Farkas János-Növényvédelmi Toxikológia PDF

SAPIENTIA – ERDÉLYI MAGYAR TUDOMÁNYEGYETEM
MŰSZAKI ÉS HUMÁNTUDOMÁNYOK KAR - MAROSVÁSÁRHELY

NÖVÉNYORVOSI SZAK
Növényvédelmi kémia és toxikológia

vizsgareferátum
Készítette:
Farkas János
MAROSVÁSÁRHELY, 2022.
1.Spektrumok
1.1 Az infravörös spektroszkópia az egyik leggyakrabban használt analitikai módszer

egy adott vegyület szerkezetének azonosítására. Az infravörös spektrumok jelölése fentről lefele
történik, mivel az áteső hullámokat és nem az elnyelés mértékét mérjük.
A vegyület beazonosításának kiindulópontja az volt, hogy tudtuk, hogy valamilyen alifás,
vagy aromás vegyületünk van. A táblázat szerint a C-H kötések megnyúlásából keletkező rezgések
a 2500-3300-as hullámhossz tartományban keletkeznek. A képen látható IR spektrum esetében a
3000-es érték fölött megjelenik egy jól elkülönülő csúcs, amely jellegzetesen az alkil csoportokra
jellemző. A kicsivel az 1200-as érték felett megjelenő másik erőteljes csúcs a C-O kötés
megnyúlásának jellemzője lehet.
1. ábra: Infravörös spektrum
2
1.2 Tömegspektrum
A mellékelt ábrán egy magmágneses rezonancia spektroszkópia (NMR: Nuclear Magnetic

Resonance) módszerével készült spektrum látható.
Az NMR spektroszkópia alapja, hogy az atommagokat elektronok veszik körbe, amelyekre hat az
alkalmazott külső mágneses tér, az atomban elhelyezkedő magok mindig gyengébb mágneses
teret érzékelnek a külső mágneses térnél. Ez a jelenség a kémiai árnyékolás.Az árnyékolt magok
rezonanciafrekvenciája (f) eltolódik a nem-árnyékolthoz (f0) képest.
Az eltolódás mértékét ppm-ben adjuk meg (parts per million).
2. ábra: Tömegspektrum
3
A mellékelt MNR spektrum esetében jól elkülönül 1-ppm-nél egy kettős csúcs. Ez egy
alkilcsoportot jelöl, pontosabban a két csúcs két darab metil csoporttal azonos CH3.
A másik jellegzetes spektrum a 4-es értéknél jelentkező 7 csúcsban elkülönülő spektrum. Ez egy
CH-hez kapcsolódó két metil csoportot jelöl, vagyis egy izopropil csoport.
A 2 ppm értéknél megjelenő csúcs az izopropil csoporthoz kapcsolódó hidroxilcsoportot (jelöli).
Mivel a spektrumunkon más csoport nem jelenik meg ebből következtethetünk arra, hogy
vegyületünk, egy izopropil csoportból és a hozzá kapcsolódó hidroxilcsoportból áll.
Következés képpen megállapíthatjuk, hogy vegyületünk az izopropil-alkohol vagy más
néven 2-propanol,mely szobahőmérsékleten folyékony, forráspontja pedig 82.3 °C (PubChem).
3. ábra az izopropil-alkohol szerkezete
4
2.Malotion és származékának tulajdonságai
2.1 2,3-Bis(hexanoylthio)propylphosphomethanol (a megadott mol file
alapján)
Összegképlete: C16 H31 O6 PS2
Molekulatömeg: 414.52g/mol
Halmazállapota:
forráspontja: 392.81 °C
olvadáspontja: -7.61°C
2.2 Környezeti paraméterek
Vízben való oldhatósága:0.1502 mg/L 25 °C-on (nagyon gyengén oldódik).
Sűrűsége: 1.2076 g/cm3 20 °C-on
Log Kow (Oktanol víz megoszlási hányados): 4.94 Ez az érték azt mutatja, hogy a molekula
zsíroldékony.
Felezési idő talajban: 75 nap(1800 óra Epiweb) más források 17 napot említnek.
LogKoc (Talaj-kötődési koefficiens) (logKoc): 4.94–es oktanol-víz megoszlási hányadosból

számolva 654. Ez azt jelenti, hogy a talajhoz kevéssé kötődik.
BCF (Biokoncentrációs faktor): 844.6 L/kg ami azt jelenti, hogy a vegyület bioakkumulatív
2.3 A Malation hatásmechanizmusa

A malation egy nem szisztemikus, széles spektrumú organofoszfát alapú rovarirtó szer,
gátolja az eukarióták acetilkolin –észteráz aktivitását. A malation mérgező a vízi szervezetekre, de
viszonylag alacsony toxicitással bír a madarakra és emlősökre nézve. A malation fő metabolitjai
mono- és dikarbonsav-származékok, a malaoxon pedig egy kisebb metabolit. Azonban a malaoxon
a legerősebb kolinészteráz-gátló. A kolinészterázok katalizálják az acetilkolin neurotranszmitter
kolinná és ecetsavvá történő hidrolízisét, amely reakció szükséges ahhoz, hogy a kolinerg neuron
5
aktiválódása után visszatérjen nyugalmi állapotába. Alapvető funkciója miatt a kolinészteráz
működését megzavaró vegyszerek erős idegmérgek, izomgörcsöket és végső soron halált okoznak.
4.ábra:Acetilkolin-észteráz szerkezete
Enzim kódja: EC 3.1.1.7
6
3.Melléklet
CAS Number: (null)
SMILES : C(SP(=S)(OC)OC)(CC(=O)OC(C)C(C)C)C(=O)OC(C)C(C)C
CHEM : C:\Users\janos\Downloads\Farkas_Janos.mol
MOL FOR: C16 H31 O6 P1 S2
MOL WT : 414.52
------------------------------ EPI SUMMARY (v4.11) --------------------------
Physical Property Inputs:
Log Kow (octanol-water): ------
Boiling Point (deg C) : ------
Melting Point (deg C) : ------
Vapor Pressure (mm Hg) : ------
Water Solubility (mg/L): ------
Henry LC (atm-m3/mole) : ------
KOWWIN Program (v1.68) Results:
===============================
Log Kow(version 1.68 estimate): 4.94
MOL WT : 414.52
7
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 8 | -CH3 [aliphatic carbon] | 0.5473 | 4.3784
Frag | 1 | -CH2- [aliphatic carbon] | 0.4911 | 0.4911
Frag | 5 | -CH [aliphatic carbon] | 0.3614 | 1.8070
Frag | 2 | -C(=O)O [ester, aliphatic attach] |-0.9505 | -1.9010
Frag | 1 | S=P [thio=phosphorus] |-0.6587 | -0.6587
Frag | 2 | -O-P [aliphatic attach] |-0.0162 | -0.0324
Frag | 1 | -S-P [sulfur, phosphorus attach] | 0.6270 | 0.6270
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 4.9404
MPBPVP (v1.43) Program Results:
===============================
Experimental Database Structure Match: no data
MOL WT : 414.52
------------------------ SUMMARY MPBVP v1.43 --------------------
8
Boiling Point: 392.81 deg C (Adapted Stein and Brown Method)
Melting Point: -130.93 deg C (Adapted Joback Method)
Melting Point: 115.70 deg C (Gold and Ogle Method)
Mean Melt Pt : -7.61 deg C (Joback; Gold,Ogle Methods)
Selected MP: -7.61 deg C (Mean Value)
Vapor Pressure Estimations (25 deg C):
(Using BP: 392.81 deg C (estimated))
(MP not used for liquids)
VP: 3.01E-006 mm Hg (Antoine Method)
: 0.000401 Pa (Antoine Method)
VP: 1.24E-005 mm Hg (Modified Grain Method)
: 0.00166 Pa (Modified Grain Method)
VP: 2.55E-005 mm Hg (Mackay Method)
: 0.00339 Pa (Mackay Method)
Selected VP: 1.24E-005 mm Hg (Modified Grain Method)
: 0.00166 Pa (Modified Grain Method)
-------+-----+--------------------+----------+---------
TYPE | NUM | BOIL DESCRIPTION | COEFF | VALUE
9
-------+-----+--------------------+----------+---------
Group | 8 | -CH3 | 21.98 | 175.84
Group | 1 | -CH2- | 24.22 | 24.22
Group | 5 | >CH- | 11.86 | 59.30
Group | 2 | -O- (nonring) | 25.16 | 50.32
Group | 2 | -COO- (ester) | 78.85 | 157.70
Group | 1 | -S- (nonring) | 69.42 | 69.42
Group | 1 | >P=S | 100.00 | 100.00
Corr | 1 | Diester-type | -35.00 | -35.00
* | | Equation Constant | | 198.18
=============+====================+==========+=========
RESULT-uncorr| BOILING POINT in deg Kelvin | 799.98
RESULT- corr | BOILING POINT in deg Kelvin | 665.97
| BOILING POINT in deg C | 392.81
-------------------------------------------------------
-------+-----+--------------------+----------+---------
TYPE | NUM | MELT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------+----------+---------
Group | 8 | -CH3 | -5.10 | -40.80
Group | 1 | -CH2- | 11.27 | 11.27
Group | 5 | >CH- | 12.64 | 63.20
Group | 2 | -O- (nonring) | 22.23 | 44.46
Group | 2 | -COO- (ester) | 53.60 | 107.20
Group | 1 | -S- (nonring) | 34.40 | 34.40
10
Group | 1 | >P=S | -70.00 | -70.00
Corr | 1 | Diester-type | -130.00 | -130.00
* | | Equation Constant | | 122.50
=============+====================+==========+=========
RESULT | MELTING POINT in deg Kelvin | 142.23
Special-limit| MELTING POINT in deg Kelvin | 142.23
| MELTING POINT in deg C | -130.93
-------------------------------------------------------
Water Sol from Kow (WSKOW v1.42) Results:
========================================
Water Sol: 0.1502 mg/L
MOL WT : 414.52
---------------------------------- WSKOW v1.42 Results ------------------------
Log Kow (estimated) : 4.94
Log Kow (experimental): not available from database
Log Kow used by Water solubility estimates: 4.94
11
Equation Used to Make Water Sol estimate:
Log S (mol/L) = 0.796 - 0.854 log Kow - 0.00728 MW + Correction
(used when Melting Point NOT available)
Correction(s): Value
-------------------- -----
No Applicable Correction Factors
Log Water Solubility (in moles/L) : -6.441
Water Solubility at 25 deg C (mg/L): 0.1502
WATERNT Program (v1.01) Results:
===============================
Water Sol (v1.01 est): 2.5375 mg/L
MOL WT : 414.52
-------+-----+--------------------------------------------+----------+---------
TYPE | NUM | WATER SOLUBILITY FRAGMENT DESCRIPTION | COEFF |

VALUE
12
-------+-----+--------------------------------------------+----------+---------
Frag | 8 | -CH3 [aliphatic carbon] |-0.3213 | -2.5702
Frag | 1 | -CH2- [aliphatic carbon] |-0.5370 | -0.5370
Frag | 5 | -CH [aliphatic carbon] |-0.5285 | -2.6426
Frag | 2 | -C(=O)O [ester, aliphatic attach] | 0.5757 | 1.1515
Frag | 1 | S=P [thio=phosphorus] | 0.8774 | 0.8774
Frag | 2 | -O-P [aliphatic attach] |-0.3827 | -0.7653
Frag | 1 | -S-P [sulfur, phosphorus attach] |-0.9761 | -0.9761
Const | | Equation Constant | | 0.2492
-------+-----+--------------------------------------------+----------+---------
Log Water Sol (moles/L) at 25 dec C = -5.2131
Water Solubility (mg/L) at 25 dec C = 2.5375
ECOSAR Program (v1.11) Results:
===============================
ECOSAR Version 1.11 Results Page
CAS Num:
ChemID1:
MOL WT : 414.52
13
Log Kow: 4.940 (EPISuite Kowwin v1.68 Estimate)
Log Kow: (User Entered)
Log Kow: (PhysProp DB exp value - for comparison only)
Melt Pt: (User Entered for Wat Sol estimate)
Melt Pt: (deg C, PhysProp DB exp value for Wat Sol estimate)
Wat Sol: 0.1502 (mg/L, EPISuite WSKowwin v1.43 Estimate)
Wat Sol: (User Entered)
Wat Sol: (PhysProp DB exp value)
--------------------------------------
Values used to Generate ECOSAR Profile
--------------------------------------
Log Kow: 4.940 (EPISuite Kowwin v1.68 Estimate)
Wat Sol: 0.1502 (mg/L, EPISuite WSKowwin v1.43 Estimate)
--------------------------------------
ECOSAR v1.11 Class-specific Estimations
--------------------------------------
Esters
Esters, Dithiophosphates
Predicted
ECOSAR Class Organism Duration End Pt mg/L (ppm)
14
=========================== ================== ======== ======
==========
Esters : Fish 96-hr LC50 1.063 *
Esters : Daphnid 48-hr LC50 1.613 *
Esters : Green Algae 96-hr EC50 0.431 *
Esters : Fish ChV 0.043
Esters : Daphnid ChV 0.473 *
Esters : Green Algae ChV 0.287 *
Esters : Fish (SW) 96-hr LC50 1.350 *
Esters : Mysid 96-hr LC50 0.312 *
Esters : Fish (SW) ChV 0.329 *
Esters : Mysid (SW) ChV 0.057
Esters : Earthworm 14-day LC50 609.195 *
Esters, Dithiophosphates : Fish 96-hr LC50 0.083
Esters, Dithiophosphates : Daphnid 48-hr LC50 0.00096
Esters, Dithiophosphates : Green Algae 96-hr EC50 0.381 *
Esters, Dithiophosphates : Fish ChV 0.013
Esters, Dithiophosphates : Daphnid ChV 0.000137 !
Esters, Dithiophosphates : Green Algae ChV 0.146 !
=========================== ================== ======== ======

==========
Neutral Organic SAR : Fish 96-hr LC50 0.779 *
(Baseline Toxicity) : Daphnid 48-hr LC50 0.580 *
: Green Algae 96-hr EC50 1.328 *
15
: Fish ChV 0.105
: Daphnid ChV 0.120
: Green Algae ChV 0.636 *
Note: * = asterisk designates: Chemical may not be soluble enough to
measure this predicted effect. If the effect level exceeds the
water solubility by 10X, typically no effects at saturation (NES)
are reported.
NOTE: ! = exclamation designates: The toxicity value was estimated through
application of acute-to-chronic ratios per methods outlined in
the ECOSAR Methodology Document provided in the ECOSAR Help Menu.
------------------------------
Class Specific LogKow Cut-Offs
------------------------------
If the log Kow of the chemical is greater than the endpoint specific cut-offs
presented below, then no effects at saturation are expected for those endpoints.
Esters:
------
Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50, Mysid LC50)
Maximum LogKow: 6.0 (Earthworm LC50)
Maximum LogKow: 6.4 (Green Algae EC50)
16
Maximum LogKow: 8.0 (ChV)
Esters, Dithiophosphates:
------------------------
Maximum LogKow: 5.0 (LC50)
Maximum LogKow: 6.4 (EC50)
Baseline Toxicity SAR Limitations:
---------------------------------
Maximum LogKow: 5.0 (Fish 96-hr LC50; Daphnid LC50)
Maximum LogKow: 6.4 (Green Algae EC50)
HENRYWIN (v3.20) Program Results:
=============================
Bond Est : 4.59E-009 atm-m3/mole (4.65E-004 Pa-m3/mole)
Group Est: Incomplete
17
MOL WT : 414.52
--------------------------- HENRYWIN v3.20 Results --------------------------
----------+---------------------------------------------+---------+----------
CLASS | BOND CONTRIBUTION DESCRIPTION | COMMENT | VALUE
----------+---------------------------------------------+---------+----------
HYDROGEN | 31 Hydrogen to Carbon (aliphatic) Bonds | | -3.7100
FRAGMENT | 9 C-C | | 1.0467
FRAGMENT | 2 C-CO | | 3.4114
FRAGMENT | 4 C-O | | 4.3419
FRAGMENT | 1 C-S | | 1.1056
FRAGMENT | 2 CO-O | | 0.1429
FRAGMENT | 2 O-P | | 0.7861
FRAGMENT | 1 S-P | | 0.6334
FRAGMENT | 1 P=S | | -1.0317
----------+---------------------------------------------+---------+----------
RESULT | BOND ESTIMATION METHOD for LWAPC VALUE | TOTAL | 6.726
----------+---------------------------------------------+---------+----------
HENRYs LAW CONSTANT at 25 deg C = 4.59E-009 atm-m3/mole
= 1.88E-007 unitless
= 4.65E-004 Pa-m3/mole
--------+-----------------------------------------------+------------+--------
| GROUP CONTRIBUTION DESCRIPTION | COMMENT | VALUE
18
--------+-----------------------------------------------+------------+--------
| 8 CH3 (X) | | -4.96
| 1 CH2 (C)(CO) | | -0.15
| 2 CH (C)(C)(C) | | 0.48
| 2 CH (C)(C)(O) | | 0.24
| 2 CO (C)(O) | | 8.18
| 2 O (C)(CO) | | -1.06
| MISSING Value for: CH (C)(S)(CO)
| MISSING Value for: S (P)(C)
| MISSING Value for: P (=S)(O)(O)(S)
| MISSING Value for: O (C)(P)
| MISSING Value for: O (C)(P)
--------+-----------------------------------------------+------------+--------
RESULT | GROUP ESTIMATION METHOD for LOG GAMMA VALUE | INCOMPLETE |

2.73
--------+-----------------------------------------------+------------+--------
For Henry LC Comparison Purposes:
Exper Database: none available
User-Entered Henry LC: not entered
Henrys LC [via VP/WSol estimate using User-Entered or Estimated values]:
HLC: 4.503E-005 atm-m3/mole (4.562E+000 Pa-m3/mole)
VP: 1.24E-005 mm Hg (source: MPBPVP)
WS: 0.15 mg/L (source: WSKOWWIN)
19
Log Octanol-Air (KOAWIN v1.10) Results:
======================================
Log Koa: 11.667
MOL WT : 414.52
--------------------------- KOAWIN v1.10 Results --------------------------
Log Koa (octanol/air) estimate: 11.667
Koa (octanol/air) estimate: 4.641e+011
Using:
Log Kow: 4.94 (KowWin est)
HenryLC: 4.59e-009 atm-m3/mole (HenryWin est)
Log Kaw: -6.727 (air/water part.coef.)
LogKow : ---- (exp database)
LogKow : 4.94 (KowWin estimate)
Henry LC: --- atm-m3/mole(exp database)
Henry LC: 4.59e-009 atm-m3/mole (HenryWin bond estimate)
20
Log Koa (octanol/air) estimate: 11.667 (from KowWin/HenryWin)
BIOWIN (v4.10) Program Results:
==============================
MOL WT : 414.52
--------------------------- BIOWIN v4.10 Results ----------------------------
Biowin1 (Linear Model Prediction) : Biodegrades Fast
Biowin2 (Non-Linear Model Prediction): Biodegrades Fast
Biowin3 (Ultimate Biodegradation Timeframe): Weeks-Months
Biowin4 (Primary Biodegradation Timeframe): Days
Biowin5 (MITI Linear Model Prediction) : Does Not Biodegrade Fast
Biowin6 (MITI Non-Linear Model Prediction): Does Not Biodegrade Fast
Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast
Ready Biodegradability Prediction: NO
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE
------+-----+--------------------------------------------+---------+---------
21
Frag | 2 | Ester [-C(=O)-O-C] | 0.1742 | 0.3484
Frag | 1 | Phosphate ester | 0.3139 | 0.3139
MolWt| * | Molecular Weight Parameter | | -0.1973
Const| * | Equation Constant | | 0.7475
============+============================================+=========+=
========
RESULT | Biowin1 (Linear Biodeg Probability) | | 1.2125
============+============================================+=========+=
========
------+-----+--------------------------------------------+---------+---------
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 4.0795 | 8.1590
============+============================================+=========+=
========
RESULT | Biowin2 (Non-Linear Biodeg Probability) | | 1.0000
============+============================================+=========+=
========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
------+-----+--------------------------------------------+---------+---------

22
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1402 | 0.2804
============+============================================+=========+=
========
RESULT | Biowin3 (Survey Model - Ultimate Biodeg) | | 2.7173
============+============================================+=========+=
========
------+-----+--------------------------------------------+---------+---------
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.2290 | 0.4579
============+============================================+=========+=
========
RESULT | Biowin4 (Survey Model - Primary Biodeg) | | 4.1730
============+============================================+=========+=
========
Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks
(Primary & Ultimate) 2.00 -> months 1.00 -> longer
23
------+-----+--------------------------------------------+---------+---------
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.3437 | 0.6875
Frag | 8 | Methyl [-CH3] | 0.0004 | 0.0033
Frag | 1 | -CH2- [linear] | 0.0494 | 0.0494
Frag | 5 | -CH- [linear] | -0.0507 | -0.2534
============+============================================+=========+=
========
RESULT | Biowin5 (MITI Linear Biodeg Probability) | | 0.1205
============+============================================+=========+=
========
------+-----+--------------------------------------------+---------+---------
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 2.4462 | 4.8923
Frag | 8 | Methyl [-CH3] | 0.0194 | 0.1554
Frag | 1 | -CH2- [linear] | 0.4295 | 0.4295
Frag | 5 | -CH- [linear] | -0.0998 | -0.4989
MolWt| * | Molecular Weight Parameter | |-11.9666
24
============+============================================+=========+=
========
RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.0345
============+============================================+=========+=
========
A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable
A Probability Less Than 0.5 indicates --> NOT Readily Degradable
------+-----+--------------------------------------------+---------+---------
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | 0.1719 | 0.3437
Frag | 8 | Methyl [-CH3] | -0.0796 | -0.6366
Frag | 1 | -CH2- [linear] | 0.0260 | 0.0260
Frag | 5 | -CH- [linear] | -0.1659 | -0.8293
============+============================================+=========+=
========
RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | 0.2670
============+============================================+=========+=
========
A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast
A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast
25
Ready Biodegradability Prediction: (YES or NO)
----------------------------------------------
Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey
model) result is "weeks" or faster (i.e. "days", "days to weeks", or
"weeks" AND the Biowin5 (MITI linear model) probability is >= 0.5, then
the prediction is YES (readily biodegradable). If this condition is not
satisfied, the prediction is NO (not readily biodegradable). This method
is based on application of Bayesian analysis to ready biodegradation data
(see Help). Biowin5 and 6 also predict ready biodegradability, but for
degradation in the OECD301C test only; using data from the Chemicals
Evaluation and Research Institute Japan (CERIJ) database.
BioHCwin (v1.01) Program Results:
==============================
MOL WT : 414.52
-------------------------- BioHCwin v1.01 Results ---------------------------
NO Estimate Possible ... Structure NOT a Hydrocarbon
26
(Contains atoms other than C, H or S (-S-))
AEROWIN Program (v1.00) Results:
===============================
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 0.00165 Pa (1.24E-005 mm Hg)
Log Koa (Koawin est ): 11.667
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 0.00181
Octanol/air (Koa) model: 0.114
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 0.0615
Mackay model : 0.127
Octanol/air (Koa) model: 0.901
AOP Program (v1.92) Results:
===========================
MOL WT : 414.52
------------------- SUMMARY (AOP v1.92): HYDROXYL RADICALS (25 deg C) --------
27
Hydrogen Abstraction = 34.5084 E-12 cm3/molecule-sec
Reaction with N, S and -OH = 53.0000 E-12 cm3/molecule-sec
Addition to Triple Bonds = 0.0000 E-12 cm3/molecule-sec
Addition to Olefinic Bonds = 0.0000 E-12 cm3/molecule-sec
Addition to Aromatic Rings = 0.0000 E-12 cm3/molecule-sec
Addition to Fused Rings = 0.0000 E-12 cm3/molecule-sec
OVERALL OH Rate Constant = 87.5084 E-12 cm3/molecule-sec
HALF-LIFE = 0.122 Days (12-hr day; 1.5E6 OH/cm3)
HALF-LIFE = 1.467 Hrs
------------------- SUMMARY (AOP v1.91): OZONE REACTION (25 deg C) -----------
****** NO OZONE REACTION ESTIMATION ******
(ONLY Olefins and Acetylenes are Estimated)
Experimental Database: NO Structure Matches
Fraction sorbed to airborne particulates (phi):
0.0941 (Junge-Pankow, Mackay avg)
0.901 (Koa method)
Note: the sorbed fraction may be resistant to atmospheric oxidation
28
KOCWIN Program (v2.00) Results:
==============================
MOL WT : 414.52
--------------------------- KOCWIN v2.00 Results ---------------------------
Koc Estimate from MCI:
---------------------
First Order Molecular Connectivity Index ........... : 11.451
Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.5694
Fragment Correction(s):
1 OrganoPhosphorus [P=S] ............... : -1.1599
2 Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939
Corrected Log Koc .................................. : 2.8156
Estimated Koc: 654 L/kg <===========
Koc Estimate from Log Kow:
-------------------------
Log Kow (Kowwin estimate) ......................... : 4.94
Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 3.6576
Fragment Correction(s):
1 OrganoPhosphorus [P=S] ............... : -0.0917
29
2 Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312
Corrected Log Koc .................................. : 3.4346
Estimated Koc: 2721 L/kg <===========
HYDROWIN Program (v2.00) Results:
================================
MOL WT : 414.52
--------------------------- HYDROWIN v2.00 Results ---------------------------
Thiophosphate: S=P-({O,S}-R)3
R1{-O-}: -CH3
R1{-O-}: -CH3
R1{-S-}: iso-Propyl-
Log Kn (/sec) = -7.3703
Kn = 4.263e-008/sec = 2.558e-006/min
= 0.0001535/hr = 0.003683/day
Log Kb (/M-sec) = -2.4364
Kb = 0.003661/M-sec = 0.2197/M-min
= 13.18/M-hr = 316.3/M-day
30
Log Ka : ** Acid-catalyzed rates can NOT be estimated at this time.
Estimated Half-Lives (for Phosphorus Ester):
-------------------------------------------
pH5 : 188.2 days
pH6 : 188 days
pH7 : 186.6 days
pH8 : 173.3 days
pH9 : 101.2 days
pH10: 19.63 days
NOTE: Fragment(s) on this compound are NOT available from the fragment
library. Substitute(s) have been used!!! Substitute R1, R2, R3,
or R4 fragments are marked with double astericks "**".
ESTER: R1-C(=O)-O-R2 ** R1: iso-Butyl-
** R2: -CH(Me)(t-Bu)
Kb hydrolysis at atom # 10: 3.912E-004 L/mol-sec
ESTER: R1-C(=O)-O-R2 ** R1: iso-Propyl-
** R2: -CH(Me)(t-Bu)
Kb hydrolysis at atom # 18: 1.015E-003 L/mol-sec
Total Kb for pH > 8 at 25 deg C : 1.406E-003 L/mol-sec
Kb Half-Life at pH 8: 15.620 years
31
Kb Half-Life at pH 7: 156.204 years
BCFBAF Program (v3.01) Results:
==============================
MOL WT : 414.52
--------------------------------- BCFBAF v3.01 --------------------------------
Summary Results:
Log BCF (regression-based estimate): 2.93 (BCF = 845 L/kg wet-wt)
Biotransformation Half-Life (days) : 0.0421 (normalized to 10 g fish)
Log BAF (Arnot-Gobas upper trophic): 1.27 (BAF = 18.5 L/kg wet-wt)
Log Kow (experimental): not available from database
Log Kow used by BCF estimates: 4.94
Equation Used to Make BCF estimate:
Log BCF = 0.6598 log Kow - 0.333 + Correction
Correction(s): Value
No Applicable Correction Factors
Estimated Log BCF = 2.927 (BCF = 844.6 L/kg wet-wt)
32
===========================================================
Whole Body Primary Biotransformation Rate Estimate for Fish:
===========================================================
------+-----+--------------------------------------------+---------+---------
TYPE | NUM | LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION | COEFF |

VALUE
------+-----+--------------------------------------------+---------+---------
Frag | 2 | Ester [-C(=O)-O-C] | -0.7605 | -1.5211
Frag | 1 | Phosphate ester (P=S type) | 0.1978 | 0.1978
Frag | 8 | Methyl [-CH3] | 0.2451 | 1.9608
Frag | 1 | -CH2- [linear] | 0.0242 | 0.0242
Frag | 5 | -CH- [linear] | -0.1912 | -0.9562
L Kow| * | Log Kow = 4.94 (KowWin estimate) | 0.3073 | 1.5184
Const| * | Equation Constant | | -1.5371
============+============================================+=========+=
========
RESULT | LOG Bio Half-Life (days) | | -1.3760
RESULT | Bio Half-Life (days) | | 0.04207
NOTE | Bio Half-Life Normalized to 10 g fish at 15 deg C |
============+============================================+=========+=
========
Biotransformation Rate Constant:
kM (Rate Constant): 16.48 /day (10 gram fish)
kM (Rate Constant): 9.265 /day (100 gram fish)
33
kM (Rate Constant): 5.21 /day (1 kg fish)
kM (Rate Constant): 2.93 /day (10 kg fish)
Arnot-Gobas BCF & BAF Methods (including biotransformation rate estimates):
Estimated Log BCF (upper trophic) = 1.267 (BCF = 18.51 L/kg wet-wt)
Estimated Log BAF (upper trophic) = 1.267 (BAF = 18.51 L/kg wet-wt)
Estimated Log BCF (mid trophic) = 1.399 (BCF = 25.08 L/kg wet-wt)
Estimated Log BAF (mid trophic) = 1.400 (BAF = 25.14 L/kg wet-wt)
Estimated Log BCF (lower trophic) = 1.440 (BCF = 27.54 L/kg wet-wt)
Estimated Log BAF (lower trophic) = 1.461 (BAF = 28.93 L/kg wet-wt)
Arnot-Gobas BCF & BAF Methods (assuming a biotransformation rate of zero):
Estimated Log BCF (upper trophic) = 3.852 (BCF = 7115 L/kg wet-wt)
Estimated Log BAF (upper trophic) = 4.934 (BAF = 8.583e+004 L/kg wet-wt)
34
Volatilization From Water
=========================
Chemical Name: C:\Users\janos\Downloads\Farkas_Janos.mol
Molecular Weight : 414.52 g/mole
Water Solubility : -----
Vapor Pressure : -----
Henry's Law Constant: 4.59E-009 atm-m3/mole (estimated by Bond SAR Method)
RIVER LAKE
--------- ---------
Water Depth (meters): 1 1
Wind Velocity (m/sec): 5 0.5
Current Velocity (m/sec): 1 0.05
HALF-LIFE (hours) : 2.597E+005 2.833E+006
HALF-LIFE (days ) : 1.082E+004 1.181E+005
HALF-LIFE (years) : 29.63 323.2
STP Fugacity Model: Predicted Fate in a Wastewater Treatment Facility
=====================================================================
=
(using 10000 hr Bio P,A,S)
35
PROPERTIES OF: C:\Users\janos\Downloads\Farkas_Janos.mol
-------------
Molecular weight (g/mol) 414.52
Aqueous solubility (mg/l) 0
Vapour pressure (Pa) 0
(atm) 0
(mm Hg) 0
Henry 's law constant (Atm-m3/mol) 4.59E-009
Air-water partition coefficient 1.87717E-007
Octanol-water partition coefficient (Kow) 87096.4
Log Kow 4.94
Biomass to water partition coefficient 17420.1
Temperature [deg C] 25
Biodeg rate constants (h^-1),half life in biomass (h) and in 2000 mg/L MLSS (h):
-Primary tank 0.00 9720.98 10000.00
-Aeration tank 0.00 9720.98 10000.00
-Settling tank 0.00 9720.98 10000.00
STP Overall Chemical Mass Balance:
---------------------------------
g/h mol/h percent
Influent 1.00E+001 2.4E-002 100.00
Primary sludge 4.66E+000 1.1E-002 46.61
36
Waste sludge 2.84E+000 6.9E-003 28.44
Primary volatilization 5.57E-007 1.3E-009 0.00
Settling volatilization 1.34E-006 3.2E-009 0.00
Aeration off gas 3.30E-006 8.0E-009 0.00
Primary biodegradation 1.40E-002 3.4E-005 0.14
Settling biodegradation 3.70E-003 8.9E-006 0.04
Aeration biodegradation 4.87E-002 1.2E-004 0.49
Final water effluent 2.43E+000 5.9E-003 24.29
Total removal 7.57E+000 1.8E-002 75.71
Total biodegradation 6.64E-002 1.6E-004 0.66
Level III Fugacity Model (Full-Output):
=======================================
Chem Name : C:\Users\janos\Downloads\Farkas_Janos.mol
Molecular Wt: 414.52
Henry's LC : 4.59e-009 atm-m3/mole (Henrywin program)
Vapor Press : 1.24e-005 mm Hg (Mpbpwin program)
Log Kow : 4.94 (Kowwin program)
Soil Koc : 654 (KOCWIN MCI method)
Mass Amount Half-Life Emissions
37
(percent) (hr) (kg/hr)
Air 0.0287 2.93 1000
Water 13.7 900 1000
Soil 85.8 1.8e+003 1000
Sediment 0.491 8.1e+003 0
Fugacity Reaction Advection Reaction Advection
(atm) (kg/hr) (kg/hr) (percent) (percent)
Air 7.35e-013 316 13.4 10.5 0.446
Water 3.51e-014 491 637 16.4 21.2
Soil 1.54e-013 1.54e+003 0 51.4 0
Sediment 3.8e-014 1.96 0.458 0.0653 0.0153
Persistence Time: 1.55e+003 hr
Reaction Time: 1.99e+003 hr
Advection Time: 7.16e+003 hr
Percent Reacted: 78.3
Percent Advected: 21.7
Half-Lives (hr), (based upon Biowin (Ultimate) and Aopwin):
Air: 2.933
Water: 900
Soil: 1800
Sediment: 8100
Biowin estimate: 2.717 (weeks-months)
38
Advection Times (hr):
Air: 100
Water: 1000
Sediment: 5e+004
39
4.Felhasznált irodalom
https://pubchem.ncbi.nlm.nih.gov/
http://webbook.nist.gov/chemistry/
http://ttk.pte.hu/analitika/letoltesek/jegyzet/ch04s02.html
http://www.biofizika.aok.pte.hu/data/2019/0227/056/NMR%20e%CC%81s%20ESR%20Spektr
oszko%CC%81pia%20handout.pdf
https://www.genome.jp/dbget-bin/www_bget?enzyme+3.1.1.7
https://pubchem.ncbi.nlm.nih.gov/compound/Isopropyl-alcohol#section=Taste
https://en.wikipedia.org/wiki/Isopropyl_alcohol
http://npic.orst.edu/factsheets/malagen.html
40
Tartalomjegyzék
1.Spektrumok .......................................................................................... 2
1.1 Az infravörös ................................................................................... 2
1.2 Tömegspektrum.............................................................................. 3
2.Malotion és származékának tulajdonságai ......................................... 5
2.1 2,3-Bis(hexanoylthio)propylphosphomethanol (a megadott mol
file alapján) ............................................................................................ 5
2.2 Környezeti paraméterek .............................................................. 5
2.3 A Malation hatásmechanizmusa .................................................... 5
3.Melléklet ............................................................................................ 7
4.Felhasznált irodalom .......................................................................... 40
41

Farkas János-Növényvédelmi Toxikológia PDF

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Farkas János-Növényvédelmi Toxikológia PDF

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SAPIENTIA – ERDÉLYI MAGYAR TUDOMÁNYEGYETEM

MŰSZAKI ÉS HUMÁNTUDOMÁNYOK KAR - MAROSVÁSÁRHELY

Növényvédelmi kémia és toxikológia

1.1 Az infravörös spektroszkópia az egyik leggyakrabban használt analitikai módszer

1. ábra: Infravörös spektrum

A mellékelt ábrán egy magmágneses rezonancia spektroszkópia (NMR: Nuclear Magnetic

3. ábra az izopropil-alkohol szerkezete

2.2 Környezeti paraméterek

Vízben való oldhatósága:0.1502 mg/L 25 °C-on (nagyon gyengén oldódik).

Sűrűsége: 1.2076 g/cm3 20 °C-on

LogKoc (Talaj-kötődési koefficiens) (logKoc): 4.94–es oktanol-víz megoszlási hányadosból

2.3 A Malation hatásmechanizmusa

Enzim kódja: EC 3.1.1.7

MOL FOR: C16 H31 O6 P1 S2

------------------------------ EPI SUMMARY (v4.11) --------------------------

Physical Property Inputs:

Log Kow (octanol-water): ------

Boiling Point (deg C) : ------

Melting Point (deg C) : ------

Vapor Pressure (mm Hg) : ------

Water Solubility (mg/L): ------

Henry LC (atm-m3/mole) : ------

KOWWIN Program (v1.68) Results:

Log Kow(version 1.68 estimate): 4.94

MOL FOR: C16 H31 O6 P1 S2

TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE

Frag | 8 | -CH3 [aliphatic carbon] | 0.5473 | 4.3784

Frag | 1 | -CH2- [aliphatic carbon] | 0.4911 | 0.4911

Frag | 5 | -CH [aliphatic carbon] | 0.3614 | 1.8070

Frag | 2 | -C(=O)O [ester, aliphatic attach] |-0.9505 | -1.9010

Frag | 1 | S=P [thio=phosphorus] |-0.6587 | -0.6587

Frag | 2 | -O-P [aliphatic attach] |-0.0162 | -0.0324

Frag | 1 | -S-P [sulfur, phosphorus attach] | 0.6270 | 0.6270

Const | | Equation Constant | | 0.2290

Log Kow = 4.9404

MPBPVP (v1.43) Program Results:

Experimental Database Structure Match: no data

MOL FOR: C16 H31 O6 P1 S2

------------------------ SUMMARY MPBVP v1.43 --------------------

Melting Point: -130.93 deg C (Adapted Joback Method)

Melting Point: 115.70 deg C (Gold and Ogle Method)

Mean Melt Pt : -7.61 deg C (Joback; Gold,Ogle Methods)

Selected MP: -7.61 deg C (Mean Value)

Vapor Pressure Estimations (25 deg C):

(Using BP: 392.81 deg C (estimated))

(MP not used for liquids)

VP: 3.01E-006 mm Hg (Antoine Method)

: 0.000401 Pa (Antoine Method)

VP: 1.24E-005 mm Hg (Modified Grain Method)

: 0.00166 Pa (Modified Grain Method)

VP: 2.55E-005 mm Hg (Mackay Method)

: 0.00339 Pa (Mackay Method)

Selected VP: 1.24E-005 mm Hg (Modified Grain Method)

: 0.00166 Pa (Modified Grain Method)

TYPE | NUM | BOIL DESCRIPTION | COEFF | VALUE

Group | 8 | -CH3 | 21.98 | 175.84

Group | 1 | -CH2- | 24.22 | 24.22

Group | 5 | >CH- | 11.86 | 59.30

Group | 2 | -O- (nonring) | 25.16 | 50.32

Group | 2 | -COO- (ester) | 78.85 | 157.70

Group | 1 | -S- (nonring) | 69.42 | 69.42

Group | 1 | >P=S | 100.00 | 100.00

Corr | 1 | Diester-type | -35.00 | -35.00