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Chemical
classification
Some pesticides
have similar properties based on their chemical structure. Such
chemicals belong to the same chemical class and frequently
have similar toxicological modes of action. This page gives brief
descriptions of the different chemical classes and provides representative
chemical structures for most classes.
Chemical
Class Descriptions
Representative
Chemical Structures
Insecticides
Herbicides
Microbiocides
Fungicides
Rodenticides
About
the Data: Accuracy, Currency, Comprehensiveness and Source
Chemical
Class Descriptions (alphabetical)
|
Chemical
Class
|
Description |
|
1,3-Indandione
|
Rodenticides
that act as anticoagulants. High acute toxicity. Indandione
structure, with substituents. Representative chemical structure
here. |
|
2,6-Dinitroaniline
|
Herbicidal
compounds containing a dinitroaniline functional group. While
these compounds are not acutely toxic to animals, many of them
are possible human carcinogens.
Representative chemical structure here. |
|
Alkyl
phthalate
|
Compounds
derived from phthalic acid. Used as insecticides and insect
repellents, as well as softeners in plastics manufacturing.
Some of these compounds are suspected endocrine
disruptors. Representative chemical structure here. |
|
Anilide
|
Herbicidal
compounds with an anilide functional group. These compounds
have potential to leach into groundwater. Examples are propanil
and flufenacet. Representative chemical structure here. |
|
Azole
|
Fungicidal
compounds, a few of which are carcinogenic. Representative chemical
structures here. |
|
Benzimidazole
|
Fungicidal
compounds with a benzimidazole group. Benomyl and thiabendazole
are examples. Representative chemical structure here. |
|
Benzoic
acid
|
Compounds
with a benzoic acid functional group. Many of these are herbicides.
Examples are chloramben and dicamba. Representative chemical
structures here. |
|
Benzoyl
urea
|
Herbicidal
compounds with a urea functional group having a benzoyl substituent.
Frequently found as groundwater contaminants. Diflubenzuron
and Triflumuron are examples. Representative chemical structure
here. |
|
Bipyridilium
|
Herbicides
containing two pyridine rings, joined through a C-C bond. Most
are acutely toxic to mammals. Paraquat is a bipyridilium compound.
Representative chemical structures here. |
|
Bis-Carbamate
|
Compounds
containing two carbamate moieties. Typically herbicides. Representative
chemical structure here. |
|
Botanical
|
Pesticides
derived from plants. These pesticides are typically a plant's
natural defense against insects or fungi. Examples are nicotine
and pyrethrins. Some of these compounds are quite toxic. |
|
Carboxamide
|
Fungicidal
compounds. Carboxin and flutolanil are examples. Representative
chemical structure here. |
|
Chelating
agent
|
A compound that binds tightly to metal ions, generally increasing
the water solubility of the ion. Chelation can also reduce the
bioavailability of a metal ion by making it less reactive in
biological systems. EDTA is the most widely used chelating agent
in pesticide formulations. |
|
Chlorinated
phenol
|
Chlorinated
aromatic alcohols typically used as microbiocides, fungicides,
algaecides, or wood preservatives. Some of these compounds are
carcinogenic and/or extremely toxic. Representative chemical
structure here. |
|
Chloroacetanilide
|
Herbicidal
compounds with a chloroacetanilide functional group. These compounds
are frequently found with their breakdown products as contaminants
in groundwater. Examples are alachlor and metolachlor. Representative
chemical structures here. |
|
Chlorophenoxy
acid/ ester
|
Herbicidal
compounds such as 2,4-D and 2,4,5-T. Many chlorophenoxy compounds
are suspected endocrine
disruptors. Representative chemical structure here. |
|
Chloropyridinyl
|
Triclopyr
and its salts are members of this chemical class of herbicidal
compounds.These compounds are commonly used on new-growth forests.
Structure of the parent compound here.
|
|
Coumarin
|
Rodenticides
that act as anticoagulants. Cinnamic acid lactone structure.
Representative chemical structure here.
|
|
Cyclohexenone
|
A relatively
new class of herbicidal compounds. While most have not been
thoroughly evaluated, tralkoxydim has been rated as a Likely
carcinogen by the U.S. EPA. Representative chemical
structure here. |
|
Diacylhydrazine
|
A
relatively new class of insecticide that is persistent in
the environment and may pose substantial ecological risks.
Methoxyfenozide and tebufenozide are examples. There is some
evidence these compounds may be endocrine
disruptors. Representative chemical structure here.
|
|
Dicarboximide
|
Fungicidal
compounds. Vinclozolin and iprodione are examples. Representative
chemical structure here. |
|
Dinitrophenol
|
Herbicidal
and fungicidal compounds. Many are very acutely toxic, as well
as being reproductive and developmental toxicants.
Representative chemical structure here. |
|
Dithiocarbamate
|
Typically
fungicides with a carbamate structure where sulfurs replace
both oxygens in the amide functional group. Examples are maneb,
metam sodium, and ziram. These compounds are not cholinesterase
inhibitors. Representative chemical structures here.
|
|
Halogenated
organic
|
A
diverse array of compounds composed mainly of carbon, hydrogen,
and fluorine, chlorine, and/or bromine. Used as fumigants, fungicides,
solvents and propellants. |
|
Imidazolinone
|
A
relatively new class of herbicidal compounds, with low acute
toxicity to animals. Representative chemical structure here. |
|
Inorganic
|
Any
chemical compound not containing hydrocarbon moieties and
not one of the toxic metals. Inorganic compounds of toxic metals--mercury,
arsenic, cadmium, chromium, tin, lead, and silver--are listed
separately (see below). Examples of inorganics are lime, phosphoric
acid, and sulfuryl fluoride. |
|
Inorganic-Arsenic
|
Arsenic-containing
compounds that do not have arsenic-carbon bonds. These compounds
are generally extremely toxic, causing acute toxicity, cancer,
and developmental toxicity. |
|
Inorganic-Cadmium
|
Cadmium-containing
compounds that do not have cadmium-carbon bonds. These compounds
are generally extremely toxic, causing acute toxicity, cancer,
reproductive and developmental toxicity. |
|
Inorganic-Chromium
(VI)
|
Chromium-containing
compounds that do not have chromium-carbon bonds, where the
chromium atom is hexavalent (Cr+6). These compounds are extremely
toxic, causing acute poisoning, cancer, reproductive and developmental
toxicity. |
|
Inorganic-Lead
|
Lead-containing
compounds that do not have lead-carbon bonds. These compounds
are extremely toxic, causing acute neurotoxicity, cancer, reproductive
and developmental toxicity. |
|
Inorganic-Mercury
|
Mercury-containing
compounds that do not have mercury-carbon bonds. These compounds
are generally extremely toxic, causing acute toxicity, cancer,
and developmental toxicity. |
|
Inorganic-Silver
|
Silver-containing
compounds that do not have silver-carbon bonds. Most are used
as microbiocides. |
|
Inorganic-Zinc
|
Zinc-containing
compounds that do not have zinc-carbon bonds. Most are used
as microbiocides or fungicides. |
|
Microbial
|
Pesticides
composed of a particular species of microbe, e.g. Bacillus
thuringiensis. Generally, these microbes produce a toxin
that is the "active ingredient" that kills a pest.
Microbial pesticides are typically very selective, affecting
only the target pest. |
|
N-Methyl
carbamate
|
Compounds
(mostly insecticides) with an N-methyl amide functional group.
Most N-methyl carbamates are strong cholinesterase
inhibitors which cause neurotoxicity in both insects and
humans. N-methyl carbamates are the most acutely toxic of
all carbamate pesticides. Representative chemical structure
here.
|
|
Naphthalene
acetic acid
|
Plant
growth regulators with low acute toxicity. Representative
chemical structures here. |
|
Oil
- essential
|
Oils
with pesticidal properties extracted from plants. Examples are
cinnamon, peppermint, jasmine, and lavender oils. |
|
Oil
- vegetable
|
Oils
extracted from plants such as soybeans and corn and used as
insecticides. They work by smothering the insects. |
|
Organoarsenic
|
Arsenic-containing
compounds with an organic moiety bound directly to arsenic.
These compounds are generally extremely toxic, with many used
as chemical warfare agents. |
|
Organochlorine
|
Compounds,
mostly insecticides, composed primarily of carbon, hydrogen,
and chlorine. Organochlorines are typically very persistent
in the environment and are known for bioaccumulating or building
up in sediments, plants and animals. Many organochlorines are
also suspected endocrine
disruptors. Representative chemical structures here. |
|
Organomercury
|
Mercury-containing
compounds with an organic moiety bound directly to mercury.
These compounds are generally extremely toxic, causing acute
toxicity, cancer, and developmental toxicity. |
|
Organophosphorus
|
Compounds,
mostly insecticides, that contain a phosphorus atom bound to
organic substituents, either alkyl or alkoxy groups. Most organo-phosphorus
pesticides are cholinesterase
inhibitors which cause neurotoxicity in both insects and
humans. Representative chemical structures here. |
|
Organotin
|
Tin-containing
compounds with an organic moiety bound directly to tin. These
compounds are generally extremely acutely toxic and are also
known to be endocrine
disruptors. Examples are tributyltin or triphenyltin salts. |
|
Other
carbamate
|
Compounds
(mostly insecticides) with an amide functional group with substituents
besides methyl groups. Many of these carbamates are mild cholinesterase
inhibitors which cause neurotoxicity in both insects and
humans. Representative chemical structure here. |
|
Petroleum
derivative
|
Compounds
derived from crude oil through a distillation process. Frequently
used as solvents, adjuvants, and insecticides. Depending on
the level of refinement, petroleum derivatives often contain
carcinogenic substances. |
|
Pheromone
|
Insect
sex-attractant hormones used to disrupt mating. These compounds
are used in very small quantities and are very selective for
a particular insect species. Their chemical structure is typically
a long-chain alcohol, aldehyde or ester with at least one double
bond. Representative chemical structures here.
Cornell University hosts an excellent web site on pheromones.
|
|
Phosphonoglycine
|
Herbicidal
organophosphorus compound. These compounds inhibit a plant-specific
enzyme and have low acute toxicity to mammals. Glyphosate and
its salts and esters (active ingredients in Roundup products)
belong to this class of compounds. Representative structure
here. |
|
Pyrazole
|
A
relatively new class of insecticide that is persistent in the
environment and may pose substantial ecological risks. Chlorfenapyr
(Pirate) is an example. Representative chemical structure here. |
|
Pyrethroid
|
Synthetic
insecticides (typically cyclopropane carboxylates) structurally
similar to pyrethrins, which are naturally occurring insecticidal
compounds. Many pyrethroids are suspected endocrine
disruptors. Representative chemical structures here. |
|
Pyridinecarboxylic
acid
|
Herbicidal
compounds with low acute toxicity. Representative chemical structure
here. |
|
Quaternary
ammonium
|
Ammonium
salts with four alkyl or aryl groups, typically used as microbiocides
or algaecides. Representative chemical structure here. |
|
Silicone
|
Synthetic
oils with a silicon-oxygen backbone. Used as antifoaming agents
and emulsifiers. |
|
Soap
|
Compounds
with surfactant or detergent properties. Used as insecticides
and adjuvants. |
|
Substituted
benzene
|
Fungicidal
compounds with a benzene ring substituted with various substituents.
Some of these compounds are very toxic wood preservatives such
as pentachloro-nitrobenzene (PCNB) and hexachlorobenzene. Representative
chemical structure here.
|
|
Sulfonyl
urea
|
Herbicidal
compounds with a urea functional group having a sulfonyl substituent.
Frequently found as groundwater contaminants. Bensulfuron-methyl
and rimsulfuron are examples. Representative chemical structure
here. |
|
Thiocarbamate
|
Typically
herbicides with a carbamate structure where sulfur replaces
one of the oxygens in the amide functional group. Examples are
cycloate, butylate, and molinate. These compounds are weak cholinesterase
inhibitors. Representative chemical structure here. |
|
Triazine
|
Typically
herbicides or microbiocides containing a triazine ring. Frequently
found in groundwater, along with their transformation products.
Representative chemical structure here. |
|
Uracil
|
Herbicidal
compounds derived from uracil. Frequently found as groundwater
contaminants. Bromacil and terbacil are examples. Representative
chemical structure here. |
|
Urea
|
Herbicidal
compounds with a urea functional group. Frequently found as
groundwater contaminants. Diuron and linuron are examples. Some
of these compounds are carcinogenic. Representative chemical
structures here. |
Coming
soon
Fungicides:
- Mercaptobenzothiazole
- Pyrimidine
- Substituted Benzene
- Thiophthalimide
- Strobin
Herbicides:
- Amide
- Phosphinico amino
acid
Microbiocides/Wood
Preservatives (mostly):
- Alkyl Amino Propane
- Chlorinated Phenol
- Hydantoin
- Isothiazolone
- Phenol
- Quaternary Ammonium
Compounds
Oils,
soaps, solvents, adjuvants:
- Alcohol/Ether
- Polyalkoxy Compound
Other:
- Carbohydrate
- Cellulose derivative
Representative
Chemical Structures
Insecticides
Alkyl
Phthalates
Chloronicotinyl
Compounds
Diacylhydrazines
N-Methyl
Carbamates
Organochlorine
Compounds
Organophosphorus
Compounds
Other
Carbamates
Pheromones
Pyrazoles
Pyrethroids
Herbicides
2,6-Dinitroanilines
Anilides
Aryoxyphenoxy
proprionic acids
Benzoic
Acids
Benzoyl
Ureas
Bipyridilium
Compounds
Bis-Carbamates
Chloroacetanilide
Chlorophenoxy
Acids/Esters
Chloropyridinyls
Cyclohexenones
Dinitrophenols
Imidazolinones
Naphthalene
Acetic Acid Derivatives
Phosphonoglycines
Pyridinecarboxylic
Acids
Sulfonyl
Ureas
Thiocarbamates
Triazines
Ureas
Uracils
Microbiocides
Chlorinated
Phenols
Hydantoins
Isothiazolones
Phenols
Quaternary
Ammonium Compounds
Fungicides
Azoles
Benzimidazoles
Carboxamides
Dicarboximides
Dithiocarbamates
Substituted
Benzenes
Rodenticides
Coumarins
1,3-Indandiones
Alkyl
Phthalates
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Chloronicotinyl
Compounds
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Diacylhydrazines

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N-Methyl
Carbamates
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Organochlorine
Compounds
Organochlorine
compounds do not have a common chemical structure, but all of them
have multiple carbon-chlorine bonds.
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Organophosphorus
Compounds
The general
chemical structures associated with organophosphorus pesticides
are:

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Other
Carbamates

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Pheromones
Many pheromones
have a long-chain alkyl component with one or more double bonds
and a terminal alcohol, ester, or aldehyde functional group.

Others are
more variable in structure. Some examples are shown below.

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Pyrazoles

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Pyrethroids
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2,6-Dinitroanilines

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Anilides
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Aryloxyphenoxy
proprionic acids

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Benzoic
Acids
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Benzoyl
Ureas
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Bipyridilium
Compounds
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Bis-Carbamates
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Chlorophenoxy
Acids/Esters
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Chloroacetanilide
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Chloropyridinyl
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Cyclohexenones

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Dinitrophenols

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Imidazolinone

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Naphthalene
Acetic Acid Derivatives
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Phosphonoglycines

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Pyridinecarboxylic
Acids
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Sulfonyl
Ureas
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Thiocarbamates
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Triazines
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Ureas
The general structure
is a urea unit with substituents:

Some specific
examples are diuron and tebuthiuron.

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Uracils
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Chlorinated
Phenols
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Quaternary
Ammonium Salts
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Azoles
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Benzimidazoles
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Carboxamides
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Dicarboximides
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Dithiocarbamates
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Substituted
Benzenes
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Coumarins
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1,3-Indandiones
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About
the Data: Accuracy,
currency, comprehensiveness and source
This dataset is maintained by PAN staff by evaluation of chemical
structure, and research using the references listed below. Last
updated December 11, 2003. PAN staff will continue to add to this
list and update it at least annually.
References:
- Chem Finder, CambridgeSoft Corporation. Viewed on
April 8, 2005.
- The Pesticide Manual, 11th edition, C. D. S. Tomlin, Ed., British Crop Protection Council (Farnham, Surrey, UK, 1997).
- Merck Index, 12th edition, Merck Publishing Group (Rahway, NJ, 1996).
- A. Wood, Compendium
of Pesticide Common Names, Copyright © 1995-2003. Viewed on
April 8, 2005.
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Last updated
April 7, 2005
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