USE OF N-BENZYLBENZAMIDE-BASED COMPOUND AS HERBICIDE

Abstract

An N-benzylbenzamide-based compound as shown below or its salt which may be used as a herbicide is provided.

##STR00001##

The N-benzylbenzamide-based compound or its salt serves as a pigment synthesis inhibitor for controlling weeds in field crop growing places or non-farming crop places. Furthermore, the compound may form an agricultural herbicide with an agriculturally accepted carrier. Still further, the compound also serves an agricultural herbicide in a manner of a mixed formulation with a further herbicidal active component, particularly atrazine. The N-benzylbenzamide-based compound or its salt has high herbicidal activity, and can be used to control weeds that are resistant to existing herbicides, which thereby exhibits a good synergistic effect when combined with a further herbicidal active component.

Claims

1. An herbicide comprising a N-benzylbenzamide-based compound of following general formula (I) or (II) or its salt as a component, ##STR00015## wherein in the general formula (I) or (II), R.sub.0 is selected from methyl or methoxy; R.sub.1 is selected from hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, halo C.sub.1-C.sub.4 alkyl, halo C.sub.1-C.sub.4 alkoxy, halogen or cyano; R.sub.2, R.sub.3 and R.sub.4 are each independently selected from hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, halogen, cyano, halo C.sub.1-C.sub.4 alkyl, halo C.sub.1-C.sub.4alkoxy or methylsulfonyl; and X is selected from C or N.

2. The herbicide according to claim 1, wherein in the general formula (I) or (II), R.sub.0 is selected from methyl or methoxy; R.sub.1 is selected from hydrogen, methyl, methoxy, fluorine, chlorine, bromine or cyano; R.sub.2, R.sub.3 and R.sub.4 are each independently selected from hydrogen, methyl, methoxy, fluorine, chlorine, bromine, cyano or methylsulfonyl; and X is selected from C or N.

3. The herbicide according to claim 1, wherein the N-benzylbenzamide-based compound of general formula (I) is prepared by a reaction Scheme I in a suitable solvent and a suitable alkaline condition with a synthetic scheme as follows: ##STR00016## the reaction Scheme I is carried out in a suitable solvent, and the suitable solvent is selected from tetrahydrofuran, acetonitrile, toluene, xylene, N,N-dimethylformamide, dichloromethane, chloroform or pyridine; a suitable alkali is selected from triethylamine, pyridine, potassium carbonate or sodium hydroxide; a reaction temperature is between ice bath and a boiling temperature of the solvent; and a reaction time is 30 minutes to 20 hours.

4. The herbicide according to claim 1, wherein the N-benzylbenzamide-based compound of general formula (II) is prepared by a reaction Scheme II in a suitable solvent and a suitable alkaline condition with a synthetic scheme as follows: ##STR00017## the reaction Scheme II is carried out in a suitable solvent, and the suitable solvent is selected from tetrahydrofuran, acetonitrile, toluene, xylene, N,N-dimethylformamide, dichloromethane, chloroform or pyridine; a suitable alkali is selected from triethylamine, pyridine, potassium carbonate or sodium hydroxide; a reaction temperature is between ice bath and a boiling temperature of the solvent; and a reaction time is 30 minutes to 20 hours.

5. The herbicide according to claim 1, wherein the N-benzylbenzamide-based compound serves as a pigment synthesis inhibitor to control weeds in field crop growing places or non-farming crop places.

6. The use according to claim 5, wherein the weeds comprise: Sinapis, Brassica, Galium, Stellaria, Chenopodium, Kochia, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirsium, Sonchus, Solanum, Veronica, Datura, Viola, Papaver, Centaurea, Galinsoga, Rotala, Lindernia, Sesbania, Trifolium, Abutilon, Lamium, Matricaria, Artemisia, Pharbitis, Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Monochoria, Fimbristylis, Sagittaria, Scirpus, Paspalum, Ischaemum, Agrostis, Alopecurus, Cynodon, Commelina, Brachiaria or Leptochloa.

7. The herbicide according to claim 5, wherein the weeds are barnyard grass, pondweed, Monochoria vaginalis, Cyperus difformis, Scirpus planiculmis, Leptochloa chinensis, Avena fatua, Digitaria sanguinalis, goosegrass, green bristlegrass, Alopecurus aequalis, flixweed, Capsella bursa pastoris, Lepidium apetalum, Humulus scandens, Polygonum aviculare, Convolvulus arvensis, Fallopia convolvulus, Cyperus rotundus, Chenopodium album, Polygonum lapathifolium, Amaranthus retroflexus, Portulaca oleracea, Amaranthus blitum, Cuscuta chinensis, piemarker, Galium spurium, Eclipta prostrata, Xanthium strumarium, bermudagrass, cogon, Solanum nigrum, Myosoton aquaticum, Chromolaena odorata, Ageratum conyzoides, Rotala rotundifolia, Artemisia argyi, dandelion, Erigeron annuus, Hemisteptia lyrata, Artemisia capillaris, Ixeris polycephala, field thistle, setose thistle, Elsholtzia ciliata, woundwort or Acalypha australis.

8. An agricultural herbicide composition, wherein a herbicidal component of the composition is the N-benzylbenzamide-based compound or its salt according to claim 1, and the composition further comprises an agriculturally acceptable carrier.

9. An agricultural herbicide mixed formulation, wherein a herbicidal component of the mixed formulation is the N-benzylbenzamide-based compound or its salt according to claim 1, and the mixed formulation further comprises a herbicidal component serving as an acetyl-CoA carboxylase inhibitor, an acetolactate synthase inhibitor, an auxin herbicide, a carotenoid biosynthesis inhibitor, a photosynthesis inhibitor, or a cell wall biosynthesis inhibitor.

10. The mixed formulation according to claim 9, wherein the herbicidal components in the mixed formulation are the N-benzylbenzamide-based compound or its salt and atrazine in a weight ratio from 1:10 to 10:1.

Description

DETAILED DESCRIPTION

[0049] For easy understanding of the purpose, technical solutions and effects of the present disclosure, the present disclosure will now be further described in detail in conjunction with examples.

[0050] (I). Synthesis of N-Benzylbenzamide-Based Compound

Example 1: Preparation of N-(3-fluorobenzylamine)-2-methoxybenzamide (Compound A01)

[0051] ##STR00007##

[0052] 125 g (1.0 mol) of 3-fluorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 230 g of product with a yield of 88.8%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.24 (d, J=8.0 Hz, 2H), 7.45 (t, J=8.0 Hz, 1H), 7.27-7.31 (m, 1H), 7.03-7.14 (m, 3H), 6.90-6.99 (m, 2H), 4.68 (d, J=5.0 Hz, 2H), 3.93 (s, 3H).

Example 2: Preparation of N-(4-fluorobenzyl)-2-hydroxyaniline (Compound A02)

[0053] ##STR00008##

[0054] 125 g (1.0 mol) of 4-fluorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 220 g of product with a yield of 84.9%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.23-8.25 (m, 1H), 8.18 (br, 1H), 7.44-7.47 (m, 1H), 7.32-7.35 (m, 2H), 6.97-7.11 (m, 4H), 4.59 (d, J=5.5 Hz, 2H), 3.92 (s, 3H).

Example 3: Preparation of N-(3,5 difluorobenzyl)-2-methoxybenzamide (Compound A03)

[0055] ##STR00009##

[0056] 143 g (1.0 mol) of 3,5-fluorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 245 g of product with a yield of 88.4%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.18-8.34 (m, 2H), 7.46-7.52 (m, 1H), 7.08-7.14 (m, 1H), 7.01 (d, J=8.3 Hz, 1H), 6.88 (d, J=6.1 Hz, 2H), 6.67-6.75 (m, 1H), 4.67 (d, J=6.0 Hz, 2H), 3.97 (s, 3H).

Example 4: Preparation of N-(3-chloro-5-fluorobenzyl)-2-methoxybenzamide (Compound A07)

[0057] ##STR00010##

[0058] 159 g (1.0 mol) of 3-chloro-5-fluorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 260 g of product with a yield of 88.7%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.19-8.33 (m, 2H), 7.48 (t, J=6.9 Hz, 1H), 7.07-7.16 (m, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.88 (d, J=6.1 Hz, 2H), 6.69 (t, J=8.9 Hz, 1H), 4.66 (d, J=6.0 Hz, 2H), 3.97 (s, 3H).

Example 5: Preparation of N-(3-chlorobenzyl)-2-methoxybenzamide (Compound A09)

[0059] ##STR00011##

[0060] 141 g (1.0 mol) of 3-chlorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 260 g of product with a yield of 94.5%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.00-8.28 (m, 2H), 7.45-7.51 (m, 1H), 7.35 (t, J=1.7 Hz, 1H), 7.22-7.31 (m, 3H), 7.05-7.14 (m, 1H), 6.99 (d, J=8.3 Hz, 1H), 4.67 (d, J=5.8 Hz, 2H), 3.95 (s, 3H).

Example 6: Preparation of 2-methoxy-N-(3-methylbenzyl)benzamide (Compound A14)

[0061] ##STR00012##

[0062] 121 g (1.0 mol) of 3-methylbenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 170 g (1.0 mol) of 2-methoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 210 g of product with a yield of 82.4%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.26 (dd, J=7.8, 1.9 Hz, 1H), 8.18 (br, 1H), 7.44-7.48 (m, 1H), 7.20-7.28 (m, 1H), 7.14-7.20 (m, 2H), 7.06-7.13 (m, 2H), 6.97 (d, J=8.3 Hz, 1H), 4.66 (d, J=5.7 Hz, 2H), 3.92 (s, 3H), 2.35 (s, 3H).

Example 7: Preparation of N-(3-fluorobenzyl)-2,5-dimethoxybenzamide (Compound A22)

[0063] ##STR00013##

[0064] 125 g (1.0 mol) of 3-fluorobenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 200 g (1.0 mol) of 2,5-dimethoxybenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 260 g of product with a yield of 90.0%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 8.37 (s, 1H), 7.79 (d, J=3.3 Hz, 1H), 7.32-7.27 (m, 1H), 7.12 (d, J=7.7 Hz, 1H), 7.09-7.03 (m, 1H), 7.00 (dd, J=8.9, 3.3 Hz, 1H), 6.97-6.87 (m, 2H), 4.66 (d, J=5.8 Hz, 2H), 3.88 (d, J=2.7 Hz, 3H), 3.80 (d, J=2.9 Hz, 3H).

Example 8: Preparation of 3-methyl-N-(3-methylbenzyl)benzamide (Compound B14)

[0065] ##STR00014##

[0066] 121 g (1.0 mol) of 3-methylbenzylamine and 150 g (1.5 mol) of triethylamine were dissolved in 1.5 L of toluene, and stirred for 30 minutes in ice bath, and then 154 g (1.0 mol) of 3-methylbenzoyl chloride dissolved in 500 ml of toluene was added dropwise before being stirred at room temperature for 1.5 hours; the mixture was washed by adding 200 ml of saturated sodium bicarbonate solution and then washed with 200 ml of deionized water and 200 ml of saturated brine in sequence, dried with anhydrous sodium sulfate, and then subjected to reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography to obtain 212 g of product with a yield of 88.7%. .sup.1H NMR (500 MHz, CDCl.sub.3) δ 7.62 (s, 1H), 7.59-7.54 (m, 1H), 7.31 (d, J=4.7 Hz, 2H), 7.24 (d, J=7.6 Hz, 1H), 7.19-7.14 (m, 2H), 7.12 (d, J=7.6 Hz, 1H), 6.36 (s, 1H), 4.61 (d, J=5.6 Hz, 2H), 2.39 (s, 3H), 2.35 (s, 3H)

[0067] (II). Preparation of Herbicide or Herbicidal Composition Comprising the N-Benzylbenzamide-Based Compound

Example 9: Wettable Powders with 10% of the N-Benzylbenzamide-Based Compound (Compound B14)

[0068] Components and proportions thereof in the wettable powders:

TABLE-US-00003 Compound B14 10% Sodium lauryl sulfate  3% Sodium Lignosulfonate  3% Naphthalenesulfonic acid formaldehyde condensate  5% Light calcium carbonate balance.

[0069] The added amount of each component was in the percentage by weight, and the active compounds were added in an amount on 100% basis. The compound B14 and other components were thoroughly mixed and pulverized by a jet mill to obtain a wettable powder product comprising 10% of the N-benzylbenzamide-based compound (compound B14).

Example 10: Water Emulsion with 10% of the N-Benzylbenzamide-Based Compound (Compound A09)

[0070] Components and proportions thereof in the water emulsion:

TABLE-US-00004 Compound A09  10% Ethylene glycol   5% Nonylphenol polyglycol ether   3% Sodium Lignosulfonate   5% Carboxymethyl cellulose   1% 75% silicone oil water emulsion 0.4% Water balance.

[0071] The added amount of each component was in the percentage by weight, and the active compounds were added in an amount on 100% basis. The compound A09 and other components were mixed thoroughly in a stirred tank to obtain a water emulsion product comprising 10% of the N-benzylbenzamide-based compound (compound A09).

Example 11: Oil Dispersion with 10% of the N-Benzylbenzamide-Based Compound (Compound A85)

[0072] Components and proportions thereof in the oil dispersion:

TABLE-US-00005 Compound A85 10% Rhodia V0/02N 12% Organobentonite  3% White carbon black  3% Citric acid  2% Methyl oleate balance

[0073] The added amount of each component was in the percentage by weight, and the active compounds were added in an amount on 100% basis. The compound A85 and other components were mixed thoroughly in a stirred tank to obtain an oil dispersion product comprising 10% of the N-benzylbenzamide-based compound (compound A85).

Example 12: Emulsifiable Concentrate with 10% of the N-Benzylbenzamide-Based Compound (Compound B07)

[0074] Components and proportions thereof in the emulsifiable concentrate:

TABLE-US-00006 Compound B07 10% Calcium dodecylbenzene sulfonate  4% Agricultural Emulsifier 600# 10% Methyl oleate balance

[0075] The added amount of each component was in the percentage by weight, and the active compounds were added in an amount on 100% basis. The compound B07 and other components were mixed thoroughly in a stirred tank to obtain an emulsifiable concentrate product comprising 10% of the N-benzylbenzamide-based compound (compound B07).

[0076] Several herbicides comprising the N-benzylbenzamide-based compound provided by Examples 9-12 were merely an illustration for the preparation of the herbicide or the herbicidal composition formulation comprising the N-benzylbenzamide-based compound.

[0077] (III). Efficacy Test of the Herbicide or Herbicidal Composition Comprising the N-Benzylbenzamide-Based Compound

Example 13: Synergistic Test of Compound A02 with Atrazine

[0078] Seeds of green bristlegrass were sown in plastic pots with a diameter of 9 cm, and each pot was sown with 20 seeds that were covered with 0.5 cm of soil and cultivated in a greenhouse at 25-35° C. under natural light and natural humidity. When the green bristlegrass was in the stage where 3 to 4 leaves were grown, applying the agent with an automatic spraying system. 29 treatments were provided in total, in which there were four single-agent treatments with a single agent of A02 at 50, 100, 200, 400 g(a.i.)/ha; four single-agent treatments with a single agent of atrazine at 400, 800, 1200, 1600 g(a.i.)/ha, and 20 treatments with mixed formulations at a dosage of 900 g(a.i.)/ha, in which two single agents were mixed in different proportions; and a blank control (spraying water). Each treatment was repeated 4 times. The overground part of all weeds in each treatment was cut 21 days after the treatment, and the fresh weight was weighed to calculate the controlling effect represented by fresh weight. The combined effect by mixing two agents was evaluated by the Gowing method. The theoretical and measured controlling effects (represented by fresh weight) of the two single agents mixed in different proportions were E and E.sub.0 respectively. E=X+Y−XY/100, where X and Y represent the measured controlling effects represented by fresh weight of the two single agents, respectively. The combined effect was additive effect when −5.0%≤E.sub.0−E≤5.0%, synergistic effect when E.sub.0−E>5.0%, and antagonistic effect when E.sub.0−E<−5.0%.

TABLE-US-00007 TABLE 3 Synergistic effect as achieved by mixing A02 and atrazine in different proportions for controlling green bristlegrass A02 + Atrazine, 900 g(a.i.)/ha Proportions 20 + 1 19 + 2 18 + 3 17 + 4 16 + 5 15 + 6 14 + 7 13 + 8 12 + 9 11 + 10 E.sub.0 − E 5.6% 7.2% 7.5% 8.0% 8.6% 8.5% 9.3% 9.2% 9.6% 9.6% Proportions 10 + 11 9 + 12 8 + 13 7 + 14 6 + 15 5 + 16 4 + 17 3 + 18 2 + 19 1 + 20 E.sub.0 − E 10.0% 11.6% 11.3% 11.8% 12.0% 14.0% 17.6% 16.2% 9.3% 5.0%

[0079] The results in Table 3 showed that the mixture of A02 and atrazine has a significant synergistic effect on the controlling effect of green bristlegrass. When the proportions of A02 and atrazine were 4+17, E.sub.0−E=17.6%, and when the proportions of A02 and atrazine were 3+18, E.sub.0−E=16.2%, which showed an obvious synergistic effect.

Example 14: Herbicidal Activity Test for Indoor Pre-Emergence Soil Treatment

[0080] The herbicidal activity test for indoor pre-emergence soil treatment was performed with some of the N-benzylbenzamide-based compounds of general formula I or II with reference to the method of NY/T 1155.3-2006. Neutral sandy loam soil having an organic content of ≤2% was added to fill ⅘ of the pot, and the soil was completely moistened by infiltrating irrigation from the bottom of the pot. The seeds of the test weed were evenly spread on the soil surface, and then covered by 0.5 cm to 2.0 cm of soil depending on the seed size. Representative compounds in the examples were used to prepare emulsifiable concentrates (10%), and spray treatments to the soil were performed 24 hours after the sowing with the test agents diluted with water, at a spraying dosage of 150 g(a.i.)/ha. Then, the results were investigated by visual inspection 21 days after the treatments. The herbicidal activity of the agent was evaluated on a scale of 1-9 levels according to the symptoms and severity of damage to the test weeds.

[0081] Level 1: weed free;

[0082] Level 2: equivalent to 0 to 2.5% of the weed in the blank control area;

[0083] Level 3: equivalent to 2.6 to 5% of the weed in the blank control area;

[0084] Level 4: equivalent to 5.1 to 10% of the weed in the blank control area;

[0085] Level 5: equivalent to 10.1 to 15% of the weed in the blank control area;

[0086] Level 6: equivalent to 15.1 to 25% of the weed in the blank control area;

[0087] Level 7: equivalent to 25.1 to 35% of the weed in the blank control area;

[0088] Level 8: equivalent to 35.1 to 67.5% of the weed in the blank control area; and

[0089] Level 9: equivalent to 67.6 to 100% of the weed in the blank control area.

[0090] Table 4 shows the pre-emergence herbicidal activities of the test compounds against the weeds.

TABLE-US-00008 TABLE 4 Weed control effects of the pre-emergence soil treatments of some of the N-benzylbenzamide-based compounds (150 g a.i./ha) Herbicidal Activity Barnyard Green Digitaria Amaranthus Humulus Compound grass bristlegrass sanguinalis retroflexus Piemarker scandens A01 1 1 1 3 3 4 A02 1 2 1 3 2 4 A03 1 1 2 1 1 2 A07 1 2 1 1 1 3 A09 1 2 2 2 1 3 A14 2 1 2 2 1 3 A22 1 2 1 2 2 4 A23 1 1 1 2 2 4 A24 1 1 1 1 1 1 A28 1 1 1 1 1 2 A29 1 1 2 1 1 2 A35 1 1 2 1 1 2 A85 1 1 1 2 1 3 A87 2 1 2 2 2 3 A89 1 1 2 1 1 2 A91 1 1 2 1 1 2 A92 1 1 1 1 1 2 A94 1 1 1 1 1 2 B01 2 1 1 1 2 2 B02 1 1 2 1 2 2 B07 1 1 1 2 1 3 B08 2 2 2 1 2 2 B14 1 1 2 2 1 3 B15 1 2 1 2 1 3 B22 1 1 1 1 1 2 B27 1 1 1 1 1 1 B30 1 1 1 1 1 2 Isoxaflutole 1 1 1 1 1 1

[0091] The data in Table 4 showed that the test compounds had a good controlling effect on both monocotyledonous weeds and dicotyledonous weeds at a dosage of 150 g(a.i.)/ha, and after the weeds emerged, the seedlings showed albino symptoms, and then gradually withered and died. In addition, the better the light and temperature conditions, the better the effect.

Example 15: Herbicidal Activity Test for Indoor Post-Emergence Spraying on Stems and Leaves

[0092] The post-emergence herbicidal activity test was performed with some of the N-benzylbenzamide-based compounds of general formula I or II with reference to the method of NY/T 1155.4-2006. Neutral sandy loam soil having an organic content of 3% was added to fill ⅘ of the pot, and the soil was completely moistened by infiltrating irrigation from the bottom of the pot. The seeds of the test weed were evenly spread on the soil surface, and then covered by 0.5 cm to 2.0 cm of soil depending on the seed size. After the sowing, the weed was moved to a greenhouse for regular cultivation. Representative compounds in the examples were used to prepare emulsifiable concentrates (10%), and spray treatments were performed at a dosage of 150 g(a.i.)/ha in the stage where 2 leaves and 1 bud were grown for monocotyledonous weeds and the stage where 3 to 5 true leaves were grown for broadleaf weeds. Then, the results were investigated by visual inspection 21 days after the treatments. The herbicidal activity of the agent was evaluated on a scale of 1-9 levels according to the symptoms and severity of damage to the test weeds.

[0093] Level 1: all dead;

[0094] Level 2: equivalent to 0 to 2.5% of the weed in the blank control area;

[0095] Level 3: equivalent to 2.6 to 5% of the weed in the blank control area;

[0096] Level 4: equivalent to 5.1 to 10% of the weed in the blank control area;

[0097] Level 5: equivalent to 10.1 to 15% of the weed in the blank control area;

[0098] Level 6: equivalent to 15.1 to 25% of the weed in the blank control area;

[0099] Level 7: equivalent to 25.1 to 35% of the weed in the blank control area;

[0100] Level 8: equivalent to 35.1 to 67.5% of the weed in the blank control area; and

[0101] Level 9: equivalent to 67.6 to 100% of the weed in the blank control area.

[0102] Table 5 shows the post-emergence herbicidal activities of the test compounds against the weeds.

TABLE-US-00009 TABLE 5 Weed control effects of post-emergence soil treatments with some of the N-benzylbenzamide-based compounds (150 g a.i./ha) Herbicidal Activity Barnyard Green Digitaria Amaranthus Humulus Compound grass bristlegrass sanguinalis retroflexus Piemarker scandens A01 1 1 1 1 1 1 A02 1 2 1 1 1 1 A03 1 1 2 1 1 1 A07 1 2 1 1 1 1 A09 1 2 1 1 1 1 A14 2 1 1 1 1 1 A22 1 2 1 1 1 1 A23 1 1 1 1 1 1 A24 1 1 1 1 1 1 A28 1 1 1 1 1 1 A29 1 1 1 1 1 1 A35 1 1 1 1 1 1 A85 1 1 1 1 1 1 A87 2 1 1 1 1 1 A89 1 1 1 1 1 1 A91 1 1 1 1 1 1 A92 1 1 1 1 1 1 A94 1 1 1 1 1 1 B01 2 1 1 1 1 1 B02 1 1 1 1 1 1 B07 1 1 1 1 1 1 B08 1 2 1 1 1 1 B14 1 1 1 1 1 1 B15 1 1 1 1 1 1 B22 1 1 1 1 1 1 B27 1 1 1 1 1 1 B30 1 1 1 1 1 1 Mesotrione 1 1 1 1 1 1

[0103] The data in Table 5 showed that the test compounds had a good controlling effect on both monocotyledonous weeds and dicotyledonous weeds at a dosage of 150 g(a.i.)/ha, and the weeds exhibited characteristic albinism symptoms caused by the pigment synthesis inhibitors 1 to 3 days after the treatment, and then gradually withered and died. In addition, the better the light and temperature conditions, the better the effect.

Example 16: Post-Emergence Herbicidal Activity Test of Some of the Compounds of General Formula I or II in a Paddy Field

[0104] The post-emergence herbicidal activity test was performed in a paddy field with some of the N-benzylbenzamide-based compounds of general formula I or II with reference to the method of GB/T 17980.40-2000. The soil texture of the test paddy field was medium soil, which had an organic content of 2.0% and a pH value of 6.5 in the cultivation layer. Spray treatments were performed in the stage where 4 leaves to 5 leaves were grown for the rice seedlings which was about 1 month after the sowing. Representative compounds in the examples were used to prepare emulsifiable concentrates (10%), and spray treatments were performed with the concentrates in water at a dosage of 150 g(a.i.)/ha, and repeated 4 times for each treatment, and the area was 50 m.sup.2. 25 g/L of penoxsulam suspension was used as a control agent and applied at a dosage of 250 g(a.i.)/h. The results were investigated by a value estimating survey method 15 days and 30 days after the treatments. The relative weed population quantities were estimated by comparing each agent treated area with an adjacent blank control area, and the results of which were investigated with the following grading standard method using the overall coverage of the weed population as an indicator.

[0105] Level 1: weed free;

[0106] Level 2: equivalent to 0 to 2.5% of the weed in the blank control area;

[0107] Level 3: equivalent to 2.6 to 5% of the weed in the blank control area;

[0108] Level 4: equivalent to 5.1 to 10% of the weed in the blank control area;

[0109] Level 5: equivalent to 10.1 to 15% of the weed in the blank control area;

[0110] Level 6: equivalent to 15.1 to 25% of the weed in the blank control area;

[0111] Level 7: equivalent to 25.1 to 35% of the weed in the blank control area;

[0112] Level 8: equivalent to 35.1 to 67.5% of the weed in the blank control area; and

[0113] Level 9: equivalent to 67.6 to 100% of the weed in the blank control area.

[0114] Table 6 shows the post-emergence herbicidal activities of the test compounds against the weeds.

TABLE-US-00010 TABLE 6 Post-emergence weed control effects of some of the N-benzylbenzamide- based compounds against weeds in the paddy field (150 g a.i./ha) Herbicidal activity 15 days after treatment 30 days after treatment Broadleaf Broadleaf Compound Gramineae weed Cyperaceae Gramineae weed Cyperaceae A01 2 1 1 2 2 2 A02 1 1 1 1 1 1 A03 2 1 2 1 2 1 A07 2 2 1 2 1 2 A09 2 2 1 2 2 2 A14 1 1 1 2 2 2 A22 1 2 2 1 1 1 A23 1 1 1 1 1 1 A24 1 1 1 1 1 1 A28 2 1 2 1 1 1 A29 2 1 1 1 1 2 A35 2 1 1 1 2 2 A85 2 1 1 1 1 1 A87 2 1 1 1 1 1 A89 1 1 1 1 1 1 A91 2 1 1 2 1 1 A92 2 1 1 2 1 1 A94 2 1 1 2 1 2 B01 2 1 2 2 2 2 B02 2 1 1 2 1 1 B07 2 1 1 2 1 1 B08 2 2 1 2 1 1 B14 1 1 1 1 1 1 B15 2 1 1 1 1 2 B22 1 1 1 1 1 1 B27 1 1 1 1 1 1 B30 1 1 1 1 1 2 Penoxsulam 2 2 2 1 1 2

[0115] The data in Table 6 showed that the test compounds in the table had a good controlling effect on weeds in the paddy field. The controlling effects 15 days after performing the treatments with compounds A02, A14, A23, A24, A89, B14, B22, B27, B30 on the gramineous weed, broadleaf weed and cyperaceous weed all reached level 1.

Example 17: Field Test for Weed Control in a Corn Field with Some of the Compounds of General Formula I or II

[0116] The weed control efficacy field test was performed in a corn field with some of the N-benzylbenzamide-based compounds of general formula I or II with reference to the method of GB/T 17980.42-2000. The soil texture of the test corn field was sandy loam soil, which had an organic content of 2.0% and a pH value of 6.5 in the cultivation layer. Spray treatments were performed in the stage where 2 leaves to 5 leaves were grown for the corns after the sowing. Representative compounds in the examples were used to prepare emulsifiable concentrates (10%), and spray treatments were performed with the concentrates in water at a dosage of 150 g(a.i.)/ha, and repeated 4 times for each treatment, and the area was 20 m.sup.2. Oil dispersion with 25% of mesotrione was used as a control agent and applied at a dosage of 150 g(a.i.)/h. The results were investigated by visual inspection 21 days after the treatments. The herbicidal activities of the agents were evaluated on a scale of 1-9 levels according to the symptoms and severity of damage to the test weeds.

[0117] Level 1: weed free;

[0118] Level 2: equivalent to 0 to 2.5% of the weed in the blank control area;

[0119] Level 3: equivalent to 2.6 to 5% of the weed in the blank control area;

[0120] Level 4: equivalent to 5.1 to 10% of the weed in the blank control area;

[0121] Level 5: equivalent to 10.1 to 15% of the weed in the blank control area;

[0122] Level 6: equivalent to 15.1 to 25% of the weed in the blank control area;

[0123] Level 7: equivalent to 25.1 to 35% of the weed in the blank control area;

[0124] Level 8: equivalent to 35.1 to 67.5% of the weed in the blank control area; and

[0125] Level 9: equivalent to 67.6 to 100% of the weed in the blank control area.

[0126] Table 7 shows the herbicidal activity of each compound.

TABLE-US-00011 TABLE 7 Post-emergence weed control effects of some of the N-benzylbenzamide-based compounds against weeds in the corn field (150 g a.i./ha) 30 days after treatment (%) Green Barn- bristle- yard Goose Digitaria Chenopodium Portulaca Amaranthus Solanum Convolvulus Acalypha Nutgrass Compound grass grass grass sanguinalis album oleracea retroflexus nigrum arvensis australis flatsedge A01 1 2 2 2 1 1 1 2 1 2 2 A02 1 1 1 1 1 1 1 1 1 1 1 A03 2 1 2 1 1 1 1 1 1 2 2 A07 2 2 2 2 1 1 1 2 1 2 2 A09 2 2 1 2 1 1 1 2 2 2 2 A14 1 1 1 2 1 1 1 2 1 2 2 A22 2 2 2 1 1 1 1 2 1 2 2 A23 1 2 2 2 1 1 1 2 1 2 3 A24 1 1 2 2 1 1 1 2 1 3 3 A28 1 1 2 2 1 1 1 2 1 2 2 A29 2 1 2 2 1 1 1 2 2 1 2 A35 2 1 2 2 1 1 1 2 2 2 2 A85 1 1 2 2 1 1 1 2 1 1 2 A87 1 1 2 2 1 1 1 2 1 2 2 A89 1 1 2 2 1 1 1 2 1 1 2 A91 2 1 2 2 1 1 1 2 1 2 2 A92 2 1 1 2 1 1 1 2 1 2 2 A94 2 1 1 2 1 1 1 2 2 2 3 B01 1 1 1 1 1 1 1 2 2 2 2 B02 1 1 2 2 1 1 1 2 1 2 2 B07 2 1 2 2 1 1 1 2 1 2 2 B08 1 1 1 1 1 1 1 1 1 1 1 B14 1 1 1 1 1 1 1 1 1 1 1 B15 2 1 2 2 1 1 1 1 2 1 2 B22 1 1 2 2 1 1 1 2 1 1 2 B27 1 1 1 1 1 1 1 1 1 1 1 B30 1 1 1 1 1 1 1 1 1 1 1 Mesotrione 1 1 2 2 1 1 1 1 1 2 1

[0127] The data in Table 7 showed that the test compounds in the table had a good controlling effect on weeds in the corn field. The controlling effects 21 days after treatments of the compounds A02, B08, B14, B27, and B30 on green bristlegrass, barnyard grass, goosegrass, Digitaria sanguinalis, Chenopodium album, Portulaca oleracea, Amaranthus retroflexus, Solanum nigrum, Convolvulus arvensis, Acalypha australis and nutgrass flatsedge all reached level 1.

Example 18: Field Test for Weed Control in a Corn Field with Some of the Compounds of General Formula I or II Tank-Mixed with Atrazine

[0128] The weed control efficacy field test was performed in a corn field with some of the N-benzylbenzamide-based compounds of general formula I or II tank-mixed with atrazine with reference to the method of GB/T 17980.42-2000. The soil texture of the test corn field was sandy loam soil, which had an organic content of 2.0% and a pH value of 6.5 in the cultivation layer. Spray treatments were performed in the stage where 2 leaves to 5 leaves were grown for the corns after the sowing. Representative compounds in the examples were used to prepare emulsifiable concentrates (10%), tank-mixed with a suspension with 40% of atrazine for secondary absorption, and then spray treatments were performed with the mixture in water, and repeated 4 times for each treatment, and the area was 20 m.sup.2. The suspension with 40% of atrazine was used as a control agent and applied at a dosage of 600 g(a.i.)/h. The results were investigated by visual inspection 21 days after the treatments. The herbicidal activities of the agents were evaluated on a scale of 1-9 levels according to the symptoms and severity of damage to the test weeds. Table 8 shows the herbicidal activity of each compound.

TABLE-US-00012 TABLE 8 Post-emergence weed control effects in the corn field of some of the compounds of general formula I or II tank-mixed with atrazine Herbicidal activity (%) Barn- Green Dosage yard bristle- Digitaria Goose Chenopodium Portulaca Amaranthus Solanum Pie Nutgrass Treatment g (a.i.)/ha grass grass sanguinalis grass album oleracea retroflexus nigrum marker flatsedge A01 + atrazine  75 + 375 1 1 1 2 1 1 1 1 1 1 A02 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 A03 + atrazine 150 + 300 1 1 1 2 1 2 1 1 1 1 A07 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A09 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A14 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 A22 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 A23 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 A24 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A28 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 A29 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 A35 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 A85 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 A87 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 A89 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A91 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A92 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 A94 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 B01 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 B02 + atrazine 150 + 300 1 1 1 1 1 1 1 1 1 1 B07 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 B08 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 B14 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 B15 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 B22 + atrazine 100 + 350 1 1 1 1 1 1 1 1 1 1 B27 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 B30 + atrazine  75 + 375 1 1 1 1 1 1 1 1 1 1 40% of atrazine 600 4 4 4 4 1 1 1 1 1 3 suspension

[0129] The data in Table 8 showed that the compounds of general formula I or II tank-mixed with atrazine in a certain ratio had controlling effects of up to level 1 on the weeds in the corn filed, such as green bristlegrass, barnyard grass, goosegrass, Digitaria sanguinalis, Chenopodium album, Portulaca oleracea, Amaranthus retroflexus, Solanum nigrum, piemarker and nutgrass flatsedge. The suspension having 40% of atrazine used at a dosage of 600 g(a.i.)/ha had a controlling effect of up to level 1 on broadleaf grasses, but had a poor controlling effect on gramineous weeds and nutgrass flatsedge. The compound of general formula I or II tank-mixed with atrazine in a certain ratio significantly improved the controlling effects on gramineous weeds and nutgrass flatsedge, and even had a controlling effects of up to level 1 on older gramineous weeds and nutgrass flatsedge, which are basically resistant to atrazine.

Example 19: Field Test for Weed Control in a Corn Field with Mixed Formulations Including Some of the Compounds of General Formula I or II and Atrazine

[0130] The post-emergence weed control effect field test was performed in a corn field with mixed formulations of some of the compounds of general formula I or II and atrazine with reference to the method of NY/T 1155.4-2006. Post-emergence stem and leaf spraying treatments were performed in the stage where 4 leaves were grown for the corns at a dosage of 30 kg per mu. The results were investigated by visual inspection 21 days after the treatments. The herbicidal activities of the agents were evaluated on a scale of 1-9 levels according to the symptoms and severity of damage to the test weeds. The suspension with 40% of atrazine was used as a control agent and applied at a dosage of 600 g(a.i.)/h. Table 9 shows the herbicidal activities.

TABLE-US-00013 TABLE 9 Post-emergence weed control effect in the com field of the mixed formulations including some of the compounds of general formula I or II and atrazine Herbicidal activity (%) Barn- Green Dosage yard bristle- Digitaria Goose Chenopodium Portulaca Amaranthus Solanum Pie Nutgrass Treatment g (a.i.)/ha grass grass sanguinalis grass album oleracea retroflexus nigrum marker flatsedge A01 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A02 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion A03 + atrazine oil 150 + 300 1 1 1 2 1 2 1 1 1 1 dispersion A07 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A09 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A14 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion A22 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion A23 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion A24 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A28 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion A29 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion A35 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion A85 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion A87 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion A89 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A91 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A92 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion A94 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion B01 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion B02 + atrazine oil 150 + 300 1 1 1 1 1 1 1 1 1 1 dispersion B07 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion B08 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion B14 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion B15 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion B22 + atrazine oil 100 + 350 1 1 1 1 1 1 1 1 1 1 dispersion B27 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion B30 + atrazine oil  75 + 375 1 1 1 1 1 1 1 1 1 1 dispersion 40% of atrazine 600 4 4 4 4 1 1 1 1 1 3 suspension

[0131] The data in Table 9 showed that the mixed formulations as prepared by the compounds of general formula I or II and atrazine had controlling effects of up to level 1 at a dosage of 450 g (a.i.)/ha on the weeds in the corn filed, such as green bristlegrass, barnyard grass, goosegrass, Digitaria sanguinalis, Chenopodium album, Portulaca oleracea, Amaranthus retroflexus, Solanum nigrum, piemarker and nutgrass flatsedge.

[0132] The use of the N-benzylbenzamide-based compound as a herbicide according to the present disclosure has been described through specific examples. Those skilled in the art may learn from the content of the present disclosure and appropriately change the raw materials, process conditions and other factors to achieve corresponding other purposes. In addition, the related changes do not deviate from the content of the present disclosure, and all similar replacements and changes are obvious to those skilled in the art, and are considered to be included in the scope of the present disclosure.