Relationship between safening activity of dymron and fenclorim to pretilachlor and glutathione S-transferase activity in rice

Dymron [1‐(α,α‐dimethybenzyl)‐3‐(p‐tolyl)urea] and fenclorim (4,6‐dichloro‐2‐phenylpyrimidine) were found to exhibit a safening activity on the growth of rice (Oryza sativa L.) seedlings against pretilachlor [2‐chloro‐2′,6′diethyl‐N‐(2‐propoxyethyl)acetanilide] injury. By pretilachlor treatment at 10^–6 and 10^–5 mol L^–1, the elongation of the third leaves of rice seedlings was reduced by approximately 20 and 40%, and that of the fourth leaves was reduced by approximately 40 and 80%, respectively. Upon the treatment of dymron at 3 × 10^–6 and 10^–5 mol L^–1 in combination with pretilachlor, the growth inhibition was half alleviated in the third leaves, and the length of the fourth leaves was almost recovered from 10^–6 mol L^‐1 pretilachlor injury, and was 20–25% recovered from 10^–5 mol L^–1 pretilachlor injury. Upon the treatment of fenclorim at 3 × 10^–6 and 10^–5 mol L^–1 in combination with pretilachlor, the growth inhibition of rice seedlings was almost alleviated in both the third and the fourth leaves. This result indicated that dymron and fenclorim showed almost the same safening effect on the fourth leaf growth against 10^–6 mol L^‐1 pretilachlor injury, although fenclorim showed higher effects at higher concentrations of pretilachlor. Glutathione S‐transferase (GST) activities in rice seedlings were investigated after being treated with a herbicide and safener. By pretilachlor treatment at 10^–6 and 10^–5 mol L^–1, the GST activity was approximately 32 and 72% increased in roots, respectively, and a little increased (7–13%) in shoots of two‐leaf‐stage rice seedlings. By dymron treatment at 3 × 10^–6?10^–5 mol L^–1, the GST activity was 2–30% increased in roots, but was not increased in shoots. By their combination treatment, the GST activity was almost the same or less than that by treatment with pretilachlor alone. In contrast, by fenclorim treatment alone, the GST activity was 43–52 and 33–45% increased in roots and shoots of rice seedlings, respectively. By the combination treatment of pretilachlor and fenclorim, the GST activity was increased 73–126% in shoots and 101–139% in roots, and was much more increased in both shoots and roots compared with treatment of pretilachlor or fenclorim alone. It was found that dymron showed less effect in increasing the GST activity than fenclorim. It is also suggested that dymron did not increase the GST activity in shoots but did increase it slightly in roots, and showed almost no effect on GST increase by pretilachlor in shoots, or rather reduced the increase in roots. From the above results, fenclorim and dymron may have different mechanisms of safening effects on the protection of rice seedlings against pretilachlor injury.     

Differential safening activity of dymron and fenclorim on pretilachlor injury in rice seedlings in soil

The safening activity of dymron [1-(α,α-dimethylbenzyl)-3-( p -tolyl)urea] and fenclorim [4,6-dichloro-2-phenylpyrimidine] on the phytotoxic activity of pretilachlor [2-chloro-2',6'-diethyl- N- (2-propoxyethyl)acetanilide] on rice seedlings was examined in both water and soil culture. The safening activity of fenclorim in water culture was greater than that of dymron, whereas the activity of fenclorim in soil was lower than that of dymron. The fenclorim concentration in soil water was lower than that of dymron at all times when determined after the application at the same concentrations. The phytotoxic activity of pretilachlor and the safening activities of dymron and fenclorim were well correlated with the concentration of each in soil water but not with the amount in total soil. The adsorption of fenclorim on soil solids was greater than those of dymron and pretilachlor. It was suggested that both the phytotoxic activity of pretilachlor and the safening activities of dymron and fenclorim were dependent on their concentrations in soil water, which were primarily dominated by the adsorption on soil.     

Effect of CGA 123407 as a safener for pretilachlor in rice (Oryza sativa L.). Recordings of elongation rates of single rice leaves

The elongation rates of single attached leaves of rice (Oryza saliva L.) were recorded. The effect of pretilachlor on the elongation rates and the safening effect of CGA 123407 [4, 6-dichloro-2-phenyl-pyrimidine] were evaluated. Both chemicals were applied to the roots in a nutrient solution. Pretilachlor reduced leaf elongation in concentrations as low as 300 μg^?1 (9–6 × 10^?7 M) but. for combination trials with the safener, 3 mg 1^?1 (9–6 × 10^?6 M) was used. in combination with pretilachlor the safener prevented damage in very low concentrations. The ratio of pretilachlor to safener, 30:1, was sufficient when both chemicals were given to roots in nutrient solution, although for field work the ratio of 3:1 is recommended. The safener alone did not influence the elongation rate of rice leaves in the concentrations used. When pretilachlor was given to the roots and CGA 123407 to the shoot, some delay in the herbicidal action was recorded but even with high concentrations of the safener no continuous safening effect was achieved. CGA 123407 was also effective when given previous to the herbicide. This proved true even with a 2-day interval between safener uptake and application of the herbicide. When pretilachlor was given first, the safener effected recovery to various degrees when given 1–4 days after the herbicide application. When pretilachlor was given for a limited period of time only (1–3 days) and was subsequently removed from the nutrient solution, recovery of the plant occurred. It is speculated that the safener either helps this recovery or else competitively prevents the herbicide from occupying the sites of action or from keeping them occupied for a long period of time.     

Involvement of cytochrome P‐450 enzyme activity in the selectivity and safening action of pyrazosulfuron‐ethyl

To investigate the selectivity and safening action of the sulfonylurea herbicide pyrazosulfuron‐ethyl (PSE), pyrazosulfuron‐ethyl O‐demethylase (PSEOD) activity involving oxidative metabolism by cytochrome P‐450 was studied in rice (Oryza sativa L cv Nipponbare) and Cyperus serotinus Rottb. Cytochrome P‐450‐dependent activity was demonstrated by the use of the inducers 1,8‐naphthalic anhydride and ethanol, the herbicides PSE, bensulfuron‐methyl, dimepiperate and dymron, or the inhibitor piperonyl butoxide (PBO). Growth inhibition in C serotinus seedlings was more severe than that in rice seedlings. O‐Dealkylation activities of PSE were induced differently in rice and in C serotinus, with distinctly higher activity in rice seedlings. The induced PSEOD activities were slightly inhibited by PBO in rice seedlings, whereas they were strongly inhibited in C serotinus seedlings. Dimepiperate and dymron were effective safeners of rice against PSE treatment. Treatments with herbicide alone resulted in less induction of PSEOD activity compared with combined treatments of the herbicide and safener. PSEOD activity in rice seedlings induced with herbicide alone was strongly inhibited by PBO, whereas it was weakly inhibited in rice seedlings induced with combinations of PSE and two safeners. These results suggest that O‐demethylation by cytochrome P‐450 enzymes may be involved in the metabolism of PSE and may contribute to its selectivity and safening action. Furthermore, these results suggest the existence of a multiple form of cytochrome P‐450 in plants. © 2001 Society of Chemical Industry     

Effect of pretilachlor and fenclorim on carbohydrate and protein formation in relation to their persistence in rice

The persistence of pretilachlor applied to rice singly or in combination with the safener fenclorim was investigated in connection with starch, glucose and protein formation. The addition of fenclorim to pretilachlor did not reduce the accumulation of the latter, but reduced its persistence in rice shoots, while the presence of pretilachlor did not affect the persistence of fenclorim, but significantly increased its accumulation in the shoots. Therefore the safening effect of fenclorim consisted of a more rapid detoxification of pretilachlor. Over the period of pretilachlor and fenclorim detoxification, decreases in starch content, partially counterbalanced by increases of free glucose, and decreases in total protein content were observed in pretilachlor-treated shoots; decreases in both starch and free glucose, as well as in total protein content, were observed in fenclorim -treated shoots compared with the untreated controls. The decreases in starch and total glucose appeared to be a direct consequence of reduced glucokinase and ribulose-1,5-bisphosphate carboxylase activity, and the decrease in total protein an indirect consequence of reduced glutamine synthetase and glutamate synthase activity, in response to pretilachlor and fenclorim treatments.     

The effect of CGA 43089 as a safener of metolachlor in sorghum (Sorghum bicolor) (Recordings of elongation rates on single sorghum leaves)

The influence of metolachlor [2-chloro-6-ethyl-N-(2-methoxyl-methylethyl)acet-o-toluidide] on sorghum (Sorghum bicolor Moench.) is first demonstrated in order to be able to show the difference observed when this herbicide is applied together with CGA 43089. The effect of various concentrations (in nutrient solution) and of various exposure times on the elongation rate of single leaves is demonstrated. The safener CGA 43089 (x-(cyanomethoximino)-benzacetonitrile] showed no effect on the elongation rates when used in normal concentrations. The combined application of safener and metolachlor (concentration ratio 1:3) prevented the growth reductions due to metolachlor. When the safener was applied before metolachlor the safening action was as good as that of the combined application. When the safener was applied 1 or 2 days after the herbicide the safening effect was diminished. Plant uptake of the safener over a period of 3 days was sufficient to prevent the action of metolachlor but the safening effect was reduced when the interval between the end of safener application and the beginning of the herbicide application was increased. The conclusion drawn regarding the mode of action is that CGA 43089 does not interfere with herbicide uptake into the plant. The safener is, however, able to reduce the active amount of herbicide when present at the right time at the site of effect.     

Chemical control of weedy rice in precise hill‐direct‐seeded rice in South China

Precise hill‐direct‐seeded rice, which is both cost‐ and labor‐saving, is based on the direct seeding of rice by using a precision rice hill‐drop drilling machine. Weedy rice (Oryza sativa f. spontanea), also known as “red rice”, is a major weed in precise hill‐direct‐seeded rice, causing an ≤80% yield loss and a reduction in grain quality. The aim of this study was to evaluate the control efficiency of weedy rice by pretilachlor (a pre‐emergence herbicide) and fenclorim (a safener) and their safety for precise hill‐direct‐seeded rice in two consecutive years. The amount of rice seed germination was accelerated by soaking the seeds in the safener at 0.67 g ai L^?1 for 1 h before sowing. The pre‐emergence pretilachlor treatments were applied 2 days after sowing cultured rice. The inhibition of the shoot fresh weight of the cultured rice was reduced by 3.3, 6.4 and 7.4% with 450, 900 and 1350 g ai ha^?1 of pretilachlor at 32 days after sowing (DAS) and that of the root fresh weight was reduced by 2.6, 4.9 and 8.1%, respectively. With fenclorim and pretilachlor in a precise hill‐direct‐seeded rice field in 2010 and 2011, the weedy rice control efficiency at 32 DAS was reduced by 100 and 98.0%, respectively. The pre‐emergence pretilachlor treatments that were applied at 2 DAS were much more efficient in the weedy rice control and less inhibitory to the cultured rice growth. The rice yield was increased by 26.1–26.7% in the mechanical precise hill‐direct‐seeded rice, relative to the manual‐seeding rice, with the application of fenclorim and pretilachlor.     

Residues of the herbicide fenoxaprop‐P‐ethyl,its agronomic safener isoxadifen‐ethyl and their metabolites in rice after field application

BACKGROUND: Fenoxaprop‐P‐ethyl is a herbicide used on cereals and in particular on rice, the degradation of which leads to several relevant metabolites. The herbicide is used together with an agronomic safener such as isoxadifen‐ethyl, which also generates some metabolites. The present work was aimed at developing and validating an analytical method for the determination of the above parent compounds and their main metabolites in the edible fractions of rice. Parent compounds were extracted in acetonitrile and determined by gas chromatography with a mass spectrometer detector, while metabolites were extracted in acetonitrile and analysed by liquid chromatography tandem mass spectrometry. RESULTS: The method was validated through recovery tests in rice straw, grain and plant: accuracy was in the range 76–86% and 90–103% for parent compounds and metabolites respectively. Precision, as relative standard deviation, was in the range 3–11% and 6–17% for parent compounds and metabolites respectively. The limit of detection was 0.01 mg kg^?1 for each analyte, while the limit of quantification was set at 0.05 mg kg^?1. CONCLUSION: The analytical method is suitable for quantitative determination of each analyte considered in rice commodities. Copyright © 2010 Society of Chemical Industry     

Interaction between optical isomerism and plant pharmacological action,change of modes of action and chirality of 1-(α-methylbenzyl)-3-p-tolylurea

The optical isomers, (R)-1(α-methylbenzyl)-3-p-tolylurea ((R)-MBU) and (S)-1-(α-methylbenzyl)-3-p-tolylurea ((S)MBU), which are analogues of daimuron [1-(α,α-dimethylbenzyl)-3-p-tolylurea], a herbicide for Cyperaceae weeds and a safener for paddy rice, exhibited different biological responses. These two physiological properties of daimuron were observed separately in (R)-MBU and (S)-MBU. Only (R)-MBU had herbicidal activity against Cyperaceae weeds, while the (S)-isomer was a more effective safener against bensulfuron-methyl (BSM) injury of rice seedlings than was (R)-MBU. (S)-MBU promoted root growth of rice seedlings, but the (R)-enantiomer inhibited root growth. (S)-MBU was a more potent inhibitor than (R)-MBU on PS II reaction of spinach broken chloroplasts. Furthermore, (S)-MBU and (R)-MBU showed cross intergenus selective phytotoxicity among the Gramineae plants, Oryza sativa L. (rice, cv. Tsukinohikari, japonica), Triticum aestivum L. (wheat, cv. Norin No. 61) and Echinochloa crusgalli var. frumentacea Wight, on root growth inhibition in the dark.     

Effects of the safeners CGA 154281, oxabetrinil and fenclorim on uptake and degradation of metolachlor in corn (Zea mays L.) seedlings

Summary. The influence of three crop safeners on the uptake and degradation of ¹⁴C-metolachlor was investigated in two corn varieties. Following application of herbicide and safener together to seedling shoots the concentrations of non-metabolized ¹⁴C-metolachlor in the tissues was found to be lower in the tolerant variety LG 9 than in the susceptible variety 211A. The difference between varieties was due to differences in both uptake and degradation of ¹⁴C-metolachlor.
Following shoot application most of the radioactivity was retained in the coleoptile and the mesocotyl. Two hours after application 95% of the herbicide had been degraded in coleoptiles and mesocotyls, whereas approximately 20% of non-metabolized ¹⁴C-metolachlor was present in the enclosed developing shoot leaves. In both corn varieties the safener CGA 154281 caused a substantial lowering of tissue levels of parent ¹⁴C-metolachlor. This was primarily due to an enhanced degradation. Glutalhione- S -transfer-ase (GST) enzyme activity in shoot tissues was found to be enhanced in both varieties by CGA 154281. Oxabetrinil and fenclorim were less effective than CGA 154281 both in reducing tissue levels of non-metabolized ¹⁴C-metolachlor and in enhancing GST activity in either variety.     

除草剂安全剂对作物细胞色素P450及其他酶活性和水平的影响

综述了除草剂安全剂对作物中参与除草剂解毒作用的酶以及作为除草剂作用靶标位点酶水平与活性的影响。安全剂能增强细胞色素P450酶系统活性,诱导P450在除草剂降解中的作用;增加作物体内谷胱甘肽的含量,从而促进除草剂与谷胱甘肽的轭合而发挥解毒作用;降低由于除草剂对乙酰乳酸合成酶的抑制作用而引起的植物毒性等。     

Metolachlor (2-chloro-N-[2-ethyl-6-methylphenyl]-N-[2-methoxy-l-methylethyl] acetamide) and the metolachlor safener CGA 43089 [α-(cyanomethoximino)-benzacetonitrile] in sorghum seedlings: Correlations between morphological effects and ethylene formation

Treatment of germinating sorghum [Sorghum bicolor (L.) Moench] seeds with the grass herbicide, metolachlor (2-chloro-N-[2-ethyl-6-methylphenyl]-N-[2-methoxy-1-methylethyl] acetamide), causes growth retardation, promoted by thickening of the first leaf and thus inhibition of unfolding of secondary leaves, and increased ethylene production. Sorghum seeds pretreated with the safener CGA 43089 [α-(cyanomethoximino)-benzacetonitrile] exhibit neither morphological deformations nor ethylene production upon metolachlor treatment. Aminoethoxyvinylglycine [l-2-amino-4-(2-aminoethoxy)-trans-3-butenoic acid], a specific inhibitor of ethylene formation in higher plants, decreases ethylene formation by metolachlor-treated sorghum seedlings; the observed deformations, however, remain unchanged. Sorghum control seedlings which grow against a covering plate build up ethylene concentrations as after herbicide treatment, but without induction of the morphological symptoms. These observations suggest that the plant hormone ethylene is a symptom and not the inducer of the morphological effects visible after metolachlor treatment of sorghum seedlings.     

Induction of wheat and maize glutathione S-transferase by some herbicide safeners and their effect on enzyme activity against butachlor and terbuthylazine

The expression of glutathione S-transferase (GST) activity in wheat and maize shoots was investigated in response to treatments with the herbicide safeners benoxacor, cloquintocet-mexyl, fenchlorazole-ethyl, fenclorim, fluxofenim and oxabetrinil. These safeners significantly enhanced the GST activity towards 1-chloro-2,4-dinitrobenzene (CDNB) as a 'standard' substrate, with the exception of oxabetrinil in maize. The enhancements of GST (CDNB) activity were found to be concomitant with increases in V(max) (the reaction rate when the enzyme is fully saturated by the substrate) in wheat following cloquintocet-mexyl and fenchlorazole-ethyl treatments, and in maize following fenchlorazole-ethyl treatment. Otherwise, decreases in V(max) were observed in wheat and maize following fenclorim and fluxofenim treatments. With the exception of oxabetrinil, all the safeners significantly reduced the apparent K(M) (the substrate concentration required for 50% of maximum GST activity) of both wheat and maize GST. The V(max) and K(M) variations following safener treatments are discussed in terms of an increased expression of GST enzymes and an increased affinity for the CDNB substrate. The activity of wheat and maize GST was also assayed towards butachlor and terbuthylazine respectively; the results indicate the ability of cloquintocet-mexyl, fenchlorazole-ethyl and fluxofenim to enhance the enzyme activity in wheat and of benoxacor and fenchlorazole-ethyl to do so in maize.     

丙草胺防治直播稻田杂草稻的技术研究

为了探寻对栽培稻安全的杂草稻防除技术,采用整株测定法研究了丙草胺对杂草稻的毒力及解草啶减轻丙草胺对栽培稻药害的应用技术,并通过田间试验检验了这一技术的安全性。结果表明:丙草胺在450g/hm2时,可显著抑制杂草稻和栽培稻的生长;采用30mg/L解草啶浸种48h,可显著减轻丙草胺对栽培稻的药害,随着丙草胺施药量的增加,解草啶的保护作用逐渐减弱。田间试验结果说明:用30mg/L解草啶浸种栽培稻48h,丙草胺的施药剂量在450~675g/hm2时对栽培稻安全;当丙草胺剂量为900g/hm2时,栽培稻产量显著下降。     

Differential glutathione S-transferase isozyme activities in rice and early watergrass seedlings

Glutathione S -transferase (GST) isozymes were investigated in one-leaf-stage rice ( Oryza sativa L. cv. Nipponbare) and early watergrass ( Echinochloa oryzicola Vasing) shoots after being induced by treatment with a combination of pretilachlor [2-chloro-2',6'-diethyl-N-(2-propoxyethyl)acetanilide] and fenclorim (4,6-dichloro-2-phenylpyrimidine) using DEAE-Sephacel anion exchange chromatography. Non-treated plants contained GST isozymes that had activity to the following substrates: three isozymes for l-chloro-2,4-dinitrobenzene (CDNB), six isozymes for pretilachlor and three isozymes for fenclorim in rice shoots; and four isozymes for CDNB, three or four isozymes for pretilachlor and two or three isozymes for fenclorim in early watergrass shoots. Glutathione S -transferase isozyme activities of non-treated plants were higher in rice than in early watergrass, especially in the case of GST activity with fenclorim as a substrate. Pretreatment of rice roots with a combination of pretilachlor and fenclorim increased the activity of the constitutively expressed isozymes that exhibited activity with CDNB, pretilachlor and fenclorim. This pretreatment also caused the appearance of one new GST(fenclorim) isozyme. Pretreatment of early watergrass roots with a combination of pretilachlor and fenclorim produced almost no increase in activity of some constitutively expressed isozymes that exhibited activity to CDNB and fenclorim, although it partly increased the peaks to corresponding to pretilachlor. The induction of GST was higher in rice than that in early watergrass. These results indicated that the isozyme pattern and substrate specificity of GST isozymes in rice were different from those in early watergrass. Furthermore, the selectivity of pretilachlor between rice and early watergrass may be related to different constitutively expressed GST(pretilachlor) isozyme activities and the induction of GST(pretilachlor) isozyme activities in the combination treatment.     

The basis for the safening of clomazone by phorate insecticide in cotton and inhibitors of cytochrome P450s

Clomazone may be safely used in cotton to manage weeds when applied following treatments of the organophosphate insecticides phorate or disulfoton. The loss of chlorophyll and carotenoids with 6 days of 100 nM clomazone treatment of cotton seedlings was partially prevented with phorate in hydroponic solution in a rate-dependent manner. In a study to examine the timing of safening from a one-day clomazone (100 nM) treatment, maximum safening was achieved when phorate (50 μM) was applied the same day as clomazone. Phorate decreased metabolism of ¹⁴C-clomazone to polar metabolites in excised cotton shoots and shoots of intact cotton plants. Microsomal studies of corn shoots showed an NADPH-dependent/cytochrome P450 reaction was inhibited by phorate. Additional studies with corn microsomes, corn seedlings and cotton seedlings supported the basis of clomazone safening is the inhibition of toxic clomazone metabolism by P450 inhibitors.     

Herbicide safeners: a review

Herbicide safeners selectively protect crop plants from herbicide damage without reducing activity in target weed species. This paper provides an outline of the discovery and uses of these compounds, before reviewing literature devoted to defining the biochemical and physiological mechanisms involved in safener activity. Emphasis is placed on the effects of safeners on herbicide metabolism and their interactions with enzyme systems, such as cytochrome P₄₅₀ mono-oxygenases and glutathione-S-transferases. Attention is drawn to the potential wide-ranging applications of safeners and, in particular, their use as powerful research tools with which to identify and manipulate those mechanisms which contribute to herbicide selectivity and resistance. © 1999 Society of Chemical Industry     

Physiological responses of maize and sorghum to four different safeners for metazachlor

The ability of the herbicide safeners, BAS-145138 (1-dichloroacetyl-hexahydro-3,3,8a-trimethyl-pyrrolo(1,2a)pyrimidin-6(2H)-one), dichlormid (N,N-diallyl-2,2-dichloroacetamide), flurazole (phenylmethyl ester), and MG-191 (2-dichloromelhyl-2-methyl-1,3-dioxolane) for preventing metazachlor injury to maize (Zea mays L.) and sorghum (Sorghum bicolor L.) seedlings were compared with their effects on ¹⁴C-metazachlor metabolism to a glutathione (GSH) conjugate, effects on non-protein thiol contents (mainly GSH) and effects on Glutathione S-transferase (GST) activity in these two species. Sorghum shoot growth was reduced by 41% and maize shoot growth was reduced by 54%, by metazachlor concentrations in vermiculite nutrient culture of 0·6 μM and 7·5μM, respectively. In this system, all four compounds had significant activity as safeners for metazachlor in both sorghum and maize seedlings. BAS-145138 and flurazole were the most effective safeners in maize and sorghum, respectively. In the absence of safeners, the rate of non-enzymatic conjugation of metazachlor and GSH was much greater than the enzymatic rate. However, the rate of enzymatic conjugation of metazachlor with GSH was increased by safener treatment in both maize and sorghum. Safener effectiveness was highly correlated with increases in ¹⁴C-metazachlor uptake and metabolism in both species. Safener effectiveness was more highly correlated with safener effects on GST activity in maize or sorghum when ¹⁴C-metazachlor was used as the substrate than when the non-specific CDNB (1-chloro-2,4-dinitrobenzene) was used as the substrate. Safener effectiveness was also strongly correlated with safener effects on GSH levels in sorghum, but not in maize, possibly because of the greater importance of non-enzymatic conjugation of metazachlor with GSH in sorghum as compared to maize.     

Isolation and functional characterization in yeast of CYP72A18, a rice cytochrome P450 that catalyzes (ω-1)-hydroxylation of the herbicide pelargonic acid

Cytochrome P450 proteins play important roles in plant herbicide selectivity. Here, we demonstrate metabolism of the herbicide pelargonic acid by CYP72A18, a novel cytochrome P450 isolated from the rice Oryza sativa L. cv. Nipponbare. The CYP72A18 cDNA was cloned from rice and heterologously expressed in Saccharomyces cerevisiae AH22 cells from the alcohol dehydrogenase (ADH1) promoter. Microsomes isolated from recombinant yeast cells contained the CYP72A18, which was found to catalyze the (ω-1)-hydroxylation of the herbicide pelargonic acid. We also show that (ω-1)-hydroxypelargonic acid has reduced herbicide activity against rice seedlings. Based on these results, we suggest that CYP72A18 participates in the detoxification of the herbicide pelargonic acid in rice plants.