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Патент USA US3033898

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United States Patent 0
1
3,033,883
IC€
Patented May 8, 1962,
Mr.
.1
2
NOMENCLATURE
3,033,888 '
VINYL CYCLIC PHOSPHATES AND METHOD
OF PREPARATION
William S. Wadsworth, In, Willow Grove, and William D.
1n the Speci?cation
Emmons, Huntingdon Valley, Pa., assignors to Rohm &
Haas Company, Philadelphia, Pa., a corporation of
In the Claims
4 - chloromethyl - 4 - ethyl - propyl ene - 1 - ,8 - diehlorovinylphos -
5 - chloromethyl - 5 - ethyl - 2 ‘B -
Delaware
4 - chloromethyl ~ 4 - ethyl - propyl
5 - ehloromethyl - 5 - ethyl - 2 - a .
No Drawing. Filed Apr. 22, 1960, Ser. No. 23,897
19 Claims. (Cl. 260-461)
vmylphosphate
'
4, 4 - diehloromethylpropylene - 1 -
dichloroviuyloxy - 1, 3, 2 - dioxa -
phate
phosphorinane-2oxide
ene - 1 - a - ethoxy - ? - ehloro-'
This invention relates to new compositions of matter
and to their preparation. More especially, it deals with
10
new and useful vinyl cyclic phosphates which are sub
stituted in the 1 and 4 positions of the heterocyclic ring;
a further embodiment deals with a method for preparing
these compounds.
The compounds of the invention may be represented by
Formula I:
ethoxy - B - chlorovinyloxy - 1, 3,
2-dioxaphosphorinane-2-oxide
5, 5 - dichloromethyl - 2 - a - methyl
or}; methyl ~? - ehlorovinyl - phos
p at e
3 - ehlorovinyloiry - 1, 3, 2 - dioxa -
4- chloromethyl- 4 - acetoxymethyl
5 - ehloromethyl - 5 - acetoxy -
phosphorinane-Z-oxide
propylene - 1 -B - dichlorovinyl -
methyl - 2, B - dichlorovinyloxy -
4, 4 - dichloromethylpropylene - 1 a - ethyl 13 ~ dichlorovinyl - phos
5, 5 - dieh1oromethyl~ 2 - a - ethyl -
phosphate
1, 5a 2 - dioxaphosphorinane - 2 on e
phate
B - dichlorovinyloxy - 1, 3, 2 - di -
-
oxaphosphorinaue-Z-oxide I
4, 4 - dichloromethylpropylene - 1 -
5, 5 - diehloromethyl - 2 - a - methyl
a - methyl-B - dichlorovinylphos -
[3 - dichlorovinyloxy - 1, 3, 2 - di -
phate
oXaphosphorinane-2-oxide
>
‘EH’Z
r
o ronlonr (0) 00:0
can:
a1 Y1
Typical of the new and useful vinyl phosphates of the
invention are the following:
(I)
in which X is a halogen atom having an atomic number
ranging from 9 to 53 and including ?uorine, bromine,
chlorine, and iodine;
4-chloromethy1-4-ethy1propylene-l-B-dichlorovinyl phos
phate,
4-bromomethyl-4-ethylpropy1ene-l-B-dichlorovinyl
phos '
phate,
Z is (1) an atom of the class VIIA of the periodic
chart of the elements having an atomic number of 1 to 5 3
4-chloromethyl -' 4 - ethylpropylene-l~wethoxy - B - chloro
and including the atoms hydrogen, chlorine, ?uorine, bro
mine and iodine, (2) an alkyl group containing from 1
4 - chloromethyl-4-acetoxymethy1propylene-l-?-dichloro
vinyl phosphate,
'
vinyl phosphate,
to 4 carbon atoms, and (3) an acyloxy group in which 30 4-chloromethyl - 4 - dodecanoxymethylpropylene-l-p-di
chlorovinyl phosphate,
the acyl group contains from 1 to 12 carbon atoms;
4 - chloromethyl-4-hexanoxymethylpropylene-1-B-dichlo
R1 is a hydrogen atom, an alkyl group containing from
rovinyl phosphate,
1 to 4 carbon atoms, such as methyl, ethyl, isobutyl, iso
4-chloromethyl-4~methylpropylene - 1 - B - dichlorovinyl
propyl and the like; or R1 is an alkoxy R1O— group in
35
which R1 has been de?ned above;
4,4 - dichloromethylpropylene-l_m-methyl-?-dichlorovinyl
. Y1 is an atom of the class VIIA ofthe periodic chart
phosphate,
>
of the elements having an atomic number of 1 to 53 and
phosphate,
including the atoms, hydrogen, vchlorine, bromine, ?uorine
and iodine;
.
_
_
~
_
4 - chloromethyl-4-ethylpropylene-l-a-rnethoxy-?-chloro
vinyl phosphate,
Y2 is an atom of the class VIIA of the periodic chart 40 4-chloromethyl - 4 - ethylpropylene-l-a-butoxy-?-chloro
vinyl phosphate,
of the elements having an atomic number of 1 to 53 and
including the atoms, hydrogen, chlorine, bromine,
?uorine, and iodine; with the proviso that Y1 and Y2 are
never a hydrogen atom concurrently.
The cyclic phosphates of the invention are named in 45
accordance with the following nomenclature: ’
The atoms'in the ring are counted starting with the
phosphorous atom, followed by one of the oxygen atoms,
and then the carbon atoms. The compounds are named
phosphates to indicate that the phosphorous atom is pentavalent. The names of the compounds incorporate the
term “propylene” to specify that the compounds incorpo
4,4-dichloromethylpropylene-l-a-ethyl - ,8 - dichlorovinyl
phosphate,
'
4,4-dichloromethylpropylene-l-u-butyl - B -, dichlorovinyl
phosphate,
7.
4,4-dichloromethylpropylene-l-a-methyl - t3 - chlorovinyl
phosphate.
A further embodiment of the invention provides a
method for preparing the vinyl phosphates of the inven
tion by a method which comprises bringing together a
bicyclic phosphite of the general formula
rate three carbon atoms in the claim. The compounds
are disubstituted on the carbon in the 4-position of the
ring. The carbon atoms of the vinyl group are designated
in which Z has the de?nition given above with a com
pound of the general formula
as alpha and beta, the alpha carbon being the carbon
atom bonded to the phosphorous atom. In the claims,
the compounds are named as phosphorinanes. The cor
respondence between the two types of nomenclature used
60
is illustrated below:
,
.
. t
R: Y1
(O)CIJ—(IJ—YB
-
-'
‘
,
_
'
.
(11>
in which R1, Y1 and Y? are de?ned above‘ and X is a
s,esa,ess
V
3
r
,
4
.
suspended in an aqueous medium and applied as a spray.
halogen atom having an atomic number from 9 to 53
Also, the vinyl cyclic phosphonates of the invention may
and including ?uorine, chlorine, bromine and iodine.
The method for preparing the new vinyl phosphates is
unusual
the formbecause
of an alkyl
insteadhalide,
of splitting
it is retained
out theinhalogen
the vinyl
be formulated into self-emulsi?able or self-dispersible con
centrates or as aqueous sprays. Since the salts of .the
vinyl cyclic phosphonates of the invention are water
soluble and possess good herbicidal and fungicidal proper
ties, they olfer a particularly suitable group where aqueous
7 phosphate product,’ thus enhancing its useful properties.
In the preparation of the vinyl phosphates, the reactants
applications are desired.
are generally used in stoichiometric amounts; but an ex
cess of the compound is not detrimental to the reaction.
‘
The vinyl cyclic phosphonate of the invention may be
Preferably, the temperature is maintained in the range 10 employed as herbicides in pre-immergence or post-im
mergence applications. Generally, since the post-immer
gence applications o?er somewhat preferred control, it is
optimum temperature vbeing readily determined to suit
the recommended procedure.
best the individual reactivity of the particular reactant
The vinyl cyclic phosphonates of the invention are use
used to react with the bicyclic phosphite. When the
product is a solid, it precipitates, out of the solution; in 15 ful in controlling typical monocotyledons, such as duck
weed, pondweed, undesirable grasses and herbs and di
which case it may be separated by any suitable procedure;
cotyledons typi?ed by broad leaf plant species, such as
when the product is a liquid, it may be obtained by strip
curley dock and velvet leaf. In fungicidal tests, the vinyl
ping olf excess solvent and distilling off the product under
cyclic phosphonates of the invention were found to be,
reduced pressures. By suitable procedures, a purer prod
20 effective in the control of fungi as determined in standard
' uct may be obtained.
,
>
tests against Plzytophthora infestans, the late blight of
Typical of the starting bicyclic phosphites that are
tomato.
'
employed in accordance with the invention, there may be
In testing the herbicidal properties of the vinyl cyclic
named methyl bicyclic phosphi'te, butyl bicyclic phosphite,
phosphates of the invention against millet and wild
and ethyl bicyclic phosphite; hydroxymethyl bicyclic phos
' of 100° to 280° C., especially from 100° to 210° C., the
'phite, chloromethyl bicyclic phosphite, iodomethyl bi
25
. cyclic phosphite, bromomethyl bicyclic phosphite, ?uoro- ’
methyl bicyclic phosphite, chloroethyl bicyclic phosphite,
chlorobutyl bicyclic phosphite acetoxy bicyclic phosphite,
butanoxymethyl bicyclic phosphite, isobutyroxymethyl
bicyclic phosphite, octanoxymethyl bicyclic phosphite,
oats (monocots) and against curley dockrand velvet leaf
(dicots), it was observed that the compounds in which
Z and Y1 and Y2 are halogens exhibit very good fungicidal
activity combined'with good herbicidal effectiveness.
The following examples, in which all parts are by
30 weight, unless otherwise indicated, are offered as illus
trative of the method whereby thevinyl phosphates of the
dodecanoxymethyl bicyclic phosphite and the like.
' invention are prepared and arenot to be construed as a
These bicyclic phosphites may be prepared by a num
ber of suitable methods, such as by the general procedure
limitation thereon.
'
described in Journal of “Americal Chemical Society, 78,
6413 (1956), by Hoffman, Moore,'and Kogan as suitably 35
'
Example 1
4-chloromethyl-4-ethylpropylene - 1 - B - dichlorovinyl
phosphate is prepared by reacting 32.4 parts of ethyl
bicyclic phosphite with 29.48 parts of chloral by ‘heating
modi?ed to suit the instant situation. A method well
adapted to prepare the bicyclic phosphite is the reaction
of 'triethylphosphite with pentaerythritol with gradualre-e' with stirring the reactants at about 135° C. for three
hours. The viscous mixture which resultslis distilled at
moval of the alcohol under moderate ‘heating such as in
the range of 85° to 180° C. Another method of prepar 40 reduced pressure giving a liquid distillate of the dichloro
ing the bicyclic phosphite is by reacting phosphorus tri
vinyl phosphate having a boiling point of 147° to 149°
‘chloride with a trimethylol alkane at. reduced tempera
C. at 0.05 mm. and an up?‘ 1.4964.
tures, such‘ as from 0° to 80° (3., under a stream of nitro~
gen for the :removal of the hydrogen chloride. Other
methods known in the art may also be employed in the 45
Example 2
4,4-dichloromethylpropylene - l - B- dichlorovinyl phos
phate is prepared by adding to a reaction ?ask 18.2 parts
preparation of the bicyclic phosphites that are employed
of ‘chloromethyl bicyclic phosphite and 14.7 parts of
as ‘starting materials in accordance with the invention.’
chloral. The, solution'is heated with stirring at a tem
perature of 135° C. for four hours. On cooling and stand
In accordance with’ the invention, these bicyclic phos
phites are intimately contacted with the reactant of
lowing: chloral and a,a-dichloropropionaldehyde;’- di
ing overnight, the solution solidi?es. After recrystalliza
tion from isooctane, the white crystalline vinyl phosphate
chloro- and trichloroacetic acid alkyl esters, in which the
is obtained; it has a‘rnelting point of 48° to 50° C.
50
Formula ll. These reactants may be typi?ed'by the fol
alkyl group contains ‘from one to four carbon atoms, such
as trichloroacetic acid ethyl ester, dichloroacetic acid
methyl ester, and trichloroacetic acid butyl ester; dichloro 55
2-alkanones containing from three to seven carbon atoms
typi?ed by 1,1»dichloro-2-propanone, 1,1-dichloro-2-pen
tanone, 1,1-_dichloro.-2-heptanone, and the like.
.
.
The vinyl‘cycli‘c phosphates of the invention have a
wide variety of useful applications. Inaddition, they are 60
useful as pesticides, particularly at fungicides, insecticides
and herbicides.
'
, In combatting pests, they may be used as dusts, wet
table powders, self-dispersible concentrates, in solution or
'
Example 3
4-chlorcimethyl-4-ethylpropylene '- 1 - oz - ethoxy-?-di
chlorovinylphosphate'is prepared by heating together at
140° to 150° C. 32.4 parts of ethyl bicyclic phosphite and
38.3 parts of ethyl trichloroacetate. The product is sepa
rated by distilling under reduced pressure.
'
=
a
.
Example 4
There are reacted 36.9 parts of methyltrichloroacetatc
with 32.4 parts of ethyl bicyclic phosphite by heating to
gether at a temperature in the range of 145° to 150°C.
suspension. Compositions suitable as. dusts are prepared 65 with stirring. The resulting viscous mixture is distilled
--under reduced pressure to give 4-chloromethyl-4-ethyl
from one or more vinyl cyclic phosphonates of‘ this inven
tion dispersed in a solidcarrier, such as talc of clays. ‘ propylene-l-a-methoxy-?-dichlorovinyl phosphate.
The compound may be used an an amount ranging from
% %. to 25%.? As wettable powders‘, the vinyl cyclic phosi
7
Example 5 '_
_
There are reacted by. heating together at a temperature
phonates, in a range of about 20% to 90%, are mixed 70
of, 135° to 140°C. 33.5 parts of'methyldichloroacetate
'with about 1% to 5% of a suitable wetting agent, such
with 432.4 parts of ethyl bicyclic phosphite. The product,
as a water-soluble, surface-active polyethoxyalkylphenoxy
which is‘separated'by heating at reduced pressure, is 4
polyethoxyethanol-and about 0.5% to 3% of a suitable
chloromethyl-4-ethylpropylene - 1 -. a - methoxy-pchloro
dispersing agent, such as a formaldehyde condensed naph
1
'
thalene-sultonate: ' The wettable powder may then be 75 vinyl phosphate.
3,033,888
5
6
Example 6
CHaZ
CHQO
4,4-chloromethylpropylene - 1 - 0: ~ methyl-,B-chlorovinyl
phosphite is obtained by reacting vwith heating at 145° to
160° C. 36.4 parts of chloromethyl bicyclic phosphite and
25.2 parts of 1,1-dichloropropanone-2. The liquid prod
uct is obtained by distillation under reduced pressure.
Example 7
c \CHZO
IYI
P(O)OC=(IJ
V
_ 1 YI
.
CHzX
(I)
in which
X is a chlorine atom,
anone with 36.4 parts of chloromethyl bicyclic phosphite 10 Z is an alkyl group containing from 1 to 4 carbon
atoms,
at a temperature of 150° C. The liquid product is dis
R1 is an alkoxy group containing from 1 to 4 carbon
tilled under reduced pressure to give 4,4-dichloromethyl
There are reacted 29.4 parts of 1,1-d-ichloro-2-hex
propylene-l-u-butyl-[i-chlorovinyl phosphate.
atoms, and
‘
Y1 and Y2 are each a chlorine atom.
5. 5-chloromethyl-5~ethyl-2-a-ethoxy '- 18 - chlorovinyl
From 1,1-dichloro-2-butanone, there is obtained in a
like manner 4,4-dichloromethylpropylene-1-a - ethyl — )8
chlorovinyl phosphate.
oxy-1,3,Z-dioxaphosphorinane-Z-oxide.
'
6. A cyclic viny-l phosphate of the formula
Example 8
CHzZ
There are reacted 11.3 parts of 0:,cc-diChlOl'OP1‘OPiOI1
aldehyde with 18.2 parts of cbloromethyl bicyclic phos
20
CHgO
phite by heating at 135° C. for four hours. The product
c
which is obtained is 4,4-dichloromethylpropylene-1-19
Y!
\P (o) 0 C=(IJ
\CHzO
chlorovinyl phosphate.
R1 I"?
CH2X
Example 9
(I)
25
There are heated at a temperature of 150° C. to 160°
in which
X and Z are each a halogen atom having an atomic
number ranging from 9 to 53,
R1 is an alkyl group containing from 1 to 4 carbon
atoms, and
C. 41.2 parts of acetoxymethyl bicyclic phosphite with
14.7 parts of chloral. There is obtained 4-chloromethyl
4-acetoxymethylpropylene-l-?-dichlorovinyl phosphate.
In a like manner, there is prepared 4-ehloromethyl-4
hexanoxymethylpropylene - a,B-dichloroviny1 phosphate
Y1 and Y2 are each a chlorine atom.
from hexanoxymethyl bicyclic phosphite and chloral.
7. 5,5 - dichloromethyl - 2 - a-methyl-}8-chlorovinyloxy
We claim:
1,3,2-dioxaphosphorinaneJ-oxide.
1. A cyclic vinyl phosphate of the formula
8. A cyclic vinyl phosphate of the formula
35
CHzZ
CHBO
C
Porno
40
ranging from 9 to 53;
Y1 and Y2 are each a chlorine atom.
10. A cyclic vinyl phosphate of the formula
CHQZ
(EH20
C
atom concurrently.
2. A cyclic vinyl phosphate of the formula
CHzO
ClIuX
in in
(I)
in which X is a halogen atom having an atomic number
Z is
atomic
from 1
which
R1 Y2
'
(I)
in which
X is a chlorine atom,
HQX
ranging from 9 to 53,
|
P (O) O C=C
CHzO
Yl
P (0) 0 C=é
J>\CH,0/
60
Y1
\
I
oxy-1,3,2-dioxaphosphorinane-2-oxide.
Y1 is (1) a hydrogen atom and (2) a halogen atom of
an atomic number of 9 to 5 3; and
Y2 is (1) a hydrogen atom and (2) a halogen atom of
an atomic number of 9 to 53;
with the proviso that Y1 and Y2 are never a hydrogen
C\
.
9. S-chloromethyl-S-acetoxymethyl-2-B - dichlorovinyl
I
‘
(I)
in which
X is a chlorine atom,
Z is an acyloxy group in which the acyl group contains
from 1 to 12 carbon atoms,
R1 is an alkyl group containing from 1 to 4 carbon
atoms, and
Z is (1) a hydrogen atom, (2) a halogen atom of an
atomic number of 9 to 53, (3) an alkyl group 'con
taining from 1 to 4 carbon atoms, and (4) an acyl
oXy group in which the acyl group contains from
1 to 12 carbon atoms;
R1 is selected from the group consisting of a hydrogen
atom, an alkyl group containing from 1 to 4 carbon
atoms, and an alkoxy group containing from 1 to 4
CHzZ
is in
CHaX
in which X is a halogen atom having an atomic number
carbon atoms;
Y‘
P (O) 0 0:41
(1) a hydrogen atom, (2) a halogen atom of an
number of 9 to 53, (3) an alkyl group containing
to 4 carbon atoms, and (4) an acyloxyl group in
the acyl group contains from 1 to 12, carbon
atoms;
-
~
~
R1 is selected from the group consisting of a hydrogen
Z is an alkyl group containing from 1 to 4 carbon
atom, an alkyl group containing from 1 to 4 carbon atoms
atoms;
70 and an alkoxy group containing from 1 to 4 carbon atoms;
R1 is a hydrogen atom, and
‘Y1 is a hydrogen atom, and
p
Y1 and Y2 are each a chlorine atom.
Y2 is a halogen atom having an atomic number from
3. 5 - chloromethyl — S-ethyl - 2 ~ B - dichlorov-inyloxy
1,3,2-dioxaphosphorinane-2-oxide.
_
9 to 53.
'
4. A cyclic vinyl phosphate of the formula
75
11. 5,5-dichloromethyl-2-a-ethyl-p - dichlorovinyloxy
1,3,2-dioxaphosphorinane-2-oxide.
3,033,888
*1
Q
I
Cruz
'
C1120
,
8
Y2 is (1) a hydrogen atom and (2) a halogen atom of
an atomic number of 9 to 53;
with the proviso that Y1 and Y2 are never a hydrogen atom
12. A cyclic vinyl phosphate of the formula
Y‘
concurrently.
' '
15. Theprocess of claim 14 in which the temperature
l CHzO
IYa '
nix
.
’
'
<-
is maintained within the range of about 100° to 200° C.
16. A process for the preparation of a cyclic vinyl
phosphate of the formula of claim 14 in which
m
in which X and Z both are a halogen atom having an
R1 is a hydrogen atom, ‘
~
,
.
atomic number ranging from 9 to 53‘,
10 i. Y1 and Y2 are-each a chlorine atom, '7
X is a halogen atom having an atomic number ranging
Z'is (1) a hydrogen atom, (2) a halogen atom having
an atomic number of 9 to 53, (3) an alkyl group hav
ing from 1 to 4 carbon atoms, (4) an acyloxy group in
'which, the acyl group contains fromll to 12 carbon
atoms;
,,
,
t
.
from 9 to 53, and
bringing together equimolar amounts of Van ethyl bicyclic
phosphite of the formula CHsCtICi-lzO) 3P and chloral
' atom, an alkyl group containing from 1 to 4 carbon atoms,
and an alkoxy group containing from 1 to 4 carbon atoms;
Y1 is (l) a hydrogen atom and (2) a halogen atom hav
at a temperature in the range of. 110° to 150° C. and
separating 5-chloromethyl-5-ethyl-2 - ? - dichlorovinyloxy
V
l,3,Z-dioxaphosphorinahe-2-oxide.
Y2 is (l) a hydrogen atom and (2) a halogen atom hav
ing an atomic number of 9 to 53; '
'
propylene-1-;9-dichlorovinyl phosphate which comprises
R1 is selected from the group consisting of a hydrogen
ing an atomic number of 9 to 5 3; and
'
17. A process for preparing 4-chloromethyl-4-ethyl
15
p
‘
' 'Z is (l) a hydogen atom and (2) a halogen atom having
an atomic number of 9 to 53.
18. A‘process for the preparation of a cyclic vinyl phos
'
phate of the formula of claim 14 in which
V , with the proviso that Y1 and Y2 are never a hydrogen
atom concurrently.
'
g R1 is a hydrogen atom,
13. 5,S-dichloromethyl--2-a-methyl-ft-dichlorovinyloxy
1,3,2-dioxaphosphorinane-Z-oxide.
Y1 and Y2 are each a chlorine atom,
X is a halogen atom having an atomic number rang
25
. - 174. A process for the preparation of a cyclic vinyl phos
ing from 9 to 53, and
phate of the tormula
_
'
CHaZ
V
CHrO
.
atomic number of 9 to 53, (3) an alkyl group containing
t
CHrO
C/
‘
Z is (l) a hydrogen atom, (2) a halogen atom of an
30 rfromrl to 4 carbon atoms, and (4) an acyloxy group in
Y1
which the acyl group contains from 1 to 12 carbon atoms,
\P (0) 0 (IL-4%
which comprises reacting by bringing together at a tem
R‘ ‘If’
perature in the range of 200° to 280° C. a bicyclic phos
CHrX
phite of the formula
(I)
which comprises reacting at a temperature from 100° to
200° C. a bicyclic phosphite of the formula
in which Z is de?ned above,
with a trichloroacetic acid alkyl ester in which the allcyl
group contains from 1 to 4 carbon atoms, and separating
with a compound of the formula I v
resulting cyclic vinyl phosphate.
.49 the19.
A process for preparing 4-chloromethyl-4-ethyl
propylene-l-u-ethoxy-?-dichlorovinyl phosphate which
comprises heating together at a temperature in the range
of 140° to 150° C. an equimolar amount of an ethyl bi
cyclic phosphite of the formula CH3C(CH2O) 3P and ethyl
' rinwhich X is a halogen atom having an atomic number
ranging from 9 to 53;
, trichloroacetate, and separating the resulting cyclic vinyl
, Z ‘is (l), a hydrogen atom, (2) a halogen atom of an
‘atomic number of 9m 53, (3) an alkyl group containing
from 1 to 4 carbon atoms, and (4) an acyloxy group in
which the acyl group contains from 1 to 12 carbon atoms;
' R1 is selected from the group consisting of'a hydrogen
atom, an alkyl group containing from 1 to 4 carbon atoms,
and an alkoxy group containing from 1 to 4 carbon
atoms;
7
Y1 is (1) a hydrogen atom and (2) a halogen atom of 55
an atomic number of 9 to 53; and
phosphate.
7
References Cited in the ?le of this patent
UNITED STATES PATENTS
2,834,798
Hechenbleikner et al. _____ May 3, 1958
OTHER REFERENCES
Chemical Abstracts, 75th Decennial Index, page 4229s,
‘top of column 3.
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