First Symposium on Chemical-Biological Correlation, May 26-27, 1950 (1951) / Chapter Skim
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Relation of Structure of Diphenyl Compounds to Fungitoxicity
Relation of Structure of Diphenyl Compounds to Fungitoxicity
Pages 209-244
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From page 209... ...
A Chapman and Saul Rich Department of Plant Pathology and Botany The Connecticut Agricultural Experiment Station New Haven, Connecticut
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From page 210... ...
Diphenyl itself, for example, is a good inhibitor of growth - a poor inhibitor of spore germination. In visualizing the effect of test chemicals we should remember that a germinating spore carries its own rations.
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From page 211... ...
TABLE 1 CHEMICAL NAMES AND STRUCTURES OF TESTED DIPHENYL DERIVATIVES 4-Amino-2-chloro diphenyl ether 2-Amino diphenyl H2r 4-Amino diphenyl 4-Amino-2-phenyl phenol
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From page 212... ...
Cl Cl Cl , etc. Arochlor 1248 Mixture of trichlorodiphenyls, position of chlorines uncertain HC1 a-Benzyl-a-phenyl hydrazine hydrochloride H3C Auramine base hydrochloride CH3 QH2 CBenzyl sulfone "*
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From page 213... ...
dis ulf ide H3C' \ f s f v^n3 Bis (4-dimethyl aminophenyl) methane Bis (4-chlorophenyl)
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From page 214... ...
benzylimido methane CH3 Bis (4-methyl phenyl) sulfonic acid HO 6-Chloro-4-(3-chloro-4-hydroxy-a, a-dimethylbenzyl)
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From page 215... ...
NHNHCONHNH \ / sulfonamide 0 s -Diphenyl carbazone N - ( S Dicyclohexyl amine Diphenyl disulfide
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From page 216... ...
0 Diphenyl sulfone Diphenyl guanidine phthalate N-NH2 . HC1 AS -Diphenyl hydrazine hydrochloride Diphenyl methane C -- ( 6 Diphenyl phthalate Q-O Diphenyl sulfoxide / \ H H S H H / V / ^ -- N -- N -- C -- N -- N-/ \ Diphenyl thiocarbazide aH H S / V
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From page 217... ...
) C2H5 Ethylbenzyl aniline OH Phenyl -2 -hydroxybenzoate CH2 \ - / Ethylidene aniline Ethyl-2-benzoyl benzoate ,OH 2-Phenyl phenol HO 4-Phenyl phenol 4-HydrcKy diphenyl amine J yU^U^M3 > w 2-Phenyl phenol acetate Isopropyl diphenyl ether 2-Phenyl sodium phenate H3C V Cl, \ - / Cl ci Pentachlorophenyl-4-toluenesulfonic acid CJtrO Salicylanilide Phenyl benzoate Triphenyl guanidine
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From page 218... ...
The following bridged compounds were non-toxic: TABLE 2 LIST OF NON-TOXIC BRIDGED COMPOUNDS Benzyl disulfide Dicyclohexylamine Diphenyl amine Diphenyl benzidine s-Diphenyl carbazide Diphenyl guanidine phthalate Diphenyl methane Diphenyl phthalate 4,4-Diphenyl semicarbazide Ethyl benzyl aniline Ethylidene aniline Bis (2-diphenyl) monophenyl phosphate Triphenyl guanidine
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From page 219... ...
en fMtn inm rg ^ in ""^ ^ ^ *
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From page 220... ...
For example, Stemphylium was inhibited by very few bridged compounds with otherwise unsubstituted rings. The most effective of these was diphenyl guanidine, 0 - NHCNHNH - 0.
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From page 221... ...
• N N ^ n N ^ rsl rsJ rg •*
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From page 224... ...
Using cyclohexane for the second ring gave a strikingly opposite effect for 2-phenyl phenol than for 4-phenyl phenol. It increased rather than reduced the potency of 2-phenyl phenol to both organisms and flattened the slope.
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From page 225... ...
isopropane, and 2,3',4,5',6 biphenylpentol; respectively. Horsfall^ reports data showing that adding extra -OH units to phenol, phenyl phenol, and naphthol usually reduces the fungitoxicity.
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From page 226... ...
benzylimido methane, the toxicity is blocked again. From all this study of -NH2, we can conclude that toxicity of an amino diphenyl compound depends upon the action of a primary amine.
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From page 227... ...
disulf 4-Diamieo diprteeyl di ydroUrtloride Beezidirt base dirtydro . g g N1 -Diprteeyl beezidirt a u f i >, Comprted fill t l o i 5 i a 7 i o.
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From page 230... ...
230 o U U n u .3 3 u « , , « 0 CX iT o en 'u t 1 55 , , 00 H o u -- i rg CO 1 | x E i n .
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From page 231... ...
The resonance discussed can be prevented by substituting to give triphenyl guanidine or diphenyl guanidine phthalate. If the resonance theory is sound, these compounds should be non-toxic and they are non-toxic.
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From page 232... ...
it is clear that the result is not due merely to the larger atomic size of bromine. Hatfield'' made a study of the effect of chlorinating phenyl phenols on toxicity to Fomes annosua in culture.
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From page 233... ...
>* «J Z Z Z oooo o o o o U ZZZZ ZZZZ *
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From page 236... ...
Effect of Position of Substituent on the Ring The comparative ranking of 2 and 4 -OH substituents are as follows: 2-cyclohexyl phenol > 4-cyclohexyl phenol, 4-phenyl phenol > 2-phenyl phenol, 2-chloro-4-phenyl phenol > 4-chloro2-phenyl phenol, benzyl-4 -hydroxybenzoate > benzyl-2-hydroxybenzoate. In the case of amino substituents 4-amino diphenyl > 2-amino diphenyl and bis {4-mtrophenyl)
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From page 237... ...
Depression slide teat using Stemphyllu.il sarc.naeforme.
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From page 238... ...
It seems reasonably clear that the more reduced the sulfur, the more fungitoxic are the diphenyl compounds with sulfur bridges. If so, we deduce that the reduced sulfur must compete for oxygen with the spore and thus interfere with its respiration.
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From page 239... ...
^ reported that chlorination and phenyl phenols increased toxicity to growing mycelia. We had no halogenated amino derivatives for study.
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From page 240... ...
Some of the compounds may react with cell constituents, as for example, diphenylhydrazine with glucose. Diphenyl benzidine may react with essential metals.
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From page 241... ...
, Plant Disease Rep.
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From page 242... ...
I am wondering whether, in these closely related diphenyl compounds when there was an ammonium or a hydroxyl substitution, if there might not have been an influence on the stability of the molecule, or a difference in its absorption or penetration.
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From page 243... ...
We have the problem of what we call coverage; it is analogous to the greased pig problem whether it is better to put on concentrated mixtures thinly spread, or weak mixtures with a lot of water. In other words, if you are permitted in the country fair to have two thousand pounds of human flesh to catch the pig, is it better to have ten 200-pounders or twenty 100pounders?
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