CGA-43089 [α-(cyanomethoximino)-benzacetonitrile], CGA-92194 {α-[(1,3-dioxolan-2-yl-methyl)imino] benzeneacetonitrile}, and MON-4606 [5-thiazolecarboxylic acid, benzyl ester, 2-chloro-4-(trifluoromethyl)], applied as seed treatments at 1.25 g/kg seed, prevented yield losses in grain sorghum [Sorghum bicolor (L.) Moench.] in the field due to metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide], alachlor [2-chloro-2′, 6′-diethyl-N-(methoxymethyl)acetanilide] or acetochlor [2-chloro-N-(ethoxymethyl)-6′-ethyl-o-acetotoluidide] applied at 1.7, 2.2 and 1.7 kg/ha, respectively. CGA-92194, applied at 0.8 g/kg seed, prevented yield reduction from metolachlor applied at 4.5 kg/ha. MON-4606 was more effective in protecting grain sorghum when applied as a seed treatment than when applied in the furrow with a clay or sand granule as carrier.

Chlorsulfuron {2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino] carbonyl]-benzenesulfonamide} applied preemergence or postemergence as a soil drench retards the growth of four corn (Zea mays L.) genotypes in soil with 50% inhibition in each case at a rate of approximately 5 g ai/ha. R-25788 (N,N-diallyl-2,2-dichloroacetamide), applied at 1.0 kg ai/ha to the soil preemergence with chlorsulfuron or postemergence 2 days prior to chlorsulfuron treatment, reverses shoot growth inhibition induced by the herbicide in varying degree in ‘XL25A’ and ‘XL72B’ corn hybrids and ‘FRM017’ and ‘FR619’ inbreds, but not in soybean [Glycine max (L.) Merr., var. ‘Amsoy-71’]. Under similar conditions, flurazole [2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylic acid (phenylmethyl ester)] and CGA-92194 [α-(1,3-dioxolan-2-yl-methoxy)-imino-benzeneacetonitrile] are less effective than R-25788 in protecting corn genotypes from chlorsulfuron injury. R-25788 also partially reverses chlorsulfuron-induced root growth inhibition in XL25A and FR619 corn but not in pea (Pisum sativum L. var. ‘Dwarf Gray Sugar’). Acetohydroxyacid synthase (AHAS) is higher in both activity and the proportion that is very sensitive to in vitro chlorsulfuron inhibition when prepared from XL25A shoots than from the roots. R-25788 does not reverse the in vitro inhibition of corn acetohydroxyacid synthase (AHAS) by chlorsulfuron. Pretreatment of 5-day-old XL25A corn with R-25788 at 24 or 48 μM significantly increases AHAS activity by approximately 25% in both shoots and roots but does not change its in vitro sensitivity to chlorsulfuron. This antidote also increases the glutathione (GSH) content in roots and etiolated shoots. The R-25788-induced elevation of AHAS activity may contribute to its antidotal effect in corn.

Field studies were conducted on a Taloka silt loam (Mollic Albaqualf) to determine the effects of residual levels of metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide] on rice (Oryza sativa L.). Yield reductions could be overcome by increasing rice seeding rate, by decreasing seeding depth, or by applying the safeners CGA-43089 [α-(cyanomethoxyimino)-benzacetonitrile] or CGA-92194 [α-(1,3-dioxolan-2-yl-methoximino)-benzacetonitrile] to the rice seed. Greenhouse studies with the safeners and reduced seeding depths indicated that CGA-92194 was better than CGA-43089 for protecting rice from metolachlor injury, but reduced seeding depths did not reduce metolachlor injury.

The efficacy of the safeners naphthalic anhydride (NA), CGA-92194, and CGA-133205 as protectants of grain sorghum and of NA, R-29148, CGA-154281, and dichlormid as protectants of corn against injury from the chloroacetamide herbicide, SAN 582H, was evaluated under greenhouse conditions. SAN 582H applied alone reduced the shoot growth of ‘Funk G522DR’ and ‘Funk G623’ sorghum, but had no effect on the growth of the ‘GP-10’ genotype of sorghum. Corn (‘Northrup-King 9283’ hybrid) was considerably more tolerant than grain sorghum to SAN 582H. The rate of SAN 582H causing 50% reduction of corn shoot height (GR50) was 5.1 kg/ha as compared to 1.1 kg/ha for grain sorghum. NA applied as seed dressing at 5 or 10 g/kg seed, provided moderate protection to ‘G522DR’ and ‘G623’ sorghum and no protection to corn against SAN 582H injury. Dressing of sorghum seeds with CGA-133205 provided moderate protection to G522DR sorghum, whereas seed-applied CGA-92194 provided moderate protection to G623 sorghum against SAN 582H. The dichloroacetamide safeners R-29148, dichlormid, and CGA-154281 were all effective as protectants of corn against SAN 582H injury. These results demonstrate that, as with other chloroacetamide herbicides, the tolerance of corn and grain sorghum to SAN 582H can be enhanced with the use of safeners of the dichloroacetamide type and oxime ether type, respectively.

Certain oximes, including cyometrinil [(Z)-α-(cyanomethoxy)iminobenzeneacetonitrile], CGA-92194 [N-(1,3-dioxolan-2-yl-methoxy)-iminobenzeneacetonitrile], 2-pyridinealdoxime-O-benzyl ether (PA-B), and 2-pyridinealdoxime-O-phenethyl ether (PA-PE), which are known to protect sorghum from chloroacetanilide herbicides, increased the toxicity of the insecticide propoxur (o-isopropoxyphenyl-methyl carbamate) to a resistant strain of housefly (Musca domestica L.). Flurazole [5-thiazolecarboxylic acid, benzyl ester, 2-chloro-4-(trifluoromethyl)], a nonoxime protectant for grain sorghum, had less effect on the toxicity of propoxur than did the oximes. Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide], which can be used as a herbicide in sorghum [Sorghum bicolor (L.) Moench.] only if the seed have been treated with a protectant, also increased the toxicity of propoxur to houseflies. Commercially available insecticide synergists increase insecticide activity by inhibiting NADPH-dependent microsomal mixed-function oxidase activity. Sorghum coleoptiles possessed the enzyme system necessary to oxidize aldrin (1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4-endo-exo-5,8-dimethanonaphthalene) to dieldrin (1,2,3,4,10,10-hexachloro-6, 7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo-exo-5,8-dimethanonaphthalene), which is a standard test for oxidative metabolism in insects. Under the conditions of these tests, the aldrin epoxidase activity in sorghum coleoptiles was not affected by pretreatment with cyometrinil or flurazole.

Alachlor at 3.4 and 6.7 kg ha-1, metolachlor at 2.8 and 5.6 kg ha-1, and propachlor at 4.5 and 9.0 kg ha-1 were applied to grain sorghum in field experiments conducted in 1981 and 1982. ‘Dekalb E-59’ and ‘Pioneer 8311’ grain sorghum were tested with and without the seed protectants cyometrinil and flurazole in both experiments. ‘Funk's G-1350’ was tested with and without cyometrinil and CGA-92194 in one experiment. Alachlor and metolachlor caused serious injury (stunting and, in some instances, reductions in stand and yield) to grain sorghum without the seed protectants. Less severe injury to grain sorghum occurred with alachlor and metolachlor at high rates even in the presence of the seed protectants. The three seed protectants were equally effective in preventing crop injury. Only minor injury to grain sorghum, with or without the seed protectants, occurred with propachlor at both rates. Overall, early-season weed control was 81 to 100%; however, propachlor at the rates tested was noticeably weaker than alachlor and metolachlor against some annual grasses.

Greenhouse studies were initiated to determine the efficacy of four herbicide antidotes as protectants of corn (Zea mays L., ‘DeKalb XL72AA’ and ‘DeKalb XL67′) against injury from preemergence or early postemergence applications of the herbicides chlorsulfuron {2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino] carbonyl] benzenesulfonamide}, fluazifop-butyl {butyl-2-[4-[5-(trifluoromethyl-2-pyridinyl)oxy] phenoxy] propanoate}, or BAS 9052 OH {2-[1-(ethoxyimino)-butyl]-5-[2-(ethylthio)-propyl]-3-hydroxy-2-cyclohexene-1-one}. NA (1,8-naphthalic anhydride) was the most effective of the four antidotes in protecting corn against injury from preemergence applications of chlorsulfuron. CGA-43089 [α-(cyanomethoxy)-imino-benzeneacetonitrile] and CGA-92194 [α-(1,3-dioxolan-2-yl-methoxy)-imino-benzeneacetonitrile] partially protected corn from chlorsulfuron injury, whereas R-25788 (N,N-diallyl-2,2-dichloroacetamide] was the least effective. R-25788 offered partial to good protection to corn against injury from preemergence applications of fluazifop-butyl and BAS 9052 OH. NA, or CGA-43089, and CGA-92194 partially protected corn from fluazifop-butyl injury but their efficacy against BAS 9052 OH injury to corn was limited. In general, all four antidotes offered better protection to the thiocarbamate-tolerant ‘XL72AA’ hybrid than to the thiocarbamate-susceptible ‘XL67’ hybrid. With the exception of NA, which partially protected corn from postemergence-applied chlorsulfuron, none of the four herbicide antidotes was effective in protecting corn against injury from postemergence applications of any of the three herbicides.