JPS60193960A - N-benzoyl-n'-phenylurea compound and insecticide containing same - Google Patents
N-benzoyl-n'-phenylurea compound and insecticide containing sameInfo
- Publication number
- JPS60193960A JPS60193960A JP5009184A JP5009184A JPS60193960A JP S60193960 A JPS60193960 A JP S60193960A JP 5009184 A JP5009184 A JP 5009184A JP 5009184 A JP5009184 A JP 5009184A JP S60193960 A JPS60193960 A JP S60193960A
- Authority
- JP
- Japan
- Prior art keywords
- dichloro
- compound
- benzoyl
- difluorophenyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規なＮ−ベンゾイル−Ｎ′−フェニルウレア
系化合物及びそれらを含有する殺虫剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel N-benzoyl-N'-phenylurea compounds and insecticides containing them.
詳しくは、本発明は、一般式ＣＩ）
（式中Ｘは水素原子又はハロゲン原子であり、Ｙはハロ
ゲン原子であり、Ｚは２，６−ジクロロ−３，５−ジフ
ルオロ７エ二ル基、３．５−ジクロロ−２，６−ジフル
オロ７エエル基、２．４−ジクロロ−３，５−ジフルオ
ロフェニル基又は３．５−ジクロロ−２，４，ロートリ
フルオロフェニル基である）で表わされるＮ−ベンゾイ
ル−Ｎ′−フェニルウレア系化合物及びそれらを含有す
る殺虫剤である。Specifically, the present invention is based on the general formula CI) (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, and Z is a 2,6-dichloro-3,5-difluoro7enyl group, 3,5-dichloro-2,6-difluoro7-el group, 2,4-dichloro-3,5-difluorophenyl group, or 3,5-dichloro-2,4,rotrifluorophenyl group) N-benzoyl-N'-phenylurea compounds and insecticides containing them.
前記一般式（Ｉ）のＸ及びＹで表わされるハロゲン原子
としでは弗素、塩素、臭素、沃素が挙げられる。Examples of the halogen atoms represented by X and Y in the general formula (I) include fluorine, chlorine, bromine, and iodine.
本発明のＮ−ベンゾイル−Ｎ′−フェニルウレア系化合
物は、通常、一般式〔■〕
（式中Ｘ及びＹは前述の通りであり、Ｒ１はカルバモイ
ル基又はインシアナートカルボニル基である）で表わさ
れる化合物と、
一般式（ＩＩＩ）
２−Ｚ
（Ｉ［）
（式中Ｚは前述の通りであり、Ｒ２は、Ｒ１がカルバモ
イル基の時インシアナート基であり、Ｒ１がイソシアナ
ートカルボニル基の時アミ７基である）で表わされる化
合物とを、反応させることによって製造される。この反
応は、ベンゼン、トルエン、キシレン、クロロベンゼン
などの芳香族炭化水素類：クロロホルム、四塩化炭素、
塩化メチレン、ジクロロエタン、トリクロロエタン、ヘ
キサン、シクロヘキサン、酢酸エチルなどの環状又は非
環状脂肪族炭化水素類ニジエチルエーテル、ジオキサン
、テトラヒドロフランなどのエーテル類：アセトン、メ
チルエチルケトン、メチルイソブチルケトンなどのケト
ン類ニジメチルスルホキシド、スルホランなどの非プロ
トン性極性溶媒などの溶媒の存在下に行なわれ、反応温
度は０〜１００’Ｃ１反応時間は０．１〜２４時間であ
る。The N-benzoyl-N'-phenylurea compound of the present invention usually has the general formula [■] (wherein X and Y are as described above, and R1 is a carbamoyl group or incyanatocarbonyl group). A compound represented by the general formula (III) 2-Z (I[) (wherein Z is as described above, R2 is an incyanato group when R1 is a carbamoyl group, and when R1 is an isocyanatocarbonyl group It is produced by reacting a compound represented by amine 7 group). This reaction is effective for aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; chloroform, carbon tetrachloride,
Cyclic or acyclic aliphatic hydrocarbons such as methylene chloride, dichloroethane, trichloroethane, hexane, cyclohexane, and ethyl acetate; Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; Ni dimethyl sulfoxide The reaction temperature is 0 to 100'C1 and the reaction time is 0.1 to 24 hours.
次に本発明化合物の具体的合成例を記載する。Next, specific synthesis examples of the compounds of the present invention will be described.
合成例Ｉ Ｎ−（２，６−ジフルオロベンゾイル）−Ｎ
’ −（２，４−ジ９０ロー３，５−ジフルオロフェニ
ル）ウレアの合成
（１） ３．５−ジクロロ−２，４，６−）リフルオロ
ベンゾニトリル５．０ｇに２８％アンモニア水１００ｍ
ｆｆを冷却しながら加え、その後室温で１５時間攪拌下
に反応させた。Synthesis Example I N-(2,6-difluorobenzoyl)-N
Synthesis of -(2,4-di90-3,5-difluorophenyl)urea (1) 5.0 g of 3,5-dichloro-2,4,6-)lifluorobenzonitrile and 100 m of 28% ammonia water
ff was added while cooling, and then the reaction was allowed to proceed at room temperature for 15 hours with stirring.
反応終了後、析出した結晶を濾過し、塩化メチレンに溶
解させ、無水 硝で乾燥させた後溶媒を減圧留去した６
残査をシリカゲルカラムクロマトグラフィーで分離し、
２−アミノ−３，５−ジクロロ−４，６−シフルオロベ
ンゾニトリル０．９７ｇと４−アミノ−３，５−ジクロ
ロ−２，６−シフルオロベンゾニトリル２．４ｇを得た
。After the reaction was completed, the precipitated crystals were filtered, dissolved in methylene chloride, dried over anhydrous sulfur, and the solvent was distilled off under reduced pressure.
The residue was separated by silica gel column chromatography,
0.97 g of 2-amino-3,5-dichloro-4,6-cyfluorobenzonitrile and 2.4 g of 4-amino-3,5-dichloro-2,6-cyfluorobenzonitrile were obtained.
（２）前記（１）で得た２−７ミノー３，５−ジクロロ
−４，６−シフルオロベンゾニトリル３．７ｇを７０％
硫酸３０ｍρに溶解させ、１５０〜１６０℃で３日間攪
拌下で反応させた。反応終了後、生成物を氷水中に投入
し、塩化メチレンで抽出、抽出層を無水 硝で乾燥した
後、溶媒を減圧留去し、シリカゲルカラムクロマトグラ
フィーで分離して融点６２〜６３．５℃の２，４−ジク
ロロ−３，５−ジフルオロアニリン１．１２ｇを得た。(2) 70% of 3.7 g of 2-7 minnow 3,5-dichloro-4,6-cyfluorobenzonitrile obtained in (1) above
It was dissolved in 30 mρ of sulfuric acid and reacted at 150 to 160°C for 3 days with stirring. After the reaction was completed, the product was poured into ice water, extracted with methylene chloride, and the extracted layer was dried over anhydrous nitric acid, the solvent was distilled off under reduced pressure, and the product was separated by silica gel column chromatography to give a melting point of 62-63.5°C. 1.12 g of 2,4-dichloro-3,5-difluoroaniline was obtained.
（３）前記（２）で得た２、４−ジクロロ−３，５−ジ
フルオロアニリン０．８８に、２，６−シフルオロベン
ゾイルイソシアナー）１．０ｇ及びジオキサン１５ｍ１
２を加えた混合物を室温で１４時間攪拌下に反応させた
。反応終了後、生成物を水中に投入し、濾過しだ後熱湯
及び酢酸エチルで洗浄して融点２３７〜２４１℃の目的
物０．９８ｇを得た。(3) To 0.88 g of 2,4-dichloro-3,5-difluoroaniline obtained in (2) above, 1.0 g of 2,6-cyfluorobenzoyl isocyaner) and 15 ml of dioxane
The mixture to which 2 was added was allowed to react at room temperature for 14 hours with stirring. After the reaction was completed, the product was poured into water, filtered, and washed with hot water and ethyl acetate to obtain 0.98 g of the desired product having a melting point of 237-241°C.
前記一般的製造法及び具体的合成例に準じて製造された
化合物の具体的代表例を記載する。Specific representative examples of compounds produced according to the general production method and specific synthesis examples described above will be described.
化合物Ｎｏ、Ｉ Ｎ−（２，６−ジフルオロベンゾイル
）−Ｎ’−（２，６−ジクロロ−３，５−ジフルオロフ
ェニル）ウレア ｍ、ｐ、１８０．５−１８３℃化合物
Ｎｏ、２ Ｎ−（２，６−ジフルオロベンゾイル）−Ｎ
’ −（３，５−ジクロロ−２，６−ジフルオロ７エ二
ル）ウレア ｍ、ｐ、２１０−２１４’Ｃ化合物Ｎｏ、
３ Ｎ−（２，６−ジフルオロベンゾイル）−Ｎ’ −
（２，４−ジクロロ−３，５−ジフルオロフェニル）ウ
レア ｍ、ｐ、２３７〜２４１℃化合物Ｎｏ、４ Ｎ−
（２，６−ジフルオロベンゾイル）−Ｎ’ −（３，５
−フクロロー２，４．６．−トリフルオロフエニル）ウ
レア
鎗、ｐ、 ２０７〜２１１℃
化合物Ｎｏ、５ 、Ｎ−（２−クロロベンゾイル）−Ｎ
’ −（２，４−ジクロロ−３，５−ジフルオロフェニ
ル）ウレア ｍ、ｐ、２４１〜２４５℃
本発明化合物は、後記試験例にみる通り、殺虫剤、特に
殺昆虫剤の有効成分として優れた活性を示す。Compound No, I N-(2,6-difluorobenzoyl)-N'-(2,6-dichloro-3,5-difluorophenyl)urea m, p, 180.5-183°C Compound No, 2 N-( 2,6-difluorobenzoyl)-N
'-(3,5-dichloro-2,6-difluoro7enyl)urea m, p, 210-214'C compound No.
3 N-(2,6-difluorobenzoyl)-N'-
(2,4-dichloro-3,5-difluorophenyl)urea m, p, 237-241°C Compound No., 4 N-
(2,6-difluorobenzoyl)-N'-(3,5
- Fukuroro 2, 4.6. -trifluorophenyl)urea, p, 207-211°C Compound No. 5, N-(2-chlorobenzoyl)-N
' -(2,4-dichloro-3,5-difluorophenyl)urea m, p, 241-245°C As shown in the test examples below, the compound of the present invention is excellent as an active ingredient of insecticides, especially insecticides. Shows activity.
このものを殺虫剤の有効成分として使用するに際しては
、従来の農薬の製剤の場合と同様に農薬補助剤と共に乳
剤、粉剤、水和剤、液剤などの種々の形態に製剤するこ
とができる。これらの製剤の実際の使用に際しては、そ
のまま使用するか、または水等の希釈剤で所定濃度に希
釈して使用することができる。ここに言う農薬補助剤と
しては、タルり、カオリン、ベントナイト、珪藻土、ホ
ワイトカーボン、クレー、澱粉などの固型担体、水、ト
ルエン、キシレン、クロロベンゼン、シクロヘキサン、
ジメチルスルホキシド、ジメチルホルムアミド、アルコ
ールなどの液体希釈剤、乳化剤、分散剤、展着剤などを
挙げることができる。また必要に応じて他の農薬、例え
ば殺虫剤、殺ダニ剤、殺菌剤、植物生長調整剤などと混
用、併用することができ、この場合に一層優れた効果を
示すこともある。When this product is used as an active ingredient of an insecticide, it can be formulated into various forms such as an emulsion, a powder, a wettable powder, a liquid, etc. together with an agricultural chemical auxiliary, as in the case of conventional agricultural chemical formulations. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. The pesticide adjuvants mentioned here include solid carriers such as tar, kaolin, bentonite, diatomaceous earth, white carbon, clay, and starch, water, toluene, xylene, chlorobenzene, cyclohexane,
Examples include liquid diluents such as dimethyl sulfoxide, dimethylformamide, and alcohol, emulsifiers, dispersants, and spreading agents. Furthermore, if necessary, it can be mixed or used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, plant growth regulators, etc. In this case, even more excellent effects may be exhibited.
本発明の殺虫剤は種々の有害虫、特に有害昆虫の防除に
有効であり、施用は一般にｏ、ｏｏｉ〜１＋ＯＯＯｐｐ
ｍ、望ましくは０．０１〜５００ｐｐＩ１１の有効成分
濃度で行なう。また、家畜に対して前記有効成分を飼料
に混合して与え、その徘 物での有害虫、特に有害昆虫
の発生、生育を防除したり、或いは、昆虫の成虫に有効
成分を処理することによって卵のふ化を阻止することも
で終る。なお、水棲有害虫の場合は、上記の濃度範囲の
薬液を発生場所に散布して防除できることから、水中で
の薬液濃度範囲は上記以下でも有効である。The insecticide of the present invention is effective in controlling various harmful insects, especially harmful insects, and the application is generally o, ooi to 1+OOOOpp.
m, preferably at an active ingredient concentration of 0.01 to 500 ppI11. It is also possible to feed livestock with the above-mentioned active ingredients mixed with their feed to control the emergence and growth of harmful insects, especially harmful insects, in their wandering materials, or by treating adult insects with the active ingredients. It also ends up preventing the eggs from hatching. In the case of harmful aquatic insects, it is possible to control them by spraying a chemical solution in the above concentration range to the place where they occur, so it is effective even if the concentration range of the chemical solution in water is less than the above range.
次に本発明殺虫剤の試験例を記載する。Next, test examples of the insecticide of the present invention will be described.
試験例１
有効成分化合物の製剤品を水に分散させ、５０ｐｐｍの
濃度に調整した薬液にキャベツの葉片を約１０秒間浸漬
し、取り出して風乾した。ペトリ皿（直径９ｃＩ＋１）
に湿った濾紙を敷き、その上に葉片を置いた。そこへ２
〜３令のハスモンヨトウの幼虫を放ち、ふたをして２８
°Ｃの照明付恒温器内に放置した。放虫後８日目に生死
を判定し、下記の計算式により元止率をめて第１表の結
果を得た。Test Example 1 A preparation of an active ingredient compound was dispersed in water, and cabbage leaves were immersed in a drug solution adjusted to a concentration of 50 ppm for about 10 seconds, taken out, and air-dried. Petri dish (diameter 9cI+1)
A damp filter paper was placed on top of the filter paper, and the leaf pieces were placed on top of it. There 2
~ Release 3rd instar Spodoptera larvae and cover with a lid.
It was left in a lighted thermostat at °C. The survival rate was determined on the 8th day after the release of the insects, and the survival rate was calculated using the following formula to obtain the results shown in Table 1.
死虫数
元止率（％） ＝ −Ｘ １００
放虫後
第１表
化合物Ｎｏ、 元止率（％）
１ １００
２ １００
３ １００
４ １００
５ １００
試験例２
２〜３令のハスモンヨトウを２〜３令のフナガにがえる
こと以外は、前記試験例１の場合と同様にして試験を行
ない、第２表の結果を得た。Number of dead insects and stopping rate (%) = -X 100 Table 1 Compound No. after release, killing rate (%) 1 100 2 100 3 100 4 100 5 100 Test example 2 Two to three instars of Spodoptera The test was conducted in the same manner as in Test Example 1 above, except that the three-instar three-year-old Funagas were hatched, and the results shown in Table 2 were obtained.
第２表
化合物Ｎｏ、 元止率（％）
１ １００
２ １００
３ １００
４ １００
５ １００
試験例３
直径９ｃｍの深底シャーレに１ｏｐｐｂの濃度に調整し
た化合物Ｎｏ、３の薬液を約２５０ｍｆｆ入れ、そこへ
３令のチヵイエカの幼虫を放ち、ふたをして２８℃の照
明付恒温器内に放置した。成虫後１０日日に幼虫の生死
を調査した結果、１００％の元止率が認められた。Table 2 Compound No. Stopping rate (%) 1 100 2 100 3 100 4 100 5 100 Test Example 3 Approximately 250 mff of the chemical solution of compound No. 3 adjusted to a concentration of 1 opppb was placed in a deep-bottom petri dish with a diameter of 9 cm. Third instar Chikae mosquito larvae were released and placed in a lighted incubator at 28°C with a lid on. As a result of examining the survival of the larvae on the 10th day after they became adults, a 100% survival rate was observed.
次に本発明殺虫剤の製剤例を記載する。Next, formulation examples of the insecticide of the present invention will be described.
製剤例１
（伺 化合物Ｎｏ、２ ２０重量部
（ロ） ジ−クライト ７２重量部
（ハ） リグニンスルホン酸ソーダ ８重量部以上のも
のを均一に混合して水和剤とした。Formulation Example 1 Compound No. 2 20 parts by weight (b) Di-Cryte 72 parts by weight (c) Sodium ligninsulfonate 8 parts by weight or more were uniformly mixed to prepare a wettable powder.
製剤例２ （イ）化合物Ｎｏ、４ ５重量部 （ロ）タルク ９５重量部 以上のものを均一に混合して粉剤とした。Formulation example 2 (a) Compound No. 4 5 parts by weight (b) Talc 95 parts by weight The above ingredients were mixed uniformly to form a powder.
製剤例３
（イ）化合物Ｎｏ、５ ’ ２０重量部（ロ）Ｎ、Ｎ’
−゛ジメチルホルムアミド ７０ｍｔ部（ハ）ポリオキ
シエチレンアルキルフェニルエーテル１０重量部
以上のものを均一に混合、溶解して乳剤とした。Formulation Example 3 (a) Compound No. 5' 20 parts by weight (b) N, N'
- 70 mt parts of dimethylformamide (c) 10 parts by weight or more of polyoxyethylene alkylphenyl ether were uniformly mixed and dissolved to form an emulsion.
製剤例４
（イ）ジ−クライト ７８重量部
（ロ） β−す７タレンスルホン酸ソ一ダホルマリン綜
合物２重量部
（ハ）ポリオキシエチレンアルキルアリルサルフェート
５重量部
（ニ） ホワイトカーボン １５重量部以上の各成分の
混合物と、化合物Ｎｏ、３とを、４：１の重量割合で混
合し、水和剤とした。Formulation Example 4 (a) Di-cryte 78 parts by weight (b) 2 parts by weight of β-7talenesulfonic acid sodium formalin complex (c) 5 parts by weight of polyoxyethylene alkylaryl sulfate (d) White carbon 15 parts by weight A mixture of 1 part or more of each component and Compound No. 3 were mixed at a weight ratio of 4:1 to prepare a wettable powder.
手続補正書（方式）
％式％
１、事件の表示 昭和５９年特許願第５００９１号２、
発明の名称 Ｎ−ベンゾイル−Ｎ′−フェニルウレア系
化合物及びそれらを含有する殺虫剤
３、補正をする者
事件との関係 特許出願人
５、補正の対象 明細書全文
６、補正の内容 別紙の通り（タイプ印書したもので手
続補正書
特許庁長官 志 賀 学 殿
１、事件の表示 昭和５９年特許願第５００９１号２、
発明の名称 Ｎ−ベンゾイル−Ｎ′−フェニルウレア系
化合物及びそれらを含有する殺虫剤
３、補正をする者
事件との関係 特許出願人
６、補正の内容
（１）明細書第４頁下から５行目及び同第５頁５行目の
「無水 硝」を「無水て硝」に訂正する。Procedural amendment (method) % formula % 1, Indication of case Patent Application No. 50091 of 1982 2,
Title of the invention N-benzoyl-N'-phenylurea compounds and insecticides containing them 3. Relationship with the case of the person making the amendment Patent applicant 5. Subject of the amendment Full text of the specification 6. Contents of the amendment As attached. (Type-printed procedural amendment by Manabu Shiga, Director General of the Japan Patent Office 1, Indication of the case, Patent Application No. 50091 of 1982, 2)
Title of the invention N-benzoyl-N'-phenylurea compounds and insecticides containing them 3. Relationship with the case of the person making the amendment Patent applicant 6. Contents of the amendment (1) Page 4 of the specification, 5 from the bottom Correct "anhydrous salt" to "anhydrous salt" in line 5 and page 5, line 5.
（２）明細書第７真下から７行目の「排 物」を「徘ｚ
ｔ物」に訂正する。(2) “Excrement” on the seventh line from the bottom of the specification is “Wandering”.
Corrected to "t thing".
Claims (1)
ゲン原子であり、Ｚは２．６−ジクロロ−３，５−ジフ
ルオロフェニル基、３．５−ジクロロ−２，６−ジフル
オロフェニル基、２．４−ジクロロ−３，５−ジフルオ
ロフェニル基又は３．５−ジクロロ−２，４，６４リフ
ルオロフエニル基である）で表わされるＮ−ベンゾイル
−Ｎ’ −７！ユニルウレア化合％。 ２、一般式 （式中Ｘは水素原子又はハロゲン原子であり、Ｙはハロ
ゲン原子であり、Ｚは２，６−ジクロロ−３，５−ジフ
ルオロフェニル基、３．５−ジクロロ−２，６−ジフル
オロフェニル基、２．４−ジクロロ−３，５−ジフルオ
ロフェニル基又は３，５−ジクロロ−２，４，６−）リ
フルオロフェニル基である）で表わされるＮ−ベンゾイ
ル−Ｎ′−フェニルウレア系化合物の少なくとも一種を
有効成分として含有することを特徴とする殺虫剤。[Claims] 1. General formula (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, Z is a 2,6-dichloro-3,5-difluorophenyl group, 3.5- N-benzoyl- represented by dichloro-2,6-difluorophenyl group, 2,4-dichloro-3,5-difluorophenyl group or 3,5-dichloro-2,4,64-difluorophenyl group) N'-7! Unilurea compound%. 2. General formula (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, Z is a 2,6-dichloro-3,5-difluorophenyl group, 3,5-dichloro-2,6- N-benzoyl-N'-phenylurea represented by a difluorophenyl group, a 2,4-dichloro-3,5-difluorophenyl group, or a 3,5-dichloro-2,4,6-)lifluorophenyl group) An insecticide characterized by containing at least one type of compound as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5009184A JPS60193960A (en) | 1984-03-15 | 1984-03-15 | N-benzoyl-n'-phenylurea compound and insecticide containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5009184A JPS60193960A (en) | 1984-03-15 | 1984-03-15 | N-benzoyl-n'-phenylurea compound and insecticide containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60193960A true JPS60193960A (en) | 1985-10-02 |
Family
ID=12849372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5009184A Pending JPS60193960A (en) | 1984-03-15 | 1984-03-15 | N-benzoyl-n'-phenylurea compound and insecticide containing same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60193960A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264213A (en) * | 1988-07-08 | 1993-11-23 | Dowelanco | Process for preparing highly active water-dispersible pesticides |
| WO2003049540A1 (en) * | 2001-12-12 | 2003-06-19 | Makhteshim Chemical Works Ltd. | Water dispersible granules containing benzoylphenylurea pesticides |
-
1984
- 1984-03-15 JP JP5009184A patent/JPS60193960A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264213A (en) * | 1988-07-08 | 1993-11-23 | Dowelanco | Process for preparing highly active water-dispersible pesticides |
| WO2003049540A1 (en) * | 2001-12-12 | 2003-06-19 | Makhteshim Chemical Works Ltd. | Water dispersible granules containing benzoylphenylurea pesticides |
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