• Applied Biological Chemistry
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• v.30 no.4
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• pp.351-356
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• 1987

This study was conducted to investigate the absorption and translocation of pretilachlor [2-chloro-2, 6-diethyl-N-(n-propoxyethyl)-acetanilide] in plants and to evaluate the mobility in soil using the $^{14}C-or$ non-labelled compound in laboratory. Rice plant(Oryza sativa L.) was very tolerant to pretilachlor. Echinochloa crus-galli P. Beauv. was completely controlled by pretilachlor at 60g a.i./10a. At the 120g a.i./l0a, growth of Cyperus serotinus Rottb. and Sagittaria pygmaea Miq. was inhibited by 75% and 25%, respectively. The growth inhibition depended on absorbed amount of $^{14}C-pretilachlor$. The greatest concentration of $^{14}C$ was found in E. crus-galli, whereas the lowest was determined in rice plant. The rate of absorption and translocation in E. curs-galli was faster than in rice plan. Pretilachlor moved to 6cm deep in sandy clay loam, clay loam and loam soils, but to 10cm in sandy loam soil. In the soils herbicide-treated layer was found 0 to 2cm profile.

• Korean Journal of Weed Science
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• v.6 no.1
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• pp.59-66
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• 1986

This experiment was conducted with pot trial to evaluate effects of pretilachlor [2-chloro-2', 6'-diethyl-N(n-propoxythyl) acetanilide], pyrazoxyfen [ 1,3-dimethyl-4-(2,4-dichloro benzoyl)-5-phenacyloxy-pyrazole], pyrazolate (4-(2,4-dichloro benzoyl)-1,3-dimethyl-pyrazol-5-yl-p-toluenesulphonate] and their combinations on Echinochloa crew-galli. Herbicides were treated with different dosages under 3 cm water depth at 1st and 2nd leaf stages of E. crus-galli. E. crus-galli showed stunted symptom by treatment of pretilachlor and etiolation by treatment of pyrazoxyfen or pyrazolate after 4 days from treatment. Stunting and chlorosis degrees of E. crusgalli increased with high dosage of all herbicides at lst and 2nd leaf stage. Combination of pyrazoxyfen+pretilachlor (6+1.5)G or pyrazolate+pretilachlor (6+1.5)G showed positive synergistic effect of herbicidal action on E. crus-galli, therefore these combinations can control E. crux galli in paddy field with lower dosage than each single treatment of herbicides. Herbicidal effect of pyrazoxyfen on E. crus-galli was similar to pyrazolate in single treatment and combination with pretilachlor.

• Korean Journal of Weed Science
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• v.5 no.2
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• pp.169-174
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• 1985

Antidoting effect of 1,8-naphthalic anhydride (NA) on butachlor [2-chloro-2', 6'-diethyl-N-(butoxyethyl) acetanilide] phytotoxicity in rice was determined at different seeding depths and application rates of butachlor. The most sensitive response to NA was found in mesocotyl of rice (Oryza saliva L.). The mesocotyl length decreased with use of NA when seeded 2 to 4 cm deep, whereas no effect was obtained in plant height, root length and coleoptile length. Phytotoxic effect of butachlor to rice sown in vermiculite saturated with butachlor solutions decreased with use of NA at all seeding depths employed. However, depth protection was not observed when planted 3 to 4 cm deep without use of NA. Use of NA resulted in reduction in the phytotoxicity at concentrations of butachlor lower than 40 ppmw. The results indicated that the antidoting effect of NA was not due to reduction of mesocotyl elongation which would result in decrease in butachlor uptake through the mesocotyl.

• Applied Biological Chemistry
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• v.24 no.2
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• pp.112-119
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• 1981

The persistence of preemergence herbicides, butachlor [2-chloro-2,6-diethyl-N(butoxymethyl) acetanilide] and nitrofen(2,4-dichlorophenyl-4-nitrophenyl ether), at 10 ppm level in different soil conditions amended with organic matter and lime was studied under flooded and field moisture capacity. The microbial breakdown played a major role in the dissipation of the herbicides in soil. Nitrofen degradation in flooded soil was greatly accelerated, while it was slowed down in field moisture capacity as compared with butachlor. Increased amendment of rice straw to the soil shortened the half-life of butachlor under flooded condition, however it prolonged that of butachlor when the amendment was exceeded over 1% on dry weight basis. Liming the soil stimulated decomposition of the herbicides in the soil systems, which ap pears to be pH independent.

• The Korean Journal of Pesticide Science
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• v.13 no.2
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• pp.63-69
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• 2009

New morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 2(X=O) and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 3(X=C) to which morpholinyl or piperidinyl functional group were introduced at C-4 side chain of the 2-phenylimino-1,3-thiazoline scaffold were synthesized to investigate the effect of NH hydrogen of 2-phenylimino-1,3-thiazoline-4-acetanilide derivatives on the antifungal property against rice blast. Synthesized 30 compounds were screened against 6 kinds of typical plant fungi. Treatment of ketene dimer with chlorine followed by the reaction of morphorine or piperidine without isolation of the intermediate acetoacetylchloride gave $\gamma$-chloro-$\beta$-keto derivatives. These were reacted with thioureas to give morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines respectively in good yield (27-98%). The compound 3j, in which two fluorine atoms are substituted at ortho and para position of phenyl group of 2-phenylimino moiety and piperidinyl group is substituted at C-4, showed the highest antifungal activity (100 ppm, 90%). This result suggested that the substituent at C-4 of the 2-phenylimino-1,3-thiazolines may play a supplementary role to show the antifungal activity against rice blast.

• Korean Journal of Weed Science
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• v.4 no.2
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• pp.169-178
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• 1984

This experiment was conducted to find out selective herbicides which are safe to the rice seedlings and to provide effective weed control method in protected semi-irrigated rice seedbed. There was no crop injury in rice with benzophenap [2-(4-2, 4-dichloro-3-methylbenzoyl)-1, 3-dimethyl-pyrazol-5-yl-oxy)-4'-methyl acetophenone] (240g), pyrazoxyfene [1,3-dimethyl-4-(2,4-dichlorobenzoyl)-Sphenacyloxy pyrazole] (200g), chlormethoxynil [2,4-dichlorophenyl-4-nitro-3-methoxyphenyl ether] (180g), dimepiperate [S-(1-methyl-1-phenethyl)-piperidine-l-carbathioate] (210g), dimepiperate + probenazol [3-allyloxy-1,2-benzisothiazol-1,1-dioxide] (210 + 120g) mixture and dimepiperate + probenazol + molinate [S-ethyl-N,N-hexamethylene-thiol-carbamate] (120 + 120 + 120g) mixture at times of application studied. Butachlor [2-chloro-2',6'-diethyl-N-buthoxymethyl acetanilide] + pyrazolate [4-(2,4-dichlorbenzoyl)-1,3dimethyl-pyrazol-5-yl-p-toluene-sulfonate] (70 + 120g) mixture and butachlor + chlormethoxynil (60 + 120g) mixture caused root length to shorten and root viability to decrease. However, the crop injury was recovered at 25 days after seeding. Benzophenap, pyraxoxyfene and butachlor + pyrazolate mixture were effective for weed control when applied at 2 days before seeding. Chlormethoxynil and butachlor + chlormethoxynil mixture was very effective for controlling annual weed. Dimepiperate, dimepiperate + probenazol mixture and dimepiperate + probenazol + molinate mixture did not control most weeds except for Echinochloa crus-galli (L.) Beauv.

• Korean journal of applied entomology
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• v.16 no.3 s.32
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• pp.149-154
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• 1977

Effect of Simazine(2-chloro-4,6-bis (ethylamino)-s-triazine), Nitrofen (2, 4-dichloro-4' -nitrodi­phenylether), Propanil (:3, 4-dichloropropionanilide), and Butachlor (2-chloro-2, 6-diethyl N-(buthoxy­menthyl) acetanilide on urea hydrolysis and subsequent nitrification was investigated in an upland soil incubated at $20\pm1^{\circ}C$. 1. All the herbicides tested had no effect on the hydrolysis of urea to ammonia at the recommended rates. Butachlor, at ten and fifty times the recommended rate, and Nitrofen, at fifty times the recommeded rate, depressed urea hydrolysis, resulting in reduction of ammonia. But the depressive effects were temporary, disappearing soon. Simazine and Propanil had no detrimental effect on urea decomposition at all the treated rates. 2. Also, all the chemicals tested had no effect on the nitrification process at the recommended rates. At higher concentrations of ten and fifty times the recommended rate Butachlor and Nitrofen inhibited the oxidation of nitrite, and propanil long inhibited the oxidation of ammonium to nitrite, but was inactive against nitrite oxidizer. These inhibitive effects of the chemicals, however, disappeared in the later period of incubation. Simazine had no effect on the nitrification process at all the treated rates. 3. The trend of change in soil pH of both the treated and untreated plots well reflected the change of soil nitrogen forms during incubation. No direct effect of the chemicals on soil pH was obserbed.

• Korean Journal of Weed Science
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• v.5 no.1
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• pp.56-62
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• 1985

Effects of butachlor [N-(butoxymethyl)-2-chloro-2', 6'-diethyl acetanilide] and 1,8-naphthalic anhydride (NA) on post-germination growth, mesocotyl and root anatomy and root-cell membrane permeability of rice (Orvza saliva L.) were investigated. Lengths of mesocotyl and radicle were markedly decreased as the application rates of butachlor increased from 0.1 to 100 ppmW and NA from 1 to 100 ppmW, but there was no effect on coleoptile elongation. Application of butachlor-NA resulted in increase in coleoptile elongation, but decrease in mesocotyl elongation. Partial breakdown of cortical cells in root and mesocotyl was caused by either trutachlor or NA treatments, resulting in increase in intercellular air space. Further increase in the intercellular air space of root and mesocotyl was obtained when butachlor was applied in combination with NA. Increase in root-cell membrane permeability occurred when either butachlor or NA was applied. However, butachlor-NA treatments resulted in reduction in the permeability.

• Korean Journal of Weed Science
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• v.15 no.2
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• pp.115-120
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• 1995

This experiment was conducted in the paddy field to investigate the influence of bensulfuron (methyl-2-[[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonil]methyl]benzoate)+butachlor (N-(butoxymethyl)-2-chloro-2',6'-diethyl acetanilide) and bensulfuron+mefenacet(2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide) for seedling age of rice with Dongjinbyeo of medium-late-maturing variety, Hwaseongbyeo of medium-maturing variety and Namwonbyeo of early-maturing variety. Two herbicide applications interfered with the early growth of all rice varieties, the root was especially damaged more than the shoot. The phytotoxicity of bensulfuron+butachlor and bensulfuron+mefenacet was not significant statistically and the phytotoxicity of these herbicides for seedling age was apt to be similar, also. Twenty and 35days seedlings of Dongjinbyeo and Hawseongbyeo had more growth amount than 8days seedlings, but Namwonbyeo had opposite trend. The number of maximum tillers in the plots applied herbicides were fewer than untreated control but, the percentage of productive tillers was higher than those. Heading date for Namwonbyeo was delayed 2, 1-2 and 2-3days on 35, 20 and 8days seedlings by herbicide application, respectively.

• Korean Journal of Environmental Biology
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• v.39 no.4
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• pp.452-462
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• 2021

Pretilachlor (PRE) is a common acetanilide herbicide used worldwide. However, its effects on aquatic organisms, particularly marine photosynthetic life, are not sufficiently known. Herein, we evaluated the toxic effects of PRE by physiological and molecular parameters in the photosynthetic dinoflagellate Prorocentrum minimum. The cell density, pigment content, and photosynthetic parameters (F_v/F_m and PI_ABS) were considerably decreased with increased PRE exposure time and doses. In addition, photosynthesis-related genes, PmpsbA, PmpsaA, and PmatpB, were significantly upregulated when exposed to 1.0 mg L^-1 of PRE for 24 h (p<0.001). In 72 h treatment, the relative gene expression was significantly increased (0.1 and 0.5 mg L^-1; p<0.01). In contrast, PmrbcL was decreased or little changed compared to the controls. Reactive oxygen species (ROS) increased after 24 h exposure (p<0.001). However, the transcriptional fold-changes in glutathione S-transferase (GST) were significantly increased (0.5 and 1.0 mg L^-1; p<0.001) at 72 h. These findings suggested that the PmGST might be involved in PRE detoxification in P. minimum. In addition, PRE may affect the photosystem function in phytoplankton similar to other acetanilides, causing severe damage or cell death.