JPH0450282B2 - - Google Patents

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Publication number
JPH0450282B2
JPH0450282B2 JP7828283A JP7828283A JPH0450282B2 JP H0450282 B2 JPH0450282 B2 JP H0450282B2 JP 7828283 A JP7828283 A JP 7828283A JP 7828283 A JP7828283 A JP 7828283A JP H0450282 B2 JPH0450282 B2 JP H0450282B2
Authority
JP
Japan
Prior art keywords
parts
compound
reducer
herbicide
phytotoxicity
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.)
Expired
Application number
JP7828283A
Other languages
Japanese (ja)
Other versions
JPS59204103A (en
Inventor
Toshimi Tanaka
Masao Hayashi
Toshio Nanho
Kazuo Akihiro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Priority to JP7828283A priority Critical patent/JPS59204103A/en
Publication of JPS59204103A publication Critical patent/JPS59204103A/en
Publication of JPH0450282B2 publication Critical patent/JPH0450282B2/ja
Granted legal-status Critical Current

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Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は、一般式() (式中、R1およびR2は低級アルキル基を示し、
R3は炭素数1〜4個のアルキル基を示し、Aは
非置換メチレン鎖、非置換のエチレン鎖、または
1個若しくは2個のメチル基で置換されたエチレ
ン鎖を示す)で表わされるハロアセトアニリドの
薬害軽減剤に関する。より詳しくは、1,2−ベ
ンゾイソチアゾール−3(2H)−オン−1,1−
ジオキシドまたはその塩、あるいは一般式(I) (式中、Rは低級アルキル基または低級アルケ
ニル基を示す)で表わされる薬害軽減剤に関する
ものである。 除草剤は、そもそも選択性を利用して有用作物の
栽培区における有害な雑草を化学的手段によつて
防除するものであるが、作物と雑草間に本質的な
選択性を著わすものは少なく、多くは作物と雑草
の生育ステージの差、土壌中における作物と雑草
の種子の位置の差、葉面上のふ着の差、などを利
用して選択性を著わしている。そのため、土壌の
種類、温度、雨量などの天候、薬量などによつ
て、好ましくない副作用である薬害が生じる場合
がしばしばある。このことは、多くの除草剤、例
えばトリアジン系、尿素系、カーバメート系、フ
エノキシ系、フエノール系、そしてアセトアニリ
ド系等各除草剤にあてはまることである。 そのためにこれら除草剤の薬害軽減剤の研究が
過去多くなされ、例えば、トウモロコシの除草剤
であるEPTC(S−エチル−N,N−ジ(n)−プ
ロピルチオールカーバメート)に対し薬害軽減作
用を有するN,N−ジアリル−2,2−ジクロロ
アセトアミド〔Weed Science 21(4),292−
295(1973)〕やアラクロール(N−メトキシメチ
ル−2,6−ジエチル−α−クロロアセトアニリ
ド)に対し薬害軽減作用を有する1,8−ナフタ
リツクアンハイドライド(Weed Science 22
(1),86−90(1974))などが知られている。 除草剤として有用な化合物であることが既に公
知(特公昭48−37820号、特開昭49−54527号)の
一般式()で表わされるハロアセトアニリド
も、各種の他の除草剤と同じように薬害を生じる
ことがある。 本発明者らは、一般式()で表わされるハロ
アセトアニリドの除草剤の薬害軽減剤を探策し、
1,2−ベンゾイソチアゾール−3(2H)−オン
−1,1−ジオキシドまたはその塩、あるいは、
一般式(I)で表わされるイネいもち病防除剤と
して公知(特公昭45−38080号)の化合物が、著
しい軽減効果をあらわすことを見出した。この化
合物の薬害軽減効果をあらわす作物は、水稲をは
じめとし、一般式()で表わされる除草剤が適
用できる作物、つまりトウモロコシ、小麦、大
麦、ビール麦、陸稲、大豆、綿、ピーナツツ、テ
ンサイ等広範囲に及ぶものである。 本発明で薬害軽減剤として使用する1,2−ベ
ンゾイソチアゾール−3(2H)−オン−1,1−
ジオキシド、その塩、および一般式(I)であら
わされる化合物は、イネいもち病防除効果につい
て知られているが除草活性や薬害軽減作用につい
ては知られていない。 本発明の薬害軽減剤として使用できる化合物と
して次表のようなものがあげられる。
The present invention is based on the general formula () (In the formula, R 1 and R 2 represent lower alkyl groups,
R 3 represents an alkyl group having 1 to 4 carbon atoms, and A represents an unsubstituted methylene chain, an unsubstituted ethylene chain, or an ethylene chain substituted with one or two methyl groups. This invention relates to a drug-toxicity reducer for acetanilide. More specifically, 1,2-benziisothiazol-3(2H)-one-1,1-
Dioxide or its salt, or general formula (I) (wherein R represents a lower alkyl group or a lower alkenyl group). Herbicides use selectivity to control harmful weeds in areas where useful crops are cultivated by chemical means, but there are few that show inherent selectivity between crops and weeds. In many cases, selectivity is achieved by utilizing differences in the growth stages of crops and weeds, differences in the position of seeds of crops and weeds in the soil, and differences in attachment on the leaf surface. Therefore, depending on the type of soil, temperature, weather such as rainfall, dosage, etc., chemical damage, which is an undesirable side effect, often occurs. This applies to many herbicides, such as triazine, urea, carbamate, phenoxy, phenol, and acetanilide herbicides. For this reason, many studies have been conducted in the past on phytotoxicity reducing agents for these herbicides. N,N-diallyl-2,2-dichloroacetamide [Weed Science 21 (4), 292-
295 (1973)] and alachlor (N-methoxymethyl-2,6-diethyl-α-chloroacetanilide), weed science 22
(1), 86-90 (1974)) are known. Haloacetanilide represented by the general formula (), which is already known to be a useful compound as a herbicide (Japanese Patent Publication No. 48-37820, Japanese Patent Publication No. 49-54527), is also a compound useful as a herbicide in the same way as various other herbicides. May cause drug damage. The present inventors searched for a phytotoxicity reducer for haloacetanilide herbicides represented by the general formula (),
1,2-benzisothiazol-3(2H)-one-1,1-dioxide or a salt thereof, or
It has been found that the compound represented by the general formula (I), which is known as a rice blast control agent (Japanese Patent Publication No. 38080/1983), exhibits a remarkable alleviation effect. Crops that exhibit the phytotoxicity reducing effect of this compound include paddy rice, crops to which the herbicide represented by the general formula () can be applied, such as corn, wheat, barley, beer barley, upland rice, soybeans, cotton, peanuts, sugar beet, etc. It is wide-ranging. 1,2-Benzisothiazol-3(2H)-one-1,1- used as a drug harm reducer in the present invention
Dioxide, its salts, and the compound represented by the general formula (I) are known to have a rice blast control effect, but their herbicidal activity and herbicidal damage reducing effect are not known. Compounds that can be used as the drug-toxicity reducing agent of the present invention include those shown in the following table.

【表】 キシド
本発明の薬害軽減剤は、種々の方法で除草剤の
薬害を軽減することができる。 即ち、大豆の栽培地では播種し、ハロアセトア
ニリドの除草剤を散布する前にまたは同時に、あ
るいは後に薬害軽減剤を処理することができる
し、また薬害軽減剤を種子にコーデイングするこ
とができる。 また薬害軽減剤を適当な担体と均一混合し、活
性剤、分散剤および結合剤を添加した上で粒剤化
して使用することができる。 本発明の薬害軽減剤は剤型をその他乳剤、水和
剤、粉剤、液剤、又はフロアブルの形として用い
ることもできる。 使用する薬害軽減剤の量は、ハロアセトアニリ
ド1重量部当り0.01〜5重量部であるが、最適な
薬量については使用するハロアセトアニリドの種
類、対象作物によつてその都度検討の上決められ
る。 ハロアセトアニリド除草剤の作用性はタンパク
質生合成の阻害にあるとされているが、薬害症状
については、例えば水稲の場合、草丈抑制、新葉
抽出の阻害、縮状葉、などの症状がみられ、ひど
い時には収量に大きく影響をおよぼす。この場
合、本発明の薬害軽減剤を同時に施用すれば、除
草効果に何ら影響することなく、上記薬害症状を
著しく軽減するか、あるいは全く薬害症状が観察
されず、水稲の収量に好結果をもたらす。 本発明の薬害軽減剤は、前記一般式()で表
わされるハロアセトアニリド除草剤に有効であ
る。 一般式()で表わされるハロアセトアニリド
として次表に示すようなものがあげられる。
[Table] Oxide The phytotoxicity reducing agent of the present invention can reduce the phytotoxicity of herbicides in various ways. That is, soybean cultivation areas can be treated with a herbicide before, at the same time, or after the soybean is sown and sprayed with a haloacetanilide herbicide, and the soybean can be coated with a herbicide. Alternatively, the drug-toxicity reducing agent can be homogeneously mixed with a suitable carrier, an active agent, a dispersant, and a binder added thereto, and then granulated for use. The drug harm reducer of the present invention can also be used in other forms such as emulsions, wettable powders, powders, liquids, or flowables. The amount of the phytotoxicity reducer used is 0.01 to 5 parts by weight per 1 part by weight of the haloacetanilide, but the optimum amount is determined on a case-by-case basis depending on the type of haloacetanilide used and the target crop. It is said that the action of haloacetanilide herbicides lies in the inhibition of protein biosynthesis, but in the case of paddy rice, for example, symptoms such as reduced plant height, inhibition of new leaf extraction, and shrunken leaves are observed. In severe cases, it can greatly affect the yield. In this case, if the phytotoxicity reducing agent of the present invention is applied at the same time, the above phytotoxicity symptoms will be significantly reduced without any effect on the herbicidal effect, or no phytotoxicity symptoms will be observed at all, resulting in good results on the yield of paddy rice. . The drug damage reducer of the present invention is effective against the haloacetanilide herbicide represented by the above general formula (). Examples of the haloacetanilide represented by the general formula () include those shown in the following table.

【表】 本発明の薬害軽減剤を、一般式()で表わさ
れるハロアセトアニリド1重量部に対し、0.01〜
5重量部の範囲で含有させる。 また、剤型に応じて、担体、活性剤、分散剤、
結合剤を用い、粒剤、乳剤、水和剤、液剤とする
ことができる。 一般には、このような剤型において、上記の範
囲のハロアセトアニリドと薬害軽減剤とを、例え
ば粒剤では0.5〜5重量%、乳剤では1〜10重量
%、水和剤では2〜20重量%、粉剤では0.1〜1
重量%含有させる。 以下、実施例および試験例によつて本発明を説
明する。 実施例1 薬害軽減剤粒剤 化合物4 5部、ベントナイト 70部、タルク
21部、ドデシルベンゼンスルホン酸ソーダ 1
部、ポリオキシエチレンアルキルアリルエーテル
1部、およびリグニンスルホン酸ソーダへ2部
を混合した後、適量の水を加えて混練し、造粒機
を用いて通常の方法で造粒し、粒剤100部を得る。 実施例2 薬害軽減除草剤粒剤 化合物C 2部、化合物6 1部、ベントナイ
ト 73部、タルク 21部、リグニンスルホン酸ソ
ーダ 2部、およびドデシルベンゼンスルホン酸
ソーダ 1部を混合した後、適量の水を加えて混
練し、造粒機を用いて通常の方法で造粒し、粒剤
100部を得る。 実施例3 薬害軽減剤粉剤 化合物3 0.5部およびケイソウ土とクレー混
合物99.5部を混合粉砕し、粉剤100部を得る。 実施例4 薬害軽減除草剤水和剤 化合物D50部、化合物2 2部、ホワイトカー
ボン10部、ケイソウ土33部、リグニンスルホン酸
ソーダ3部およびドデシルベンゼンスルホン酸ソ
ーダ2部を混合粉砕して、水和剤100部を得る。 実施例5 薬害軽減除草剤乳剤 化合物A40部、化合物1 2部、オルソキシレ
ン48部および脂肪アルコールポリグリコールエー
テル10部を混合溶解して乳剤100部を得る。 試験例1 種子コーテイングによる薬害軽減効果
試験 温室内においてトウモロコシ(品種:ゴールデ
ンクロスバンタム)、小麦(品種:農林27号)大
豆(品種:フクムスメ)の各種子に化合物3を5
%含む粉剤を、種子100gに対して10gの割合粉
衣し、砂質土壌を充填したポツトに播種し、翌日
に化合物Aまたは化合物Dを所定薬量処理し、処
理後40日目に抜取り調査をおこない、薬害軽減剤
無コーテイング種子を用いた場合と生育量につい
て比較した結果を第1表に示す。
[Table] 0.01 to 1 part by weight of the drug harm reducer of the present invention is added to 1 part by weight of the haloacetanilide represented by the general formula ().
It is contained in a range of 5 parts by weight. Depending on the dosage form, carriers, active agents, dispersants,
By using a binder, it can be made into granules, emulsions, wettable powders, and solutions. In general, in such dosage forms, the haloacetanilide and the safener are contained in the above-mentioned range, for example, 0.5 to 5% by weight for granules, 1 to 10% by weight for emulsions, and 2 to 20% by weight for wettable powders. , 0.1 to 1 for powders
% by weight. The present invention will be explained below with reference to Examples and Test Examples. Example 1 Harm reducer granules Compound 4 5 parts, bentonite 70 parts, talc
21 parts, sodium dodecylbenzenesulfonate 1
1 part of polyoxyethylene alkyl allyl ether, and 2 parts of sodium lignin sulfonate are mixed, then an appropriate amount of water is added and kneaded, and the mixture is granulated using a granulator in the usual manner to form a granule of 100 parts. get the part. Example 2 Herbicide granules that reduce chemical damage After mixing 2 parts of Compound C, 1 part of Compound 6, 73 parts of bentonite, 21 parts of talc, 2 parts of sodium ligninsulfonate, and 1 part of sodium dodecylbenzenesulfonate, an appropriate amount of water was added. Add and knead and granulate using a granulator in the usual manner to form granules.
Get 100 copies. Example 3 Powder of phytotoxicity reducer 0.5 part of Compound 3 and 99.5 parts of a mixture of diatomaceous earth and clay were mixed and ground to obtain 100 parts of a powder. Example 4 Wettable powder for a herbicide that reduces chemical damage 50 parts of Compound D, 2 parts of Compound 2, 10 parts of white carbon, 33 parts of diatomaceous earth, 3 parts of sodium ligninsulfonate, and 2 parts of sodium dodecylbenzenesulfonate are mixed and ground, and mixed with water. Obtain 100 parts of Japanese medicine. Example 5 Herbicide emulsion with reduced chemical damage 40 parts of Compound A, 2 parts of Compound 1, 48 parts of orthoxylene and 10 parts of fatty alcohol polyglycol ether were mixed and dissolved to obtain 100 parts of an emulsion. Test Example 1 Test on the effect of reducing phytotoxicity by seed coating Five doses of Compound 3 were applied to each seed of corn (variety: Golden Cross Bantam), wheat (variety: Norin No. 27), and soybean (variety: Fukumusume) in a greenhouse.
% of powder at a ratio of 10g to 100g of seeds, sown in pots filled with sandy soil, treated with Compound A or Compound D at a prescribed dose the next day, and conducted a sampling survey on the 40th day after treatment. Table 1 shows the results of comparing the growth amount with the case where seeds were coated without a phytotoxicity reducer.

【表】【table】

【表】 試験例2 育苗箱処理による薬害軽減効果試験 育苗箱で生育させた水稲(品種:コシヒカリ)
が2.5葉期に到した時に、5%の粒剤に調製した
化合物6を箱あたり50gまたは100g施用し、2
時間後にあらかじめ砂質土壌を充填した9/2000
ワグネルポツトに、土をつけたままの形で水稲を
3本を1株として、ポツト当り、その2株を深さ
3cmにそう苗した。移植後5日目に化合物Bまた
は化合物Cの粒剤を所定薬量処理し、温室内で生
育させ、処理後10日目および20日目に観察調査し
た結果を第2表に示す。 水稲に対する薬害程度の表示区分は「甚害」
「大害」「中害」「小害」「微害」および「無害」の
6段階とした。
[Table] Test Example 2 Test on the effect of reducing chemical damage by nursery box treatment Paddy rice grown in a nursery box (variety: Koshihikari)
When the leaves reached the 2.5 leaf stage, 50g or 100g of Compound 6 prepared in 5% granules was applied per box.
9/2000 filled with sandy soil in advance after hours
Three paddy rice plants were planted in Wagner pots with the soil still attached, and two plants per pot were planted at a depth of 3 cm. On the 5th day after transplantation, the plants were treated with a predetermined dose of granules of Compound B or Compound C, grown in a greenhouse, and observed and investigated on the 10th and 20th days after the treatment. Table 2 shows the results. The display category for the degree of chemical damage to paddy rice is "severe damage"
There were six levels: "major harm,""moderateharm,""slightharm,""slightharm," and "harmless."

【表】 試験例3 薬害軽減剤入り除草剤の畑作圃場試験 畑地雑草が自然混在している畑地を通常の方法
で耕起、施肥(N,P2O5,K2O各1Kg/a)、お
よび整地をおこない、1区10m2(2.5m×4m)に
区画し、これにトウモロコシ、コムギ、イネ、ワ
タ、ピーナツツの種子を播種、覆土した後薬害軽
減剤2%を含む50%水和剤に調製した除草剤を所
定薬量処理した。処理後25日目に雑草に対する除
草効果および作物に対する薬害について調査し、
これを下記に示す要領で指数に換算し、これを第
3表に示す。 殺草効果; 残草量 指数 対無処理比 10 0% 9 1−3% 8 4−8% 7 9−15% 6 16−25% 5 26−35% 4 36−45% 3 46−55% 2 56−65% 1 66−75% 0 75%以上 薬害; 指数 対手取除草茎葉部乾物重抑制率 0 0% 1 1−5% 2 6−10% 3 11−20% 4 21−30% 5 31%以上
[Table] Test Example 3 Field test of herbicide containing chemical damage reducer A field where weeds naturally coexist was tilled in the usual manner and fertilized (N, P 2 O 5 , K 2 O each 1 kg/a) The land was leveled and divided into 10m2 (2.5m x 4m) plots, and corn, wheat, rice, cotton, and peanut seeds were sown and covered with soil, followed by 50% hydration containing 2% phytotoxicity reducer. A predetermined amount of the herbicide prepared as a herbicide was applied. On the 25th day after treatment, we investigated the herbicidal effect on weeds and the chemical damage to crops.
This was converted into an index as shown below, and this is shown in Table 3. Weed killing effect; Remaining weed amount index Ratio to no treatment 10 0% 9 1-3% 8 4-8% 7 9-15% 6 16-25% 5 26-35% 4 36-45% 3 46-55% 2 56-65% 1 66-75% 0 More than 75% chemical damage; Index Suppression rate of dry matter weight of weeds removed by hand to stems and leaves 0 0% 1 1-5% 2 6-10% 3 11-20% 4 21-30% 5 31% or more

【表】 試験例4 薬害軽減剤入り除草剤の水田圃場試験 水田雑草が自然混在している水田を、通常の方
法で耕起、施肥(N,P2O5,K2O各1Kg/a)、
代かきおよび整地をおこない、1区10m2(2.5m
×4m)に区画し、これに葉令2.5の水稲稚苗3本
を1株として、あぜ間隔30cm、株間隔15cmで移植
した。移植後はたん水深を3〜5cmに保ちなが
ら、雑草発芽始期(田植3日後)およびタイヌビ
エの2葉期(田植10日後)に、薬害軽減剤1%を
含む5%粒剤に調製した除草剤を所定薬量処理し
た。処理後20日目に雑草に対する除草効果および
作物に対する薬害について調査し、これを前記に
示した要領で指数に換算し第4表に示す。
[Table] Test Example 4 Paddy field test of herbicide containing chemical damage reducer A paddy field in which paddy weeds naturally coexist was plowed and fertilized using the usual method (N, P 2 O 5 , K 2 O each 1 kg/a) ),
Plowing and leveling the land, 1 ward 10m2 (2.5m
x 4 m), and three paddy rice seedlings with leaf age of 2.5 were transplanted into each with a furrow spacing of 30 cm and a plant spacing of 15 cm. After transplanting, while maintaining the water depth at 3 to 5 cm, apply a herbicide formulated into 5% granules containing 1% phytotoxicity reducer at the beginning of weed germination (3 days after rice planting) and at the 2-leaf stage of Japanese millet (10 days after rice planting). was treated with a prescribed dose. On the 20th day after treatment, the herbicidal effect on weeds and the chemical damage to crops were investigated, and the results were converted into an index as shown in Table 4 as described above.

【表】【table】

Claims (1)

【特許請求の範囲】 1 1,2−ベンゾイソチアゾール−3(2H)−
オン−1,1−ジオキシドまたはその塩、あるい
は一般式(I) (式中、Rは低級アルキル基または低級アルケ
ニル基を示す)で表わされる、一般式() (式中、R1およびR2は低級アルキル基を示し、
R3は炭素数1〜4個のアルキル基を示し、Aは
非置換のメチレン鎖、非置換のエチレン鎖、また
は1個もしくは2個のメチル基で置換されたエチ
レン鎖を示す)で表わされるハロアセトアニリド
の薬害軽減剤。
[Claims] 1 1,2-Benzisothiazole-3(2H)-
1,1-dioxide or a salt thereof, or general formula (I) (wherein, R represents a lower alkyl group or a lower alkenyl group), (In the formula, R 1 and R 2 represent lower alkyl groups,
R 3 represents an alkyl group having 1 to 4 carbon atoms, and A represents an unsubstituted methylene chain, an unsubstituted ethylene chain, or an ethylene chain substituted with 1 or 2 methyl groups) Haloacetanilide drug harm reducer.
JP7828283A 1983-05-06 1983-05-06 Agent for reducing chemical injury and herbicide with chemical injury reduced Granted JPS59204103A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP7828283A JPS59204103A (en) 1983-05-06 1983-05-06 Agent for reducing chemical injury and herbicide with chemical injury reduced

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7828283A JPS59204103A (en) 1983-05-06 1983-05-06 Agent for reducing chemical injury and herbicide with chemical injury reduced

Publications (2)

Publication Number Publication Date
JPS59204103A JPS59204103A (en) 1984-11-19
JPH0450282B2 true JPH0450282B2 (en) 1992-08-13

Family

ID=13657602

Family Applications (1)

Application Number Title Priority Date Filing Date
JP7828283A Granted JPS59204103A (en) 1983-05-06 1983-05-06 Agent for reducing chemical injury and herbicide with chemical injury reduced

Country Status (1)

Country Link
JP (1) JPS59204103A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61231284A (en) * 1985-04-03 1986-10-15 東レ株式会社 Ink jet or spray dyeing method
JPS61231285A (en) * 1985-04-03 1986-10-15 東レ株式会社 Ink jet or spray dyeing method
DE3534231A1 (en) * 1985-09-26 1987-04-02 Bayer Ag SEED SEEDS BASED ON SACCHARINE OR SACCHARINE ALKALINE METAL SALTS
AU2862997A (en) * 1996-01-11 1997-08-01 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College, The Inhibiting induced phytotoxicity in herbicides on rice
US5670450A (en) * 1997-01-02 1997-09-23 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Composition and method of using fungicides for inhibiting induced phytotoxicity in rice from halogenated aromatic herbicides
WO2000078142A2 (en) * 1999-06-17 2000-12-28 Basf Aktiengesellschaft Method for improving the resistance of cultivated plants to chemical stress
WO2007023719A1 (en) * 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent for reducing chemical injury and herbicide composition with reduced chemical injury

Also Published As

Publication number Publication date
JPS59204103A (en) 1984-11-19

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