It is a relatively low toxicity pesticide that has the potential to find its way into food, drinking water, and residential areas. 5129 0 obj
<>
endobj
5150 0 obj
<>/Filter/FlateDecode/ID[<0FA110E32FF5404497C3ECE48A21147D>]/Index[5129 36]/Info 5128 0 R/Length 109/Prev 257434/Root 5130 0 R/Size 5165/Type/XRef/W[1 3 1]>>stream
0000058395 00000 n
0000058847 00000 n
0000001548 00000 n
0000021955 00000 n
Inhalation, dermal, and oral exposure to imazaquin yielded relatively low Margin of Exposure values issued by the EPA deeming imazaquin as a minimal risk concern. It is a colorless or white solid, although commercial samples can appear brown or tan. Chronic dermal exposure to imazaquin in rabbits during a 21-day time period yielded no effects upon the rabbits. This page was last edited on 8 June 2022, at 01:35. 0000011881 00000 n
Imazaquin has a sorption coefficient of 20.[9]. A 90-day and one-year study of ingestion of imazaquin in rats also yielded no effects as well. "7J?sc0[ZtIid d`5H3C. corn herbicide symptoms injury purdue chlorosis interveinal acsl due inhibitor Adsorption is greatest at a pH nearest the pKa of the carboxylic group of imazaquin. 0000020043 00000 n
Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. 
Imazaquin inhibits the acetohydroxy acid synthase (AHAS) enzyme accountable for synthesis of the amino acids valine, leucine, and isoleucine. %PDF-1.6
%
0000017180 00000 n
Optimization ensued and the attempt to enable the production of field trial samples led to the formation of a tricyclic compound. 0000058974 00000 n 'U endstream endobj startxref 0 %%EOF 5164 0 obj <>stream 0000002745 00000 n A derivative of phthalimide showed promise when it exhibited some plant growth inhibition. The reaction starts with the NH2 group of the benzenamine adding to the second carbonyl group on diethyl 2-oxobutanedioate (diethyl oxaloacetate). 0000010315 00000 n It has a toxicity classification of III, which corresponds to only a slight toxicity. The connection to AHAS was not understood at the time. herbicida amine [7], The imidazolinone herbicides were first discovered in the 1970s. herbicides 1998 figure proposed sampling location sulfonamide sulfonylurea values selected ec50 aquatic concentration plants 31 0 obj <> endobj xref 31 43 0000000016 00000 n When applied, imazaquin halts weed growth which eventually kills the weed or causes the weed to die due to its incapability to compete with surrounding vegetation. Imazaquin has shown greater adsorption at lower pHs. 0000002515 00000 n Imazaquin may be applied pre-plant incorporated, pre-plant surface, pre-emergence, or early post-emergence.[12]. hb```^V ea rr>`?U JUskTzqIu)L->0wt `"H0wtQA0y_Ob1-C=q,mA.7ig+6f`TZ ud`~#QX` 6 endstream endobj 5130 0 obj <>/Metadata 63 0 R/Pages 5127 0 R/StructTreeRoot 70 0 R/Type/Catalog>> endobj 5131 0 obj <. 0000010078 00000 n [6] When present in soil, imazaquin is absorbed through the roots of plants where the chemical is either metabolized quickly with no effects or slowly metabolized or not metabolized at all which eventually will lead to the death of the plant. 0000061643 00000 n }vr`U<3W j|^G_9j4Jb.Vk-IW*6Y y\uu\Lk*n`C ]cTn/^k;lGF_0){b0nnb\AYIT! 0000001961 00000 n AHAS is the first enzyme in the branched-chain amino acid pathway that leads to the synthesis of amino acids leucine, isoleucine, and valine. trailer <]/Prev 258789>> startxref 0 %%EOF 73 0 obj <>stream %PDF-1.4 % hb```b``] @Q2p+r0>d4L=ksD4mM'EE Y.l[CRuFa:Y]\56A,HRLJJp 3l$7EE@v$? & LL "xH:pidn|6C^u 0000014380 00000 n hbbd```b``- 1d"DA$X5X/~,r Q.@,$mf`bd Imazamox, the last of the six, received its U.S. patent in 1994. [4] They vary in the attached ring structure. Although exposure to residential areas affects infants and children, there is no concern over its presence due to its low estimated aggregated risk which meets the FQPA safety standards. 0000017268 00000 n 0000044630 00000 n 0000004738 00000 n (6b)W#pFAW6t a=- %Q)Mz~NhlBZV o$XN{PHXt NR$6}a'u`lV ,).BH@. 0000022810 00000 n 0000058370 00000 n 0000011700 00000 n Chronic toxicity studies were also conducted upon rabbits, rats, and beagle dogs. Years later, the molecule was found to exhibit herbicidal activity. 0000009889 00000 n Imidazolinone herbicides kill plants by inhibiting acetohydroxy acid synthase (AHAS).
Imazaquin tested negative for mutagen effects, organ toxicity, and reproductive effects. Further exploration resulted in the formation of the first imidazolinone herbicide. The same reaction was performed on the original phthalimide, resulting in a compound that exhibited broad-spectrum herbicidal activity. 0000023276 00000 n
[14], Imazaquin is a non-volatile chemical leading to limited movement into soil that eventually breaks down within 46 months. [9], When imazaquin is applied to crops its main interaction is with soil humic acids. However, in the one year, dietary chronic imazaquin exposure to beagle dogs, the dogs exposed to the highest dose of imazaquin per day, 5000 ppm, experienced effects such as decreased body weight gain, skeletal myopathy, slight anemia, bone marrow hyperplasia, increased blood levels of SGOT, DSGPT and CPK, and increased liver weight. 0000044888 00000 n
HtW\I6 0000002579 00000 n
The LD50 for dogs, rats, rabbits, and female mice were each 1000mg/kg, 5000mg/kg, 2000mg/kg, and 2363mg/kg, respectively. *fT eX
endstream
endobj
32 0 obj
<><><>]/ON[34 0 R]/Order[]/RBGroups[]>>/OCGs[34 0 R]>>/Pages 28 0 R/Type/Catalog>>
endobj
33 0 obj
<>/Font<>>>/Fields[]>>
endobj
34 0 obj
<>/PageElement<>/Print<>/View<>>>>>
endobj
35 0 obj
<>/ExtGState<>/Font<>/ProcSet[/PDF/Text]/XObject<>>>/Rotate 0/Type/Page>>
endobj
36 0 obj
<>
endobj
37 0 obj
<>
endobj
38 0 obj
[/ICCBased 71 0 R]
endobj
39 0 obj
[/Separation/PANTONE#20Violet#20CV 38 0 R 61 0 R]
endobj
40 0 obj
<>stream
Imazaquin is also nontoxic to birds and fish when properly used. As for its breakdown in surface water, imazaquin has a hydrolytic half-life of 5.5 months at pH 9. At pH 3 and 5, it is stable to hydrolysis. [11] It is classified as an imidazolinone herbicide that controls weed growth through the inhibition of specific amino acids that prove to be vital for plant growth. Due to the fact that it is highly effective and selective, it is one of the most commonly used herbicides. It was found that the rate at which imazaquin aggregates on soil humic acids was most affected by the environmental pH. [5] Crop varieties have been developed through conventional breeding that are resistant to these herbicides and are marketed by BASF under the Clearfield brand. 0000008219 00000 n
0000002644 00000 n
0000009692 00000 n
[14], 3-Quinolinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-, O=C(O)c2c(nc1ccccc1c2)/C3=N/C(C(=O)N3)(C(C)C)C, Except where otherwise noted, data are given for materials in their, "3-Quinolinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]", "Multiple mechanisms are involved in new imazamox-resistant varieties of durum and soft wheat", "OSU Extension Pesticide Properties Database", "Herbicide-binding sites revealed in the structure of plant acetohydroxyacid synthase", "Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Imazaquin", https://en.wikipedia.org/w/index.php?title=Imazaquin&oldid=1092071968, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, 219 to 222C (426 to 432F; 492 to 495K). Imazaquin is primarily used as a herbicide to control weed growth on lawns and turf fields. herbicides glycel 0000002116 00000 n
[4], The imidazolinone herbicides were discovered at American Cyanamid's Medical Division during the 1950s, starting from the initial lead molecule phthalimide. It is therefore categorized as a moderately persistent pesticide. 0000010267 00000 n
w ? The first U.S. patent was awarded in 1980 for imazamethabenz-methyl. [8], Imazaquin has a water solubility of 60mg/L[9] and its half-life in soil is 60 days. This organic compound is used to control a broad spectrum of weed species. crc handbook nuts pittosporum herbicides 1991 volume magnetism brucellosis amorphous animal toxicity pesticides fish ii plant pittosporaceae hanga philippine petroleum These chemicals all feature an imidazolinone ring with a carboxylic acid group attached to the backbone. [13], A study conducted by Cornell University showed that imazaquin ingested by humans and animals was excreted within 48 hours, 94% through urine and 4% through feces. 0000006525 00000 n
0000014904 00000 n
A higher sorption coefficient means more hindrance of movement and possibly an increase in persistence as a result of protection from degradation. Harmful in contact with skin. 0000015100 00000 n
Imazaquin is a relatively nontoxic, non-carcinogenic chemical causing none to minimal eye and skin irritation if contacted upon the dermis, ingested orally, or inhaled. 
0000001156 00000 n May be harmful if swallowed. The greater the coefficient, the higher the sorption potential. 0000001836 00000 n Imazaquin, imazapyr, imazapic, and imazethpyr followed suit and received patents in 1989. 0000023424 00000 n 0000012404 00000 n [10], The sorption coefficient is a means of specifying a pesticide's tendency to bind to soil particles. The chemical breaks down microbially and is slowly reduced to carbon dioxide and metabolites. herbicides water sulfonylurea sulfonamide values selected figure calculated concentrations estimated ec25 soil crops Imazaquin along with imazamethabenz-methyl, imazapyr, imazapic, imazethapyr, and imazamox comprise the class of synthetic compounds termed the imidazolinone herbicides. At higher pHs, the hydrogen bonds and charge-transfer complexes that form during adsorption interactions are much weaker at higher pHs. 0000010832 00000 n 0000002679 00000 n 0000011791 00000 n 0000019351 00000 n 0000023345 00000 n