B156 oil A2-D111 (cis) resin
A2-B133 resin A8-D111 (trans) oil
A2-B145 amorphous resin A8-D109 62-62
A2-B134 resin A8-B35 oil
A1210-B354 220 crystalline A1023-B2 resin
A2-C2 oil A1023-B354 95-97 crystalline
A358-B1 A15-B354 resin oil
A2-D3 resin A8-B354 oil
A1208-B354 oil A8-B1067 oil
A2-D1 13 (iso? N. A) oil A8-C146 oil
A2-D1 1 (iso? N B) oil A8-C1 oil
A2-D1 14 (iso? N A) 159-160 crystalline A94-B34 108-110 crystalline
A2-D115 amorphous A94-B35 82-84 crystalline
A1025-B354 viscous A1210-B354 amorphous
A2-B1102 124-125 crystalline A2-B1105 119 crystalline
A2-B1104 165-167 crystalline amorphous A1099-B1107
A1210-B1 117-119 crystalline A2-B1123 resin
A8-B34 A8 oil -B1123 resin
A8-B1103 resin A2-B1138 oil
A8-B1063 90-92 crystalline A124 -B1 60-65 crystalline
A8-B29 crystalline oil A1170-B1 106-107
A2-C2 oil A124 -B34 oil
A8-B552 oil A124 -B35 oil
Compound No. p. f. Físc data Compound No. p. f. Físc data
A8-B156 - resin A94-B2 53-57 crystalline
A1210-B1105 145-146 glaze A2-B1174 - crystalline - amorphous A1206-B254 - amorphous A2-B1213 133-134 crystalline
A8-B134 - oil A3-B1213 - oil
A8-D36 - oil A4-B1213 - oil
A8-B1213 71-72 crystalline A2-B1214 - resin
A8-F5 - resin A2-F5 - resin
A1029-B1105 94.5-95 crystalline A2-D109 - oil
Biological Examples Example Bl: Herbicidal action before the emergence of plants (action before emergence) Monocotiiedone and dicotyledonous test plants are planted in standard soil in plastic pots. Immediately after sowing, the test substances are sprayed as aqueous suspensions (prepared with a 25 percent wettable powder (Example F3, b) according to International Publication Number WO 97/34485), or as emulsions (prepared with a concentrate in 25 percent emulsion (Example Fl, c)), in a concentration of 2 kilograms of active ingredient / hectare or 250 grams of active ingredient / hectare (500 liters of water / hectare). The test plants are then grown in the greenhouse under optimum conditions. After a trial period of 3 weeks, it is evaluated
the experiment with resistance on a 9-point scale (1 = complete damage, 9 = no effect). The figures in Figures 1 to 4 (in particular from 1 to 3) mean a good to very good herbicidal action.
Bla Table: action before emergence
compound g / ha Cyperus Ipomoea Setaria Sinapis Solanum Stelleria
A2-B1 200 2 2 1 2 2 1
A2-B1082 200 2 2 2 2 1 2 A A22 - BB11008833 2 20000 2 3 3 4 2 3
A2-B90 200 l i l i l í
A2-868 200 1 2 1 2 1 2
A2-B24 200 1 1 1 2 1 1
A2-B73 200 3 4 2 2 2 2
A2-B75 200 2 3 2 2 1 2
A2-B95 200 2 4 2 2 1 2
A2-B93 2 '0"0 2 4 2 2 1 2
A3-B1 200 2 2 4 2 3 2
A94-B1 200 1 2 2 1 1 2
A2-B1063 200 1 2 1 2 1 2
A2-B1061 200 3 3 2 2 1 2
A2-B133 200 1 2 2 2 1 2
A64-B24 200 4 4 2 2 1 2
A2-B1089 200 1 2 2 2 1 2
A2-B31 200 2 3 4 2 1 2
A2-B46 (cis) 200 1 2 1 2 1 2
A2-B46 (trans) 200 1 2 1 2 1 2
A2-B91 200 1 2 1 2 1 2
A2-B2 200 1 1 1 1 1 2 A A22 - BB2255 2 20000 2 - 3 2 2 1 2
compound g / ha CCyyppeerus omoea Setaria Sinapis Solanum Stel
A2-B1067 200 2 3 2 2 3 3
A2-B1068 200 2 2 2 2 1 2
A2-B1070 200 2 3 3 2 2 2
A2-C146 200 1 2 2 2 1 2
A2-B354 200 1 1 1 1 1 2
A34-B1 200 1 2 2 2 2 3
A9-B1 200 2 1 2 1 1 2
A184-B1 200 2 4 2 2 1 2
A184-B24 200 1 3 2 2 1 2
A3-B24 200 1 3 2 2 1 2
A A88 - BB2244 2 20000 1 2 2 2 1 3
A18-B24 200 1 1 1 1 1 2
A2-B552 200 1 2 2 2 1 2
A2-C152 200 1 1 2 2 1 2
A2-B69 200 1 4 2 2 1 1
A2-D36 200 1 2 2 2 1 1
A2-B618 200 1 1 1 2 1 1
A2-B33 200 1 3 2 2 1 3
A2-B34 200 1 3 2 2 1 2
A2-B35 200 2 4 2 2 2 2
A2-B1095 200 3 4 2 2 1 2
A2-C147 200 2 4 2 2 2 2
A2-B49 200 2 4 2 2 1 2
A2-C1 200 2 3 1 2 1 2
A2-B1100 200 1 3 1 2 1 2
A8-B2 200 1 3 2 2 1 2
A8-B1064 200 2 4 3 2 1 3
A8-B1101 200 2 4 2 2 1 1
A2-B156 200 1 2 1 2 1 2
compound g / ha CCyyppeerus Ipomoea Setaria Sinapis Solanum Stelleria
A2-B144 200 3 3 2 2 2 4
A2-B134 200 1 2 1 2 1 1
A1210-B254 200 2 3 2 1 1 2
A2-C2 200 2 3 1 1 1 1
A2-D36 200 1 2 1 2 3 1
A2-D113 (Isom A) 200 4 4 2 1 3 3
A2-D115 200 3 3 2 2 2 3
A8-B34 200 2 3 2 2 2 2
A8-B1103 200 1 3 2 1 1 2
A2-C24 200 1 2 1 1 1 2
Table Blb: action before emergence
compound g / ha Panicum Digitaria Echino. Abutilon amaranthus < Chen
A8-B1 250 2 2 2 1 1 1
A1022-B24 250 2 4 4 3 4 1
A2-B145 250 2 2 4 2 3 1
A1208-B254 250 1 1 1 1 1 1
A8-D1063 250 2 3 3 2 4 1
A8-B552 250 2 3 4 1 4 1
A8-B156 250 3 3 3 3 4 2
A1210-B1105 250 2 3 2 1 4 1
The same results are obtained when the compounds of the formula I are formulated according to Examples F2 and F4 to F8, in accordance with International Publication Number 97/34485.
Example B2: Herbicidal action after emergence; Monocotyledonous and dicotyledonous test plants are grown in the greenhouse in plastic pots containing standard soil, and in the 4 to 6-leaves stage, they are sprayed with an aqueous suspension of the test substances of the formula I, prepared with a powder 25 percent wettable (Example F3, b) according to International Publication Number WO 97/34485) or with an emulsion of test substances of formula I prepared with a 25 percent emulsion concentrate (Example Fl, c), according to International Publication Number WO 97/34485), corresponding to a concentration of 2 kilograms of active ingredient / hectare, or 250 grams of active ingredient / hectare (500 liters of water / hectare). Subsequently, the test plants are grown in the greenhouse under optimum conditions. After a test period of approximately 18 days, the test is evaluated with reference to a 9-point scale (1 = complete damage, 9 = no effect). Classification figures 1 to 4 (particularly 1 to 3) mean a good to very good herbicidal action. In this test, the compounds of formula I show a potent herbicidal action.
Table B2a: Herbicidal action after emergence;
compound g / ha Ipomoea Lolium Setaria Sinapis Solanum Stel
A2-B1 200 1 2 1 1 1 2
A2-B1082 200 1 2 2 1 1 2
A2-B1083 200 1 4 2 1 1 2
A2-B90 200 1 2 2 1 2 2
A2-868 200 1 2 2 1 1 2
A2-B24 200 1 2 2 1 2 2
A2-B73 200 1 3 2 1 1 2
A2-B75 200 2 2 3 1 2 2
A2-B95 200 1 2 2 1 2 2
A2-B93 200 1 2 2 1 2 2
A3-B1 200 1 3 2 1 1 2
A94-B1 200 1 2 2 1 1 1
A2-B1063 200 2 2 4 1 2 2
A2-B1061 200 2 2 2 1 2 2
A2-B133 200 1 2 2 1 2 2
A2-B1058 200 1 2 4 1 2 2
A64-B24 200 2 2 4 1 2 2
A64-B1 200 2 3 4 1 1 2
A2-B1089 200 1 2 2 1 1 2
A2-B31 200 2 2 2 1 2 2
A2-B1090 200 2 4 4 2 2 2
A2-B46 (cis) 200 1 4 3 1 2 2
A2-B46 (trans) 200 1 4 2 1 1 2
A2-B91 200 1 4 2 1 2 2
A2-B2 200 1 4 2 1 2 2
A2-B29 200 2 3 2 1 2 2
A2-B1066 200 1 3 2 1 2 2
A2-B25 200 1 2 2 2 1 2
A2-B1068 200 1 2 4 1 1 2
compound g / ha Ipomoea Lolii Setaria Sinapis Solanum Stelleria
A2-B107O 200 2 3 2 1 2 2
A2-B5 200 1 3 2 1 2 2
A2-C149 200 1 2 2 2 1 2
A2-C146 200 1 2 4 1 1 2
A2-B112 200 2 4 2 2 2 2
A2-B354 200 1 2 2 1 2 2
A2-E16 200 1 3 2 1 2 2
A6-B24 200 1 2 2 1 2 2
A34-B1 200 2 3 2 1 2 2
A9-B1 200 2 2 2 2 2 2
A184-B1 200 2 3 2 2 2 2
A184-B24 200 1 3 2 1 1 2
A7-B24 200 1 2 2 1 1 2
A3-B24 200 2 4 2 2 2 2
A34-B24 200 1 3 2 1 2 2
A8-B24 200 1 2 2 1 2 2
A18-B24 200 1 2 2 1 2 2
A2-C152 200 2 2 3 1 2 2
A A22 - BB2266 2 20000 1 2 2 1 2 2
A2-D36 200 2 2 2 1 2 2
A2-B618 200 1 2 2 1 2 2
A2-B49 200 2 2 2 1 2 2
A2-B1093 200 1 2 2 1 2 2
A2-B33 200 2 4 2 1 2 2
A2-B34 200 2 3 2 1 1 2
A2-B35 200 2 3 2 1 1 2
A2-B1087 200 2 4 3 1 2 2
A531-B24 200 2 2 2 1 2 2
A2-B1095 200 1 2 4 1 2 2
A2-C147 200 1 2 2 1 2 2
A2-B70 200 3 4 3 1 2 2
compound gg // hhaa I? poommoea Lolium Setaria Sinapis Solanum Stelleria
A2-B49 200 2 2 2 1 2 2
A2-C1 200 3 2 2 1 2 2
A2-B1100 200 2 2 3 2 2 2
A8-B2 200 2 2 2 1 1 3
A8-B1064 200 2 4 2 1 2 2
A8-B133 200 2 4 2 1 1 2
A8-B1101 200 2 3 2 1 2 2
A2-B1101 200 2 2 2 1 2 3
A2-B156 200 1 2 2 1 1 2
A2-B134 200 2 2 1 1 2 2
A1210-B354 200 2 2 2 1 1 2
A2-C2 200 2 1 1 1 1 1
A2-D36 200 2 1 1 1 1 1
A2-D113 (Isom.A) 200 2 1 1 1 1 2
A2-D113 (Isoia.B) 200 2 2 2 2 2 2
A2-D114 200 2 1 1 1 1 1
A2-D115 200 1 2 1 1 1 1
A8-B34 200 2 2 2 2 2 2
A8-B1103 200 1 4 1 1 1 1
A2-C24 200 1 1 1 1 1 1
Table B2a: Herbicidal action after emergence;
Panicum Digitaria Echino compound. Abutilon Xanth. ipopur. Chenop. g / ha A8-B1 250 4 3 3 3 3 3 2
A2-B1091 250 4 4 2 3 4 3 3
A2-B1094 250 2 3 2 3 3 3 2
A2-B145 250 2 2 2 3 3 3 1
A1208-B354 250 3 4 2 1 2 2 2
A1210-B1 250 2 2 2 2 2 2 1
A8-B552 250 2 3 3 2 2 2 2
A8-B156 250 2 3 3 1 2 2 1
A1210-B1 105 250 1 2 3 2 2 2 1
A8-B134 250 3 3 3 2 3 3 2
A8-D36 250 3 3 2 2 3 3 2
A2-D111 (cis) 250 2 2 4 2 1 2 2
A2-D111 (traps) 250 3 3 3 3 1 3 2
A8-D111 250 3 3 3 3 1 2 3
A8-D109 250 3 3 3 3 1 2 3
A8-F5 250 4 3 4 3 3 3 3
A2-F5 250 3 3 3 3 3 4 3
The same results are obtained when the compounds of the formula I are formulated according to the examples F2 and F4 to F8 according to International Publication Number WO 97/34485.
It is noted that in relation to this date, the best method known to the applicant to carry
In practice, said invention is the conventional one for the manufacture of the objects or products to which it refers.
Claims (17)
-
- Having described the invention as above, the content of the following claims is claimed as property: 1. A compound of the formula I characterized in that wherein: p is 0 c 1; Rs is haloalkyl of 1 to 6 carbon atoms; R2 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, vinyl which is substituted by alkoxy of 1 to 6 carbon atoms. to 2 carbon atoms-carbonyl or phenyl, or is alkinyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, ethinyl which is substituted by trimethyl silyl, hydroxyl, alkoxy of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms-carbonyl,
- Or phenyl, or is alenyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms which is substituted by halogen, or is alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 a (> carbon atoms, haloalkoxy of 1 to 6 carbon atoms, haloalkenyloxy of 3 to 6 carbon atoms, cyanoalkoxy of 1 to 4 carbon atoms, alkoxyc of 1 to 4 carbon-alkoxy atoms of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinylalkoxyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyl alkoxyl of 1 to 4 carbon atoms, alkoxyl of 1 to 4 carbonylalkyl atoms of 1 to 4 carbon atoms , thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms- sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkoxy of 1 to 4 carbon atoms-carbonyl thioalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms -sulfinyl, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms- sulfonyl, benzyl-S (0) alkyl of 1 to 6 carbon atoms-amino, dialkyl of 2 to 6 carbon atoms-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 6 carbon-amino atoms) st.phonyl, benzyloxy, benzyl, phenyl, phenoxy, thiophenyl, phenylsulfinyl, or phenylsulfonyl, it being possible for the groups containing phenyl to be substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or R2 is OS (C) n2-R2i, (R23) -S (O) n3-R22 > cyano, carbamoyl, alkoxy of 1 to 4 carbon atoms-carbonyl, formyl, halogen, thiocyanato, amino, hydroxyalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms carbon, alkyl of 1 to 4 carbon atoms - S (0) n4_alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms - carbonyloxyalkyl of 1 to 4 carbon atoms , alkoxy of 1 to 4 carbon atoms-carboni alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, benzoyloxyalkyl of 1 to 4 carbon atoms, oxiranyl from 2 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 4 carbon atoms, di- (alkyl of 1 to 4 carbon atoms) aminoalkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 12 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, or formylalkyl of 1 to 4 carbon atoms, or Rc is a monocyclic or bicyclic fused ring system of 5 to 10 members which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being linked to the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, -C = C-, -CH20-, -CH2N ( alkyl of 1 to 4 carbon atoms) -, -CH SO-, or -CH2S02, and it is not possible for each ring system to contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and it is possible that the ring system itself mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy-lo of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms , thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon atoms-thioalkyl, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfini or, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl , aminosulfonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms] aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms' amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and the substituents being on the ring nitrogen heterocyclic other than halogen;
- R3 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms carbon-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkyl of 1 to 6 carbon-amino atoms, dialkyl of 2 to 6 carbon atoms-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, dialkyl of 2 to 6 carbon atoms-aminosulfonyl, phenyl, thiophenyl, phenylsulfinyl, phenylsulfonyl, or phenoxy , it being possible that phenyl, in turn, is substituted by alkyl of 1 to 3 atoms of carbon, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or R3 is -N (R23) -S (O) n- R22 / cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms-S (0) n-alkyl of 1 to 4 carbon atoms; R is hydrogen, alkyl of 1 to 6 carbon atoms, hydroxyl, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, haloalkenyloxy of 3 to 6 carbon atoms , alkynyloxy of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxy, alkyl of 1 to 4 carbon atoms-sulfonyloxy, tosyloxy, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms carbon-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkoxy of 1 to 4 carbon atoms-carbonyl, haloalkyl of 1 to 4 carbon atoms, formyl, cyano, halogen, phenyl, or phenoxy, it being possible that phenyl, in turn, is substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, C? nitro; or R is a 5 to 10 membered monocyclic or bicyclic fused R3 ring system, which may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being, unless this is condensed, linked to the pyridine ring directly or by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, -C = C-, -CH 0-, -CH2N (alkyl of 1 to 4 carbon atoms) -, -CH2S-, -CH2SO-, or -CH2SO2-, and it is not possible for the ring system to contain more than 2 carbon atoms of oxygen, and no more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioa lkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-thioalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms carbon-carbonyl thioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms, cyanothioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 5 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalk? ilo of 1 to 6 carbon atoms-sulfonyl, aminosulfonyl, alkyl of 1 to 2 carbon atoms-aminosul fonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) carbon) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, carbon, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and the substituents on the nitrogen of the heterocyclic ring being different from halogen; R21 is alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R22 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or di- (alkyl of 1 to 4 carbon atoms) amino; R23 / R24I / independently of each other, are hydrogen or alkyl of 1 to 4 carbon atoms; n, ni, n2 / n3 and n4, independently of each other sin 0, 1 or 2; wherein: R6, R7, Rβ, and FA independently of one another, are hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6. 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-S (O) np, alkyl of 1 to 6 carbon atoms-NHS (0) 2, alkyl of 1 to 6 carbon atoms-amino, di- (alkyl of 1 to 6 carbon atoms) amino, hydroxyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms - sulfonyloxy-alkyl from 1 to 6 carbon atoms, tosyloxy alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-S (0) alkyl of 1 to 6 carbon atoms, cyanoalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkoxy of 1 to 6 carbon atoms, benzyloxyalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonylalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonyloxyalkyl of 1 to 6 carbon atoms, thiocyanatoalkyl of 1 to 6 carbon atoms, oxiranyl, alkyl of 1 to 6 carbon atoms-aminoalkyl of 1 to 6 carbon atoms , di- (alkyl of 1 to 6 carbon atoms] aminoalkyl of 1 to 6 carbon atoms, formyl-1 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms-halo, cyano, nitro, phenyl, or phenyl which is substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, carbonyl, alkoxy of 1 to 4 carbon atoms, carbonyl, amino, alkyl of 1 to 4 carbon-amino atoms, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-S (O) n-8 alkyl of 1 to 4 carbon atoms-S (O) 20, haloalkyl from 1 to 4 carbon atoms-S (O) n 5 / haloalkyl of 1 to 4 carbon atoms-S (O) 20, alkyl of 1 to 4 carbon atoms-S (O) 2 NH, alkyl of 1 to 4 atoms carbon-S (0) ni9-J (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH or cyano; or Re and 7 adjacent, or R3 and R9 are together - (CH2) m-, C (0) 0 (CH2) n2o- or -S (0) n2i (CH2) n22-; n5, ni7, nis, n? 9, and n2i, independently of each other 0, 1 or 2; n20 is 2 or 3; n22 is 2, 3 or 4; m is 2, 3, 4, 5 or 6; W is oxygen, S (0) n6, -CR11R12, -CR53R64CR65R66, -C (O) - or NRi3; R63-Rd4i Res, and Rßβ, independently of one another, are hydrogen or alkyl of 1 to 6 carbon atoms, or Res together with R7 or R9 forms a direct bond; n6 is 0, 1, or 2; R n is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl from 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms- carbonyloxyalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyloxyalkyl of 1 to 4 carbon atoms, tosyloxyalkyl of 1 to 4 carbon atoms, di- (alkoxy of 1 to 3 carbon atoms-alkyl) R ethyl, di- (C 1 -C 3 -alkyl thioalkyl) methyl, (C 1 -C 3 alkoxy) - (C 1 -C 3 alkyl-thioalkyl) methyl, oxacycloalkyl 3 to 5 carbon atoms, tiacycloalkyl of 3 to 5 carbon atoms, dioxacycloalkyl of 3 to 4 carbon atoms, dithiacycloalkyl of 3 to 4 carbon atoms, oxathiaci cloalkyl of 3 to 4 carbon atoms, formyl, alkoxy of 1 to 4 carbon atoms-carbonyl, carbamoyl, alkyl of 1 to 4 carbon atoms-aminocarbonyl, di- (alkyl of 1 to 4 carbon atoms) aminocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl, or phenyl which, in turn, may be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, amino, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-S (O) n2 ?, alkyl of 1 to 4 carbon atoms-
- S (0) 20, haloalkyl of 1 to 4 carbon atoms-S (0) n7, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0)? NH, alkyl of 1 to 4 carbon atoms-S (0) n20N (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH or cyano; n7, n20 and n2 ?, independently of each other, are 0, L or 2; or RX2, together with R6 or R9, is a group - (CH2) 0_; or is 1, 2, 3, 4 or 5; R 2 is hydrogen, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms; or R12 together with Rn is a group - (CH2) m ?; my is 2, 3, 4, 5 6 6; Rio is hydroxyl, 0 ~ M +, halogen, cyano, SCN, OCN, alkoxy of 1 to 12 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkoxyl of 1 to 4 carbon atoms, thioalkyl of 1 to 12 carbon atoms carbon, alkyl of 1 to 12 carbon atoms-sulfinyl, alkyl of 1 to 12 carbon atoms-sulfonyl, halotioalkyl of 1 to 12 carbon atoms, haloalkyl of 1 to 12 carbon atoms-sulfinyl, haloalkyl of 1 to 12 atoms carbon-sulfonyl, alkoxy of 1 to 6 carbon atoms-thioalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms-sulfinyl, alkoxy of 1 to 6 carbon atoms carbon-alkyl from 1 to 6 carbon atoms-sulfonyl, thioalkenyl of 2 to 12 carbon atoms, alkenyl of 2 to 12 carbon atoms-sulfinyl, alkenyl of 1 to 12 carbon atoms-sulfonyl, thioalkynyl of 2 to 12 carbon atoms, alkynyl of 2 to 12 carbon atoms-sulfinyl, alkynyl of 2 to 12 carbon atoms-sulfonyl, halotioalkenyl of 2 to 12 carbon atoms, haloalkenyl of 2 to 12 carbon atoms-sulfinyl, haloalkenyl of 2 to 12 carbon atoms-sulfonyl, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms-sulfinyl, C 1 -C 4 alkoxycarbonylalkyl of 1 to 4 carbon atoms-sulfonyl, (C 1 -C 4 alkoxy) 2P (O) O, C 1 -C 4 alkyl- (C 1 -C alkoxy) 4 carbon atoms) P (O) O, H (alkoxy of 1 to 4 carbon atoms) P (O) O, R? 4R15N, R14R15NNH, R? 6R? 7NC (O) O-, R16R17NC (O) NH -, alkyl of 1 to 12 carbon atoms-S (0) 2NRi3, haloalkyl of 1 to 4 carbon atoms-S (O) 2N R19, alkyl of 1 to 12 carbon atoms-S (O) 20, haloalkyl of 1 to 4 carbon atoms -S (O) 20, alkyl of 1 to 18 carbon atoms -carbonyloxy, it being possible for the alkyl group to be substituted by halogen, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, or cyano, or is alkenyl of 2 to 18 carbon atoms-carbonyloxy, alkynyl of 2 to 18 carbon atoms-carbonyloxy, cycloalkyl of 3 to 6 carbon atoms-carbonyloxy, alkoxy of 1 to 12 carbon atoms-carbonyloxy, thioalkyl of 1 to 12 carbon atoms-carbonyloxy, thioalkyl of 1 to 12 carbon atoms-carbamoyl, alkyl of 1 to 6 carbon atoms-NH (CS) N (alkyl of 1 to 6 carbon atoms) -NH-, dialkyl of 1 to 6 carbon atoms- (CS) N (alkyl of 1 to 6 carbon atoms) -NH-, benzyloxy, thiobenzyl, benzylsulfinyl, benzylsulfonyl, phenoxy, thiophenyl, phenylsulfinyl , phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, it being possible for the phenyl groups, in turn, to be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl , alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, thioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms carbon-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, alkyl of 1 to 4 carbon atoms-S (O) 20, halotioalkyl of 1 to 4 carbon atoms, haloalkyl from 1 to 4 carbon atoms-sulfinyl, haloalkyl from 1 to 4 carbon-sulfonyl atoms, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0) 2 NH, alkyl of 1 to 4 carbon atoms-S (0) 2N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano; or Rio is an Ary-thio group, Ar2-sulfinyl, Ar3-sulfonyl, -0C0-Ar4, or NH-Ar5, where? rl f Ar2, Ar3, Ar4, and Ar5, independently of each other, are a system of monocyclic or bicyclic condensed ring, 5 to 10 members, which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, it being possible for each ring system to contain no more than 2. oxygen atoms, and no more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, 6 tri-substituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms carbon, haloalq? lithium of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 carbon atoms, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 atom:; of carbon-thioalkyl, acetyl of 3 to 5 atoms of ono-thioalkyl, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosul fonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- ( alkyl of 1 to 2 carbon atoms) aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen of the heterocyclic ring are different from halogen;
- R14, Ris, Ri6 R17, and Ri8 # independently of each other, are hydrogen or alkyl of 1 to 6 carbon atoms; ns, n9, nio, nn, ni2, ni and ni4, independently of each other, are 0, 1 or 2; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-carbonyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinylcarbonyl of 1 to 4 carbon atoms , alkyl of 1 to 4 carbon atoms-sulfonylcarbonyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-carbonyl, phenylcarbonyl, or is phenyl which in turn may be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl , alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-amino, di-alkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-S (O) ni5 alkyl of 1 to 4 carbon atoms - S (O) 20, haloalkyl of 1 to 4 carbon atoms - S (0) ni6, haloalkyl of 1 to 4 carbon atoms - S (O) 20, alkyl Uilo of 1 to 4 carbon atoms-S (O) 2 NH, alkyl of 1 to 4 carbon atoms-S (O) 2 N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano; and n.i5 and ni6, independently of one another, are 0, 1 or 2; or the agrochemically tolerated salts Mt or a stereoisomer or tautomer of the compounds of the formula I. 2. A compound according to claim 1, characterized in that p is 0; R5 is haloalkyl of 1 to 6 carbon atoms; R2 is hydrogen, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl from 2 to 6 carbon atoms, cycloalcuyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 atoms of carbon-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 5 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, benzyl-S (O) n? -, alkyl of 1 to 6 carbon atoms-amino, dialkyl of 2 to 6 carbon atoms carbon-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, dialkyl of 2 to 6 carbon atoms-aminosulfonyl, phenyl, phenoxy, thiophenyl, phenylsulfinyl, or phenylsulfonyl, it being possible for the phenyl group, in turn, to be substituted by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, halogen, cyano, or nitro, or is 0S (0) n2-R2 ?, N (R23) S (0) n3-22 / cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms- S (0) n4-alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, or alkoxyl of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms; R3 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, cycloalcuyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkyl of 1 to 6 carbon-sulfinyl atoms, alkyl of 1 to 6 carbon atoms-sulfenyl, halotioalkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, alkyl of 1 to 6 carbon atoms-amino, dialkyl of 2 to 6 carbon atoms-amino, alkyl of 1 to 6 carbon atoms-aminosulfonyl, dialkyl of 2 to 6 carbon atoms-aminosulfonyl, phenyl, thiophenyl, phenylsulfinyl, phenylsulfonyl or phenoxy, it being possible that phenyl, in turn, is substituted by alkyl of 1 to 3 carbon atoms , haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, or is -N (R23) -S (O) n-R22 ? cyano, halogen, amino, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, or alkyl of 1 to 4 carbon atoms-S (O) n-alkyl of 1 to 4 carbon atoms; R 4 is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxy, thioalkyl of 1 to 4 carbon atoms alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms sulfonyl, haloalkyl of 1 to 4 carbon atoms, formyl, cyano, halogen, phenyl, or phenoxy, it being possible for phenyl, in turn , is substituted by alkyl of 1 to 3 atoms of carbon, - haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro; or R4 is a 5 to 10 membered monocyclic or bicyclic fused R3 ring system, which may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system being linked by the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, and it is not possible for the ring system to contain more than 2 oxygen atoms, and not more than 2 sulfur atoms, and it is possible for the ring system itself to be mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6. carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy from 3 to 6 carbon atoms, alkynyloxy from 3 to 6 carbon atoms, thioalkyl from 1 to 6 carbon atoms, halotioalkyl from 1 to 6 carbon atoms, thioalkenyl from 3 to 6 carbon atoms, halotioalkenyl from 3 to 6 atoms of carbon, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon-thioalkyl atoms of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl thioalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylthioalkyl of 1 to 2 carbon atoms , cyanothioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 6 carbon atoms sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms -sulphonyl, aminosul fonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, dialkyl of 2 to 4 carbon atoms-aminosul fonyl, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn , are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and where the substituents on the nitrogen in the heterocyclic ring Clico are different from halogen; R21 and R22 / independently of one another, are alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms;
- R 24 and R 5 independently of one another are hydrogen or alkyl of 1 to 4 carbon atoms; n, nx, n2, n3, and n4, independently of each other, are 0, 1 or 2; where 'R, Ri, Re, and R9, independently of one another, sor hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms-carbonyl, alkyl of 1 to 6 carbon atoms-S (0) ni7, alkyl of 1 to 6 carbon atoms-NHS (O) 2, alkyl of 1 at 6 atoms of carbon-amino, di- (alkyl of 1 to 6 carbon atoms) amino, hydroxyl, alkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms , hydroxyalkyl of 1 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms carbon-sulfonyloxyalkyl of 1 to 6 carbon atoms, tosyloxy.alkyl of 1 to 6 carbon atoms, halogen, cyano, nitro, phenyl, or phenyl which is substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, amino, alkyl of 1 to 4 carbon-amino atoms, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-s (0) ni8 / alkyl of 1 to 4 carbon atoms-S (O) 20, haloalkyl of 1 to 4 carbon atoms-S (O) n5 haloalkyl of 1 to 4 carbon atoms-S (O)? 0, alkyl of 1 to 4 carbon atoms - S (O) 2 NH, alkyl of 1 to 4 atoms carbon-S (O) ni9 (alkyl of 1 to 4 carbon atoms), halogen, nitro, ("OOH, or cyano; or adjacent R6 and R7, or R8 and R9 are together - (CH2) m; n5, ni7, nis and n? 9, independently of each other, are 0, 1 or 2; m is 2, 3, 4, 5, 6, 6; W is oxygen, S (0) ne / -CRnR? 2-, -C (0)? 3-; n6 is 0, 1 or 2; Rn is hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyloxyalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyloxyalkyl of 1 to 4 carbon atoms, tosyloxy alkyl of 1 to 4 carbon atoms, di- (alkoxy of 1 to 3 carbon atoms-alkyl) methyl, (alkyl of 1 to 3 to: carbon atoms-thioalkyl) methyl, (alkoxy of 1 to 3 carbon atoms-alkyl) - (alkyl of 1 to 3 carbon atoms-thioalkyl) ethyl, oxacycloalkyl of 3 to 5 carbon atoms carbon, cycloalkyl of 3 to 5 carbon atoms, dioxacycloalkyl of 3 to 4 carbon atoms, dithiacyloalkyl of 3 to 4 carbon atoms, oxatiaccycloalkyl of 3 to 4 carbon atoms, formyl, alkoxy of 1 to 4 carbon atoms - carbonyl, or phenyl, which in turn may be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, 1 to 4 carbon atoms - carbonyl, alkoxy of 1 to 4 carbon atoms - carbonyl, amino, alkyl of 1 to 4 carbon atoms - amino, dialkyl of 1 to 4 carbon atoms - amino, alkyl of 1 to 4 atoms of carbon-S (O) n2 ?, alkyl of 1 to 4 carbon atoms-S (O) 20, haloalkyl from 1 to 4 carbon atoms-S (0) n7, haloalkyl of 1 to 4 carbon atoms-S (0) 20, alkyl of 1 to 4 carbon atoms-S (0) 2 NH, alkyl of 1 to 4 atoms carbon-S (0) n? oN (alkyl of 1 to 4 carbon atoms), halogen, nitro, COOH, or cyano; n7, n20, and n2 ?, independently of each other, are 0, 1 or 2; or R 2, together with R 9, is a group - (CH 2) or -; or is 1, 2, 3, 4 or 5; R 12 is hydrogen, alkyl of 1 to 4 atoms or haloalkyl of 1 to 4 carbon atoms; or R12, together with RU / is a group - (CH2) m ?;
- Rio is hydroxyl, 0"MT, halogen, alkoxy of 1 to 12 carbon atoms, alkyl of 1 to 12 carbon atoms-carbonyloxy, alkenyl of 2 to 4 carbon atoms-carbonyloxy, cycloalkyl of 3 to 6 carbon atoms- carbonyloxy, alkoxy of 1 to 12 carbon atoms-carbonyloxy, alkyl of 1 to 12 carbon atoms-carbonyloxy, R23R24N-C (0) 0, alkyl of 1 to 12 carbon atoms-S (0) n8- / haloalkyl of 1 to 4 carbon atoms- S (0) n9-, alkenyl of 2 to 12 carbon atoms- S (0) nio-haloalkenyl of 2 to 12 carbon atoms- S (0) ni? - / alkynyl of 2 to 12 carbon atoms-S (0) n? 2; benzyl? Yl, phenoxy, thiophenyl, phenylsulfinyl, or phenylsulfonyl, wherein the phenyl group, in turn, can be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4. carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms-carbonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms-amino, alkyl of 1 to 4 carbon atoms-S (0) nl3, alkyl of 1 to 4 carbon atoms-5 (O) 20, haloalkyl of 1 to 4 carbon atoms S (0) ni4, haloalkyl of 1 to 4 carbon atoms -S (O) 0, alkyl of 1 to 4 carbon atoms-S (0) 2 NH, alkyl of 1 to 4 atoms of carbon-S (0) N (alkyl of 1 to 4 carbon atoms), halogen, nitro , or cyano, or is alkyl of 1 to 4 carbon atoms-S (0) 20, phenyl-S (0) 20, (alkoxy of 1 to 4 carbon atoms) 2P (0) 0, alkyl of 1 to 4 carbon atoms Alcoxyl of 1 to 4 carbon atoms) P (0) 0, or H (alkoxy of 1 to 4 atom) s carbon) P (0) 0; n.8 / n9, child, nn, ni2, ni3 and ni4, independently of each other, are 0, 1 or 2; Ri3 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or phenyl, which in turn may be substituted by alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 atoms carbon, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-carbonyl, alkoxy of 1 to 4 carbon atoms carbonyl, alkyl of 1 to 4 carbon atoms-amino, dialkyl of 1 to 4 carbon atoms- amino, alkyl of 1 to 4 carbon atoms-S (O) n? 5, alkyl of 1 to 4 carbon atoms-S (O) 20, haloalkyl of 1 to 4 carbon atoms-S (O) n? 6 , haloalkyl of 1 to 4 carbon atoms-S (O) 20, alkyl of 1 to 4 carbon atoms-S (O) 2 NH, alkyl of 1 to 4 carbon atoms-S (O) 2N (alkyl of 1 to 4 carbon atoms), halogen, nitro, or cyano; is and ni6, independently of one another, are 0, 1 6 2; or the agrochemically tolerated M + salts, or all the stereoisomers and tautomers of the compounds of the formula I. 3. A compound according to claim 1, characterized in that Rio is hydroxyl or 0"M + A compound according to claim 1, characterized in that W is oxygen, -CR11R12- or -C (O). 5. A compound according to claim 1, characterized in that W is oxygen, and
- Re, R7, Rβ, and Rg, independently of one another, are hydrogen or alkyl of 1 to 3 carbon atoms. 6. A compound according to claim 1, characterized in that W is -C (0) - and Re, R7, Re, and R9, independently of each other, without alkyl of 1 to 3 carbon atoms. 7. A compound according to claim 1, characterized in that R2 is hydrogen and R3 is methyl. 8. A compound according to claim 1, characterized in that: R 2 is methyl, ethyl, normal propyl, isopropyl, vinyl, methoxymethyl, methoxytributyloxymethyl, ethoxycarbonyloxymethyl, acetoxymethyl, propionyloxymethyl, chloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, or cyanomethyl. 9. A compound according to claim 1, characterized in that R4 is hydrogen or methyl.
- 10. A compound according to claim 1, characterized in that R5 is trifluoromethyl, difluorochloromethyl, pentafluoroethyl, heptafluoropropyl, or difluoromethyl.
- 11. A compound according to claim 1, characterized in that: R3 is hydrogen, R 2 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, cyclopropyl, alkenyl of 2 to 3 carbon atoms, haloalkenyl of 2 to 3 carbon atoms, alkynyl of 2 to 3 carbon atoms , allyl, alkoxy of 1 to 2 carbon atoms-alkyl of 1 to 2 carbon atoms, thioalkyl of 1 to 2 carbon atoms-alkyl of 1 to 2 carbon atoms, cyanoalkyl of 1 to 2 carbon atoms, alkoxy 1 a 2 carbon atoms-carbonylalkyl of 1 to 2 carbon atoms, alkyl of 1 to 4 carbon atoms, carbonyloxyalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, allyloxy , propargyloxy, thioalkyl from 1 to 3 carbon atoms, alkyl of 1 to 3 carbon atoms-sulfinyl, or cyano.
- 12. A compound of the formula Illa characterized by that: R5o? is haloalkyl of 1 to 6 carbon atoms; R3o? it is hydrogen; R401 is hydrogen or alkyl of 1 to 6 carbon atoms; and R2o? is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkyl of 2 to 6 carbon atoms, or -vinyl substituted by alkoxy of 1 to 2 carbon atoms-carbonyl or by phenyl, alkynyl of 2 to 6 carbon atoms, or haloalkynyl of 2 to 6 carbon atoms; or ethynyl or alenyl of 3 to 6 carbon atoms substituted by tri-ethylsilyl, hydroxyl, alkoxy of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms-carbonyl, or by phenyl; or cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by halogen, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-S (O) n 4 -alkyl of 1 to 4 carbon atoms, cyanoalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms carbon, oxiranyl, alkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 4 carbon atoms, dialkyl of 1 to 4 carbon atoms-aninoalkyl of 1 to 4 carbon atoms, hydroxy-alkyl of 1 to 4 carbon atoms , thioalkyl of 1 to 12 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, or formyl-alkyl of 1 to 4 carbon atoms, or R2o? is a 5 to 10 membered monocyclic or bicyclic fused ring system which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the ring system linked to the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, -C = C-, -c: H20-, -CH2N (alkyl of 1 to 4 atoms carbon) -, -CH2S-, -CH2SO-, or -CH2S02-, and it is not possible for each ring system to contain more than 2 oxygen atoms and more than 2 carbon atoms of sulfur, and it is possible that the ring system itself mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms carbon, alkynyl of 3 to 6 carbon atoms, haloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon volumes, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, alkylthio of 1 to 6 carbon atoms, halothioalkyl 1 to 6 carbon atoms, thioalkenyl 3 to 6 carbon atoms carbon, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon atoms-thioalkyl, alkoxy of 3 to 6 carbon atoms -carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl, alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon-sulfonyl atoms, aminosulfonyl, alkyl of 1 to 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms Aminosulfonyl, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenzene, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are different from halogen; and X is halogen or cyano.
- 13. A compound of the formula XVIa: characterized in that: Rsoi is haloalkyl of 1 to 6 carbon atoms; R301 is hydrogen; R401 is hydrogen or alkyl of 1 to 6 carbon atoms; Y R201 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms-alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkyl? enyl of 2 to 6 carbon atoms, or vinyl substituted by alkoxy of 1 to 2 carbon atoms-carbonyl or by phenyl, alkynyl of 2 to 6 carbon atoms, or haloalkynyl of 2 to 6 carbon atoms; or ethynyl or alenyl of 3 to 6 carbon atoms substituted by trimethylsilyl, hydroxyl, alkoxy of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms-carbonyl, or by phenyl; or cycloalkyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms substituted by halogen, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-S (O) n 4 -alkyl of 1 to 4 atoms carbon, cyano-alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, thiocyanate of 1 to 4 carbon atoms, oxiranyl, alkyl of 1 to 4 carbon atoms -aminoalkyl of 1 to 4 carbon atoms, dialkyl of 1 to 4 carbon atoms-aninoalkyl of 1 to 4 carbon atoms, hydroxy-alkyl of 1 to 4 carbon atoms, thioalkyl of 1 to 12 carbon atoms-carbonylalkyl of 1 to 4 carbon atoms, or formyl-alkyl of 1 to 4 carbon atoms, or R20? is a 5 to 10 membered monocyclic or bicyclic fused ring system which may be aromatic or may be partially saturated, and may contain from 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, the system being of ring bound with the pyridine ring by means of an alkylene group of 1 to 4 carbon atoms, -CH = CH-, -C = C-, -CH20-, -CH2N (alkyl of 1 to 4 carbon atoms) - , -CH? S-, -CH? SO-, or -CH2S02-, and it is not possible for each ring system to contain more than 2 oxygen atoms and more than 2 carbon atoms of sulfur, and it is possible that the system ring itself this mono-, di-, or trisubstituted by alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms carbon, alkynyl of 3 to 6 carbon atoms, haloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 3 to 6 carbon atoms, alkynyloxy of 3 to 6 carbon atoms, mercapto, thioalkyl of 1 to 6 carbon atoms, halotioalkyl of 1 to 6 atoms of carbon, thioalkenyl of 3 to 6 carbon atoms, halotioalkenyl of 3 to 6 carbon atoms, thioalkynyl of 3 to 6 carbon atoms, alkoxy of 2 to 5 carbon atoms-thioalkyl, acetyl of 3 to 5 carbon atoms-thioalkyl, alkoxy of 3 to 6 carbon atoms-carbonylthioalkyl, cyano of 2 to 4 carbon atoms-thioalkyl alkyl of 1 to 6 carbon atoms-sulfinyl, haloalkyl of 1 to 6 carbon atoms-sulfinyl, alkyl of 1 to 6 carbon atoms-sulfonyl, haloalkyl of 1 to 6 carbon atoms-sulfonyl, aminosulfonyl, alkyl of 1 at 2 carbon atoms-aminosulfonyl, di- (alkyl of 1 to 2 carbon atoms) aminosulfon ilo, di- (alkyl of 1 to 4 carbon atoms) amino, halogen, cyano, nitro, phenyl, and thiobenzyl, it being possible that phenyl and thiobenzyl, in turn, are substituted on the phenyl ring by alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, halogen, cyano, or nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are different from halogen; and X is halogen or cyano, with the proviso that, when R50? is trifluoromethyl, and simultaneously R30? and F401 are hydrogen, then R201 is different from alkyl of 1 to 6 carbon atoms.
- 14. A herbicidal and plant growth inhibiting composition, characterized in that it has a herbicidally active content of a compound of the formula I on an inert carrier.
- 15. A method for controlling unwanted vegetation, characterized in that a herbicidally active amount of an active ingredient of the formula I, or of a composition comprising this active ingredient, is applied to the plants or to their environment.
- 16. A method for inhibiting the growth of plants, characterized in that a herbicidally active amount of an active ingredient of the formula I, or a composition comprising this active ingredient, is applied to the plants or to their environment.
- 17. The use of a composition according to claim 14, characterized in that it controls the undesired growth of plants. SUBSTITUTE PIRIDINE HERBICIDES SUMMARY OF THE INVENTION The compounds of the formula I wherein the substituents are as defined in claim 1, and the agrochemically tolerated salts MJ all the steroisomers and tautomers of the compounds of formula I are suitable for use as herbicides.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH2547/98 | 1998-12-23 |
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MXPA01006486A true MXPA01006486A (en) | 2001-12-13 |
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